Winchester, MA Real Estate | Winchester, MA Just Listed Homes for Sale

Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably under $1M. 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2.5 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Owners JUST put in an unused half bathroom on the first floor PERFECT for entertaining and preserving the privacy of your 2nd floor bathrooms. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Minutes from the iconic, and picturesque downtown Winchester where you'll find quaint coffee shops, local boutiques, and even a Commuter rail stop! Quick entry to Boston, Burlington, and the surrounding metro Boston area via nearby I95, Rt2, Rt3. Like spending your free time outdoors? You are mere minutes from the Medford Fells, one of Greater Boston's greenest and most resident friendly (humans and dogs alike) stretches of nature. Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS). Some of the previously prepared conceptual expansion plans are in the photos, the rest are available for review upon request.

258 Cross St, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.

$3,800

3 Beds ⋅ 3 Baths ⋅ 73575703 MLS

This beautifully maintained residence offers a unique opportunity to lease a comfortable and stylish home.This residential property, built in 1997, offers 1367 square feet of inviting, move-in ready space, presenting an open floor plan living room, dining area and kitchen with hardwood floors and lots of windows with natural sunlight. Modern kitchen white cabinets, quartz counters, range, dishwasher, refrigerator, microwave and disposal. First floor half bath with tiled floor, linen closet and washer and dryer hook ups. Second floor with 2 bedrooms, double closets, hard wood floors and full bath with tiled tub and shower and tiled floor. Third floored en-suite bedroom, double closets and bathroom with walk-in shower and tiled floor, and hardwood floors. Full unfinished basement for exercise and storage. Enjoy 4 car parking and grassy area for relaxing. Convenient to Shopping, Winchester Center, Schools, Horn Pond, Restaurants and Major Highway access. Tenant is responsible to purchase trash permit at Winchester Transfer Station. The cost is 330.00 for year and is located at 15 McKay Ave, Winchester, MA 01890

52 Sheridan Circle Unit 52, Winchester

Listing courtesy of Listing Agent: Robin Griffiths from Listing Office: J. Mulkerin Realty.

$769,000

2 Beds ⋅ 2 Baths ⋅ 73575558 MLS ⋅ ['Wedgewood Place Condominiums'] BLDG.

Don't miss this beautifully appointed 2-bedroom, 2 bath unit at Wedgewood Place, a waterfront condominium community that is centrally located in downtown Winchester. Magnificent new kitchen with custom cabinets, quartz counter tops and stainless-steel appliances that looks out at a bright and sunny, spacious open living and dining room and small home office area. Featuring a wood burning fireplace and a private balcony with exceptional views of the pool and garden, perfect for your morning coffee. Beautiful wide plank hardwood floors throughout. Custom vanities and quartz counter tops in both bathrooms. The generous Primary bedroom features custom walk-in closet and large en-suite with separate vanity area. Fresh paint and new light fixtures are among the many upgrades. New elevators and upgraded pool. One level living at its best. Enjoy the serene setting of Wedge Pond and park area right next door or take a short stroll to Winchester's amazing shops and restaurants. Public transportation outside your front door, short walk to train, 2 stops, 20 min and you are in Boston. Covered parking! Additional storage in garage.

666 Main St Unit 310, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.

$3,450

2 Beds ⋅ 3 Baths ⋅ 73575497 MLS

Welcome to this spacious 2-bedroom, 2.5-bath townhome in a highly desirable Winchester location with beautiful views of Wedge Pond. Offering multiple levels of living space, this home provides plenty of room to spread out, work from home, and relax.The main level features an open kitchen and dining area, creating a comfortable and functional space for everyday living and entertaining. Step outside to the beautiful private patio, perfect for enjoying your morning coffee, dining outdoors, or simply unwinding.Upstairs, you'll find two generously sized bedrooms, while the home also includes a dedicated office and a fully finished basement, providing flexible additional space for a home office, family room, gym, playroom, or recreation area.Enjoy an excellent location close to Winchester High School, public transportation, and the commuter rail, making travel into Boston convenient. Outdoor enthusiasts will love being near Wedge Pond, with opportunities for fishing, canoeing, and enjoying the waterfront surroundings.With 2 bedrooms, 2.5 baths, an office, finished basement, pond views, outdoor space, and convenient access to transportation, this spacious Winchester rental offers a wonderful combination of location, flexibility, and comfort.

60 Lake Street Unit J, Winchester

Listing courtesy of Listing Agent: Shannon Jenkins from Listing Office: RE/MAX Realty Experts.

$775,000

3 Beds ⋅ 2 Baths ⋅ 73575116 MLS

Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym, or additional living space. The kitchen opens directly to the generous dining room and features granite countertops, stainless steel appliances, and access to the deck. A full bathroom completes the first level. Upstairs, you’ll find three bedrooms, another full bathroom, and convenient laundry. This spacious home also offers a shared fenced-in yard, off-street parking for two cars, and additional storage in the basement. Abundant public transportation plus the charming shops and restaurants of Winchester Center, as well as elementary, middle, and high schools all at your fingertips. Welcome home to Winchester!

189 Washington St Unit 2, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,599,000

5 Beds ⋅ 3 Baths ⋅ 73575069 MLS

Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases timeless architectural character, generously proportioned rooms, and an abundance of natural light. The inviting front to back living room features a fireplace and serves as a wonderful gathering space, along with formal dining room, eat in kitchen, 1/2 bath plus a sunroom/den and a home office! The upper floors offer 5 spacious bedrooms & provide exceptional flexibility for family, guests, office space, or future customization. Enjoy the rear deck and the vast lot with lush grass, gorgeous perennial gardens and flowering trees offering plenty of space for outdoor entertaining, gardening or expansion. With this home's beautiful brick exterior, classic charm, substantial lot, and premier location, it offers an exceptional opportunity to renovate, reimagine, and create your dream home!

143 Arlington Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$4,299,000

5 Beds ⋅ 6 Baths ⋅ 73574948 MLS

Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!

4 Dartmouth, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,300,000

4 Beds ⋅ 3 Baths ⋅ 73574928 MLS

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,300,000

4 Beds ⋅ 3 Baths ⋅ 73574929 MLS

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street Unit 465, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,800

1 Beds ⋅ 1 Baths ⋅ 73574849 MLS

AVAILABLE NOW! Bright and inviting second-floor studio at Parkview Condominiums! Rent includes heat, hot water, electricity, and air conditioning. Additional amenities include storage, an outdoor swimming pool, on-site laundry, and one parking space. An additional parking pass may be purchased. Tenant is responsible for obtaining renters insurance. First month’s rent, last month’s rent, security deposit are required. Virtual Staging used.

200 Swanton St Unit 240, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.

$1,299,000

4 Beds ⋅ 2 Baths ⋅ 73574477 MLS

Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen with direct access to the picturesque backyard. Three generously sized bedrooms and a full bath complete the main level. Upstairs, a fourth bedroom is complemented by an unfinished storage room with excellent potential for a fifth bedroom, home office, or additional living space.The walkout lower level adds even more flexibility with a family room featuring a second fireplace, half bath, dedicated laundry room, mudroom, and direct access to the oversized two-car garage. Two additional storage areas provide the opportunity to create a home office, gym, playroom, workshop, or finished living space. With substantial square footage throughout, there is plenty of room to adapt the home to your needs. Beautiful custom moldings, well-proportioned rooms, abundant natural light, and a well-designed floor plan add warmth and character throughout. Recent improvements include a new roof, spray foam insulation, updated windows, and newer appliances. Outside, the park-like backyard is a true retreat, highlighted by a spectacular 20' x 40' in-ground pool, patio area, and exceptional privacy while abutting the Lynch School fields. Just moments from the Horn Pond Recreation Area, enjoy convenient access to walking trails, scenic views, playgrounds, fishing, and year-round outdoor recreation. With the newly constructed Lynch Elementary School nearby, along with shopping and major commuting routes, this home offers an ideal blend of privacy, recreation, and everyday convenience.

253 Pond St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$2,995,000

5 Beds ⋅ 6 Baths ⋅ 73574330 MLS

A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout is equally suited for everyday living and entertaining. At the heart of the home, the chef's kitchen features custom cabinetry, Thermador appliances, an oversized island, and a spacious walk-in pantry. The primary suite is a true retreat with a spa-inspired bath and generous walk-in closet, while multiple additional bedrooms offer the privacy of en suite baths. Downstairs, ceilings exceeding 10 feet elevate an expansive finished lower level with tremendous flexibility for a media room, gym, au pair or guest accommodations, or additional living space. Designed by Salt and Stone Co. and complete with a two-car garage, this is a home defined by craftsmanship, presence, and details rarely found in new construction.

8 Priscilla Lane, Winchester

Listing courtesy of Listing Agent: The Pezzano Group from Listing Office: Rise Signature Homes.

$3,149,000

7 Beds ⋅ 8 Baths ⋅ 73573670 MLS

Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

37 Mayflower Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$975,000

4 Beds ⋅ 3 Baths ⋅ 73573734 MLS

Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large, remodeled kitchen with dining area. Appreciate the large windows in the living room. Charming details complement modern improvements. The primary suite is large enough to have an office setup within the space. Primary and hall bath have been updated. Looking for outdoor space? Whether you love the Middlesex Fells, want to have friends over for al fresco dining or do a little gardening, this is the home for you. Condo expenses are split between the 2 units. Town Center, schools, commuter rail, restaurants, shopping and the farmers market are all just a few blocks away. Boston and Cambridge are less than 9 miles away from this spot conveniently located to 93 and 95.

199 Washington Street Unit 199, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,650,000

5 Beds ⋅ 4 Baths ⋅ 73573887 MLS

Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

117 Highland, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,249,000

5 Beds ⋅ 4 Baths ⋅ 73574117 MLS

Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by two gas fireplaces and central air. The luxurious primary suite features soaring ceilings, a walk-in closet, spa-like bath and private balcony. Three additional bedrooms offer generous proportions and ample closet space, while a conveniently located laundry room completes the second level. The ground floor provides a flexible living space ideal for guests, an au pair suite, or a recreation room. A whole-house generator offers added peace of mind. Ideally located approximately an equal distance to both Winchester and Arlington centers.

11 Locke St, Winchester

Listing courtesy of Listing Agent: Lesley Smith from Listing Office: Barrett Sotheby's International Realty.

$3,000

2 Beds ⋅ 1 Baths ⋅ 73573205 MLS

Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of closet spaces. Private storage space and laundry in the building. In ground pool and beautiful out door spaces. Off street parking space and huge guest parking lot. Easy access to Rte. I95, Rte. I93, "T" and Boston. Walking distance to shopping, Winchester town center and many more. HEAT , HOT WATER AND ELECTRICITY ARE INCLUDED IN THE RENT. EASY TO SHOW!

200 Swanton Street Unit T35, Winchester

Listing courtesy of Listing Agent: Nuri Tirana from Listing Office: Tirana Real Estate Group.

$1,800

1 Baths ⋅ 73573095 MLS

Desirable direct-entry terrace level studio at the Parkview Condominiums - near Winchester Center. This updated unit offers convenient walk-out access with a private covered patio perfect for enjoying the outdoors & offers direct views of the duck pond & courtyard gardens. This oversized studio offers ample space for dining, living & bedroom areas! Amenities include a pool for hot summer days and an on-site laundry room. Close to town location with easy access to the grocery store, restaurants, shops & train to Boston. Rent includes all utilities + 1 parking space. No pets. 2 person occupancy maximum.

200 Swanton Unit T30, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.

$2,199,000

4 Beds ⋅ 4 Baths ⋅ 73572955 MLS

Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor features a bright, open layout with an effortless flow from room to room, creating an ideal setting for both elegant entertaining and comfortable everyday living. Thoughtful details throughout include a spacious pantry and dedicated mudroom, blending style with exceptional functionality. Upstairs, four bedrooms include a luxurious primary suite designed as a private retreat, complete with a beautifully appointed bath and oversized walk-in shower. Convenient second-floor laundry and well-designed secondary bedrooms make this level as practical as it is polished. The finished lower level offers another impressive dimension of living space, perfect for a media room, home gym, playroom, office or guest retreat. With 3.5 beautifully finished baths, a two-car garage, and a rear deck ideal for outdoor dining and entertaining, every level of the home has been thoughtfully considered. All of this is set in one of Winchester’s most convenient locations—just minutes from Winchester Center, the commuter rail, shops, dining and schools. Classic character, completely renewed. Modern luxury without sacrificing warmth. 19 Hancock Street is a rare opportunity to enjoy the best of Winchester living in a home that feels both established and entirely new.

19 Hancock Street, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$1,749,000

5 Beds ⋅ 4 Baths ⋅ 73572890 MLS

A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with Silestone quartz countertops, upgraded cabinetry, and direct deck access. Upstairs, two ensuite bedrooms anchor the floor plan, including a generous primary suite with a large jetted soaking tub, vanity, and walk-in closet. Three additional bedrooms and a family bath complete the level. Hardwood floors run throughout, a second fireplace warms the lower-level bonus room, and ductless mini-splits deliver year-round comfort throughout the house. The walk-out lower level offers a versatile bonus room with its own exterior entrance, ideal for a home office, gym, media room, playroom, or guest suite. Three decks extend the living space outdoors for entertaining and dining above the private backyard, and an attached two-car garage adds everyday ease. Set on a quiet street with easy access to commuter rail, downtown Winchester, parks, and bike or jog trails, this is a rare chance to live in your dream home in a community that has it all.

17 Churchill Rd, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.

$675,000

2 Beds ⋅ 2 Baths ⋅ 73572854 MLS

Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all off, you have a private outdoor patio with water views! One deeded parking space included with an additional second space available for $40 per month. Prime location - walk to downtown restaurants, commuter rail, schools, supermarket, beach, and much more. Updates include kitchen (2020) downstairs bathroom (2023) new windows (2026) heating (2020)

60 Lake St Unit E, Winchester

Listing courtesy of Listing Agent: Shaundize Moosavizadeh from Listing Office: Coldwell Banker Realty - Boston.

$1,679,900

3 Beds ⋅ 2 Baths ⋅ 73572791 MLS

Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen features a substantial wood center island, handmade pocket plantation shutters that disappear seamlessly behind custom cabinetry, updated countertops and backsplash, a concealed illuminated bar cabinet, beverage fridge, and dual-zone wine fridge. Paned-glass pocket doors can separate the kitchen or open it to the adjoining dining and family rooms, where radiant-heated floors create a warm, inviting setting and a wall of windows connects the interior space beautifully to the surrounding landscape. The family room’s custom cherry entertainment center, finished with copper paneling and ebony inlays, reflects the extraordinary attention to detail found throughout. A formal living room with fireplace and custom millwork provides a separate space to gather or unwind. Tucked into a private wing are three well-proportioned bedrooms with hardwood floors and generous closets, along with a renovated full bath featuring a double vanity, deep soaking tub, and radiant-heated floor. The finished lower level offers remarkable flexibility with a media room wired for surround sound, exercise room, second full bath, laundry, mudroom area, abundant temperature-controlled storage, and direct access to an oversized two-car garage with workspace. Outside, the backyard and stone patio provide an equally peaceful and private extension of the interior living space. Mature plantings, stone walls, a potting shed, and an irrigation system complete this wide, one-third-acre lot. Central air, central vacuum, extensive built-ins and storage, plus new interior doors and crown molding throughout the bedroom wing add comfort and convenience. Polished, distinctive, and genuinely inviting, 5 Willowdale Road is a home of enduring quality that feels every bit as special as it looks. NO OPEN HOUSES, shown By Private Appointment only.

5 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.

$2,049,000

4 Beds ⋅ 4 Baths ⋅ 73572687 MLS

Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the surrounding living spaces. A formal living room with fireplace, spacious den, sun-filled dining area, & inviting sunroom create an ideal layout for both everyday living & entertaining, while a first-floor bedroom & full bath offer flexibility for guests, or home office. Upstairs includes three spacious bedrooms, including a serene primary suite with spa-like bath & dual walk-in closets, plus second-floor laundry. The finished lower level expands your living space with room for a gym, playroom, or media retreat, complete with a half bath & mudroom. A turnkey home designed to fit the way you live today

26 N Gateway, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$1,699,000

3 Beds ⋅ 2 Baths ⋅ 73572661 MLS

Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living and dining rooms, plus a bedroom & full bath. The formal dining room offers flexibility to serve as a fourth bedroom, if desired. Upstairs are two generously sized bedrooms with hardwood floors and ample closet space, along with a spacious hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$3,000

3 Beds ⋅ 1 Baths ⋅ 73572192 MLS

Welcome to 341 Washington St, Winchester, MA! This spacious 3-bedroom, 1-bath apartment offers a comfortable and convenient layout in a desirable Winchester location.The unit features laundry, parking for 2 cars, and access to a backyard, providing extra space to relax and enjoy the outdoors.Conveniently located near local shops, restaurants, schools, public transportation, and major routes, making commuting and everyday errands easy.Property Features: 3 Bedrooms 1 Full Bathroom Laundry 2-Car Parking BackyardMove in cost: 1st Month & Security due at signing contract. A great opportunity to enjoy comfortable living in Winchester. Schedule your showing today!Lease 12 monthsTenants pay for gas & Electricity and Trash disposalOwner pays water & sewer

341 Washington St Unit 2, Winchester

Listing courtesy of Listing Agent: Claudia Morais from Listing Office: P&Co Real Estate.

$3,200

2 Beds ⋅ 2 Baths ⋅ 73572062 MLS

Freshly painted and move in ready, 2 bed, 2 bath unit is located in the highly desirable Wedgewood Place. This unit boasts an open concept kitchen, dining and living room complete with a fireplace and alcove perfect for a home office. . The primary suite offers walk in closet closet space and private bath with tub and shower. Second bedroom, additional full bath and washer and dryer complete this unit. Enjoy the convenient location, minutes to public transportation, Winchester Center, schools, library, restaurants and shops while relaxing in the quiet serenity of your covered balcony overlooking the beautiful downtown Winchester. Excellent credit required, first, last, and security, no pets. One covered parking spot included #8.

666 Main St Unit 208, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$619,000

3 Beds ⋅ 4 Baths ⋅ 73571573 MLS

Great opportunity to live on a quiet side street conveniently located near the town center and Elizabeth C. McDonald Field, featuring tennis courts, ball fields, basketball courts, and a playground. This well-maintained 3-bedroom, 3.5-bath townhouse offers 1,225 sq. ft. of comfortable living space. The charming home features high ceilings and a functional multi-level layout with a bright living area, spacious kitchen, two generously sized bedrooms, and a large office. Numerous updates were completed in 2023, including hardwood flooring, a finished attic, five ductless mini-split AC units, and renovated bathrooms. A new roof was installed in 2024. Additional updates include a high-efficiency gas boiler and hot water system installed in 2019. Conveniently located within walking distance to the newly built Lynch Elementary School and Winchester High School, with easy access to local shops, restaurants, and major routes. A wonderful opportunity to enjoy comfortable living in highly desirable Winchester!

23 Shepard Ct Unit 23, Winchester

Listing courtesy of Listing Agent: Ning Sun from Listing Office: United Real Estate, LLC.

$1,099,000

4 Beds ⋅ 3 Baths ⋅ 73571480 MLS

Tucked on a quiet side street just north of Main Street, this circa-1853 antique pairs the character of a classic Winchester home with the space of a beautiful, sun-filled addition (completed in 2003): A lovely farmer's porch welcomes you and, once inside, hardwood and tile floors run through the main living spaces. Front rooms include a quaint sitting room and private office. A gas fireplace adds warmth in the family room off the kitchen, which has a slider out to a generous sized deck overlooking the serene back yard. Fresh paint throughout means there is nothing to do but move in. The same addition brought two bedrooms (primary with en suite bath), a walk-in closet, and updated kitchen cabinetry. Out back, a wood deck steps down to a spacious fenced yard with a built-in tree house, a garden area, storage shed, and in-ground sprinkler system. Central air conditioning, gas heat, town water and sewer, a one-year-old hot water tank, a partially finished, heated basement, a walk-up attic, and a four-car driveway. The location is the real headline: walk to the commuter rail, the bus, and Winchester Center's shops and restaurants, with the park, bikeway, and conservation trails minutes away. Newly renovated Lynch Elementary, McCall Middle and Winchester High School.

24 Richardson St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$1,050,000

5 Beds ⋅ 3 Baths ⋅ 73571418 MLS

Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!

257 Cross Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$11,500

5 Beds ⋅ 3 Baths ⋅ 73570878 MLS

Beautiful newer construction 4/5 bedroom *furnished or *unfurnished home with an attached garage, ideally situated on a gorgeous 11,000+ sq. ft. lot in a wonderful neighborhood with easy access to Route 93 and Boston. This spacious and inviting home offers a flexible floor plan, including a first-floor bedroom with a full bath, perfect for guests, a home office, or additional living space. The heart of the home is the oversized marble kitchen featuring a large center island, stainless steel appliances, gas cooking, and plenty of space for gathering. The kitchen opens to a warm and welcoming family room with a fireplace, while a mudroom provides convenient direct access from the garage. A formal dining room and gleaming hardwood floors complete the main level. Upstairs you’ll find four generously sized bedrooms, including a beautiful primary suite with a soaking tub and separate spa-like shower, plus an additional family room with plantation shutters. Enjoy the private backyard and patio, perfect for entertaining, grilling, and relaxing outdoors. Located in the desirable Muraco Elementary School district and convenient to Winchester Center, commuter routes, shopping, dining, and more. A wonderful opportunity to rent a spacious, beautifully maintained home in Winchester! Flexible lease terms!

10 Bellevue Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$3,895

2 Beds ⋅ 1 Baths ⋅ 73570662 MLS

Beautiful condo style apartment for rent on picturesque Church Street. A lovely 2nd floor unit, generously sized with hardwood floors throughout. Walk upstairs to an open vestibule perfect for reading a good book with direct access to the covered front porch. Living room with faux fireplace opens to a bright and airy home office or a classic dining room with period built-in cabinet. Oversized gas-cooking kitchen, 2bedrooms and full tiled bath finish this welcoming apartment. All new windows and brand new 2nd floor laundry room off the kitchen. Available for occupancy Oct 1st.

77 Church Street Unit A, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,699,000

5 Beds ⋅ 4 Baths ⋅ 73568493 MLS

Built in 2019 and perfectly positioned near downtown Winchester and the commuter rail, this 5 bed, 3.5 bath Colonial offers a bright, open layout with oversized windows, newly installed custom interior shutters and great natural light throughout. The large living room flows into the dining room, making the first floor great for everyday living and entertaining. The kitchen features a 2025 Thermador appliance package and oversized breakfast nook, with access to the deck, patio and fully fenced yard. Exterior work and fencing were completed in 2022, with mature evergreens and the newer fence creating a private and serene outdoor setting. Upstairs, the spacious primary suite includes a walk-in closet and en-suite bath with soaking tub and standing shower. Two additional bedrooms, a Jack-and-Jill bathroom and laundry room complete the second floor, with two more bedrooms and a full bath on the third. Ample storage throughout the home, including custom closets and additional storage tucked under the eaves on the third floor. Solar panels with Tesla Powerwalls and a HEATED DRIVEWAY are great added features. The unfinished basement with 8'+ ceilings offers excellent potential for future living space.

30 Farrow St, Winchester

Listing courtesy of Listing Agent: Carlisle Group from Listing Office: Compass.

$1,098,000

3 Beds ⋅ 2 Baths ⋅ 73566405 MLS

Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..

$1,999,000

4 Beds ⋅ 3 Baths ⋅ 73565817 MLS

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High St, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$4,400

3 Beds ⋅ 2 Baths ⋅ 73564765 MLS

Rare opportunity to rent an exceptionally spacious home on historic Church Street in the heart of Winchester! Offering over 2000 sq. ft. of living space, this charming Victorian features 3 generous bedrooms, 1.5 baths, a grand foyer, spacious living and dining rooms, and an eat-in kitchen with granite countertops and gas cooking. High ceilings, hardwood floors, original architectural details and a decorative fireplace add to the home's character. Enjoy a private wraparound farmer's porch, in-unit washer/dryer, ample closet space and two off-street driveway parking spaces. Pet friendly. Ideally located less than half a mile from Winchester Center and approximately 0.3 mile from the commuter rail, with shops, restaurants and cafés nearby. A beautiful combination of space, character and convenience!

79 Church St Unit 1, Winchester

Listing courtesy of Listing Agent: Anna Mean from Listing Office: AC Realty.

$1,880

1 Baths ⋅ 73564703 MLS

Welcome to 200 Swanton Street, Unit 738—a top-floor studio condominium offering comfortable, convenient, and low-maintenance living. All utilities are included, making monthly expenses simple. Enjoy laundry facilities in the building, additional storage downstairs for an extra fee, and a pool.

200 Swanton Unit 738, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.

$4,100

4 Beds ⋅ 2 Baths ⋅ 73563763 MLS

This luxurious townhome is now available for immediate occupancy. Spanning two floors, it boasts an exceptional layout. The main floor is particularly impressive, featuring a primary bedroom, an additional bedroom, Open Concept living room and dining area, and a bright, inviting eat-in kitchen. The kitchen is equipped with ample cabinets, counter space, and stainless steel appliances. Natural light floods the home, highlighting the beautiful hardwood floors throughout. The property also includes two full bathrooms, unique spots for multiple work stations or an office, and much more. The Town of Winchester is a commuters dream with easy access to downtown Boston. Either drive or take the MBTA Bus of Commuter Rail Train. Additional amenities include two driveway parking spots, common use of the backyard plus limited basement storage. All applicants must be 18 years of age or older and complete a Rental Application. EXCELLENT credit, income, and references are required. The lease signing requires First month's rent $4,200 and a Security deposit of $4,200.

7 Park Ave Unit 7, Winchester

Listing courtesy of Listing Agent: Christopher L. Barnard from Listing Office: Barnard Real Estate Advisors, LLC.

$3,500

3 Beds ⋅ 1 Baths ⋅ 73563669 MLS

**Flexible lease terms** Prime location close to town! Spacious and beautifully maintained 3-bedroom first floor unit in the heart of Winchester, with a full driveway! This great home offers a blend of classic character and thoughtful updates. This unit has always been owner occupied and is in meticulous condition .. featuring generously sized rooms with high ceilings, oversized windows, hardwood floors, beautiful original woodwork, crown molding, and timeless architectural details. The layout includes a welcoming living room with a wood-burning fireplace, dining room with wainscoting, sunroom, updated kitchen with upgraded cabinets and countertops, and an updated full bath. The kitchen includes a range, dishwasher, refrigerator, and freezer, with washer and dryer also available. Additional features include pantry and storage space, an enclosed porch/patio & a great back yard. Ideally located near downtown Winchester, with convenient access to shops, restaurants, parks, walking and biking trails, schools, public transportation, and the commuter rail. A spacious home combining historic charm, modern updates, and a convenient Winchester location.

303 Washington Street Unit 1, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$3,295,000

6 Beds ⋅ 7 Baths ⋅ 73563095 MLS

Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an impressive oversized living and dining space that flows seamlessly into the chef’s kitchen, featuring a Thermador appliance package, wine chiller, wet bar, and custom finishes. The adjoining family room is anchored by an electric fireplace, while a private home office and first-floor guest suite add versatility to the floor plan. Upstairs, four bedrooms each feature private en-suite baths, including a spacious primary retreat with a beautifully appointed bath and oversized custom walk-in closet. The finished lower level expands the living space with a media room ideal for movie nights, an additional bedroom, and full bath. Outdoors, a private fenced backyard and patio create the perfect setting for relaxing and entertaining. Pella windows and thoughtfully selected finishes can be found throughout. Ideally situated in a desirable Winchester neighborhood just down the street from Ambrose Elementary School and moments from downtown Winchester’s restaurants, shops, cafés, and commuter rail service to Boston’s North Station. A sophisticated new construction offering that combines space, style, and an exceptional Winchester location.

2 Atherton Rd, Winchester

Listing courtesy of Listing Agent: Peter Kasseris from Listing Office: Serhant.

$2,700

1 Beds ⋅ 1 Baths ⋅ 73562666 MLS

Best rental on the market in Winchester! This Beautifully updated one bedroom and one bathroom condo is avaiable for rent. The enter island kitchen opens up to a bright living and dining room area. This home boasts of all new kitchen appliances, heat pump (heat and AC), efinished hardwood floors, & recessed dimmable lighting. California closets in both closets in the bedroom, laundry room with washer dryer in unit and entryway to provide ample storage. Walk in laundry room with extra storage is a bonus! Enjoy the convenient location to the commuter rail, library, town restaurants, & shops.

115 Washington Unit 1B, Winchester

Listing courtesy of Listing Agent: Leah Polacke from Listing Office: Gamut Group LLC.

$1,329,000

3 Beds ⋅ 3 Baths ⋅ 73562273 MLS

110 Thornberry Road. Strong west side location near Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. An exceptional opportunity to establish roots in Winchester. 2021 Natural Gas Brute FT Floor Standing Boiler. Replacement windows. Central cooling. 200 amp electric. Updated Kitchen w Double oven. Prefinished hardwood floors. Therma-Tru French doors flow from the dining room to a window-lined bonus room off the dining room provides flexible year-round living space. In-ground swimming pool.

110 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Mark Kiklis from Listing Office: Kiklis Real Estate, LLC.

$2,499,000

4 Beds ⋅ 5 Baths ⋅ 73555666 MLS

Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704

54 Squire Road, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.

$2,500

2 Beds ⋅ 1 Baths ⋅ 73561836 MLS

This great first floor 2 bedroom home is bright and spacious. The entry hall leads to living room, dining room, and kitchen The full bath is flanked by 2 bedrooms. Eat in kitchen with pantry is spacious enough to have a dining table. Tenant pays for gas heat, electricity, hot water, snow removal & refuse removal. Landlord pays for landscaping (grounds maintenance), water, sewer & provides laundry in the basement. 2 car tandem assign parking. Available 9/1/26. Showings are:Wed, 8/12 5-6pmThurs., 8/13 3:30-4:15Fri., 8/14 11am-12 noonPhotos are from 2nd floor unit and represent similar condition and layout.

24 Lebanon Unit 1, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$949,999

4 Beds ⋅ 2 Baths ⋅ 73561829 MLS

Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens effortlessly into a bright eat-in kitchen — an inviting space for both everyday living and entertaining. Two well-sized bedrooms with ample closet space and a full bath complete the main level, kept comfortable year-round by central air-conditioning.The lower level offers exceptional flexibility with its own private in-law suite, featuring a warm, fireplaced living room, two bedrooms with plush wall-to-wall carpeting, and a full bath — ideal for extended family, guests, or additional living space.Outside, enjoy a level, easy-to-maintain backyard, convenient off-street parking, and a one-car garage. Ideally located just minutes from Skillings Field and McDonald Field, this home offers wonderful access to local recreation, with Lynch Elementary only 0.8 miles away and the scenic Horn Pond Recreation Area close at hand. Enjoy the convenience of nearby Winchester Hospital, easy access to Route 3, and commuter rail service for a smooth trip into Boston. A home that blends comfort, versatility, and an unbeatable location — a must-see that won't last long. Showings begin 8/22 @ Open House 1:30-3PM

96 Loring Ave, Winchester

Listing courtesy of Listing Agent: Jeremy Smith from Listing Office: StartPoint Realty.

$3,450,000

6 Beds ⋅ 5 Baths ⋅ 73561703 MLS

Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the oversized three car garage into the stunning mudroom & into the most fabulous home that has hit the market in quite some time. Wide plank oak flooring, high ceilings & tasteful finishes throughout. The family room feature wall has custom arched inset bookshelves & cabinetry with led lighting, gas fireplace & plenty of windows to enjoy views of the gorgeous yard. Enjoy conversations & cocktails in the stylish lounge featuring elegant arched details, a custom wet bar & wine fridge. Oversized sliders to spacious deck draw you to the gorgeous 1/2 acre level lot with **room for pool ** pool shown is virtual image*. The first floor also offers a bedroom or home office option; The second floor features 5 large bedrooms & 3 full baths w/ soaring ceilings in every room; the primary being a dreamy retreat showcasing a spa like porcelain bath w 10' shower & 2 shower heads with soaking tub, bidet toilet & walk in closet! Second floor laundry w/sink & custom cabinetry make doing laundry a joy. The lower level offers plenty of space for media room, game room plus space for a home gym & full bath! This exceptional home is a must see ~the top quality finishes and stunning design will not disappoint!

7 Hutchinson Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$3,200,000

5 Beds ⋅ 6 Baths ⋅ 73561372 MLS

Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort. From the moment you arrive, the home’s striking historical columns, wraparound porch, circular driveway, and natural stone detailing create an unforgettable first impression. Inside, every space has been thoughtfully crafted with premium finishes and custom design elements throughout. The showstopping chef’s kitchen features paneled Thermador appliances, a stunning La Cornue induction range, and a custom white oak island that seamlessly anchors the heart of the home. Formal and informal living spaces flow beautifully together, highlighted by exposed chimneys, restored 1800s double doors, multiple fireplaces, floor-to-ceiling windows, and rich hardwood flooring. The luxurious primary suite serves as a private retreat, complete with a tray ceiling, fireplace, spa-inspired bath with radiant heated floors, soaking tub, oversized custom shower, and an impressive walk-in closet with built-in island storage. Additional bedrooms offer ensuite and Jack-and-Jill bath configurations, while the finished third floor provides flexible living with cathedral ceilings, sitting area, and office space.Designed with entertainment and lifestyle in mind, the finished lower level features a custom movie theater, wet bar, wine room, and additional pantry storage. Above the detached two-car garage, finished bonus rooms with a full bath create the ideal space for a home office, gym, studio, or guest accommodations.Blending historic character with cutting-edge efficiency, the home has undergone an extensive structural rebuild and offers fully electric, energy-efficient living with multi-zone heat pumps, EV-ready garage spaces, radiant heated bathroom floors, Pella windows, and premium construction materials throughout. A rare opportunity to own a truly distinctive luxury residence in one of Winchester’s most sought-after neighborhoods.

18 Ridge St, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.

$3,200

3 Beds ⋅ 2 Baths ⋅ 73561319 MLS

Great opportunity to rent this spacious 3-bedroom duplex offering three levels of living space, tucked away on a quiet dead-end street. Freshly painted throughout, the unit features new flooring, an updated kitchen equipped with a stove, dishwasher, and refrigerator, three generously sized bedrooms, and 1.5 bathrooms. The basement offers additional storage space, with a washer and dryer available if needed. The property also includes off-street parking for up to two vehicles.

5 Quigley Court Unit 5, Winchester

Listing courtesy of Listing Agent: Anna Mean from Listing Office: AC Realty.

$3,200

2 Beds ⋅ 2 Baths ⋅ 73560790 MLS

Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features a walk-in closet, private bath, and separate vanity area, while the second bedroom and updated guest bath provide flexibility for guests or a home office. New hardwood floors & new carpet in bedrooms, in unit laundry, central air, parking, extra storage, and access to the community pool. The professionally managed elevator building. Located near Winchester Center’s restaurants, shops, commuter rail, parks, and everyday conveniences! move right in and enjoy!

666 Main Street Unit 315-3, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$3,500

3 Beds ⋅ 2 Baths ⋅ 73560549 MLS

Spacious and well-maintained 3-bedroom, 2-bath townhouse featuring three levels of living space, with a large private yard and a storage shed. Enjoy hardwood floors throughout, a fully equipped kitchen with stainless steel appliances, and a finished basement with laundry and abundant storage space. The property includes 4 off-street parking spaces on a paved driveway. Conveniently located with an easy commute to Boston and access to Winchester's highly regarded schools and community amenities.No smoking. First month's rent, last month's rent, and a security deposit are due upon lease signing.

28 East St Unit 28, Winchester

Listing courtesy of Listing Agent: Jennifer Zhao from Listing Office: HMW Real Estate, LLC.

$3,100

2 Beds ⋅ 2 Baths ⋅ 73560458 MLS

Welcome to this charming 2-bedroom, 1.5-bath rental located on the desirable west side of Winchester. Offering three levels of living space, this home provides plenty of room to spread out and enjoy a comfortable, flexible layout. Beautiful hardwood floors add warmth and character throughout, while the level, partially fenced backyard provides a wonderful private outdoor space for relaxing, entertaining, or enjoying the warmer months. Situated in a welcoming Winchester neighborhood with convenient access to local amenities, schools, shopping, dining, commuter routes, and all that this sought-after community has to offer. Enjoy the space and privacy of a home combined with an excellent Winchester, MA location. Schedule your showing today!

7 Ridge Street, Winchester

Listing courtesy of Listing Agent: Shannon Jenkins from Listing Office: RE/MAX Realty Experts.

$4,950

5 Beds ⋅ 2 Baths ⋅ 73560281 MLS

Welcome to this spacious 3-story Colonial, where timeless curb appeal meets modern living. A bluestone path invites you to the main entry, setting the tone for a home designed for both comfort and sophistication. Inside, expansive living and dining rooms showcase wood trim and custom built-ins, while hardwood floors and oversized replacement windows flood the space with natural light. The heart of the home is a fully equipped kitchen featuring granite counters and a premium appliance suite: Sub-Zero refrigerator, Wolf gas range, and Bosch dishwasher. 3/4 bath on the main level. Upstairs, a spacious layout offers 4 bedrooms and 1 bathroom, perfect for families or those seeking generous space. The third floor includes a bedroom & a bonus office ideal for remote work or a quiet retreat. Outside, enjoy a private yard with a shed, plus parking for 4 cars. Located just 8 miles from Boston and moments from the Wedgemere train Station. You’ll be close to outstanding public and private schools, downtown Winchester, Upper Mystic Lake, Winchester Boat Club, Winchester Country Club, Ginn Field Park, and a variety of shopping, dining, and scenic nature trails. Additional features include a washer and dryer with dry storage in the basement. Tenant pays utilities; pets will be considered. Immediate availability.

79 Bacon St Unit 79, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.

$3,700

4 Beds ⋅ 2 Baths ⋅ 73559841 MLS

Spacious 4-bedroom, 2-bath apartment available for immediate occupancy in a two-family home just minutes from Winchester Center. Please note: This is NOT a single-family home. This unique unit occupies the entire first floor and finished lower level. The main level features hardwood floors throughout, a living room, dining room, two spacious bedrooms, a full bath, and an eat-in kitchen with a new refrigerator and dishwasher. The finished lower level offers a large family room, two additional bedrooms, a second full bath, laundry, and ample storage. Private driveway with parking for up to 3 cars, patio, and shared backyard. Conveniently located near Winchester Center, shopping, restaurants, commuter rail, and major routes.

10-12 Webster St Unit 1, Winchester

Listing courtesy of Listing Agent: Ryan Kelly from Listing Office: Real Broker MA, LLC.

$6,000

3 Beds ⋅ 3 Baths ⋅ 73559660 MLS

This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail drawers, and Blum hardware. Additional upgrades include Harvey windows and doors, sleek Kuzco modern lighting, and Italian tile finishes that bring a touch of elegance to every room. With 3 full baths, 3 generous bedrooms, and multiple living areas, there's plenty of room to spread out. The home also offers a two-car garage and ample storage. Set on almost half an acre lot, this home is close to shopping, schools, medical facilities, public transportation and highway access. Convenience and style.

25 Berkshire Dr, Winchester

Listing courtesy of Listing Agent: McCaul & Mounsif Real Estate Group from Listing Office: McCaul & Mounsif Real Estate Group LLC.

$2,800

2 Beds ⋅ 1 Baths ⋅ 73557966 MLS

All utilities included (heat, hot water, and electricity) in this top-floor 2-bedroom, 1-bath condo with stunning views over the treetops and duck pond. Its 7th-floor perch offers exceptional privacy, quiet, and floor-to-ceiling, south-facing windows that fill the home with natural light. One cat allowed. The kitchen and bath were fully renovated several years ago, and the entire unit has been freshly painted. This elevator building features a swimming pool, newly renovated laundry rooms with convenient app-operated machines, and one parking space (additional parking available for a fee). Less than a mile to Winchester Center's cafés, restaurants, shops, and the MBTA commuter rail into Boston. The newly built Lynch Elementary School and grocery store are both approximately ½ mile away. Enjoy quick access to I-93, as well as the scenic trails and natural beauty of Middlesex Fells Reservation and Horn Pond. Available for immediate occupancy. No dogs permitted.

200 Swanton St Unit 705, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.

$5,500

3 Beds ⋅ 3 Baths ⋅ 73557783 MLS

Welcome to this spacious and charming Colonial offering beautiful architectural character, a flexible floor plan, and generous living space across multiple levels.Step into the welcoming foyer and discover a bright, inviting home featuring a fireplaced living room with beamed ceilings and oversized windows, complemented by a sun-filled adjoining sunroom.The beautiful kitchen features granite countertops, ample workspace, and a cozy breakfast nook with convenient access to the side yard. A separate home office and full bathroom on the first floor provide additional flexibility for working from home, guests, or everyday living.Upstairs, the spacious primary bedroom includes a walk-in closet and en-suite bathroom, along with an additional adjoining room that can serve as a nursery, private office, dressing room, or guest space. Two additional generously sized bedrooms, a full family bathroom, and a spacious landing with additional closet storage complete the second floor.The lower level offers an unheated bonus/family room with a decorative fireplace, laundry area, additional storage, and direct access to the two-car garage.Outside, enjoy a beautiful, spacious fenced backyard, perfect for relaxing, entertaining, and outdoor activities.Conveniently located near Middlesex Fells Reservation and all that Winchester has to offer, this home combines space, character, privacy, and convenience in a highly desirable residential setting.

111 Highland Ave, Winchester

Listing courtesy of Listing Agent: Michelle Li from Listing Office: Zhensight Realty LLC.

$1,549,000

3 Beds ⋅ 3 Baths ⋅ 73556633 MLS

Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!

50 Holland Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$3,600,000

7 Beds ⋅ 8 Baths ⋅ 73556474 MLS

Spectacular ground-up NEW construction estate on expansive, large level lot of 24,688sf, ready for move in, located on a quiet Winchester cul-de-sac. Newly completed, this exceptional residence spans more than 7,000 square feet across impeccably finished levels. Ideally positioned on a quiet cul-de-sac on over half an acre of land in one of Winchester’s most desirable locations, the home offers an extraordinary combination of new construction, refined design, privacy, and convenience, just moments from Winchester Country Club. Designed with entertaining in mind, the residence features seven spacious bedrooms and 7.5 designer baths, providing beautifully appointed private retreats for family and guests. At the heart of the home is an outstanding chef’s dream kitchen, thoughtfully designed with custom cabinetry, expansive preparation and gathering spaces, double oven, top-of-the-line 48" Wolf gas stove, Sub-Zero fridge, 2 Bosch dishwashers. steam oven, built in microwave and wine fridge. The kitchen flows seamlessly into expansive, light-filled lamily, living and dining areas, creating an inviting setting for large gatherings, celebrations, and relaxed everyday living. The flexible floor plan is perfectly suited to today’s lifestyle, with dedicated spaces for a professional home office, private fitness studio, and expansive recreation wing. Set in a lush, private lot with a three-car garage, this large lot property also offers excellent potential for a future pool and outdoor entertaining oasis. A rare opportunity to own a substantial, newly built entertainer’s home in an ideal Winchester setting, close to the town center, dining, schools, recreational amenities, hiking trails, and Wright Locke Farm. Ready to move in and enjoy!

11 Viking Road, Winchester

Listing courtesy of Listing Agent: Post Advisory Group from Listing Office: Engel & Volkers Boston.

$2,100,000

4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ ['The Ledges'] BLDG.

Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home offers an elegant first-floor primary suite w/ dual walk-in closets and a stunning spa-inspired bath. Meticulously reimagined from top to bottom, every element of this extraordinary renovation was thoughtfully curated using the finest imported designer finishes and bespoke craftsmanship, creating an unparalleled level of luxury. The dramatic open-concept main level is highlighted by soaring vaulted ceilings, a fireplaced living room w/ a custom-designed mantel, & walls of glass that open to a private deck overlooking breathtaking western sunsets & tranquil natural surroundings. The designer kitchen is a true showpiece, featuring premium finishes, a sun-filled breakfast area, & seamless flow into the elegant dining room, ideal for both intimate gatherings & entertaining.The second floor offers 3 rooms including a spacious bedroom, beautifully renovated full bath, loft ideal for a home office, & an additional sitting room/TV room or guest space. The walk-out lower level it’s another suite in itself offering a spacious family room, second kitchenette, dining area, game room, additional bedroom with double closets, a luxurious spa bath, oversized laundry room, and abundant storage. Step outside to a private patio surrounded by peaceful, picturesque grounds, creating the perfect retreat for relaxing or entertaining. Ideally located w/ easy access to Winchester Center, Whole Foods, major highways, restaurants, and shops, this exceptional home offers luxury living just 7 miles from downtown Boston.

7 Wainwright Road Unit 113, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,749,000

3 Beds ⋅ 4 Baths ⋅ 73555777 MLS

Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing or entertaining. Step outside to enjoy the beautifully fenced-in yard, offering a private outdoor retreat for play, pets, gardening, or gatherings. Everyday convenience continues with a mudroom located directly off the driveway, multiple off-street parking spaces, and a two-car garage. The finished lower level includes a full bathroom and versatile flex space perfect for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. Thoughtfully renovated from top to bottom, this home features all new systems for peace of mind and effortless modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.

1 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$849,000

3 Beds ⋅ 2 Baths ⋅ 73555218 MLS

Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

15 Clark St, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.

Winchester, MA Just Listed Homes for Sale

Newest Winchester, MA Just Listed Homes for Sale

REAL BROKER MA LLC

Address

Contact

Follow