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1 Plymouth Rd., Winchester
$3,299,000
7 Beds ⋅ 8 Baths ⋅ 73585058 MLS
$50,000 BUYER INCENTIVE!!! Our seller is offering buyers a $50K credit to be used as you want. Buy down your mortgage rate, order upgrades, pay closing costs. Choice is yours! Ideally situated in one of Winchester’s most serene neighborhoods, this exceptional residence offers impressive scale, thoughtful design, and remarkable versatility in a quiet, peaceful setting. It also represents one of Winchester's best values, with tremendous square footage and an au-pair/in-law apartment. Surrounded by beautiful homes and a sense of established elegance, this is a property designed to feel both private and welcoming. Thoughtfully expanded and beautifully built, the home offers 7 bedrooms and 7.5 baths, with generous living spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, a stunning chef’s kitchen opens seamlessly to a dramatic fireplaced living room with soaring cathedral ceilings, creating a warm and inviting gathering space filled with natural light. There is also a family room, also with a fireplace and large picture windows, allowing for an abundance of sunlight. Explore further and you'll find a huge butler's pantry, a must-have feature in today's homes. There is also a wet bar with a beverage fridge. This is a home that has been very thoughtfully designed for how today's buyers actually live, but what truly distinguishes it is the flexibility of design. A private two-bedroom suite offers its own living area, office, wet bar, and full bath, providing an exceptional option for an au pair, extended stays, guests, returning college students or a more private living arrangement. The finished lower level adds even more space for recreation, fitness, entertaining, or simply spreading out. Beautifully proportioned rooms, exceptional functionality, and a serene neighborhood setting come together to create a home that feels substantial yet comfortable, sophisticated yet wonderfully livable. The natural light is exceptional, and outside, an oversized lot offers plenty of play space and a deck to hang out on. Just moments from Mullen Field, close to the town center and trains and an easy trip to Lexington or Cambridge, 1 Plymouth offers a rare opportunity to enjoy exceptional space and privacy in one of Winchester’s most sought-after neighborhoods.

1 Plymouth Rd., Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
2 Wyman Ct Unit 1, Winchester
$3,900
3 Beds ⋅ 2 Baths ⋅ 73582725 MLS
Spacious and full of character, this 3-bedroom, 1.5-bath apartment is located in a beautiful Colonial Revival home just minutes from Winchester Center. Inside, you'll find well-proportioned bedrooms, expansive living and dining areas, a cozy den, and an eat-in kitchen. Additional highlights include both front and back porches and driveway parking for two cars. Conveniently located near Ambrose Elementary School and within walking distance of Winchester Center's shops, cafés, restaurants, and commuter rail station, this home offers the perfect blend of space, charm, and everyday convenience. *Last bedroom to be emptied by end of weekend and porch to be painted next week.

2 Wyman Ct Unit 1, Winchester

Listing courtesy of Listing Agent: Remianna Hearns from Listing Office: Coldwell Banker Realty - Cambridge.
1 Overlook Way, Winchester
$1,650,000
4 Beds ⋅ 3 Baths ⋅ 73581571 MLS
NEW Photos! Welcome to One Overlook Way in Winchester. This home is located on a 1/3 acre corner lot on a short cul-de-sac off High Street- a premier location close to Ambrose Elementary School and the Winchester Country Club. Don't miss this spacious 4+ bedroom center-entrance Colonial. with a thoughtfully designed circular flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen with room to add an island or large table also opens naturally into the comfortable family room - with gas fireplace, custom built-ins, a new split AC and access to the back and side yard! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a split AC, private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a second home office, hangout zone or storage. The finished lower level adds another playroom, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished storage space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

1 Overlook Way, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
666 Main Street Unit 217, Winchester
$700,000
2 Beds ⋅ 2 Baths ⋅ 73581469 MLS ⋅ ['Wedgewood Place'] BLDG.
Easy one-floor living in Winchester Center with garage parking for one car! Fabulous location near town center, TRAIN, shopping, restaurants, schools and library. Enjoy the open layout with extra wall of beautiful kitchen cabinets, large peninsula/eating bar, fireplace, balcony and a nook for a desk or whatever you wish. Large primary bedroom has two windows, large walk-in closet and full bath. Second bedroom is across hall from laundry and bath with shower. Air handler and condenser replaced in 2022. Central air throughout. Hot water heater and water shutoff installed - 2018. The additional storage unit is off the main lobby for easy access. Amenities include 2 elevators, inviting POOL and onsite rubbish pickup. Perfect home for first time buyers, downsizers, anyone commuting to Boston or in search of a vibrant town center lifestyle. New budget meets conventional financing guidelines!

666 Main Street Unit 217, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
7 Conant Unit 19, Winchester
$3,500
2 Beds ⋅ 2 Baths ⋅ 73580293 MLS
Available NOW! Welcome to your oasis at The Willows at Winchester. This fully gut-renovated, first-floor corner unit offers seamless single-level living at its finest. The Living Space offers open-concept layout featuring rich hardwoods, a gourmet chef's kitchen, dining area and living room w/ a cozy gas fireplace opening to your private patio. The Bedrooms: A lavish primary suite with a walk-in closet and spa-like glass shower, plus a bright second bedroom and an upgraded full bath.The Perks: In-unit laundry, an oversized private garage with a massive storage loft, and resort-style amenities (heated pool, gym, and clubhouse).Perfectly situated just minutes from Winchester Center, Route 93, and the commuter rail, Boston train & scenic nature trails. A rare turnkey gem where modern comfort meets premium lifestyle.

7 Conant Unit 19, Winchester

Listing courtesy of Listing Agent: Ides Figueiredo from Listing Office: Coldwell Banker Realty - Brookline.
34 Charles Road Unit 34, Winchester
$3,500
3 Beds ⋅ 2 Baths ⋅ 73580052 MLS
Bright and sunny 3 bedroom /1.5 bathroom town home in a quiet neighborhood in Winchester to rent. It features a nice floor plan with a new foyer/mudroom entrance, a spacious living room and dining area, a kitchen which can directly access to the beautiful back yard. The second floor offers three good sized bedrooms. The basement offers plenty storage space with included washer and dryer. Fenced backyard provides a great private space for outdoor entertainments or dining. Great opportunity to move into Winchester and take advantage of the great schools, cozy community and close proximity to Boston. The location is very convenient and close to schools, shopping and highway access.

34 Charles Road Unit 34, Winchester

Listing courtesy of Listing Agent: WINN Rental Team from Listing Office: WINN Real Estate & Consulting.
666 Main Unit 310, Winchester
$3,900
2 Beds ⋅ 2 Baths ⋅ 73579935 MLS
2 bedroom, 2 bath condo with *Flexible Leasing Terms* 6-12 months. Located at Wedgewood Place, a waterfront condominium community that is centrally located in downtown Winchester. Beautifully updated, overlooking beautiful pool and garden area. Garage parking. Steps to town, stores and restaurants as well as public transportation, just a short ride to Boston.

666 Main Unit 310, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.
200 Swanton St Unit 708, Winchester
$1,878
1 Baths ⋅ 73579736 MLS
Sunny top-level studio apartment available now at desirable Parkview Condominiums in Winchester! This bright and open studio features a spacious layout with sliders to a balcony overlooking the beautifully landscaped grounds and pond. Enjoy a well-maintained kitchen and bath, ample closet space, and one assigned parking spot (extra spot can be rented). The community offers a pool, picnic area, laundry facilities, and on-site management. Heat, hot water, and electricity included! Conveniently located near Winchester Center, Horn Pond, and major routes. Renters insurance required. first, last and security for move in.

200 Swanton St Unit 708, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
9 Priscilla Ln, Winchester
$1,325,000
4 Beds ⋅ 2 Baths ⋅ 73579538 MLS
1st OPEN HOUSE! SUNDAY, OCTOBER 4th, 11:30am-1:00pm! Timeless New England charm meets prime Winchester living at 9 Priscilla Lane. Tucked along a quiet, tree-lined neighborhood on Winchester’s East side, this inviting 4-bedroom home offers the perfect balance of suburban tranquility, outdoor adventure, and seamless connectivity.Inside, the sun-drenched home features rich hardwood floors, a gorgeous kitchen, wood burning fireplace, flexible living areas, and an intuitive layout designed for both daily relaxation and effortless entertaining. Step outside to an expansive, private backyard—a sunlit haven perfect for weekend barbecues, garden projects, or crisp New England evenings.Outdoor enthusiasts will love living moments away from the endless hiking, trail running, and scenic escapes of the Middlesex Fells Reservation. For commuters, rapid access to I-93 and Route 128/I-95, combined with nearby Commuter Rail stations, makes reaching Boston, Cambridge, or local tech hubs exceptionally fast and direct. Complete with proximity to top-rated Winchester public schools and vibrant downtown dining and shops, this property delivers the quintessential North Shore lifestyle in an unmatched location. MAKE 9 PRISCILLA LANE YOUR HOME TODAY!

9 Priscilla Ln, Winchester

Listing courtesy of Listing Agent: Robert Del Greco from Listing Office: Compass.
200 Swanton St Unit 727, Winchester
$399,000
1 Beds ⋅ 1 Baths ⋅ 73579389 MLS ⋅ ['Parkview Condominiums'] BLDG.
Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and electricity, as well as access to the in-ground swimming pool. A private basement storage unit is also included for added convenience. With its comfortable layout, private balcony, pond and garden views, included utilities, and convenient location, this move-in-ready condo is a great opportunity you won’t want to miss!

200 Swanton St Unit 727, Winchester

Listing courtesy of Listing Agent: Alice Zheng from Listing Office: Shore Real Estate LLC.
7 Lakeview Terrace, Winchester
$2,400,000
6 Beds ⋅ 4 Baths ⋅ 73578443 MLS
RARE WATERFRONT OPPORTUNITY on Upper Mystic Lake with spectacular sunset views! Tucked away on Lakeview Terrace, this special 1910 home offers a combination rarely found in Winchester: waterfront living, privacy, beautiful southwest light and exceptional convenience. Gracious rooms, period details and quality craftsmanship give the home wonderful character, while its generous layout offers an exciting opportunity to update and create something truly special. The home features 5-6 bedrooms, a home office and expansive living spaces designed to take advantage of the lake views. The kitchen, renovated some years ago, was thoughtfully positioned so the view can be enjoyed while preparing meals. An unfinished lower level with high ceilings offers additional possibilities. Just steps from Wedgemere Commuter Rail Station, 1/2 mile to Shannon Beach and less than a mile to Winchester Center via the Tri-Community Bikeway. A remarkable setting, beautiful sunsets and an opportunity that may not come again for years. Don't delay your visit!

7 Lakeview Terrace, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
36 Elmwood Ave Unit 11, Winchester
$1,350,000
2 Beds ⋅ 3 Baths ⋅ 73578288 MLS ⋅ ['Allegro Condominium'] BLDG.
Introducing 36 Elmwood Avenue, Unit 11 - a penthouse residence at Allegro with Winchester Center's shops, restaurants & commuter rail right outside your door. Built in 2021, this 2 bedroom / 2.5 bath home w/ 2 GARAGE PARKING SPACES offers 1,573 sqft and the best layout in the building. Loads of upgrades throughout! The open living, dining & kitchen area is bright and great for entertaining, with a living room wall finished in custom wood detailing. The home chef will enjoy Thermador appliances & plenty of counter space. Designer lighting has been added throughout. Big bonus: custom-made plantation shutters on the windows, an upgrade most buyers would otherwise pay for after closing. Several closets have been outfitted w/ custom organizing systems, so storage is already done for you. Both bedrooms have their own en suite baths, and a half bath is on hand for guests. Smart light switches throughout, in-unit laundry w/ washer & dryer, a private balcony, and private storage in the garage. Allegro is a secure elevator building w/ intercom & camera entry plus a heated garage, so no scraping or shoveling on winter mornings. Leave the car downstairs and walk to the train, dinner & coffee.

36 Elmwood Ave Unit 11, Winchester

Listing courtesy of Listing Agent: The Rasner Group from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.
30 Willowdale Rd, Winchester
$3,200,000
8 Beds ⋅ 7 Baths ⋅ 73577116 MLS
$50,000 BUYER INCENTIVE!!! Our seller is offering buyers a $50K credit to be used as you want. Buy down your mortgage rate, order upgrades, pay closing costs. Choice is yours! A rare expression of quality, craftsmanship, and enduring style, 30 Willowdale Road presents an exceptional opportunity to own a newly constructed residence in one of Winchester’s most coveted neighborhoods. Set on a beautifully proportioned, large and level lot, this remarkable home has been thoughtfully conceived to offer the space, sophistication, and effortless lifestyle expected of a truly exceptional property.From the moment you enter, the quality is unmistakable. Gracious proportions, refined architectural details, exceptional craftsmanship, and carefully curated finishes create a home designed not simply for today, but with a sense of lasting beauty that will transcend trends for years to come. Every space feels considered, polished, and substantial, with an elevated yet welcoming character throughout.At the heart of the home, a spectacular chef’s kitchen pairs custom finishes with premium Viking appliances, creating a beautiful gathering place for everyday living and entertaining. Expansive living spaces flow naturally from one to the next, equally suited to intimate evenings, holiday celebrations, and a house full of family and friends. 8 bedrooms and 6.5 baths provide extraordinary flexibility, privacy, and comfort, with abundant space for guests, home offices, fitness, recreation, and the evolving needs of modern life. Outside, the expansive level grounds are a luxury unto themselves, offering wonderful possibilities for outdoor entertaining, recreation, gardens, and the simple pleasure of having room to breathe. A two-car garage and the ease and efficiency of brand-new construction further enhance the lifestyle.Sophisticated without being showy and luxurious without sacrificing warmth, 30 Willowdale Road is the kind of home that feels exceptional today and will remain so for generations. A rare combination of location, land, craftsmanship, and enduring quality in a premier Winchester neighborhood.

30 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
258 Cross St, Winchester
$919,000
4 Beds ⋅ 3 Baths ⋅ 73575764 MLS
MASSIVE PRICE IMPROVEMENT!!! A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 4 bedrooms, 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides bedrooms 3 and 4 that allow you to expand your work and life styles, as your life changes, without needing to move. The bedrooms work well as kids rooms, guest suites, home office / gym, hobby spaces or all of the above! Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

258 Cross St, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.
52 Sheridan Circle Unit 52, Winchester
$3,650
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.
60 Lake Street Unit J, Winchester
$3,250
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.
189 Washington St Unit 2, Winchester
$765,000
3 Beds ⋅ 2 Baths ⋅ 73575116 MLS
SELLERS WILL PRE-PAY 1 YEAR OF CONDO FEE! 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.
4 Dartmouth, Winchester
$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.
465 Washington Street, Winchester
$1,250,000
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.
465 Washington Street Unit 465, Winchester
$1,250,000
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.
37 Mayflower Road, Winchester
$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.
117 Highland, Winchester
$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.
200 Swanton Street Unit T35, Winchester
$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.
19 Hancock Street, Winchester
$2,149,000
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.
17 Churchill Rd, Winchester
$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.
60 Lake St Unit E, Winchester
$660,000
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.
4 Churchill Road, Winchester
$1,499,000
4 Beds ⋅ 2 Baths ⋅ 73572661 MLS
Price Change!! **Open House this weekend or call for private showings** Great offering~ Extensively rebuilt and expanded, this impeccably maintained 4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room w/living area and dining area 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 room w/ fplc, plus 2 spacious bedrooms & full bath. offering flexibility for various uses. Upstairs are two additional generously sized bedrooms with hardwood floors and ample closet space, along with a full 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.
666 Main St Unit 208, Winchester
$2,900
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.
24 Richardson St, Winchester
$1,049,000
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.
10 Bellevue Avenue, Winchester
$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.

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