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$3,600
3 Beds ⋅ 2 Baths ⋅ 73575968 MLS
Welcome to this charming Winchester home! Nestled amidst lush greenery, it exudes classic ranch style and is located in the sought-after Muraco School District, near Horn Pond and Middlesex Fells Reservation. Just a 20-minute drive to downtown Boston, this location offers both convenience and tranquility. Renovated in 2022, it consists of modern upgrades including stainless steel appliances, an updated AC system, and a new gas water heating system. Step into the beautiful garden leading to the spacious kitchen with new quartz countertops and Imitation wood grain tiles. The open-concept living room features gleaming hardwood floors. Two bright bedrooms and an office/den provide cozy spaces, while the expansive basement offers endless possibilities. Outside, stone pathways lead to the well-maintained backyard with a swing and picnic area, perfect for outdoor gatherings. Don't miss the chance to make this dream home yours!

235 Forest St, Winchester

Listing courtesy of Listing Agent: Lin Wu from Listing Office: JW Real Estate Services, LLC.
$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.
$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.
$1,299,000
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.
$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.
$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.
$3,200
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.
$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..
$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.
$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.
$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.
$3,200
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.
$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.
$849,000
3 Beds ⋅ 2 Baths ⋅ 73553626 MLS
Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and effortless entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or a 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 Center commuter rail, and major routes, this home embodies the very best of Winchester living. No HOA fee.

15 Clark St Unit 15, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.
$685,000
2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.
NEW PRICE! Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new chandelier. Spacious primary bedroom has LARGE WALK-IN CLOSET plus a sink and linen closet before the entry to the water closet where you'll find a large tub. Second bedroom/office has double closet and is across hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR and find NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (all recently done in 2026), NEW WASHER AND DRYER 2025 and NEW HOT WATER HEATER (2024). Love the COVERED PARKING in the garage below the building, association POOL, two ELEVATORS plus the convenience of being only one flight of stairs up from the street level. Location near town center, TRAIN, shopping, restaurants, schools and library is superb.

666 Main Street Unit 211, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$4,200
3 Beds ⋅ 2 Baths ⋅ 73550305 MLS
Beautifully renovated single-family home on a quiet cul-de-sac in desirable Winchester. Situated on a spacious 9,500± sq. ft. lot, this move-in-ready home features newly finished hardwood floors throughout, an open-concept living and dining area, an updated kitchen with gas cooking, a cozy family room with a wood-burning fireplace, and a full bath on the main level. Upstairs offers three spacious bedrooms and a newly renovated full bath. Conveniently located near schools, parks, shopping, and major commuter routes. Tenant is responsible for all utilities, snow removal, and lawn maintenance. First month’s rent, one month’s security deposit, credit/background check, proof of income, and photo ID required.

22 Baldwin St, Winchester

Listing courtesy of Listing Agent: Qian Han from Listing Office: JW Real Estate Services, LLC.
$950,000
3 Beds ⋅ 2 Baths ⋅ 73549935 MLS
Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

47 Water Street, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.
$789,000
2 Beds ⋅ 2 Baths ⋅ 73546074 MLS ⋅ ['50-52 Middlesex St Townhomes'] BLDG.
Completely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy white oak hardwood floors, a stunning chef's kitchen with quartz countertops and full-height backsplash, Bosch stainless steel appliances, and beautifully designed baths with custom tile and premium Kohler fixtures. Additional upgrades include a new roof, central A/C and heat, recessed lighting, and all-new systems throughout. Winchester is renowned for its award-winning schools, charming New England downtown filled with shops, restaurants, and cafés, easy commuter rail access to Boston, and convenient proximity to major highways—offering the perfect blend of suburban tranquility and city convenience.

50 Middlesex Street Unit 50, Winchester

Listing courtesy of Listing Agent: The North Star Group from Listing Office: Keller Williams Realty Evolution.
$649,900
2 Beds ⋅ 2 Baths ⋅ 73543744 MLS ⋅ ['Wedgewood Place'] BLDG.
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, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$849,000
4 Beds ⋅ 2 Baths ⋅ 73542597 MLS
Charming and Spacious Custom Built Mid-Century Bungalow offers a terrific opportunity to live in Winchester! Do you want to send your children to the award-winning public schools? Need an in-law apt.? Generously sized, sun-drenched, freshly painted rooms with high ceilings and hardwood floors, beautiful architectural details, and two fireplaces. A private, flat backyard perfect for growing gardens and outdoor fun. A fully finished lower-level creates excellent 2nd living space for your needs. In-town location convenient to the Boston Commuter Rail and all picturesque downtown Winchester offers. Come see all this sweet, unspoiled Mid-Century home on a dead-end street!

84 Oak Street, Winchester

Listing courtesy of Listing Agent: John E. Magazzu from Listing Office: Charlesgate Realty Group LLC.
$2,900
3 Beds ⋅ 2 Baths ⋅ 73534454 MLS
Three bedrooms and an office in this two floor, second floor unit in Winchester. Open kitchen with pantry, spacious living room. Two bedrooms on this main level. Upstairs two more rooms. Two full baths and laundry in the basement. One car garage parking and plenty of space for several cars. Shareable backyard. All of this in the Muraco School District.

63-65 Harvard Street Unit 2, Winchester

Listing courtesy of Listing Agent: Beth Sager Group from Listing Office: Keller Williams Realty Boston Northwest.
$3,200
2 Beds ⋅ 2 Baths ⋅ 73525728 MLS
LOCATION! LOCATION! LOCATION! Here is your opportunity to live in a quiet and beautifully renovated townhouse in the heart of Winchester, MA. Walking distance to all local schools, parks, downtown shops and restaurants, the commuter rail, tennis courts, and right next to Wedge Pond; where you can enjoy year round fun whether it’s swimming in the summer, or ice skating in the winter. The first floor features granite countertops, stainless steel appliances, hardwood floors, & natural sunlight throughout. With an open concept kitchen and dining room, living room w/ built in shelving and closet, and complete with a half bath. Upstairs you will find 2 spacious bedrooms, one with dual closets and the other w/ walk-in closet and built in shelving. The carpeted lower level is complete w/ a family room, and large laundry room w/ extra storage space. Easy access to Rte 93, 128, and Boston, communal picnic area on site.

60 Lake St Unit D, Winchester

Listing courtesy of Listing Agent: Clara Wu from Listing Office: United Real Estate, LLC.
$4,200
3 Beds ⋅ 2 Baths ⋅ 73515502 MLS
Available now, Spacious 3 bedroom, 1.5 bathroom single family home for rent in the heart of Winchester. This house offers a large first floor, an updated kitchen with ample cabinet space, and a private fenced backyard perfect for entertaining. The property also features a two car garage, providing additional storage and convenience. Enjoy the convenience of being just steps away from a top-rated elementary school, playground, and other amenities. Public transportation and shopping are also nearby. Don't miss your chance to make this beautiful, spacious and well-appointed home yours.

16 Nathaniel Rd, Winchester

Listing courtesy of Listing Agent: Yu Li from Listing Office: Blue Ocean Realty, LLC.
$4,800
3 Beds ⋅ 2 Baths ⋅ 73507654 MLS
Move in date: Now. Tenant pays all utilities (gas, heat, electricity, cold/hot water and trash disposal). Lead Paint: Certified Treated. 2 off street parking. Central AC ,Pets negotiable. Laundry in the unit. 12-month lease minimum Move-in costs: First month's rent, one month's rent as a security deposit, Last month rent Welcome to 17 Russell Road, a well-maintained single-family home tucked away on a quiet one-way street in one of Winchester’s desirable family neighborhoods. Enter through a welcoming mudroom with radiant floor heat and bead board walls, leading into a bright main level featuring hardwood floors, a sun-filled living room with cozy bow window seating, and a functional kitchen with ample cabinet and counter space. Dining room sliders open to a private deck overlooking a fully fenced, tree-lined backyard — ideal for entertaining or outdoor play.

17 Russell Rd, Winchester

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

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