Winchester MA Real Estate & Homes for Sale

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Beds:
3
Baths:
2.00
Sq.Ft.:
2,421
Status:
Active
MLS#:
73572661
Type:
Single Family
Lot size:
0.23 Acres
Year built:
1954
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

COMMUTER OPEN HOUSE! Friday 4-5:30 9/25 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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,411
Status:
Active
MLS#:
73571480
Type:
Single Family
Lot size:
0.19 Acres
Year built:
2003
Courtesy: Keller Williams Realty Boston Northwest 781-862-2800
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
3.00
Sq.Ft.:
2,801
Status:
Active
MLS#:
73571418
Type:
Single Family
Lot size:
0.24 Acres
Year built:
1960
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,657
Status:
Active
MLS#:
73566405
Type:
Single Family
Lot size:
0.12 Acres
Year built:
1905
Courtesy: Kwan Realty Inc. 646-384-1343
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ADDITIONAL INFORMATION

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.AI-generated virtual staging. Furniture and decor are digitally added for illustration purposes only.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,757
Status:
Active
MLS#:
73565817
Type:
Single Family
Lot size:
0.29 Acres
Year built:
1931
Courtesy: Better Homes and Gardens Real Estate - The Shanahan Group 781-729-9030
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,459
Status:
Active
MLS#:
73562273
Type:
Single Family
Subdivision:
West Side
Lot size:
0.46 Acres
Year built:
1974
Courtesy: Kiklis Real Estate, LLC 781-933-2500
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ADDITIONAL INFORMATION

Key upgrades include 200-amp electrical service, a 2021 Brute natural gas boiler and replacement windows. The updated kitchen features stone counters, stainless appliances and a double oven. On Winchester's West Side, this 3-bedroom, 2.5-bath home offers 2,459 sq. ft., including a finished lower level. Enjoy hardwood floors, two fireplaces, central air and a year-round sunroom.The 0.46-acre property includes a patio, in-ground pool and two-car garage. Nearby are Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. Some photos are virtually staged.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,450
Status:
Active
MLS#:
73555666
Type:
Single Family
Lot size:
0.59 Acres
Year built:
2016
Courtesy: The Marino Group Collection 781-990-8880
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ADDITIONAL INFORMATION

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

Beds:
4
Baths:
2.00
Sq.Ft.:
2,326
Status:
Active
MLS#:
73561829
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1951
Courtesy: StartPoint Realty 978-422-3999
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ADDITIONAL INFORMATION

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

Beds:
6
Baths:
5.00
Sq.Ft.:
5,735
Status:
Active
MLS#:
73561703
Type:
Single Family
Subdivision:
West Side
Lot size:
0.41 Acres
Year built:
2026
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

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!

Beds:
5
Baths:
6.00
Sq.Ft.:
5,295
Status:
Active
MLS#:
73561372
Type:
Single Family
Lot size:
0.47 Acres
Year built:
2026
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,640
Status:
Active
MLS#:
73556633
Type:
Single Family
Lot size:
0.15 Acres
Year built:
1960
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

Private showings available! Resort living just steps from the town center! Completely remodeled with 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 primary 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!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,640
Status:
Active
MLS#:
73556476
Type:
Condo
Year built:
1995
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

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.

Beds:
7
Baths:
8.00
Sq.Ft.:
7,429
Status:
Active
MLS#:
73556474
Type:
Single Family
Subdivision:
West side, on a cul de sac
Lot size:
0.57 Acres
Year built:
2026
Courtesy: Engel & Volkers Boston 617-936-4194
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ADDITIONAL INFORMATION

Spectacular ground-up NEW construction set on an expansive, level lot of 24,688 square foot lot at the end of a quiet Winchester cul-de-sac. Newly completed and ready for immediate occupancy, this exceptional residence offers more than 7,000 square feet of beautifully finished living space, combining impressive scale, 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 a chef’s kitchen, thoughtfully designed with custom cabinetry, generous preparation and gathering spaces, and an impressive suite of appliances including a 48" Wolf gas stove, Sub-Zero fridge, double ovens, 2 Bosch dishwashers. steam oven, built in microwave and wine fridge. The kitchen flows seamlessly into expansive, light-filled lamily, living and dining spaces, 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 area. Set on more than half an acre of private grounds, the property also features a three-car garage, and excellent potential for a future pool and exceptional outdoor entertaining spaces. A rare opportunity to own a substantial, newly built home in an ideal Winchester setting, conveniently located near the town center, dining, schools, recreational amenities, hiking trails, Winchester Country Club and Wright Locke Farm.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,340
Status:
Active
MLS#:
73555218
Type:
Single Family
Year built:
1880
Courtesy: Coldwell Banker Realty - Milton 617-696-4430
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,340
Status:
Active
MLS#:
73553626
Type:
Condo
Year built:
1880
Courtesy: Coldwell Banker Realty - Milton 617-696-4430
View additional info

ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,170
Status:
Active
MLS#:
73553517
Type:
Condo
Year built:
1982
Courtesy: Berkshire Hathaway HomeServices Commonwealth Real Estate 781-729-7777
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,356
Status:
Active
MLS#:
73549935
Type:
Single Family
Lot size:
0.13 Acres
Year built:
1940
Courtesy: Leading Edge Real Estate 781-979-0100
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,494
Status:
Active
MLS#:
73549877
Type:
Condo
Year built:
1975
Courtesy: Coldwell Banker Realty - Lexington 781-862-2600
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ADDITIONAL INFORMATION

Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The finished lower level offers a family room, half bath, oversized closets, and an in-unit laundry area with additional storage. Enjoy easy access to the 2,600-acre Middlesex Fells Reservation, offering miles of scenic walking, running, and biking trails.

Beds:
1
Baths:
1.00
Sq.Ft.:
388
Status:
Active
MLS#:
73548413
Type:
Condo
Year built:
1964
Courtesy: Cameron Real Estate Group 781-486-3180
View additional info

ADDITIONAL INFORMATION

Welcome to effortless living in the most desirable community of Winchester. This beautifully updated studio condominium at The Parkview Condominiums offers an exceptional opportunity to own the most affordable home in Winchester. Rarely offered sunny side lobby level. You'll find a thoughtfully renovated interior featuring a stunning new kitchen with white shaker cabinetry, gleaming quartz countertops, stainless steel appliances, and a peninsula that's perfect for casual dining or entertaining. Enjoy your private balcony overlooking peaceful water gardens—the perfect spot to enjoy your morning coffee, unwind with a glass of wine, or dine al fresco. Residents enjoy beautifully landscaped grounds, a sparkling swimming pool, picnic area, two convenient laundries and private parking. Just minutes away is Winchester Center, with its cozy shops, pubs and train to Boston. So many activities so close to home Most exceptional value around. Ideal for a first-time buyer, downsizer or investor.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,036
Status:
Active
MLS#:
73546074
Type:
Condo
Lot size:
0.16 Acres
Year built:
1920
Courtesy: Keller Williams Realty Evolution 781-395-5600
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ADDITIONAL INFORMATION

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.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,210
Status:
Active
MLS#:
73545952
Type:
Single Family
Lot size:
0.3 Acres
Year built:
1941
Courtesy: Gibson Sotheby's International Realty 781-648-3500
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ADDITIONAL INFORMATION

Space where you need it, flexibility where you want it. This extensively renovated 5-bedroom Colonial offers a rare combination of a first-floor bedroom, two upstairs suites, finished lower level, attached 2-car garage, and nearly 1/3 acre, all just minutes from Winchester Center. Sophisticated and comfortable, the home features beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level offers hardwood floors and thoughtful architectural details, with a spacious eat-in kitchen featuring an island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, mudroom, half bath, and first-floor bedroom provide exceptional flexibility. Upstairs are two impressive suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, a full bath, and laundry. The finished lower level offers a spacious family room with fireplace and ample storage. An attached 2-car garage completes this exceptional home, conveniently located near Winchester Center’s shops, restaurants, commuter rail, and major routes.

Beds:
5
Baths:
3.00
Sq.Ft.:
4,071
Status:
Active
MLS#:
73544924
Type:
Single Family
Lot size:
0.52 Acres
Year built:
1959
Courtesy: Real Broker MA, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,025
Status:
Active
MLS#:
73543744
Type:
Condo
Year built:
1982
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

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!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,083
Status:
Active
MLS#:
73542597
Type:
Single Family
Lot size:
0.15 Acres
Year built:
1962
Courtesy: Charlesgate Realty Group LLC 978-664-3000
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ADDITIONAL INFORMATION

$5000 Closing Costs Credit to Buyer closing by Oct. 31st. Best Value in Winchester! 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 this sweet, unspoiled Mid-Century home on a dead-end street!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,690
Status:
Active
MLS#:
73541775
Type:
Single Family
Lot size:
0.28 Acres
Year built:
1850
Courtesy: MA Properties 844-962-7767
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ADDITIONAL INFORMATION

Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday living and entertaining. The living room is full of natural light, with a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The spacious, thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, and laundry. A convenient side entry provides direct access to the first of two driveways, the deck, and the large, private backyard beyond. The deck overlooks a fully fenced backyard that offers the perfect setting for relaxation, recreation, and entertaining. The flexible floor plan is designed to fit a variety of needs with a versatile main level bedroom, a sunny and cheerful space with hardwood floors and direct access to the first of three full bathrooms. The bathroom, also accessible from the hall, offers a dual sink vanity and tiled tub with a shower. A convenient laundry area adds the finishing touch to the main level. Designed with comfort and functionality in mind, the second level features a private primary suite, two additional bedrooms, a family room, and a full family bathroom, all connected by a wide central hallway. The primary bedroom offers a large walk-in closet and an updated bathroom featuring a dual sink vanity and a beautifully tiled shower. The family bedrooms are full of natural light with hardwood floors and ample closets, sharing the family bathroom with a tub and shower. One of the bedrooms also works well as an office if needed. Double French doors open to the inviting family room, where cozy carpeting and a large window overlooking the backyard create the perfect space to relax. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this special property offers a prime location just moments from the Middlesex Fells Reservation, the town center, the commuter rail and Muraco ES. Nothing left to do but move right in.

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Andrea D. Conner, License 1?0?0?0?1?8?8, Xome Inc., License 9622, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. Copyright © 2026 MLS Property Information Network, Inc. All rights reserved.



Winchester Real Estate

Winchester is located in Massachusetts. Winchester, Massachusetts has a population of 22,875. Winchester is more family-centric than the surrounding county with 48.34% of the households containing married families with children. The county average for households married with children is 35.9%.

The median household income in Winchester, Massachusetts is $184,844. The median household income for the surrounding county is $111,790 compared to the national median of $69,021. The median age of people living in Winchester is 42.4 years.

Winchester Weather

The average high temperature in July is 82.3 degrees, with an average low temperature in January of 19 degrees. The average rainfall is approximately 46.9 inches per year, with 52.7 inches of snow per year.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $1,825,000
    12.9%
    change since last quarter
  • # Active listings

    64
    30-day change

Winchester Schools and Demographics

Education near Winchester, MA

City County
High School Graduates 97.52 93.57
College Degree - 2 year 3.07 5.86
College Degree - 4 year 75.47 57.77
Graduate Degree 28.51 19.76
Expenditures per Student 23,560 23,560
Students per Teacher 12 12

Elementary Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Ambrose Elementary School KG - 05 458 13.5 01890
Brackett KG - 05 497 16.3 02476
Brooks School PK - 05 534 13.2 02155
Christopher Columbus PK - 05 471 11.8 02155
Clyde Reeves PK - 05 512 15.7 01801
Cyrus E Dallin KG - 05 456 15.4 02476
Daniel P Hurld KG - 05 217 14.5 01801
Goodyear Elementary School KG - 05 322 12.8 01801
Hardy KG - 05 392 16.4 02474
John A Bishop KG - 05 415 16.8 02474
John J McGlynn Elementary School PK - 05 559 13.2 02155
Lincoln Elementary School KG - 05 408 13.1 01890
Linscott-Rumford KG - 05 213 13.9 01801
Lynch Elementary School PK - 05 524 12.6 01890
Malcolm White KG - 05 336 14.7 01801
Mary D Altavesta KG - 05 235 10.8 01801
Menotomy Preschool PK - PK 57 9.5 02476
Milton Fuller Roberts PK - 05 576 13.2 02155
Muraco Elementary School KG - 05 406 12.6 01890
Shamrock PK - 05 350 13.2 01801
Thompson KG - 05 392 16 02474
Vinson-Owen Elementary School KG - 05 427 13.5 01890
Wyman KG - 05 189 13.5 01801

Middle Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Daniel L Joyce Middle School 06 - 08 528 10.6 01801
John F Kennedy Middle School 06 - 08 527 11.7 01801
John J. McGlynn Middle School 06 - 08 476 9.7 02155
Madeleine Dugger Andrews 06 - 08 494 11.5 02155
McCall Middle School 06 - 08 1,073 14.1 01890
Ottoson Middle School 06 - 08 1,107 12.7 02476

High Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Arlington High School 09 - 12 1,217 13.8 02476
Curtis-Tufts 09 - 12 22 5 02155
Medford High School 09 - 12 1,176 12 02155
Winchester High School 09 - 12 1,209 14.1 01890
Woburn High 09 - 12 1,332 13.8 01801

Demographics near Winchester, MA

City County
Neighborhood Type Suburban
Population 22,875 1,623,411
Population Density 3,793 1,985
Median Age 42.4 38.5
People per Household 2.8 2.5
Median Household Income 184,844 111,790
Average Income per Capita 90,356 58,399

Real estate near Winchester