Winchester, MA Homes for Sale

Rich History

Winchester, MA is known for its rich history, dating back to the 17th century when it was first settled. With many historic homes and buildings still standing, the town offers a unique blend of old-world charm and modern amenities. Real estate in Winchester often includes beautifully preserved historic homes, making it a popular choice for buyers looking for a piece of history.

Desirable Location

Located just 8 miles north of Boston, Winchester offers a convenient location for those looking to commute to the city for work or leisure. With easy access to major highways and public transportation, residents can enjoy the quiet suburban lifestyle of Winchester while still being close to the bustling city of Boston. This prime location makes Winchester real estate highly sought after.

Strong Housing Market

The real estate market in Winchester, MA is strong, with high demand for homes in the area. The town's excellent schools, beautiful parks, and vibrant community make it a desirable place to live for families and individuals alike. With a mix of historic homes, modern condos, and spacious single-family houses, Winchester offers a variety of options for buyers at different price points.

Community Amenities

Winchester boasts a range of community amenities, including excellent schools, recreational facilities, and numerous parks and green spaces. Residents can enjoy outdoor activities like hiking, biking, and picnicking in the town's many parks, or take advantage of the nearby Mystic Lakes for boating and water sports. With a strong sense of community and plenty of activities to enjoy, Winchester is a great place to call home.

Investment Potential

Real estate in Winchester, MA offers strong investment potential, with property values steadily increasing over the years. As a highly desirable town with a prime location and excellent schools, Winchester is a popular choice for buyers looking to invest in real estate. Whether purchasing a home to live in or as a rental property, Winchester offers a solid return on investment and the opportunity for long-term growth.

Our website features the best Winchester, MA real estate search for homes available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Avg. No of Beds

Avg. No of Baths

Avg. Living Ft²

Avg. Listing Price

Cost per ft²

Days on Market

Winchester, MA Popular Searches

Winchester, MA Homes by Price

Winchester, MA Homes by # of Bedroom(s)

Winchester, MA Homes by # of Bathroom(s)

Curious about what’s happening in the Winchester, MA real estate market? Sign up for a Winchester, MA Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Winchester, MA Homes for Sale

$2,299,000

4 Beds ⋅ 5 Baths ⋅ 73555666 MLS

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

54 Squire Road, Winchester

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

$919,999

4 Beds ⋅ 2 Baths ⋅ 73561829 MLS

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

96 Loring Ave, Winchester

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

$3,450,000

6 Beds ⋅ 5 Baths ⋅ 73561703 MLS

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

7 Hutchinson Road, Winchester

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

$3,200,000

5 Beds ⋅ 6 Baths ⋅ 73561372 MLS

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

18 Ridge St, Winchester

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

$3,350

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! Home is heated by oil.

7 Ridge Street, Winchester

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

$4,850

5 Beds ⋅ 2 Baths ⋅ 73560281 MLS

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

79 Bacon St Unit 79, Winchester

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

$3,700

4 Beds ⋅ 2 Baths ⋅ 73559841 MLS

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

10-12 Webster St Unit 1, Winchester

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

$6,000

3 Beds ⋅ 3 Baths ⋅ 73559660 MLS

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

25 Berkshire Dr, Winchester

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

$1,549,000

3 Beds ⋅ 3 Baths ⋅ 73556633 MLS

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!

50 Holland Street, Winchester

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

$3,600,000

7 Beds ⋅ 8 Baths ⋅ 73556474 MLS

Spectacular ground-up NEW construction 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.

11 Viking Road, Winchester

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

$1,999,000

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

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

7 Wainwright Road Unit 113, Winchester

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

$1,749,000

3 Beds ⋅ 4 Baths ⋅ 73555777 MLS

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

1 Town Way, Winchester

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

$664,000

2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.

Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER (2026) for improved energy efficiency and beauty, now with a fabulous price improvement. The kitchen features UPDATED APPLIANCES, GRANITE COUNTERS with an eating bar and PANTRY CLOSET, open to the living room with a fireplace and the dining room with a NEW CHANDELIER. The spacious primary bedroom has a LARGE WALK-IN CLOSET, a sink area before the entry to the water closet where you’ll find a large tub. The second bedroom/office offers DOUBLE CLOSET and is across the hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR, NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (2026), NEW WASHER AND DRYER (2025) and NEW HOT WATER HEATER (2024). Benefit from COVERED PARKING in the garage below the building, the association POOL, TWO ELEVATORS, and the convenience of being only one flight of stairs up from street level. The location near town center, TRAIN, shopping, restaurants, schools and library is superb. Great layout, garage parking, ideal location, and numerous recent improvements make this a wonderful opportunity. New budget conforms to lending guidelines. Make your appointment to see this today!

666 Main Street Unit 211, Winchester

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

$899,000

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.

$600,000

3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ['Winchester Green'] BLDG.

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.

247 Washington St Unit 11, Winchester

Listing courtesy of Listing Agent: Heejeong Joo from Listing Office: Coldwell Banker Realty - Lexington.

$769,000

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.

$2,175,000

5 Beds ⋅ 3 Baths ⋅ 73544924 MLS

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.

9 Plymouth Rd, Winchester

Listing courtesy of Listing Agent: Steph Crawford Group from Listing Office: Real Broker MA, LLC.

$1,950

1 Beds ⋅ 1 Baths ⋅ 73543231 MLS

The sought after Parkview Condominium! Prime Winchester Location ! Living room with glass sliders to balcony overlooking a calming and picturesque landscaped wildlife garden and pond with ducks & swans. Rent includes ALL utilities - heat, cold & hot water, electricity and 1 gated parking space! No pets. No smoking of any substances. Large bedroom for a king-size bed or twins and includes a walk-in closet. A sparkling bath with updated countertop, mirror, and lighting. Separate parking area for guests. Amenities: A fenced-in inground pool with landscaped grounds. 2 laundry rooms on each side of the building. Professionally management on-site. Close to town shops, restaurants, and commuter rail to Boston. Explore the nearby Tri-Community Greenway! Come Home! Sweet Home!

200 Swanton Street Unit 416, Winchester

Listing courtesy of Listing Agent: Ai Cheng Goh from Listing Office: Z. Realty.

$2,700

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.

$1,025,000

3 Beds ⋅ 3 Baths ⋅ 73519082 MLS

GREAT OPPORTUNITY TO BUILD EQUITY!! LOW PRICE!!! Charming Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

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

$3,000

2 Beds ⋅ 1 Baths ⋅ 73516177 MLS

Welcome to 63 Holland St in Winchester! This beautifully renovated 2-bedroom, 1-bath townhome offers the perfect blend of classic charm and modern updates, featuring hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom showcases a walk-in tiled shower with a custom glass door for a sleek, contemporary feel. Additional highlights include an in-unit washer and dryer, private driveway parking, extra basement storage, professional management, and access to a shared backyard space. Water and sewer are included. Conveniently located near shops, restaurants, and public transportation, this home provides comfortable living in one of Winchester's most desirable neighborhoods.

63 Holland St Unit 63, Winchester

Listing courtesy of Listing Agent: Issam Dib from Listing Office: Skyline Realty.

$1,110,000

5 Beds ⋅ 3 Baths ⋅ 73515601 MLS

Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside.

63-65 Harvard Street, Winchester

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

$3,950

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.

$2,100,000

6 Beds ⋅ 5 Baths ⋅ 73510713 MLS

Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves as the anchor for the expansive living and dining areas. The primary sanctuary is a true showstopper, featuring soaring ceilings and a boutique-style walk-in closet of legendary proportions. With six bedrooms and spa-inspired baths, there is plenty of space for multiple uses and configurations. From the lower-level recreation room with patio access to the proximity to Wedge Pond and the Middlesex Fells, this home is designed for indoor and outdoor leisure. Enjoy the convenience of nearby local shopping and easy access to the surrounding areas.

6 Ivy Circle, Winchester

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

$4,000

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..

$349,900

1 Beds ⋅ 1 Baths ⋅ 73500952 MLS ⋅ ['The Parkview Condominium'] BLDG.

Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for dining and entertaining. Large living room with a glass slider leading to a private balcony overlooking a view of beautifully landscaped grounds. Unit also includes 1 parking space, storage space in the basement, and on-site laundry room. Condo fee includes; heat. hot water, electric, A/C, water/sewer, landscape, & snow removal. Other amenities include gated entry, on-site management, plus the swimming pool with picnic/BBQ area. minutes away from town center, shops, restaurants, bus stop, & the commuter rail t-stop. Close to outdoor trails, major highways, and easy access to the city of Boston

200 Swanton St Unit 717, Winchester

Listing courtesy of Listing Agent: Cameron Moniz from Listing Office: Coldwell Banker Realty - Lexington.

$2,750,000

6 Beds ⋅ 7 Baths ⋅ 73500890 MLS

Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.

14 Nassau Drive, Winchester

Listing courtesy of Listing Agent: Weidong Li from Listing Office: WINN Real Estate & Consulting.

$950,000

2 Beds ⋅ 2 Baths ⋅ 73497739 MLS ⋅ ['83 Church St Condominiums'] BLDG.

Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal chandeliers & wall sconces. The thoughtfully renovated kitchen features granite countertops, custom cabinetry, stainless steel appliances, & opens to a stylish butler’s pantry complete w/wine fridge, sink, & in-unit washer/dryer. Upstairs, both bedrooms offer HW flooring, updated lighting, & skylight w/shade. Bathrooms have been tastefully updated. Additional highlights include updated electrical, gas line connection, & integrated sound wiring.Includes one car garage, an additional outdoor parking space & basement storage w/bonus cedar closet.Turnkey home near town center, shops & commuter rail. Some photos are virtually staged.

83 Church Street Unit 15, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$450,000

2 Beds ⋅ 1 Baths ⋅ 73496844 MLS

BACK ON MARKET DUE TO FINANCING ! PARKVIEW WINCHESTER CONDOMINIUMS! 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 CONDOMINIUM FEE. EASY TO SHOW! OPEN HOUSE ON SATURDAY 11: 00 -- 1:00 PM AND SUNDAY 12:00--2:00 PM

200 Swanton Street Unit T35, Winchester

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

$2,195,000

5 Beds ⋅ 4 Baths ⋅ 73496396 MLS

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

276 High Street, Winchester

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

$3,200,000

6 Beds ⋅ 6 Baths ⋅ 73482275 MLS

**OPEN HOUSE SUNDAY 1-2pm Oct 25 **HOME JUST COMPLETED!! ** This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer kitchen w/white oak flooring, vaulted ceilings, skylights, oversized island, gorgeous family room with gas fireplace & walls of windows showcasing the beauty of the natural, private setting w/sliders that lead to a large deck. A formal living room, dining room & a FIRST FLOOR bedroom suite plus fabulous mudroom direct entry from spacious 2 car garage complete the main level! The 2nd floor offers 4 generous BR's including a luxurious primary suite, 2 additional full baths & convenient second floor laundry. The above grade/ walk-out lower level adds exceptional flexibility w/ *Au- pair or In-law suite* media room, home office, exercise room, bedroom & full bath Enjoy all the area has to offer including restaurants, shops, schools, train to Boston, Bike-paths & more! 7 miles from Boston!

9 Albamont Road, Winchester

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

Start Your Search

Prev
1
2
of 2
Next

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, landlords 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, leasing or renting 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, leasing or renting. 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.

Winchester, MA Homes for Sale

Rich History

Desirable Location

Strong Housing Market

Community Amenities

Investment Potential

Newest Winchester, MA Homes for Sale

How much is your home worth?

How much is your home worth?

REAL BROKER MA LLC

Address

Contact

Follow