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Single Family Homes for Sale in Winchester, MA

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Welcome to your dedicated resource for single family homes for sale in Winchester, MA. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winchester, MA agent, Marc Fiore specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the single family properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Single Family Homes for Sale in Winchester, MA

$3,450,000
6 Beds ⋅ 5 Baths ⋅ 73561703 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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.
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 73556633 MLS ⋅ ACTIVE Status
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 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 ⋅ ACTIVE Status
Spectacular ground-up NEW construction estate on expansive, large level lot of 24,688sf, ready for move in, located on a quiet Winchester cul-de-sac. Newly completed, this exceptional residence spans more than 7,000 square feet across impeccably finished levels. Ideally positioned on a quiet cul-de-sac on over half an acre of land in one of Winchester’s most desirable locations, the home offers an extraordinary combination of new construction, refined design, privacy, and convenience, just moments from Winchester Country Club. Designed with entertaining in mind, the residence features seven spacious bedrooms and 7.5 designer baths, providing beautifully appointed private retreats for family and guests. At the heart of the home is an outstanding chef’s dream kitchen, thoughtfully designed with custom cabinetry, expansive preparation and gathering spaces, double oven, top-of-the-line 48" Wolf gas stove, Sub-Zero fridge, 2 Bosch dishwashers. steam oven, built in microwave and wine fridge. The kitchen flows seamlessly into expansive, light-filled lamily, living and dining areas, creating an inviting setting for large gatherings, celebrations, and relaxed everyday living. The flexible floor plan is perfectly suited to today’s lifestyle, with dedicated spaces for a professional home office, private fitness studio, and expansive recreation wing. Set in a lush, private lot with a three-car garage, this large lot property also offers excellent potential for a future pool and outdoor entertaining oasis. A rare opportunity to own a substantial, newly built entertainer’s home in an ideal Winchester setting, close to the town center, dining, schools, recreational amenities, hiking trails, and Wright Locke Farm. Ready to move in and enjoy!

11 Viking Road, Winchester

Listing courtesy of Listing Agent: Post Advisory Group from Listing Office: Engel & Volkers Boston.
$1,749,000
3 Beds ⋅ 4 Baths ⋅ 73555777 MLS ⋅ ACTIVE Status
Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing or entertaining. Step outside to enjoy the beautifully fenced-in yard, offering a private outdoor retreat for play, pets, gardening, or gatherings. Everyday convenience continues with a mudroom located directly off the driveway, multiple off-street parking spaces, and a two-car garage. The finished lower level includes a full bathroom and versatile flex space perfect for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. Thoughtfully renovated from top to bottom, this home features all new systems for peace of mind and effortless modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.

1 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$849,000
3 Beds ⋅ 2 Baths ⋅ 73555218 MLS ⋅ ACTIVE Status
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 ⋅ ACTIVE Status
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.
$899,000
3 Beds ⋅ 2 Baths ⋅ 73549935 MLS ⋅ PRICE CHANGED Status
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.
$1,899,000
5 Beds ⋅ 4 Baths ⋅ 73545952 MLS ⋅ ACTIVE Status
As close to new construction as you’ll find, this exceptional Colonial was comprehensively renovated in 2016, with numerous additional improvements since. Sophisticated and comfortable, the home offers beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level features hardwood floors, elegant architectural details, and thoughtfully designed spaces. At the center of the home is a spacious eat-in kitchen with island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, first-floor bedroom, mudroom, and half bath provide both functionality and flexibility. Upstairs are two impressive primary suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, full bath, and laundry room. The finished lower level includes a spacious family room with fireplace and ample storage. An attached 2-car garage completes this exceptional home, conveniently located just minutes from Winchester Center’s shops, restaurants, commuter rail, and major routes.

79 Grove St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$2,400,000
5 Beds ⋅ 3 Baths ⋅ 73544924 MLS ⋅ ACTIVE Status
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.
$849,000
4 Beds ⋅ 2 Baths ⋅ 73542597 MLS ⋅ ACTIVE Status
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.
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 73541775 MLS ⋅ ACTIVE Status
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.

423 Washington St, Winchester

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.
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