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$1,549,000
3 Beds ⋅ 3 Baths ⋅ 73556633 MLS
Completely remodeled with exceptional 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
Spectacular ground-up new construction estate on a quiet Winchester cul-de-sac near Wright Locke Farm. Newly completed, this exceptional residence spans more than 7,000 square feet across four impeccably finished levels. Ideally positioned on a quiet cul-de-sac 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 a chef’s dream kitchen, thoughtfully designed with custom cabinetry, expansive preparation and gathering spaces, double over, and top-of-the-line Wolf and Sub-Zero appliances. The kitchen flows seamlessly into expansive, light-filled 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, the 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, and Winchester Country Club.

11 Viking Road, Winchester

Listing courtesy of Listing Agent: Post Advisory Group from Listing Office: Engel & Volkers Boston.
$2,100,000
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.
$2,299,000
7 Beds ⋅ 5 Baths ⋅ 73556122 MLS
Exceptional craftsmanship defines this majestic home in The Flats, where beautifully-preserved architectural details blend seamlessly w/ modern livability. A showstopping foyer welcomes you w/ a sweeping staircase, exquisite millwork, graceful arched openings & leaded glass windows. You’ll find quarter-sawn oak floors, rich woodwork, generously scaled windows & impressive ceiling height throughout. The expanded eat-in kitchen includes granite, SS appliances, island, office area & steps to a custom mudroom. The main level also includes elegant living, dining & family rooms, a butler's pantry, & ½ bath. The 2nd floor showcases a dramatic landing w/ continuously curved railing & has 4 large bedrooms & two full baths, including a spacious primary suite w/ full bathroom and walk-in closet. 3 bedrooms & a full bath complete the 3rd floor. The finished lower level w/ recreation room, mudroom w/ built-in lockers, and full bathroom offers endless possibilities. Recent updates include Pella windows throughout (2020), new & upgraded heating system (2024), and exterior siding, paint & shutters (2020). Set on a flat, oversized lot featuring a bluestone patio w/ seating wall. Located in a highly-coveted neighborhood and less than a mile from the newly built Lynch elementary school, town center & train.This magnificent home pairs timeless character with today’s amenities.

42 Wildwood Street, Winchester

Listing courtesy of Listing Agent: Carolyn Walsh from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,799,000
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.
$1,125,000
5 Beds ⋅ 3 Baths ⋅ 73555597 MLS
Thoughtfully updated 1870 home with a versatile footprint offering many options for multi-generational living, a grand home office setup, dedicated au pair quarters, or separately rented as an Accessory Dwelling Unit (ADU). Elegant renovations have preserved the home's original historic character while seamlessly incorporating today's modern luxuries. A charming farmer's porch welcomes you into the main living area, featuring 8 rooms, 4 bedrooms, and 1.5 baths. The beautifully renovated 2024 eat-in kitchen showcases timeless cabinetry, quartz countertops, a functional butcher block island, custom blue-and-white tile backsplash, an exterior-vented gas range, and direct access to a new 2024 TimberTech deck. Interior highlights include an inviting living room with a striking embossed tin ceiling, a flexible first-floor bedroom or office featuring floor-to-ceiling windows, and gorgeous wide-plank flooring. The walk-out lower-level family room adds excellent bonus space with direct access to the backyard, while three additional bedrooms sit on the second floor. The full bath was tastefully renovated in 2020 with vintage-inspired washstand sinks, and the unfinished basement provides laundry space and storage. The separate, fully integrated living area is ideal for extended family, guests, an au pair, or rental income. This bright secondary suite offers a sunlit living room with its own deck access, an eat-in kitchen, full bath, and a spacious second-floor bedroom. Original pine floors on main level and carpet in bedroom. Modern mini-split heating and A/C units provide year-round climate control throughout both distinct living areas. The main home also features gas baseboard and radiator heat, while the suite is independently served by radiator heat. Outside, a patio and three off-street parking spaces complete this exceptional property. The location is an absolute commuter's dream, situated just a short stroll to vibrant Winchester Center, boutique shops, local cafés, and acclaimed restaurants. Commuters will love being near two MBTA Commuter Rail stations, offering a quick two-stop ride straight into Boston's North Station. Best of all, this property sits within the highly sought-after Lynch Elementary School district, placing you directly inside Winchester's top-rated, award-winning public school system. This rare property truly offers the perfect combination of timeless historic charm, high-end modern updates, and outstanding lifestyle versatility.

8 Oak Street, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
$1,125,000
5 Beds ⋅ 3 Baths ⋅ 73555245 MLS
Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

8-10 Oak St, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
$849,000
3 Beds ⋅ 2 Baths ⋅ 73555218 MLS
Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

15 Clark St, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.
$2,225,000
4 Beds ⋅ 4 Baths ⋅ 73554545 MLS
Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail, Lincoln Elementary School and the Middlesex Fells Reservation with miles of trails, hiking, running and The Sheepfold dog park. The traditional yet open layout features an updated kitchen, spacious living and dining areas, refreshed baths, fresh paint and updated mechanical systems. A versatile bonus room with a private staircase offers endless possibilities as a home office, media room, guest space, playroom or fitness area. The finished lower level with half bath adds valuable living space. Enjoy outdoor living on the wraparound deck overlooking a private backyard with mature landscaping.

6 Davey Ln, Winchester

Listing courtesy of Listing Agent: Gretchen Papineau from Listing Office: Coldwell Banker Realty - Andovers/Readings Regional.
$1,150,000
4 Beds ⋅ 3 Baths ⋅ 73554139 MLS
Classic center-entrance Colonial set on a cul-de-sac with a wonderful sense of flow and everyday function. The main level offers formal living and dining rooms, a spacious front-to-back fireplaced family room with first-floor laundry and half bath, plus a bright kitchen with island, dining area, and direct access to the deck. Upstairs, the primary suite includes a walk-in closet and private bath, complemented by three additional bedrooms and a full bath. A two-car under garage connects to the unfinished basement, offering excellent storage and future possibilities. Central air, gas heat, hardwood floors, and a level lot complete this inviting home.

11 Williams Cir, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 73554036 MLS
New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new deck railings, a freshly painted finished lower level with brand-new carpeting, and the seller will replace the second-floor HVAC system, providing valuable peace of mind for the next owner. Inside, you'll find sun-filled living spaces, an updated kitchen, generously sized bedrooms, and a versatile finished lower level ideal for a family room, home office, gym, or playroom. The true showstopper is the spectacular backyard retreat. Designed for entertaining and everyday enjoyment, the private outdoor oasis features a heated saltwater pool with a beautiful waterfall, an expansive patio, mature landscaping, and an outdoor entertaining area rough-plumbed for a future outdoor kitchen—making it easy to create the backyard you've always envisioned. Ideally located just minutes from Winchester Center, top-rated schools, shopping, dining, parks, and commuter routes, this is a rare opportunity to own a turnkey home with outstanding updates, exceptional outdoor amenities, and an unbeatable Winchester location.

241 Ridge St, Winchester

Listing courtesy of Listing Agent: Team Lillian Montalto from Listing Office: Lillian Montalto Signature Properties.
$849,000
3 Beds ⋅ 2 Baths ⋅ 73553626 MLS
Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and effortless entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or a dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester Center commuter rail, and major routes, this home embodies the very best of Winchester living. No HOA fee.

15 Clark St Unit 15, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.
$700,000
2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.
Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new chandelier. Spacious primary bedroom has LARGE WALK-IN CLOSET plus a sink and linen closet before the entry to the water closet where you'll find a large tub. Second bedroom/office has double closet and is across hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR and find NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (all recently done in 2026), NEW WASHER AND DRYER 2025 and NEW HOT WATER HEATER (2024). Love the COVERED PARKING in the garage below the building, association POOL, two ELEVATORS plus the convenience of being only one flight of stairs up from the street level. Location near town center, TRAIN, shopping, restaurants, schools and library is superb.

666 Main Unit 211, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,099,000
5 Beds ⋅ 3 Baths ⋅ 73553083 MLS
Exceptional two-family opportunity with incredible potential to renovate/expand! Situated on a large, level corner lot with frontage on both Cross Street and Verplast Avenue, this property offers endless possibilities for investors, builders, or owner-occupants. The first-floor unit features a fireplaced living room, an updated kitchen, three bedrooms, 1.5 baths and sunroom overlooking the expansive backyard. The second unit offers a spacious and flexible layout with a living room, kitchen, 2 bedrooms, laundry room and full bath. The generous lot, separate entrances, and existing footprint create an ideal opportunity to modernize the current two-family, expand the living space, or explore redevelopment possibilities. Whether you're looking for a strong income property or your next renovation project, this property is full of potential and ready for its next chapter!

257 Cross St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$950,000
3 Beds ⋅ 1 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.
$729,000
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.
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 73549484 MLS
Completely renovated in 2021, this stunning 3-bedroom, 2.5-bath townhouse offers the comfort and feel of a single-family home with three levels of beautifully finished living space. The open and inviting floor plan features hardwood floors throughout, modern finishes, and abundant natural light. The spacious third-floor primary suite provides a private retreat with spacious walk in closet and its own full bath. Second floor features 2 ample sized bedrooms, full bath and laundry. Step outside through the sliding glass doors to a newly installed stone patio and backyard—perfect for relaxing, entertaining, or outdoor dining. Additional highlights include two off-street parking spaces and thoughtful updates throughout. Ideally located just moments from the Winchester Center commuter rail station, vibrant downtown shops and restaurants, Winchester High School, and the brand-new Lynch Elementary School, this move-in ready home offers the perfect combination of style, space, and convenience.

52 Salem Street Unit 52, Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$288,750
1 Beds ⋅ 1 Baths ⋅ 73548413 MLS ⋅ ['The Parkview'] BLDG.
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.

200 Swanton Unit L8, Winchester

Listing courtesy of Listing Agent: Stephen DeConto from Listing Office: Cameron Real Estate Group.
$2,999,000
5 Beds ⋅ 4 Baths ⋅ 73548103 MLS
Must see this stunning move in ready waterfront gem! Perfectly sited at the end of Wedgemere on Winter Pond, offering over 80 feet of direct water frontage w/ expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this home presents a rare opportunity to enjoy water activities such as kayaking, paddle-boarding, fishing, ice skating and hockey all while being just minutes from Winchester Center and the train to Boston; homes like this rarely come to market. Custom designed and lovingly owned by the original family, this home is now ready for its next chapter. Offering a beautiful flowing layout w/ gleaming hardwood floors, large rooms, featuring floor-to-ceiling bay windows with stunning views, 5 bedrooms, 2 full & 2 half baths, 4 fireplaces, a walk-out lower level rec room, & a gorgeous fenced yard with steps to the water. Truly a special setting that seamlessly combines privacy, views & accessibility in Winchesters TOP neighborhood!

10 Dartmouth Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,064,000
4 Beds ⋅ 2 Baths ⋅ 73547513 MLS
Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as well as a mudroom and a full bath. The fenced backyard is perfect for entertaining. Upstairs, four bedrooms each offer generous closet space. The lower level--with new half bath, new carpet, laundry and storage--is ideal for a media space or playroom. Newer roof, tankless water heater, and a new 200-amp electrical panel provide peace of mind. Close proximity to Horn Pond Reservation, trails, and parks, and easy access to Boston via rail and bus. A rare chance to own a fully updated home in a truly special neighborhood.

46 Clark St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$799,000
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.
$1,899,000
5 Beds ⋅ 4 Baths ⋅ 73545952 MLS
Sophisticated and comfortable, this updated Colonial 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 updated 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 and a convenient location just minutes to Winchester Center’s vibrant 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.
$2,500,000
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.
$649,900
2 Beds ⋅ 2 Baths ⋅ 73543744 MLS ⋅ ['Wedgewood Place'] BLDG.
Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features a walk-in closet, private bath, and separate vanity area, while the second bedroom and updated guest bath provide flexibility for guests or a home office. New hardwood floors & new carpet in bedrooms, in unit laundry, central air, parking, extra storage, and access to the community pool. The professionally managed elevator building. Located near Winchester Center’s restaurants, shops, commuter rail, parks, and everyday conveniences! move right in and enjoy!

666 Main Street Unit 315, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$888,000
4 Beds ⋅ 2 Baths ⋅ 73542597 MLS
Charming and Spacious Custom Built Mid-Century Bungalow offers a wonderful opportunity to live in Winchester ! Do you want to send your children to the award-winning public schools? Need an in-law? Generously sized, sun-drenched, freshly painted rooms with hardwood floors and beautiful architectural details, and two fireplaces. A terrific, 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 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
Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The inviting living room is enhanced by a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, laundry, and steps out to the deck and fully fenced, private backyard. A versatile main level bedroom provides direct access to the first of three full bathrooms, while the primary suite on the second level offers a walk-in closet and an updated bathroom with a dual sink vanity and tiled shower. French doors open to the inviting family room with a bay window. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this home offers a prime location moments from the Fells Reservation, the town center, commuter rail, and Muraco ES.

423 Washington St, Winchester

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.
$999,900
4 Beds ⋅ 2 Baths ⋅ 73541288 MLS
A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown

258 Cross Street, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.
$2,300,000
4 Beds ⋅ 5 Baths ⋅ 73541163 MLS
Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations.. Ideally located just minutes from Winchester's highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living—this is a rare opportunity in one of Winchester's most sought-after neighborhoods.

14 Hillside Ave, Winchester

Listing courtesy of Listing Agent: Rebecca Huang from Listing Office: William Raveis R.E. & Home Services.
$1,099,000
3 Beds ⋅ 2 Baths ⋅ 73530959 MLS
Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for den, home office or playroom area. First floor half bath. Upstairs features 3 well proportioned bedrooms and a full bath, hardwood floors throughout, partially finished basement with bonus room, 2 car garage and ample driveway parking, sunny back yard. Freshly painted exterior,Showings delayed until Tenant moves out. Please schedule starting July 2nd.

150 Cambridge Street, Winchester

Listing courtesy of Listing Agent: Diane Plunkett from Listing Office: Plunkett Properties.
$1,675,000
5 Beds ⋅ 4 Baths ⋅ 73538393 MLS
Excellent New Price! Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and powder room complete this level. Upstairs, the generous primary suite includes full bath and convenient laundry and is complemented by four additional bedrooms and a family bath. A walk-up attic provides flexible bonus space and storage, while the finished lower level offers a spacious family room, bonus room, and kitchenette with ADU potential. Enjoy the private backyard retreat complete with a fully fenced yard and pristine in-ground pool, plus two-car attached garage. An extraordinary opportunity to enjoy space, comfort, and refined living in one of Winchester’s most sought-after neighborhoods, a short stroll to the incredible nature at the Fells Reservation.

117 Highland Ave, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

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