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$2,100,000
4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ NEW Status ⋅ ['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.
$1,799,000
3 Beds ⋅ 4 Baths ⋅ 73555777 MLS ⋅ NEW 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.
$1,599,000
4 Beds ⋅ 4 Baths ⋅ 73554036 MLS ⋅ ACTIVE Status
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.
$2,999,000
5 Beds ⋅ 4 Baths ⋅ 73548103 MLS ⋅ ACTIVE Status
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.
$1,899,000
5 Beds ⋅ 4 Baths ⋅ 73545952 MLS ⋅ ACTIVE Status
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.
$1,675,000
5 Beds ⋅ 4 Baths ⋅ 73538393 MLS ⋅ ACTIVE Status
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.
$2,099,000
4 Beds ⋅ 4 Baths ⋅ 73538052 MLS ⋅ ACTIVE Status
Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the surrounding living spaces. A formal living room with fireplace, spacious den, sun-filled dining area, & inviting sunroom create an ideal layout for both everyday living & entertaining, while a first-floor bedroom & full bath offer flexibility for guests, or home office. Upstairs includes three spacious bedrooms, including a serene primary suite with spa-like bath & dual walk-in closets, plus second-floor laundry. The finished lower level expands your living space with room for a gym, playroom, or media retreat, complete with a half bath & mudroom. A turnkey home designed to fit the way you live today

26 N Gateway, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$2,499,000
5 Beds ⋅ 4 Baths ⋅ 73526460 MLS ⋅ ACTIVE Status
Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR, mudroom, stylish 1/2 bath & home office/sunroom complete this floor. Upstairs you'll find five spacious bedrooms and two full baths including the most perfect primary suite w/gorgeous bath plus a sitting room. Many updates include new hardwood floors, new high end Pella windows, updated electrical, heating and cooling systems finished lower level offers excellent recreation Enjoy the great landscaped yard with patio, lawn and sports court! For sure a favorite gathering spot for family and friends.

78 Bacon Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,399,000
5 Beds ⋅ 4 Baths ⋅ 73525195 MLS ⋅ ACTIVE Status
Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient laundry add flexibility for guests or multigenerational living. Upstairs, the luxurious master retreat boasts a cozy gas fireplace, expansive walk-in closet, and spa-like bath, followed by another bedroom with an ensuite bath, and two additional bedrooms sharing a Jack and Jill bath. A finished basement provides versatile space for a gym, media room, or playroom. Enjoy a charming front porch, private back deck, durable Hardy Plank exterior, and attached two-car garage. Exceptional craftsmanship and timeless curb appeal make this a must-see home! Located within the Winchester School District

53 Winford Way, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$1,099,000
3 Beds ⋅ 4 Baths ⋅ 73513572 MLS ⋅ ACTIVE Status ⋅ ['The Washington Street Condominium'] BLDG.
Experience the best of Winchester with a home that pairs exceptional value with an unbeatable location. Just moments from Winchester Center, enjoy a low-maintenance lifestyle within walking distance of downtown, the commuter rail, and all three school levels. This townhouse-style condo lives like a single-family home, offering space, flow, and flexibility across four finished levels. The open main level seamlessly connects the kitchen, dining, and living areas, highlighted by coffered ceilings, wainscoting, and a beautifully renovated kitchen with stainless steel appliances and modern finishes. Upstairs, the front-to-back primary suite features custom closets and a spa-inspired bath with a soaking tub and glass shower. The finished lower level provides the perfect flex space for a home office, media room, fitness area, or playroom. Complete with two deeded parking spaces, this is effortless living in one of Winchester's most desirable locations.

129 Washington St Unit 129, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.
$2,195,000
5 Beds ⋅ 4 Baths ⋅ 73496396 MLS ⋅ ACTIVE Status
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.

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