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$775,000
3 Beds ⋅ 2 Baths ⋅ 73575116 MLS ⋅ NEW Status
Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym, or additional living space. The kitchen opens directly to the generous dining room and features granite countertops, stainless steel appliances, and access to the deck. A full bathroom completes the first level. Upstairs, you’ll find three bedrooms, another full bathroom, and convenient laundry. This spacious home also offers a shared fenced-in yard, off-street parking for two cars, and additional storage in the basement. Abundant public transportation plus the charming shops and restaurants of Winchester Center, as well as elementary, middle, and high schools all at your fingertips. Welcome home to Winchester!

189 Washington St Unit 2, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,679,900
3 Beds ⋅ 2 Baths ⋅ 73572791 MLS ⋅ ACTIVE Status
Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen features a substantial wood center island, handmade pocket plantation shutters that disappear seamlessly behind custom cabinetry, updated countertops and backsplash, a concealed illuminated bar cabinet, beverage fridge, and dual-zone wine fridge. Paned-glass pocket doors can separate the kitchen or open it to the adjoining dining and family rooms, where radiant-heated floors create a warm, inviting setting and a wall of windows connects the interior space beautifully to the surrounding landscape. The family room’s custom cherry entertainment center, finished with copper paneling and ebony inlays, reflects the extraordinary attention to detail found throughout. A formal living room with fireplace and custom millwork provides a separate space to gather or unwind. Tucked into a private wing are three well-proportioned bedrooms with hardwood floors and generous closets, along with a renovated full bath featuring a double vanity, deep soaking tub, and radiant-heated floor. The finished lower level offers remarkable flexibility with a media room wired for surround sound, exercise room, second full bath, laundry, mudroom area, abundant temperature-controlled storage, and direct access to an oversized two-car garage with workspace. Outside, the backyard and stone patio provide an equally peaceful and private extension of the interior living space. Mature plantings, stone walls, a potting shed, and an irrigation system complete this wide, one-third-acre lot. Central air, central vacuum, extensive built-ins and storage, plus new interior doors and crown molding throughout the bedroom wing add comfort and convenience. Polished, distinctive, and genuinely inviting, 5 Willowdale Road is a home of enduring quality that feels every bit as special as it looks. NO OPEN HOUSES, shown By Private Appointment only.

5 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.
$1,699,000
3 Beds ⋅ 2 Baths ⋅ 73572661 MLS ⋅ ACTIVE Status
Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living and dining rooms, plus a bedroom & full bath. The formal dining room offers flexibility to serve as a fourth bedroom, if desired. Upstairs are two generously sized bedrooms with hardwood floors and ample closet space, along with a spacious hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,098,000
3 Beds ⋅ 2 Baths ⋅ 73566405 MLS ⋅ ACTIVE Status
Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..
$1,329,000
3 Beds ⋅ 3 Baths ⋅ 73562273 MLS ⋅ ACTIVE Status
110 Thornberry Road. Strong west side location near Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. An exceptional opportunity to establish roots in Winchester. 2021 Natural Gas Brute FT Floor Standing Boiler. Replacement windows. Central cooling. 200 amp electric. Updated Kitchen w Double oven. Prefinished hardwood floors. Therma-Tru French doors flow from the dining room to a window-lined bonus room off the dining room provides flexible year-round living space. In-ground swimming pool.

110 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Mark Kiklis from Listing Office: Kiklis Real Estate, LLC.
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 73556633 MLS ⋅ ACTIVE Status
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.
$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.
$950,000
3 Beds ⋅ 2 Baths ⋅ 73549935 MLS ⋅ ACTIVE 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.
$650,000
3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ACTIVE Status ⋅ ['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.
$1,075,000
3 Beds ⋅ 3 Baths ⋅ 73519082 MLS ⋅ ACTIVE Status
Charming antique 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.

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