0.24 mi
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
19 Gershon Way
Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining
Living Area:
3953 Sqft.
|
3
Beds,
3
Baths
|
$2,299,000 |
189 High Street
This classic Cape offers exceptional space, character, and room to make it your own. The first floor features a gracious front-to-back living room, formal dining room, and an inviting eat-in kitchen, all highlighted by hardwood floors, high ceilings, and a seamless circular layout ideal for everyday
Living Area:
2126 Sqft.
|
4
Beds,
3
Baths
|
$1,150,000 |
181 Lowell St
Historically reproduced new construction masterpiece blends a timeless design with modern comfort and efficiency. Thoughtfully crafted to honor the original Victorian-era style of this neighborhood, this exceptional 4-5 bed, 3 bath home offers elegance, functionality and character. The main level sh
Living Area:
3655 Sqft.
|
5
Beds,
3
Baths
|
$2,339,000 |
26 Berkshire Dr
Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and n
Living Area:
2316 Sqft.
|
3
Beds,
3
Baths
|
$1,475,000 |
10 Viking Rd
Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family a
Living Area:
5674 Sqft.
|
4
Beds,
4
Baths
|
$2,785,000 |
5 Azalea Road
NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef?
Living Area:
6232 Sqft.
|
5
Beds,
4
Baths
|
$1,999,000 |
16 Ridge Street
ATTENTION CONTRACTORS/BUILDERS & BUYERS LOOKING TO BUILD EQUITY~whether you do a light update/ expand or completely renovate; this well maintained 3 bedroom split entry home on a stunning 27k+ lot with a great layout and an oversized private yard offers tremendous potential! The first floor is spaci
Living Area:
1844 Sqft.
|
3
Beds,
3
Baths
|
$1,149,000 |
22 Oldham Rd
Elegantly sited on Morningside Hill, this home is a luxury-built masterpiece. Thoughtfully designed & artfully crafted, it exudes opulence & cozy comfort. A gracious entry hall welcomes you into sophisticated living, highlighted by a breathtaking two-story living room adorned with countless windows.
Living Area:
5737 Sqft.
|
5
Beds,
6
Baths
|
$3,380,000 |
22 Tyler Road
***MOVE IN FOR THE HOLIDAYS ***An exceptional NEW 6-bedroom, 5.5-bath modern farmhouse colonial, perfectly positioned in one of Lexington’s most coveted neighborhoods. Thoughtfully designed for both everyday comfort and sophisticated entertaining, this sun-drenched, southern-facing home showcases
Living Area:
5531 Sqft.
|
6
Beds,
6
Baths
|
$3,650,000 |
80 Arlington St
New roof. New landscaping. New exterior paint. New price! With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved
Living Area:
5632 Sqft.
|
5
Beds,
4
Baths
|
$3,099,000 |
15 Peachtree Road
Celebrate the Holidays in this new, stunning 7-bed, 7.5-bath transitional modern home with 4 spectacular finished levels with 6,600 SF of refined living space with wide-plank white oak floors, soaring 10 ft ceilings on 1st FL, 9' on 2nd, Fl, 8' on 3rd + LL! Custom white oak cabinetry, exposed wood
Living Area:
6600 Sqft.
|
7
Beds,
8
Baths
|
$4,170,000 |
14 Nassau Drive
Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. 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 isl
Living Area:
6968 Sqft.
|
6
Beds,
7
Baths
|
$2,850,000 |
8 Blueberry Lane
Welcome to your modern sanctuary — a beautifully crafted contemporary new home offering the perfect blend of clean architectural lines, thoughtful functionality, and luxurious comfort. This expansive 6-bedroom residence is ideal for today's lifestyle, boasting flexible living spaces and stunning d
Living Area:
7653 Sqft.
|
6
Beds,
8
Baths
|
$3,799,000 |
281 Forest St
Welcome to this stunning, fully renovated single-family home with great views from the Turkey Hill. Meticulously gut-renovated in 2025, this home seamlessly blends modern luxury with classic charm.The main floor features an open-concept layout with a chef's kitchen and a wine cellar, perfect for ent
Living Area:
3088 Sqft.
|
4
Beds,
5
Baths
|
$1,720,000 |
257 High Street
Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom bui
Living Area:
7101 Sqft.
|
5
Beds,
7
Baths
|
$3,299,000 |
14 Park Ave Ext
A charming classic house with good bones waiting for your imagination and effort to make a comfortable home for the new era. With a large land and view of Boston Skyline in distance, this home sits on a hill at a very convenient location. Only stone's throw away from the Town Center, Schools, Shops
Living Area:
1507 Sqft.
|
4
Beds,
1
Bath
|
$799,900 |
20 Amberwood Dr
Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and
Living Area:
8866 Sqft.
|
6
Beds,
8
Baths
|
$3,600,000 |
276 High Street
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
Living Area:
5006 Sqft.
|
5
Beds,
4
Baths
|
$2,299,000 |
5 Squire Rd
Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shipla
Living Area:
4696 Sqft.
|
6
Beds,
4
Baths
|
$2,000,000 |
54 Johnson Road
This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings
Living Area:
7982 Sqft.
|
7
Beds,
8
Baths
|
$3,499,000 |