0.52 mi
Distance
Explore Mount Pisgah in Winchester, Massachusetts for a natural and recreational experience. Operated by the Town of Winchester Water Department, this point of interest offers stunning views and outdoor activities. Perfect for hiking, picnicking, and enjoying nature.
| 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 |
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 |
12 Canterbury Road
Tucked along a quiet side street in the sought-after Ambrose School district, this spacious ranch offers comfort, convenience, and endless possibilities. With nearly 2,000 square feet of living space, the home features seven rooms, including a large living room w/ fireplace that anchors the easy, na
Living Area:
1942 Sqft.
|
3
Beds,
3
Baths
|
$1,200,000 |
5 Wood Lane
Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cy
Living Area:
2443 Sqft.
|
3
Beds,
3
Baths
|
$1,950,000 |
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 |
32 Woodside Road
Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice sk
Living Area:
2587 Sqft.
|
3
Beds,
3
Baths
|
$1,549,000 |
15 Wildwood Street
Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for th
Living Area:
4104 Sqft.
|
6
Beds,
3
Baths
|
$2,275,000 |
53 Bacon Street
Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open flo
Living Area:
2865 Sqft.
|
3
Beds,
3
Baths
|
$1,499,000 |
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 |
40 Foxcroft Road
An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a
Living Area:
6367 Sqft.
|
6
Beds,
5
Baths
|
$3,799,000 |
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 |
44 Cabot Street
Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceiling
Living Area:
6028 Sqft.
|
6
Beds,
7
Baths
|
$3,099,000 |
104 Church Street
This charming colonial in prime flats location is full of surprises! Showcasing a stunning rear 3 story addition duplex with walls of windows & 4 rooms! Use as the primary, home office, art studio or let your children enjoy this unique space~ The first floor offers a classic layout with an expanded
Living Area:
2696 Sqft.
|
4
Beds,
2
Baths
|
$1,285,000 |
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 |
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 |
2 Everett Ave
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where
Living Area:
7043 Sqft.
|
7
Beds,
6
Baths
|
$4,174,000 |
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 |
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 |
19 Glengarry Road
A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personaliz
Living Area:
3521 Sqft.
|
6
Beds,
4
Baths
|
$1,975,000 |
20 Grove Pl
From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight
Living Area:
3294 Sqft.
|
5
Beds,
4
Baths
|
$1,869,000 |
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 |
61 Grove Street
- 2017 - STUNNING CUSTOM- BUILT HOME, COMPLETELY rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. Welcome to this easy living, maintenance free sophisticated residence. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in showe
Living Area:
4798 Sqft.
|
5
Beds,
5
Baths
|
$2,239,000 |
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 |