845 ft
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
1 Copley Street
Gracious Center Entrance colonial situated in top Flats location on a desirable corner lot. This home has all the charm of yesteryear and has many custom features including a beautiful front staircase with window seats, hardwood floors and sunny rooms. Attractive cherry cabinet kitchen with granit
Living Area:
2998 Sqft.
|
7
Beds,
3
Baths
|
$1,725,000 |
7-7A Brooks St
This stately Victorian offers an exceptional blend of preserved character and modern functionality across its generous, well-appointed layout. Sunlit rooms highlight hardwood floors, detailed millwork, bay windows, and a graceful fireplace, creating a warm and elegant flow throughout the main level.
Living Area:
4122 Sqft.
|
6
Beds,
4
Baths
|
$2,275,000 |
29 Shepard Ct
Offers due Tuesday, 11/25 @ 10am. With 6 bedrooms & 5 full baths, this beautifully crafted new construction located at the end of a cul-de-sac delivers refined style, a modern layout & effortless living. The open layout showcases a chef’s kitchen with an oversized island, quartz counters & Thermad
Living Area:
4594 Sqft.
|
6
Beds,
5
Baths
|
$2,399,000 |
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 |
89 Wildwood St
Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cab
Living Area:
4929 Sqft.
|
7
Beds,
6
Baths
|
$2,299,000 |
139 High Street
This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with co
Living Area:
1302 Sqft.
|
3
Beds,
2
Baths
|
$999,000 |
8 Felsdale Close
Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells'
Living Area:
3658 Sqft.
|
4
Beds,
3
Baths
|
$2,075,000 |
237 Swanton Street
NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. F
Living Area:
4334 Sqft.
|
5
Beds,
4
Baths
|
$2,149,000 |
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
|
$2,600,000 |
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 |
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 |
380 Cross St
This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The
Living Area:
1938 Sqft.
|
4
Beds,
2
Baths
|
$949,000 |
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 |
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 |
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 |