370 ft
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
46 Church St
Welcome to 46 Church Street. This spacious, beautifully maintained, Paul Whitney built home is just outside the heart of Winchester center with easy access to the commuter rail, schools, restaurants, and shopping. Offering flexible living areas and abundant room throughout, the residence features
Living Area:
3475 Sqft.
|
4
Beds,
4
Baths
|
$1,999,000 |
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 |
19 Town Way
Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artfu
Living Area:
5257 Sqft.
|
5
Beds,
6
Baths
|
$2,999,000 |
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 |
6 Marchant Road
Updated 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, the train, and route to Boston. The first floor offers an ideal layout with an updated kitchen, stainless steel appliances & island w seating open to a lovely famil
Living Area:
2153 Sqft.
|
3
Beds,
3
Baths
|
$1,350,000 |
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 |
8 Priscilla Ln
Welcome to 8 Priscilla Ln, Winchester—a brand-new 5 bed, 5.5 bath luxury home designed by Salt & Stone Co where elevated craftsmanship meets everyday comfort. Spanning 6,500 ± sq ft, this home features a chef’s kitchen with custom cabinetry, premium appliances, and an oversized center island fl
Living Area:
6500 Sqft.
|
5
Beds,
6
Baths
|
$3,250,000 |
53 Winford Way
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 coz
Living Area:
5083 Sqft.
|
5
Beds,
4
Baths
|
$2,799,000 |
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
27,000 SF lot!!! Set far back from the street~ Don't miss this opportunity! Whether looking to lightly update/ expand or completely renovate; this well maintained 3 bedroom split entry home with a stunning oversized private yard offers tremendous potential! The first floor is spacious with large sun
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 |
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 |
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 |
19 Shirley Rd
Welcome to this stunning, fully reimagined modern home nestled on a quiet east Medford street. Newly rebuilt -and occupied by a local developer with a reputation for high-end craftsmanship, this home showcases thoughtful design and luxury at every turn. With approximately 4800 sq ft, the residence o
Living Area:
4800 Sqft.
|
4
Beds,
6
Baths
|
$1,699,000 |