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| Address | Bed / Bath | Listing Price |
|---|---|---|
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 |
209 Washington St
Charm and character meet modern living in this beautifully renovated & expanded Victorian townhome just steps from Winchester Center. Fully updated in 2013/14 with new kitchen, baths, wiring, all systems, roof, and windows—and enhanced in 2023 with a redesigned patio, landscaping, fencing, and flo
Living Area:
3141 Sqft.
|
5
Beds,
4
Baths
|
$1,499,000 |
14 Ash St
Welcome to 14 Ash Strret, a classic Colonial located in the highly desirable Horn Pond Neighborhood. This tradt'l 3 bdrm, 1.5 bath home blends timeless character w/the right updates to create a warm & functional living space. A front entry area is the perfect transition to an open concept living, di
Living Area:
1520 Sqft.
|
3
Beds,
2
Baths
|
$749,900 |
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 |
82 Hillcrest Parkway
Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly
Living Area:
1882 Sqft.
|
3
Beds,
3
Baths
|
$1,650,000 |
44 Main Street
Sweet curb appeal abounds this well maintained ranch style home on the Winchester line. Enter through the attached 1 car garage or beautiful composite front steps into the bright living area which includes a fireplace living room, formal dining room and kitchen with sparkling granite countertops. H
Living Area:
1029 Sqft.
|
2
Beds,
1
Bath
|
$589,900 |
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 |
50 Lincoln Street
This beautiful Victorian home, featuring an inviting front porch, stunning period detail including wainscoting, original tin ceilings, custom built-ins, and three fireplaces is not to be missed! Maple hardwood floors flow through an open-concept layout to a spacious eat-in kitchen with a lovely expo
Living Area:
2004 Sqft.
|
4
Beds,
2
Baths
|
$1,200,000 |
18 Middlesex St
A masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of-the-art amenities.Step into a grand foyer, where a striking curved staircase sets the stage for the home’s sophisticated ambiance. Expansive living and entertaining space
Living Area:
5233 Sqft.
|
4
Beds,
5
Baths
|
$2,795,000 |
29 Porter St
Step into this beautifully renovated Colonial in the heart of Woburn—where timeless charm meets modern living. The sunlit foyer opens to a chef-inspired kitchen with granite countertops, a spacious island, and abundant cabinetry. An open floor plan connects the dining room to the composite deck an
Living Area:
1822 Sqft.
|
3
Beds,
3
Baths
|
$799,000 |
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 |
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 |
61 Mt Pleasant St
Welcome to modern elegance in this stunning Farmhouse that offers 3,814 sq ft of contemporary style blended with farmhouse charm, featuring 5 potential bedrooms and 3.5 bathrooms. The heart of this home is its luxurious kitchen, complete with a 8-foot island, cooktop, wall ovens, beverage fridge and
Living Area:
3814 Sqft.
|
5
Beds,
4
Baths
|
$1,399,900 |
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 |
571 Washington St
Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Design
Living Area:
1425 Sqft.
|
3
Beds,
1
Bath
|
$898,000 |
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 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 |
5 Bacon St
This stunning Victorian home, in the style of Painted Ladies w/ soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & Boston. The house lives as a harmonious single family with a second ki
Living Area:
4385 Sqft.
|
6
Beds,
4
Baths
|
$2,190,000 |
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 |
4 Chestnut St
Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blu
Living Area:
4474 Sqft.
|
4
Beds,
5
Baths
|
$1,990,000 |
7-9 Cleveland Rd
Welcome to this outstanding home set on a spacious 20,817 sf lot in desirable Winchester. This property presents a wealth of possibilities, whether you're looking to live in it as a single-family home, have a need for an in-law apartment, or maintain it as a multi-family residence. The 1st level boa
Living Area:
2578 Sqft.
|
5
Beds,
3
Baths
|
$1,149,000 |