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' Winchester, MA Living Area: 3658 Sqft.	4 Beds, 3 Baths	$2,075,000
6 Marchant Road Beautiful 3 bed, 2.5 bath home set on a generous 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 family ro Winchester, MA Living Area: 2153 Sqft.	3 Beds, 3 Baths	$1,350,000
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 Winchester, MA Living Area: 4334 Sqft.	5 Beds, 4 Baths	$2,149,000
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 Winchester, MA Living Area: 1942 Sqft.	3 Beds, 3 Baths	$1,200,000
446 Highland Ave Charming Spanish-style home in desirable Winchester! This unique property features a beautiful terracotta roof and timeless architectural details. The first floor welcomes you with a foyer which leads to an astounding great room, perfect for entertaining or hosting family gatherings. The kitchen ope Winchester, MA Living Area: 2033 Sqft.	2 Beds, 2 Baths	$999,000
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 Winchester, MA Living Area: 3141 Sqft.	5 Beds, 4 Baths	$1,499,000
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 Winchester, MA 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 Winchester, MA Living Area: 1882 Sqft.	3 Beds, 3 Baths	$1,650,000
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 Winchester, MA Living Area: 6500 Sqft.	5 Beds, 6 Baths	$3,250,000
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 Woburn, MA Living Area: 1029 Sqft.	2 Beds, 1 Bath	$589,900
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 Winchester, MA 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 Winchester, MA 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 Winchester, MA 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 Winchester, MA 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 Winchester, MA Living Area: 5233 Sqft.	4 Beds, 5 Baths	$2,795,000
39 Town Way Discover all this gorgeous new construction home in top East Side location will offer! Designed with today’s lifestyle in mind, this home features a flexible open floor plan perfect for entertaining & everyday living / A great opportunity for you to customize the finishes & bring your vision to li Winchester, MA Living Area: 5709 Sqft.	6 Beds, 7 Baths	$3,199,000
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 Winchester, MA 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 Winchester, MA 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 Winchester, MA Living Area: 2696 Sqft.	4 Beds, 2 Baths	$1,285,000
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 Winchester, MA 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 Winchester, MA 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 Winchester, MA 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 Winchester, MA 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 Winchester, MA Living Area: 3294 Sqft.	5 Beds, 4 Baths	$1,869,000
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 Winchester, MA Living Area: 4798 Sqft.	5 Beds, 5 Baths	$2,239,000
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 Winchester, MA 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 Winchester, MA Living Area: 2578 Sqft.	5 Beds, 3 Baths	$1,149,000

Winchester, Massachusetts, United States

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Homes for sale near Keller Williams Realty, Winchester, MA, USA

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