Luxury Houses For Sale In Winchester - Boston, MA

Results 1 - 21 of 21
18 Kirk St

$1,099,900

18 Kirk St - Winchester, Massachusetts United States
Beds: 4   Baths: 3.00   FT2: 2,653   Lot Size: 7,501   Lot Acres: 0.17   County: Middlesex   
Welcome to 18 Kirk! In the beautiful town of Winchester, just 9 miles from Boston and only 26 miles to NH! The best of both worlds. This home includes 2 bedrooms on the upper level, 1 on the main and 1 in the basement, all floors having a full bath and with the basement having its own exterior door ...
43 Mayflower Rd.

$1,550,000

43 Mayflower Rd. - Winchester, Massachusetts United States
Beds: 4   Baths: 3.00   FT2: 4,190   Lot Size: 20,020   Lot Acres: 0.46   County: Middlesex   
Sunny, bright and spacious! This residence is tailor-made for hosting gatherings. The open concept living and dining room is adjacent to the chef's kitchen, complete with high end appliances, ample counter space and 2 skylights. But the real gem is the 4 season room just off the kitchen offering a t...
37 Canterbury Road

$1,599,000

37 Canterbury Road - Winchester, Massachusetts United States
Beds: 4   Baths: 2.50   FT2: 3,527   Lot Size: 16,483   Lot Acres: 0.38   County: Middlesex   
Welcome home! Nestled on a huge, fenced-in lot in a sought-after neighborhood, this picturesque 4 bed, 2 1/2 bath home has it all. A spacious eat-in-kitchen with granite peninsula opens to a sun-filled family room boasting French sliders out to an elegant bluestone patio. The first floor also featur...
9 South Gateway

$1,599,000

9 South Gateway - Winchester, Massachusetts United States
Beds: 6   Baths: 4.00   FT2: 3,250   Lot Size: 10,132   Lot Acres: 0.23   County: Middlesex   
Welcome to this spacious home nestled in a cul-de-sac in top neighborhood featuring 6 large bedrooms & 4 full bathrooms. An inviting living room w/fireplace & picture window showcases the great views & allows sunlight to flow through into the formal dining room. Updated kitchen w/views of great yard...
67 WILDWOOD STREET

$1,649,500

67 WILDWOOD STREET - Winchester, Massachusetts United States
Beds: 3   Baths: 3.50   FT2: 3,011   Lot Size: 12,837   Lot Acres: 0.29   County: Middlesex   
Yes you can have it all. Winchester Flats, corner of Yale Street location. Exquisite move in ready gracious home, that will truly impress. Excellent layout, with a first floor bedroom and bath, walk in shower and double sink vanity. Spacious and sunny living room with a fireplace, dining room, and ...
49 Ledyard Road

$1,679,000

49 Ledyard Road - Winchester, Massachusetts United States
Beds: 4   Baths: 3.00   FT2: 3,050   Lot Size: 13,390   Lot Acres: 0.31   County: Middlesex   
Welcome to this charming 4 bd, 3 br home situated on a gorgeous oversized lot on the desirable East side! Step inside this updated home to discover a warm & inviting layout designed for both family time & entertaining. The open floor plan seamlessly connects the kitchen & dining to a stunning family...
40 Wainwright Road
New

$1,699,000

40 Wainwright Road - Winchester, Massachusetts United States
Beds: 4   Baths: 2.50   FT2: 2,853   Lot Size: 21,048   Lot Acres: 0.48   County: Middlesex   
Discover the allure of this beautiful home nestled on an oversized 21,000sf private lot abutting conservation! This exceptional and meticulously maintained home boasts a flawless layout designed for comfort and functionality with large flowing rooms perfect for hosting parties & family gatherings. T...
2 Chestnut Street

$1,699,000

2 Chestnut Street - Winchester, Massachusetts United States
Beds: 4   Baths: 3.50   FT2: 3,171   Lot Size: 11,090   Lot Acres: 0.25   County: Middlesex   
Top location close to Winchester Center! This 4 bd, 3.5 br home is situated on a generous lot, offering abundance of space & functional floor plan for multi-generational or au-pair living. Greeted by a sunlit interior, showcasing hardwood floors & a cozy fireplace, creating a warm & inviting atmosph...
30 Glen Road

$1,999,000

30 Glen Road - Winchester, Massachusetts United States
Beds: 6   Baths: 2.50   FT2: 3,892   Lot Size: 24,341   Lot Acres: 0.56   County: Middlesex   
Welcome to your dream home nestled on highly sought-after Glen Road! This charming 1910 house boasts modern updates while showcasing timeless elegance. With 6 BR, 2 1/2 BA, & over 1/2 acre of picturesque land, this property has it all.The 1st floor boasts a grand entryway opening to an updated eat-i...
6 Loring Court

$1,999,000

6 Loring Court - Winchester, Massachusetts United States
Beds: 4   Baths: 3.50   FT2: 4,055   Lot Size: 6,600   Lot Acres: 0.15   County: Middlesex   
Must see this gorgeous 4 bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open flr plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating/ quartz countertops, high-end appliances and walk in...
204 Highland Ave

$1,999,000

204 Highland Ave - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 4,274   Lot Size: 12,846   Lot Acres: 0.29   County: Middlesex   
Imagine living at the foot of the Fells, surrounded by a natural setting while being close to the Muraco School, trains, and the town center. This gorgeous Colonial sits high on a hill, surrounded by custom rock walls, a stone patio, and mature landscaping. With 5 bedrooms, including a first-floor g...
6 Lakeview Rd

$2,499,000

6 Lakeview Rd - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 4,300   Lot Size: 11,600   Lot Acres: 0.27   County: Middlesex   
Located on one of the most desirable streets in Winchester is this 5 bedroom home with amazing views of Mystic Lake close to Wedgemere Station, Shannon Beach, and restaurants downtown. Through the front door you'll be impressed with beautiful in-laid hardwood floors that flow through the dining room...
89 Wildwood Street

$2,499,000

89 Wildwood Street - Winchester, Massachusetts United States
Beds: 7   Baths: 5.50   FT2: 4,800   Lot Size: 10,075   Lot Acres: 0.23   County: Middlesex   
NEW CONSTRUCTION!! Must see this gorgeous 7 bed 5.5 bath home w/ thoughtful design & high end finishes! This luxury home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen features an oversized island with seating/ quartz count...
49 Oxford Street

$2,599,000

49 Oxford Street - Winchester, Massachusetts United States
Beds: 7   Baths: 3.50   FT2: 5,616   Lot Size: 13,939   Lot Acres: 0.32   County: Middlesex   
Perfectly situated in one of Winchester's most prestigious neighborhoods, 'The Flats,' this 7 bedroom home has an expansive lot w/ welcoming patio, fire pit & large level yard perfect for family fun! The 1st floor is stunning w/an abundance of picturesque windows that flood the living space w/ natur...
4 Davey Ln

$2,600,000

4 Davey Ln - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 5,267   Lot Size: 13,508   Lot Acres: 0.31   County: Middlesex   
Step into refined living with this gorgeous 5-bedroom, 4.5-bathroom colonial home tucked away on a quiet cul-de-sac. You'll be greeted by a spacious layout with a chef's kitchen featuring a top-of-the-line 48" Sub Zero refrigerator/freezer, a gas range topped with a stylish hood, and a cozy breakfas...
1 Alice Lane

$2,699,000

1 Alice Lane - Winchester, Massachusetts United States
Beds: 6   Baths: 5.50   FT2: 5,524   Lot Size: 10,684   Lot Acres: 0.25   County: Middlesex   
NEW CONSTRUCTION!! Must see this gorgeous 6 bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open flr plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating/ quartz countertops, high-end app...
20 Bellevue Avenue

$2,699,000

20 Bellevue Avenue - Winchester, Massachusetts United States
Beds: 6   Baths: 6.50   FT2: 6,300   Lot Size: 10,001   Lot Acres: 0.23   County: Middlesex   
NEW CONSTRUCTION! This spacious 6 bed, 6.5 bath home by a top local builder has it all! With over 6,300sf of living space you won't want to miss this stunning home. The first flr offers a gourmet kitchen w/ oversized island w/ seating/ quartz countertops, high-end appliances, & breakfast nook/dinin...
4 Abby Road

$2,798,000

4 Abby Road - Winchester, Massachusetts United States
Beds: 4   Baths: 4.50   FT2: 5,471   Lot Size: 10,023   Lot Acres: 0.23   County: Middlesex   
Presenting Winchester's newest luxury new construction home, 4 Abby Road. The first floor features a formal dining room, fireplaced family room, and an eat-in kitchen with a gorgeous island & wet bar. The large mudroom, conveniently located off the garage, provides seamless access to the home. Addit...
276 High Street

$2,830,000

276 High Street - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 6,595   Lot Size: 19,998   Lot Acres: 0.46   County: Middlesex   
This fabulous house is in a beautiful and unique location, perched on a small hill with a secluded half-acre lot in a very quiet cul-de-sac area near the Winchester/Lexington line, far away from any road traffic and offering excellent privacy. There are 4 floors of living space containing 5 bedroom...
27 Everett Ave

$4,399,000

27 Everett Ave - Winchester, Massachusetts United States
Beds: 6   Baths: 5.50   FT2: 7,431   Lot Size: 28,027   Lot Acres: 0.64   County: Middlesex   
This is one of the most notable and distinguished homes on Everett Avenue, with preeminent siting and curb appeal. Designed by famous architect Robert Coit, this residence combines the magnificence of early 1900s architecture with today's modern amenities. Completely renovated in 2023/2024, this res...
15&Lot227 Vinson Circle

$6,500,000

15&Lot227 Vinson Circle - Winchester, Massachusetts United States
Beds: 6   Baths: 6.50   FT2: 8,805   Lot Size: 42,577   Lot Acres: 0.98   County: Middlesex   
Visionary New Construction has begun! Quality and 1st class design define this rare legacy residence.Spectacular interpretation of a modern colonial designed by acclaimed architect & built by Master Builder.Impeccably positioned on one of the highest points in Winchester & commanding seasonal skylin...