Homes For Sale In Winchester - Boston, MA

Results 1 - 29 of 29
25 Hemingway St

$979,900

25 Hemingway St - Winchester, Massachusetts United States
Beds: 3   Baths: 2.00   FT2: 1,890   Lot Size: 6,564   Lot Acres: 0.15   County: Middlesex   
Discover the potential of this charming and well-maintained 2-story Cape-style home, offering both comfort and privacy in a highly desirable Winchester location. Conveniently situated near a public elementary school, public transportation, healthcare services, and a variety of dining options, this h...
89 Mystic Valley Parkway, Apt 89

$1,156,900

89 Mystic Valley Parkway, Apt 89 - Winchester, Massachusetts United States
Beds: 5   Baths: 2.50   FT2: 3,220   Lot Size: 12,196   Lot Acres: 0.28   County: Middlesex   
Price Adjustment to Assessed Value!!Victorian townhome condo with a single-family feel in fabulous downtown location! Ideally situated in close proximity to trains, schools, restaurants & everything Winchester Center has to offer! Front porch welcomes you into this lovingly cared for home blending o...
6 Governors Avenue

$1,199,000

6 Governors Avenue - Winchester, Massachusetts United States
Beds: 3   Baths: 1.50   FT2: 1,883   Lot Size: 7,488   Lot Acres: 0.17   County: Middlesex   
Welcome to this impeccably maintained & beautifully updated Colonial on large lot near the town center. This home blends charm w/ modern convenience, featuring 3 spacious bedrooms & 1.5 baths w/ a great floor plan. The first level features a sun-drenched living room that flows into an inviting dinin...
37 Tufts Road

$1,249,000

37 Tufts Road - Winchester, Massachusetts United States
Beds: 4   Baths: 2.50   FT2: 1,969   Lot Size: 10,546   Lot Acres: 0.24   County: Middlesex   
Beautifully renovated home with open concept main living area including elegantly updated kitchen with quartz countertops, professional grade range and wine refrigerator. Primary suite includes cathedral ceilings and oversized (8' high) sliders opening up to private balcony with views of Leonard Pon...
28 Thornberry Road

$1,449,000

28 Thornberry Road - Winchester, Massachusetts United States
Beds: 4   Baths: 2.00   FT2: 2,245   Lot Size: 15,002   Lot Acres: 0.34   County: Middlesex   
Welcome to 28 Thornberry! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the ho...
7 Thornberry Road

$1,499,000

7 Thornberry Road - Winchester, Massachusetts United States
Beds: 5   Baths: 2.00   FT2: 3,033   Lot Size: 15,298   Lot Acres: 0.35   County: Middlesex   
Welcome to this newly renovated contemporary home, nestled in the highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfort...
78 Middlesex Street

$1,595,000

78 Middlesex Street - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 2,650   Lot Size: 3,864   Lot Acres: 0.09   County: Middlesex   
Amazing transformation of a Classic Colonial carefully reimagined for today's busy lifestyle. Living room with gas fireplace opens to the family room, oversized hi-end kitchen with island, stainless & granite, dining room with sliders to the yard with a stone patio for outside entertaining, a mud ro...
31 Girard Road

$1,599,000

31 Girard Road - Winchester, Massachusetts United States
Beds: 4   Baths: 2.50   FT2: 3,158   Lot Size: 23,949   Lot Acres: 0.55   County: Middlesex   
Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you'll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen...
40 Foxcroft Rd

$1,675,000

40 Foxcroft Rd - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 2,000   Lot Size: 14,431   Lot Acres: 0.33   County: Middlesex   
Garrison Colonial nestled in the highly desirable Flats neighborhood of Winchester! This 3-bedroom, 2.5-bath home offers plenty of potential, with additional space in the walk-up attic and a large backyard. Classic brick fireplaces in first floor living room and in basement. With the existing 2,000 ...
10 Marshall Rd

$1,875,000

10 Marshall Rd - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 3,376   Lot Size: 11,073   Lot Acres: 0.25   County: Middlesex   
Fully renovated in 2012,this charming colonial is nestled on a side street near Winchester Center, both train stations and local schools.Step into a welcoming ,traditional foyer that leads to the living room, complete with custom built-ins, a cozy fireplace and French doors opening to a sunroom bat...
189 Mystic Valley Pkwy

$1,899,900

189 Mystic Valley Pkwy - Winchester, Massachusetts United States
Beds: 6   Baths: 2.50   FT2: 3,543   Lot Size: 8,011   Lot Acres: 0.18   County: Middlesex   
Nestled in a coveted location just moments from the heart of downtown Winchester, the stunning Barstow House boasts a unique Mansard roof & timeless colonial architecture. This historic gem features a versatile floorplan designed for modern living while preserving its classic charm. The first level ...
11 Plymouth Road

$1,949,000

11 Plymouth Road - Winchester, Massachusetts United States
Beds: 4   Baths: 3.50   FT2: 3,611   Lot Size: 25,835   Lot Acres: 0.59   County: Middlesex   
NEW PRICE! Magnificent Brick Colonial, perfectly situated at the end of a quite dead-end street, abutting conservation that offers unmatched privacy and tranquility. The gorgeous, spacious foyer leads into the beautiful front to back living room with a warm and inviting fireplace. The well-appointe...
9 S Gateway

$2,188,000

9 S Gateway - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 3,450   Lot Size: 10,132   Lot Acres: 0.23   County: Middlesex   
Completely renovated colonial style home on a quiet cul-de-sac within walking distance to downtown Winchester! This home features 5 bedrooms, 3.5 bathrooms and an attached 2 car garage. The first floor offers kitchen, dining, living room and den/study. The flexible first floor also has a bedroom ...
18 Dix Street

$2,199,000

18 Dix Street - Winchester, Massachusetts United States
Beds: 4   Baths: 2.50   FT2: 3,048   Lot Size: 13,713   Lot Acres: 0.31   County: Middlesex   
Elegant and timeless, this beautifully renovated colonial in the heart of Winchester Center offers the perfect blend of classic design and modern luxury. With a high-end chef's kitchen featuring an oversized island, the home's open floor plan seamlessly connects to a spacious family room and dining ...
58 Wedgemere Avenue

$2,399,000

58 Wedgemere Avenue - Winchester, Massachusetts United States
Beds: 5   Baths: 2.50   FT2: 3,008   Lot Size: 14,488   Lot Acres: 0.33   County: Middlesex   
Welcome to this stunning English Tudor with incredible curb appeal situated on desirable Wedgemere Avenue! Nestled on a lush oversized lot with gorgeous flowering trees & perennial gardens; this enchanting home has been lovingly maintained & nicely updated inside and out. The first level features a ...
5 Girard Rd

$2,425,000

5 Girard Rd - Winchester, Massachusetts United States
Beds: 4   Baths: 4.00   FT2: 5,721   Lot Size: 18,526   Lot Acres: 0.43   County: Middlesex   
Experience the pinnacle of refined living at 5 Girard Road, a custom built Contemporary Colonial in Winchester, MA. This captivating home boasts 4 bedrooms and 4 bathrooms. Tasteful architecture and custom woodwork create a timeless and sophisticated ambiance, home faces south for abundance of natur...
92 Hillcrest Pkwy

$2,499,999

92 Hillcrest Pkwy - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 4,048   Lot Size: 11,474   Lot Acres: 0.26   County: Middlesex   
This exquisite, custom-built home from local master builder boasts a grand two-story foyer, a spacious chef's kitchen seamlessly flows into a vaulted ceiling family room, & an open concept living room & dining room perfect for entertaining. Upstairs, discover a luxurious primary bedroom suite w/expa...
50 Winford Way

$2,599,000

50 Winford Way - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 4,270   Lot Size: 10,019   Lot Acres: 0.23   County: Middlesex   
Stunning new construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the l...
18 Middlesex St

$2,695,000

18 Middlesex St - Winchester, Massachusetts United States
Beds: 4   Baths: 4.50   FT2: 5,233   Lot Size: 10,812   Lot Acres: 0.25   County: Middlesex   
European inspired and masterfully crafted, showcases sophisticated design and top-of-the-line systems. A well appointed floor plan awaits with grand scale rooms and elegant detail. Enter through the magnificent foyer, featuring a beautiful curved staircase that leads into the formal living room and ...
15 Churchill Road

$2,699,000

15 Churchill Road - Winchester, Massachusetts United States
Beds: 4   Baths: 4.50   FT2: 5,501   Lot Size: 20,023   Lot Acres: 0.46   County: Middlesex   
Indulge in modern luxury with this 2024 masterpiece, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the ...
31 Lawson Rd

$2,749,000

31 Lawson Rd - Winchester, Massachusetts United States
Beds: 4   Baths: 3.50   FT2: 5,218   Lot Size: 10,485   Lot Acres: 0.24   County: Middlesex   
Welcome to this gracious Colonial, seamlessly blending traditional charm with modern amenities, perfect for today's lifestyle. Located in one of Winchester's most desirable neighborhoods, you'll enjoy easy access to top-rated schools, the commuter rail, and downtown. This home showcases deep molding...
16 Ardley Place

$2,799,000

16 Ardley Place - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 4,324   Lot Size: 20,064   Lot Acres: 0.46   County: Middlesex   
Beautiful & magnificent, this colonial single family offers a perfect blend of timeless elegance and contemporary amenities. Situated at the end of a serene cul-de-sac & private hilltop oasis just minutes from the new Lynch Elementary School opening in 2025. Enjoy proximity to Horn Pond recreation a...
14 Nassau Dr.

$2,899,000

14 Nassau Dr. - Winchester, Massachusetts United States
Beds: 6   Baths: 5.50   FT2: 6,968   Lot Size: 18,637   Lot Acres: 0.43   County: Middlesex   
Absolutely stunning custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18' high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double...
8 Chestnut St

$3,299,000

8 Chestnut St - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 5,366   Lot Size: 16,335   Lot Acres: 0.38   County: Middlesex   
This iconic vintage farmhouse seamlessly blends historic charm with modern luxury. Spanning over 5,366 sq. ft., this home has been completely renovated and thoughtfully expanded for today's lifestyle. Featuring 5 bedrooms, 4 full and 2 half baths, every inch exudes elegance and comfort. The designer...
2 Chestnut St

$3,649,000

2 Chestnut St - Winchester, Massachusetts United States
Beds: 5   Baths: 5.00   FT2: 5,500   Lot Size: 11,090   Lot Acres: 0.25   County: Middlesex   
This spacious 5-bed, 5 bath home is located just outside the heart of downtown. In one of Winchester's most sought-after locations, this unique opportunity is scheduled for completion in July 2025. Construction begins in November, offering the rare opportunity for buyers to personalize finishes and...
6 Lakeview Road

$3,769,000

6 Lakeview Road - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 5,768   Lot Size: 11,578   Lot Acres: 0.27   County: Middlesex   
Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town's most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Reconstructed and designed by RENEW, a company commit...
20 Amberwood Dr

$3,898,000

20 Amberwood Dr - Winchester, Massachusetts United States
Beds: 6   Baths: 7.00   FT2: 8,866   Lot Size: 23,274   Lot Acres: 0.53   County: Middlesex   
Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliance...
27 Everett Ave

$3,899,000

27 Everett Ave - Winchester, Massachusetts United States
Beds: 5   Baths: 5.50   FT2: 7,431   Lot Size: 28,027   Lot Acres: 0.64   County: Middlesex   
One of the most notable and distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. 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 r...
54 Johnson Road

$4,399,000

54 Johnson Road - Winchester, Massachusetts United States
Beds: 7   Baths: 7.50   FT2: 7,982   Lot Size: 20,016   Lot Acres: 0.46   County: Middlesex   
Step into this stunning, newly constructed home that redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends beauty w/ ease of living. The 8' arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom r...