Homes For Sale In Winchester - Boston, MA

Results 1 - 41 of 41
5 Bates Road
New

$850,000

5 Bates Road - Winchester, Massachusetts United States
Beds: 5   Baths: 2.00   FT2: 1,918   Lot Size: 6,491   Lot Acres: 0.15   County: Middlesex   
Priced to sell! Amazing opportunity! This home is in a desirable location just steps away from Muraco Elementary School. Feel free to put some renovations into this home to make it your own or move right in. This home features two separate living room spaces with fireplaces, three bedrooms on the fi...
9 Upland Rd

$998,000

9 Upland Rd - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 1,468   Lot Size: 5,001   Lot Acres: 0.11   County: Middlesex   
Welcome to 9 Upland Rd, a beautiful and newly renovated colonial. As you enter the home, you'll be greeted by the dining room, which flows effortlessly into the renovated white kitchen- featuring stainless steel appliances and an island that separates the two rooms. On your way to the spacious firep...
32 Tufts Rd

$999,000

32 Tufts Rd - Winchester, Massachusetts United States
Beds: 3   Baths: 1.50   FT2: 2,139   Lot Size: 6,904   Lot Acres: 0.16   County: Middlesex   
Nestled in Winchester's prestigious neighborhood, this charming Garrison Colonial home is a suburban paradise! Enjoy unrivaled convenience with its prime location near Muraco School, Leonard Field, and enjoy the natural beauty of the nearby Middlesex Fells Reservation. This home is located on an exp...
7 Grant Rd

$999,000

7 Grant Rd - Winchester, Massachusetts United States
Beds: 3   Baths: 2.00   FT2: 2,034   Lot Size: 10,006   Lot Acres: 0.23   County: Middlesex   
A Wonderful home to make your own! Or Contractors, envision the future! Enter into the Living Room with a beautiful bow window overlooking the front. The Dining Room is open to the Living Room making a spacious entertaining area. The kitchen is centrally located to all rooms and has access to the ...
1 Orient St

$1,120,000

1 Orient St - Winchester, Massachusetts United States
Beds: 3   Baths: 1.50   FT2: 2,664   Lot Size: 8,028   Lot Acres: 0.18   County: Middlesex   
Welcome to this recently renovated, charming 3 bedroom 1.5 bath home centrally located in a desirable side-walked neighborhood! Providing the perfect balance of city and suburban living, walking distance to schools, downtown, parks, playgrounds, and the bike path, with easy access to 93 + Commuter R...
18 Kirk St

$1,150,000

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   
One of the best deals on price per square foot for Winchester, AND18 Kirk St has everything you could ask for! Located on a dead-end street, in walking distance to McDonald field with its baseball field, tennis and basketball courts. Less than a mile walk to downtown shops and restaurants and the ou...
246 Washington Street, Apt 246

$1,175,000

246 Washington Street, Apt 246 - Winchester, Massachusetts United States
Beds: 4   Baths: 1.50   FT2: 2,660   Lot Size: 99,999   Lot Acres: 2.30   County: Middlesex   
Move right in and enjoy this lovely 4 bedroom townhome close to downtown with incredible curb appeal and feel of a single family! You will love to call this great property home, offering side by side living with plenty of privacy! The first floor features a beautiful flowing first floor w/ high ceil...
5 Clearwater Rd

$1,199,000

5 Clearwater Rd - Winchester, Massachusetts United States
Beds: 4   Baths: 2.50   FT2: 2,713   Lot Size: 11,108   Lot Acres: 0.26   County: Middlesex   
Opportunity abounds at this East Hill Colonial in a highly sought-after neighborhood where new construction goes for well over $2 million. Available for the first time in 50 years, this cherished home offers a wide-spanning floor plan and perfect canvas for creating a modern living space. The sunny ...
6 Ivy Cir

$1,315,000

6 Ivy Cir - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 2,307   Lot Size: 10,350   Lot Acres: 0.24   County: Middlesex   
Enjoy all Winchester has to offer in this Colonial at the end of a cul-de-sac with a near center location. Hardwood floors in the living room, dining room, bedrooms and hallways. The large family room adjacent to the kitchen has a vaulted ceiling with walls covered in authentic barn board and atta...
8 Glenwood Avenue, Apt 8

$1,360,000

8 Glenwood Avenue, Apt 8 - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 2,225   Lot Size: 7,100   Lot Acres: 0.16   County: Middlesex   
Newly constructed 3-bedroom townhouse. First floor has great open floor plan with hardwood floors throughout. Kitchen features all stainless steel appliances, granite countertops, center island, and dining area. Living room has gas fireplace. Sliding door grants access to deck and back yard. Second ...
18 Forest Street

$1,399,000

18 Forest Street - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 2,365   Lot Size: 6,499   Lot Acres: 0.15   County: Middlesex   
Welcome to this custom built home w/ a fabulous yard abutting town field/conservation! Stunning open floor plan, ideal for hosting gatherings, seamlessly connecting all of your spaces for modern living! The kitchen is a chefs dream which boasts custom cabinetry, high-end GE appliances, quartz counte...
82 Church St

$1,449,000

82 Church St - Winchester, Massachusetts United States
Beds: 4   Baths: 4.50   FT2: 2,465   Lot Size: 8,495   Lot Acres: 0.20   County: Middlesex   
Great Single Family Alternative! ONE LUXURY TOWNHOME JUST SOLD AND ONLY ONE UNIT IS LEFT AND IS READY TO MOVE IN! Do not miss your opportunity to have all the conveniences of urban living in one of the finest suburban neighborhoods surrounding Boston. Enjoy 2,500 spacious square feet spread over fou...
34 Eaton Street

$1,450,000

34 Eaton Street - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 2,577   Lot Size: 5,950   Lot Acres: 0.14   County: Middlesex   
Incredible sun-filled home with beautiful details inside and out! Sought after location close to TOWN, TRAIN, SCHOOLS, LIBRARY and MIDDLESEX FELLS. Coveted WalkScore of "Very walkable". Gracious front porch, high ceilings, bullseye molding, gorgeous wood floors and lovely details to please the dis...
32 Woodside Road

$1,575,000

32 Woodside Road - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 2,562   Lot Size: 18,117   Lot Acres: 0.42   County: Middlesex   
Nestled along Winchesters beloved Winter Pond, this beautiful home offers the 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 skating, f...
16 Marshall Rd

$1,595,000

16 Marshall Rd - Winchester, Massachusetts United States
Beds: 4   Baths: 3.00   FT2: 2,866   Lot Size: 17,193   Lot Acres: 0.39   County: Middlesex   
**OFFER ACCEPTED--OPEN HOUSE CANCELLED 9/24**. This meticulously maintained 4 bedroom, 3 bath modern home opens with a thoughtful, sunlit layout featuring multiple living spaces including, a stone fireplace, oversized skylights, rich hardwood floors and an updated kitchen equipped with premium appl...
1 Socrates Way

$1,799,000

1 Socrates Way - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 5,123   Lot Size: 44,688   Lot Acres: 1.03   County: Middlesex   
Welcome to your private retreat at Chez Brazo. Nestled on a spacious 1+ acre lot, this property offers a serene environment that is hidden from passersby. Upon entering the driveway, a picturesque scene unfolds with lush greenery & beautifully landscaped yard.The main level features a spacious livin...
8 Olde Lyme Rd

$1,799,000

8 Olde Lyme Rd - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 4,603   Lot Size: 17,119   Lot Acres: 0.39   County: Middlesex   
Get ready to live your dream life! This house isn't just a home; it's a lifestyle upgrade with everything you could ever want. Step inside and prepare to be amazed by the huge family room, perfect for hosting Netflix marathons and epic game nights. The open kitchen and dining room are ready for your...
12 Ardley Place

$1,849,000

12 Ardley Place - Winchester, Massachusetts United States
Beds: 3   Baths: 2.50   FT2: 2,846   Lot Size: 20,277   Lot Acres: 0.47   County: Middlesex   
Rare opportunity to own this newly renovated 3/4 bedroom home in a truly special, picturesque neighborhood! This spacious home with stunning great room featuring walls of windows & vaulted ceilings, has been tastefully updated combining modern amenities with 1930s charm. A lovely front entry with s...
5 Swan Road

$1,999,000

5 Swan Road - Winchester, Massachusetts United States
Beds: 7   Baths: 3.00   FT2: 4,090   Lot Size: 20,038   Lot Acres: 0.46   County: Middlesex   
Must see this one of a kind home nestled into Myopia hill, a top Winchester neighborhood! Customize this rare gem offering grand yet intimate shared family spaces, plus a 3 room in law or au-pair suite w/ separate entry. Stunning formal dining, living room with fireplace & beautiful molding detail, ...
148 Highland Ave

$2,450,000

148 Highland Ave - Winchester, Massachusetts United States
Beds: 5   Baths: 3.50   FT2: 4,583   Lot Size: 10,015   Lot Acres: 0.23   County: Middlesex   
Extraordinary 5 bed, 3.5 bath Arts & Crafts Colonial, steps to The Fells. Total kitchen renovation in 2019 created chefs kitchen with 48' dual fuel Wolf range, double ovens, high velocity hood, Sub-Zero fridge, marble counters/backslash & 2 bev coolers and new 1/2 bath. Cherry hardwood on 1st & 2nd ...
27 Brooks Street

$2,499,000

27 Brooks Street - Winchester, Massachusetts United States
Beds: 4   Baths: 2.50   FT2: 4,650   Lot Size: 12,824   Lot Acres: 0.29   County: Middlesex   
This gorgeous custom home in coveted Brooks neighborhood features a fabulous floor plan with stunning finishes! Thoughtfully designed w/ a dramatic living room featuring vaulted ceilings & floor to ceiling windows w/ fplc, formal dining, open concept sun-drenched kitchen w/ custom cabinetry, chefs a...
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...
3 Priscilla Lane

$2,525,000

3 Priscilla Lane - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 5,724   Lot Size: 10,115   Lot Acres: 0.23   County: Middlesex   
Must see this fabulous +/- 5000 sf modern colonial! This newly constructed 5 bed, 4.5 bath home by premiere local builder is one of a kind & offers space & style that will impress! From the moment you enter you will feel the quality & appreciate the beautiful unique craftsmanship; features include a...
18 Alden Lane

$2,595,000

18 Alden Lane - Winchester, Massachusetts United States
Beds: 5   Baths: 5.50   FT2: 6,338   Lot Size: 10,019   Lot Acres: 0.23   County: Middlesex   
Treetop views and top of the line construction! This 5+ bedroom, 5.5 bathroom beauty is located in the coveted Lincoln Elementary School District. The first level consists of a formal living room, open concept family room and dining room, gourmet kitchen with pantry, 1.5 bathrooms, 1st floor bedroom...
11 Priscilla Lane

$2,598,000

11 Priscilla Lane - Winchester, Massachusetts United States
Beds: 6   Baths: 5.50   FT2: 6,323   Lot Size: 10,119   Lot Acres: 0.23   County: Middlesex   
Stunning 6 bed, 5.5 bath NEW CONSTRUCTION Colonial. on quiet side st, minutes to Rte 3, I-93, Winchester Center & The Middlesex Fells. Thoughtfully designed with first floor suite style bedroom off main living area plus expansive second floor primary suite. Gorgeous transomed windows welcome sun thr...
18 Middlesex St

$2,599,000

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   
This extraordinary property is privately situated, yet, just minutes from Boston. 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 charm. Enter through the magnificent foyer, f...
50 EMERSON ROAD

$2,599,000

50 EMERSON ROAD - Winchester, Massachusetts United States
Beds: 4   Baths: 3.50   FT2: 4,051   Lot Size: 23,370   Lot Acres: 0.54   County: Middlesex   
Don't miss this stately young Colonial beautifully sited atop a hillside in this sought-after West Side neighborhood. The home is brilliantly designed with open floor plan that integrates indoor and outdoor living space including a covered patio and in-ground pool. Other design features include en-s...
228 Ridge St

$2,649,000

228 Ridge St - Winchester, Massachusetts United States
Beds: 5   Baths: 5.50   FT2: 6,265   Lot Size: 15,085   Lot Acres: 0.35   County: Middlesex   
This stunning new construction colonial showcases a sprawling 6,265 sf of luxurious living space, offering ample room for entertaining & comfortable everyday living. With 5 beds, 5.5 baths & a 2-car garage, this home is designed to accommodate your family's every need. The grand foyer welcomes you w...
108 Arlington St
New

$2,699,000

108 Arlington St - Winchester, Massachusetts United States
Beds: 5   Baths: 5.50   FT2: 5,830   Lot Size: 10,293   Lot Acres: 0.24   County: Middlesex   
Luxury New Construction close to the Winchester Country Club! The combination of classic elements & modern convenience make this home stand apart from the rest. Double front entry doors lead to the open living room & thoughtfully designed kitchen with double wall-ovens, gas top range, direct vent ho...
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...
1 Alice Lane

$2,799,000

1 Alice Lane - Winchester, Massachusetts United States
Beds: 5   Baths: 5.00   FT2: 5,000   Lot Size: 10,684   Lot Acres: 0.25   County: Middlesex   
NEW CONSTRUCTION!! Must see this gorgeous 5 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...
3 Sheffield Rd
New

$2,800,000

3 Sheffield Rd - Winchester, Massachusetts United States
Beds: 6   Baths: 3.50   FT2: 3,755   Lot Size: 20,661   Lot Acres: 0.47   County: Middlesex   
Amazing 1907 six bedroom three and one half bath Colonial Revival located in one of Winchesters finest neighborhoods.This home is a tribute to yesteryear with its custom detail and design, magnificent woodwork, high coffered ceilings ,beautiful hardwood floors and four fireplaces.Imagine entertaini...
10 North Gateway

$2,899,000

10 North Gateway - Winchester, Massachusetts United States
Beds: 5   Baths: 5.50   FT2: 6,067   Lot Size: 10,467   Lot Acres: 0.24   County: Middlesex   
Welcome to the market 10 North Gateway, a stunning new construction property in a neighborhood that everyone in Winchester LOVES! Enter in and immediately be greeted by a gorgeous 2 story foyer with access to your formal living room. The kitchen features an oversized island and is open to the firepl...
319 Main St

$2,899,900

319 Main St - Winchester, Massachusetts United States
Beds: 8   Baths: 5.50   FT2: 6,484   Lot Size: 19,558   Lot Acres: 0.45   County: Middlesex   
Introducing 319 Main Street...a remarkable colonial showcasing exquisite craftsmanship & details throughout! Situated in a prime location, this stately home offers a grand front brick porch providing a perfect spot to relax & enjoy warm summer evenings! Upon entering be greeted wi/stunning coffered ...
30 Wedgemere Avenue

$2,975,000

30 Wedgemere Avenue - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 4,263   Lot Size: 15,220   Lot Acres: 0.35   County: Middlesex   
This stately home is situated on the second block of prestigious Wedgemere Avenue, one of Winchesters' most desired addresses. This stunning home is situated on a meticulously maintained lot with gorgeous landscape, cozy private spaces offering an abundance of undeniable curb appeal. This home showc...
11 Brooks St.

$3,099,000

11 Brooks St. - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 5,208   Lot Size: 35,283   Lot Acres: 0.81   County: Middlesex   
Embrace elegance, relish a private setting & enjoy one of Winchester's finest neighborhoods! Main level open floor plan showcases a kitchen replete w/luxury ~ Quartz counters, Laurier Max cabinetry, walk-in pantry & the culinary technology of Gagganeau appliances. An expansive LR w/gas fpl & custom ...
19 SOCRATES WAY

$3,299,000

19 SOCRATES WAY - Winchester, Massachusetts United States
Beds: 5   Baths: 4.50   FT2: 5,678   Lot Size: 21,436   Lot Acres: 0.49   County: Middlesex   
ULTIMATE DESIRABLE LOCATION - CUSTOM BUILT HOME - PRISTINE CONDITION - 7 MILES to BOSTON - HALF ACRE LOT - PERFECT FLAT LOT - RARE FIND in WINCHESTER - SPACE for YOUR EVERY DESIRE . Having 14 Rooms - 5+ Bedrooms, 4 Full Bathrooms and 2 Half Bathrooms - 3 floors of finished living space with a magnif...
23 Lawson Rd
New

$3,675,000

23 Lawson Rd - Winchester, Massachusetts United States
Beds: 6   Baths: 4.50   FT2: 5,757   Lot Size: 13,730   Lot Acres: 0.32   County: Middlesex   
Step inside elegance in this 5,757 sq ft smart home nestled on spacious 14,000 sq ft lot! First floor welcomes you w/ grand entrance, a custom office on the right, and a formal dining room adorned w/ grand crown molding. Flow effortlessly into the dream kitchen, boasting custom cabinets, a Wolf rang...
8 Niles Lane

$5,200,000

8 Niles Lane - Winchester, Massachusetts United States
Beds: 8   Baths: 7.50   FT2: 7,497   Lot Size: 25,043   Lot Acres: 0.57   County: Middlesex   
MAJESTIC LAKEFRONT ESTATE! Situated directly on the Mystic lake w/ expansive yard & breathtaking views offering the most gorgeous and serene setting in all of Winchester. This 21+ room custom home includes 7/8 bedrooms and 7.5 baths. The 2 room primary suite features 13' beamed ceiling w/ oversized ...
25 Ledgewood Rd

$5,800,000

25 Ledgewood Rd - Winchester, Massachusetts United States
Beds: 7   Baths: 4.50   FT2: 4,231   Lot Size: 117,000   Lot Acres: 2.69   County: Middlesex   
Opportunity abounds on a picturesque estate on a private road 7 miles from Boston and half mile from Winchester's center. Custom built home on 3 heavily wooded acres and meticulously maintained by one family. This unique offering is an opportunity to create a private family compound or develop the a...
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...