Middlesex, MA Homes

/42
Est $1,063,236 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,738 Sq Ft
41 Edward Dr, Winchester, MA 01890

41 Edward Dr, Winchester, MA 01890

/42
$1,688,888 Pending
- 4 Beds
- 2 Baths
- 3,838 Sq Ft
10 Blossom Hill Rd, Winchester, MA 01890

Welcome to 10 Blossom Hill Road. Tucked away in a cozy and desirable West Side Winchester neighborhood, this enchanting storybook home is full of warmth, charm, and heart. Here you will find a lovingly cared-for 4-bedroom home with a guest or in-law suite offering wonderful flexibility to suit your needs. Inside, you’ll find light-filled spaces, thoughtful updates, and timeless character that

Stephen DeConto Cameron Real Estate Group

10 Blossom Hill Rd, Winchester, MA 01890
/42
$2,950,000 Sold Jun 23, 2025
- 4,279 Sq Ft
- $689/SF
- 23 Days On Market
- 5 Beds
- 5 Baths
- Built 1914
51 Wedgemere Ave, Winchester, MA 01890

Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-placed foyer welcomes you into the home, enhanced by a new chefs kitchen w/ 10' island, custom cabinetry, & adjacent family room overlooking yard. With four floors of beautifully finished spaces, there's room for every lifestyle need. Enjoy

Kim Covino Compass

51 Wedgemere Ave, Winchester, MA 01890

/38
Est $1,074,604 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,754 Sq Ft
34 Edward Dr, Winchester, MA 01890

34 Edward Dr, Winchester, MA 01890

/27
$625,000 Pending
- 2 Beds
- 1.5 Baths
- 1,554 Sq Ft
50 Lake St Unit B, Winchester, MA 01890

Buyer's cold feet gives you a second chance to own a well-maintained 2-bed, 1.5-bath townhouse-style condo offering scenic views of Wedge Pond. The main level features hardwood floors, a spacious living area, half bath, and a kitchen with granite countertops and stainless steel appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides versatile space for a family

Andersen Group Realty Keller Williams Realty Boston Northwest

50 Lake St Unit B, Winchester, MA 01890
/15
$930,000 Sold Jun 20, 2025
- 2,333 Sq Ft
- $399/SF
- 25 Days On Market
- 4 Beds
- 3 Baths
- Built 1959
48 Tremont St, Winchester, MA 01890

Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living

Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

48 Tremont St, Winchester, MA 01890

/34
Est $1,081,531 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,859 Sq Ft
36 Edward Dr, Winchester, MA 01890

36 Edward Dr, Winchester, MA 01890

/33
$1,250,000 Pending
- 4 Beds
- 1.5 Baths
- 1,900 Sq Ft
162 Forest St, Winchester, MA 01890

Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining

Paul Cirignano The Synergy Group

162 Forest St, Winchester, MA 01890
/42
$1,187,000 Sold Jun 18, 2025
- 1,906 Sq Ft
- $623/SF
- 12 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1926
44 Forest St, Winchester, MA 01890

This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living

Kim Covino Compass

44 Forest St, Winchester, MA 01890

/37
Est $873,624 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,920 Sq Ft
47 Edward Dr, Winchester, MA 01890

47 Edward Dr, Winchester, MA 01890

/39
$1,525,000 Pending
- 3 Beds
- 2.5 Baths
- 2,850 Sq Ft
178 Mystic Valley Pkwy, Winchester, MA 01890

This carefully crafted Colonial, custom-built by Andrew Pywell, combines solid construction with a bounty of special touches and timeless charm. Delight in sun-splashed living spaces, gleaming hardwood floors, crown moldings, and a layout that balances an open flow, defined spaces and beautifully proportioned rooms across 2,850 square feet. The gracious formal living room, dining room, and

Katherine Waters-Clark Compass

178 Mystic Valley Pkwy, Winchester, MA 01890
/35
$1,750,000 Sold Jun 17, 2025
- 2,597 Sq Ft
- $674/SF
- 2 Days On Market
- 5 Beds
- 2.5 Baths
- Built 1925
18 Englewood Rd, Winchester, MA 01890

OFFER ACCEPTED - Open Houses CANCELED This stunning, sun-filled home welcomes you with a front porch facing southwest for sunset views! Move right in and enjoy so many updates - new windows, new kitchen, new shared bath, new heating and cooling systems, new exercise/mudroom, new landscaping and so much more!!! With fabulous detail and a focus on energy efficiency, this home will win your heart

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

18 Englewood Rd, Winchester, MA 01890

/31
Est $1,877,678 Not Listed For Sale
- 4 Beds
- 4 Baths
- 4,028 Sq Ft
56 Ridge St, Winchester, MA 01890

56 Ridge St, Winchester, MA 01890

/31
$1,500,000 Pending
- 4 Beds
- 2.5 Baths
- 2,506 Sq Ft
6 Highland Ave, Winchester, MA 01890

4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is

Peter Rooney Compass

6 Highland Ave, Winchester, MA 01890
/42
$2,350,000 Sold Jun 16, 2025
- 4,212 Sq Ft
- $558/SF
- 15 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1880
19 Yale St, Winchester, MA 01890

Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom

Nancy Pallotta Advisors Living - Winchester

19 Yale St, Winchester, MA 01890

/23
Est $989,245 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,548 Sq Ft
12 James St, Winchester, MA 01890

12 James St, Winchester, MA 01890

/40
$1,075,000 Pending
- 3 Beds
- 1.5 Baths
- 1,414 Sq Ft
5 Cutting St, Winchester, MA 01890

OFFER DEADLINE TUE JULY 29th 5:00PM | Exceedingly charming + in-town location to be envied. Shops, schools + both MBTA stations at your fingertips. Step up onto your porch, pass the bench swing you’re yet to install; entering into the inviting foyer w/ original stairs preserved & tall ceilings. The main level is sophisticated & functional. A front facing dining room w/ plantation shutters +

Oliver Koester Compass

5 Cutting St, Winchester, MA 01890
/36
$749,900 Sold Jun 13, 2025
- 1,545 Sq Ft
- $485/SF
- 8 Days On Market
- 2 Beds
- 2 Baths
- Built 1999
7 Conant Rd Unit 34, Winchester, MA 01890

Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of

Melanie Lentini Leading Edge Real Estate

7 Conant Rd Unit 34, Winchester, MA 01890

/38
Est $1,269,617 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,827 Sq Ft
10 James St, Winchester, MA 01890

10 James St, Winchester, MA 01890

/40
$1,199,000 Pending
- 4 Beds
- 2.5 Baths
- 2,566 Sq Ft
70 Woodside Rd, Winchester, MA 01890

Have you ever dreamed of owning a house with a white picket fence? Here it is! Eight rooms, four bedrooms, 2.5 baths. Corner lot with backyard patio, shed and one car garage. The large living room with many windows and a fireplace opens to the dining room. French doors from the dining room lead to a room that can be used as a family room, play room for the kids, or another bedroom. The

Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

70 Woodside Rd, Winchester, MA 01890
/40
$3,025,000 Sold Jun 13, 2025
- 5,198 Sq Ft
- $582/SF
- 50 Days On Market
- 6 Beds
- 5 Baths
- Built 1910
21 Sheffield W, Winchester, MA 01890

Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

Kim Covino Compass

21 Sheffield W, Winchester, MA 01890

/42
Est $908,705 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,890 Sq Ft
25 Henry St, Winchester, MA 01890

25 Henry St, Winchester, MA 01890

/28
$1,765,300 Pending
- 3 Beds
- 2.5 Baths
- 3,002 Sq Ft
44 Amberwood Dr, Winchester, MA 01890

Picture your family in this unique colonial, just one street over from the amazing Vinson-Owen school! 2 sizeable, private yards with lush grass, flagstone patios and even a dining room deck! Lots of upgrades include a new family room with brick wall, computer cubby, cathedral ceiling & mahogany deck. There's 3 bedrooms to start, including a spacious Primary Suite with walk-in closet, large

Hudson Santana Keller Williams Realty Boston Northwest

44 Amberwood Dr, Winchester, MA 01890
/37
$1,535,000 Sold Jun 12, 2025
- 2,525 Sq Ft
- $608/SF
- 5 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1965
65 Thornberry Rd, Winchester, MA 01890

Beautifully updated 4-bed, 2.5-bath ranch on a landscaped half-acre lot with attached 2-car garage. Enjoy single-level living with an open floor plan, cathedral-ceiling kitchen with granite counters, island seating, and stainless appliances. Living and dining areas flow seamlessly; cozy family room with fireplace. Sunroom with wall of windows overlooks the expansive backyard. Primary suite

Hongmei Wang HMW Real Estate, LLC

65 Thornberry Rd, Winchester, MA 01890

/26
Est $841,280 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,279 Sq Ft
28 Henry St, Winchester, MA 01890

28 Henry St, Winchester, MA 01890

/16
$858,000 Pending
- 3 Beds
- 2.5 Baths
- 1,825 Sq Ft
171 Swanton St Unit 64, Winchester, MA 01890

Turn-key end-unit townhouse in Winchester’s sought-after community! Sun-filled open layout with wood floors, quartz kitchen countertops, modern cabinets, and stainless appliances. Two renovated baths feature designer tile and sleek fixtures. Enjoy high-efficiency HVAC with Energy Recovery Ventilation, radiant-heated floors, water filtration, and in-unit laundry. Step outside to a private patio

Xiaoli Xie JKS Boston Realty LLC

171 Swanton St Unit 64, Winchester, MA 01890
/40
$1,510,000 Sold Jun 09, 2025
- 3,406 Sq Ft
- $443/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1959
7 Hutchinson Rd, Winchester, MA 01890

A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l

Kim Covino Compass

7 Hutchinson Rd, Winchester, MA 01890

/20
Est $1,093,815 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,432 Sq Ft
14 Locke St, Winchester, MA 01890

14 Locke St, Winchester, MA 01890

/35
$699,900 Pending
- 2 Beds
- 1.5 Baths
- 1,300 Sq Ft
29 Vine St Unit 7, Winchester, MA 01890

Immerse yourself in the vibrant heart of Winchester Center with this exquisite 2-bedroom, 1.5-bathroom condominium! Step into the open-concept living and dining area, where a modern touch meets downtown flair. A rare freestanding wood-burning fireplace accentuates the space, offering warmth and a touch of classic charm. Delight in the recently renovated kitchen, designed for both style and

Philip Vita Compass

29 Vine St Unit 7, Winchester, MA 01890
/23
$1,182,000 Sold Jun 09, 2025
- 1,520 Sq Ft
- $778/SF
- 24 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1929
10 Allen Rd, Winchester, MA 01890

Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the

Sally Baldwin Coldwell Banker Realty - Lexington

10 Allen Rd, Winchester, MA 01890

/17
Est $2,127,540 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,578 Sq Ft
21 Dunster Ln, Winchester, MA 01890

21 Dunster Ln, Winchester, MA 01890

/40
$3,399,000 Pending
- 5 Beds
- 4.5 Baths
- 5,250 Sq Ft
4 Norwood St, Winchester, MA 01890

Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor

Mark Donnellan Advisors Living - Winchester

4 Norwood St, Winchester, MA 01890
/41
$2,850,000 Sold Jun 09, 2025
- 4,325 Sq Ft
- $659/SF
- 8 Days On Market
- 4 Beds
- 4 Baths
- Built 1953
45 Brooks St, Winchester, MA 01890

Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4BD 4 BA home offering a classic exterior with a stunning "must see" interior; featuring formal spaces great for entertaining blended w/casual living areas both inside & out w/ walls of floor to ceiling windows capturing the elements of

Kim Covino Compass

45 Brooks St, Winchester, MA 01890

/38
Est $1,247,705 Not Listed For Sale
- 5 Beds
- 1.5 Baths
- 2,383 Sq Ft
18 Ridge St, Winchester, MA 01890

18 Ridge St, Winchester, MA 01890

/6
$1,100,000 Pending
- 4 Beds
- 2 Baths
- 2,060 Sq Ft
540-542 Washington St, Winchester, MA 01890

Great Two-Family Home in a Desirable Location! This well-maintained two-family property features a total of 4 bedrooms and 2 full bathrooms, with beautiful hardwood floors throughout. Each unit offers spacious living areas filled with natural light. The basement includes laundry hookups with washer and dryer included. Enjoy the convenience of 6 off-street parking spaces—a rare find! Situated just

Wei Wang WW Real Estate LLC

540-542 Washington St, Winchester, MA 01890
/19
$690,000 Sold Jun 06, 2025
- 1,634 Sq Ft
- $422/SF
- 20 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1999
7 Conant Rd Unit 60, Winchester, MA 01890

OPEN HOUSE Sunday, May 18: 1-3:30PM. Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and

Irene Novia Loka Matahari Real Estate LLC

7 Conant Rd Unit 60, Winchester, MA 01890

/41
Est $2,109,831 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,730 Sq Ft
2 Tanglewood Ln, Winchester, MA 01890

2 Tanglewood Ln, Winchester, MA 01890

/42
$3,249,000 Pending
- 6 Beds
- 5 Baths
- 7,005 Sq Ft
18 Wickham Rd, Winchester, MA 01890

Just 3 years young, this pristine masterpiece is nestled in a sought-after neighborhood just footsteps from the Town Forest and within walking distance of Wedgemere Station and Downtown Winchester. Step into the first floor and be captivated by the soaring ceilings. The showstopping kitchen features a SubZero fridge, a Bertazzoni 48” range, and a full eat-in area. This space flows into the family

Philip Vita Compass

18 Wickham Rd, Winchester, MA 01890
/33
$1,650,000 Sold Jun 06, 2025
- 3,338 Sq Ft
- $494/SF
- 7 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1980
34 Coolidge Rd, Winchester, MA 01890

A chance to update and create your personal design that is located in Winchester's sought after Vinson Owen School district. Set on a impressive massive manicured corner lot that has been maintained since it has been custom built by its original owners. Scenic backyard with a patio off the kitchen that spills on a large private backyard that has an inground pool. Set the stage with a large foyer

Pauline Marino Coldwell Banker Realty - Lexington

34 Coolidge Rd, Winchester, MA 01890

/22
Est $2,737,302 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,333 Sq Ft
18 Olde Village Dr, Winchester, MA 01890

18 Olde Village Dr, Winchester, MA 01890

Showing Results 161 - 200, Page 5 of 18

Massachusetts Middlesex County Winchester

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