Middlesex, MA Homes

/42
$2,349,900 Open Sat 12PM - 1:30PM
- 5 Beds
- 5 Baths
- 3,940 Sq Ft
17 Wagon Wheel Rd, Winchester, MA 01890

Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends

Yifei Wang Dreamega International Realty LLC

17 Wagon Wheel Rd, Winchester, MA 01890
/36
$11,000 per month
- 6 Beds
- 4.5 Baths
- 6,500 Sq Ft
- House for Rent
52 N Border Rd, Winchester, MA 01890

Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home has 6 bedrooms, and 5 bathrooms. The stunning foyer welcomes you to the sprawling first floor. The custom work throughout each sun filled room is exquisite. Gourmet kitchen with top of the line appliances. Generous sized rooms to entertain guests. A private home office with built

Julia Marino Archambault Real Estate

52 N Border Rd, Winchester, MA 01890
/30
$1,330,000 Sold Jun 27, 2025
- 1,629 Sq Ft
- $816/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1941
17 Mason St, Winchester, MA 01890

Nestled on a quiet, tree-lined street near Winchester’s vibrant town center, this delightful storybook colonial offers charm, character, and exceptional potential. Beautifully sited on a 10,000+ sq ft wooded lot, this three-bedroom, two-bath home invites your vision to blend timeless architectural details with thoughtful updates. A fireplaced front-to-back living room flows seamlessly into a

Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

17 Mason St, Winchester, MA 01890

/36
Est $2,291,023 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,257 Sq Ft
9 Amberwood Dr, Winchester, MA 01890

9 Amberwood Dr, Winchester, MA 01890

/39
$3,249,000 Open Sat 1:30PM - 2:30PM
- 6 Beds
- 6.5 Baths
- 6,028 Sq Ft
44 Cabot St, Winchester, MA 01890

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 ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

Andersen Group Realty Keller Williams Realty Boston Northwest

44 Cabot St, Winchester, MA 01890
/2
$4,800 per month
- 3 Beds
- 2.5 Baths
- 2,339 Sq Ft
- House for Rent
12 Trinity Rd, Winchester, MA 01890

Don't miss this opportunity to lease a beautifully maintained multi-level single-family home, ideally situated on a quiet, private dead-end street. Offering over 2,300 square feet of living space, this home features central A/C, gleaming hardwood floors throughout, a generous kitchen with an open-concept dining area—perfect for everyday living and entertaining. Step outside to enjoy the large,

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

12 Trinity Rd, Winchester, MA 01890
/35
$1,100,000 Sold Jun 27, 2025
- 3,157 Sq Ft
- $348/SF
- 20 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1866
63 Church St, Winchester, MA 01890

Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

Nancy McLaughlin Redfin Corp.

63 Church St, Winchester, MA 01890

/38
Est $1,821,663 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,218 Sq Ft
27 Amberwood Dr, Winchester, MA 01890

27 Amberwood Dr, Winchester, MA 01890

/33
$3,475,000 Open Sat 1PM - 2:30PM
- 5 Beds
- 3.5 Baths
- 5,632 Sq Ft
80 Arlington St, Winchester, MA 01890

With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement, and the chance to build instant equity through strategic upgrades. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved home offers 11 rooms, 5 bedrooms and 3.5 baths. Enjoy views from the sun-splashed eat-in

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

80 Arlington St, Winchester, MA 01890
/25
$715,000 Sold Jun 27, 2025
- 1,539 Sq Ft
- $465/SF
- 33 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1999
7 Conant Rd Unit 37, Winchester, MA 01890

Welcome to this beautifully updated corner unit townhouse-style condo, offering ample-sized rooms, abundant natural light, & hardwood floors throughout! The layout includes 5 well proportioned rooms. Kitchen, living room w/gas fireplace w/marble surround, dining room & 2.5 bathrooms, creating a comfortable & functional living space. Both bedrooms are en-suite, providing privacy & convenience,

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

7 Conant Rd Unit 37, Winchester, MA 01890

/42
Est $2,250,505 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,124 Sq Ft
9 Buckman Dr, Winchester, MA 01890

9 Buckman Dr, Winchester, MA 01890

/42
$2,975,000
- 6 Beds
- 3.5 Baths
- 5,238 Sq Ft
54 Wedgemere Ave, Winchester, MA 01890

Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive back yard featuring

Kim Covino Compass

54 Wedgemere Ave, Winchester, MA 01890
/17
$299,000 Sold Jun 27, 2025
- 450 Sq Ft
- $664/SF
- 10 Days On Market
- 1 Bed
- 1 Bath
- Built 1966
200 Swanton St Unit T4, Winchester, MA 01890

Immaculate, recently renovated Jumbo Studio Condominium with a private/direct-entry terrace level. This unit is spacious and bright, featuring a slider that leads to a private patio overlooking scenic duck ponds and lush landscaping. The large eat-in kitchen features white cabinets, with a white tiled backsplash and granite countertops. The bathroom was recently updated with new fixtures,

Michael Masci North Atlantic Realty Group

200 Swanton St Unit T4, Winchester, MA 01890

/42
Est $1,929,177 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
3 Bigelow Ave, Winchester, MA 01890

3 Bigelow Ave, Winchester, MA 01890

/37
$1,299,000
- 3 Beds
- 2 Baths
- 1,884 Sq Ft
147 Highland Ave, Winchester, MA 01890

Call for a private showing anytime! Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you w/ a spacious living room w fplc that flows seamlessly into a sun-drenched updated

Kim Covino Compass

147 Highland Ave, Winchester, MA 01890
/42
$1,350,000 Sold Jun 27, 2025
- 2,141 Sq Ft
- $631/SF
- 40 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1880
117 Mount Vernon St, Winchester, MA 01890

Available for the first time in over four decades and nestled just footsteps from Winchester Center, welcome to 117 Mount Vernon Street! As you enter, you are greeted by tall ceilings adorned with beautiful molding and a flood of natural light that fills the space with warmth and tranquility. The home offers three spacious bedrooms, including a flexible primary suite that boasts an adjoining

Philip Vita Compass

117 Mount Vernon St, Winchester, MA 01890

/42
Est $2,109,436 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,256 Sq Ft
15 Pilgrim Dr, Winchester, MA 01890

15 Pilgrim Dr, Winchester, MA 01890

/34
$1,399,900 Open Sat 12PM - 1PM
- 5 Beds
- 2 Baths
- 3,033 Sq Ft
7 Thornberry Rd, Winchester, MA 01890

Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighborhood. 15 minutes to Downtown Boston. 5 bedrooms, 2 full baths, Living, Dining PLUS family room & 2nd finished room ( play or office) ground level room heated & A/C walk access to outdoor deck & fire pit. Open concept kitchen area. Hardwood floors, 2 fireplace, 2 garage space,

salim chowdhury TAJ Mahal Realty LLC

7 Thornberry Rd, Winchester, MA 01890
/9
$2,899,000 Sold Jun 27, 2025
- 5,658 Sq Ft
- $512/SF
- 25 Days On Market
- 6 Beds
- 7.5 Baths
- Built 2025
5 Clearwater Rd, Winchester, MA 01890

Welcome to a rare opportunity to select the final finishes in your dream home right within Winchester’s most coveted neighborhoods. 5 Clearwater presents a luxurious canvas for your vision, offering 6 bedrooms, 7.5 baths, and 5,658 sq. ft. of meticulously planned living space. The spectacular floor plan seamlessly combines modern sophistication with timeless elegance, offering the perfect

Monte Marrocco Coldwell Banker Realty - Lexington

5 Clearwater Rd, Winchester, MA 01890

/40
Est $1,459,220 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,142 Sq Ft
16 Johnson Rd, Winchester, MA 01890

16 Johnson Rd, Winchester, MA 01890

/42
$3,799,900
- 7 Beds
- 7.5 Baths
- 7,429 Sq Ft
11 Viking Rd, Winchester, MA 01890

Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

The McLaren D'Agostino Team Compass

11 Viking Rd, Winchester, MA 01890
/22
$4,200,000 Sold Jun 26, 2025
- 5,208 Sq Ft
- $806/SF
- 4 Days On Market
- 6 Beds
- 5.5 Baths
- Built 2025
3 Foxcroft Rd, Winchester, MA 01890

Nearing completion! Welcome to this exquisite 6-bedroom, 5-1/2 bath residence nestled in one of Winchesters most prestigious neighborhoods. This completely rebuilt, expanded & tastefully renovated home is one of a kind, offering a perfect blend of elegance & modern sophistication for a lifestyle of luxury & comfort. Step inside to discover a beautifully designed interior that exudes charm & style

Kim Covino Compass

3 Foxcroft Rd, Winchester, MA 01890

/33
Est $2,048,669 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,603 Sq Ft
8 Olde Lyme Rd, Winchester, MA 01890

8 Olde Lyme Rd, Winchester, MA 01890

/34
$3,598,000
- 6 Beds
- 7 Baths
- 8,866 Sq Ft
20 Amberwood Dr, Winchester, MA 01890

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 appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

Dan Li Keller Williams Realty

20 Amberwood Dr, Winchester, MA 01890
/19
$3,450,000 Sold Jun 26, 2025
- 5,500 Sq Ft
- $627/SF
- 54 Days On Market
- 6 Beds
- 5 Baths
- Built 2025
2 Chestnut St, Winchester, MA 01890

Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering

Mark Donnellan Advisors Living - Winchester

2 Chestnut St, Winchester, MA 01890

/42
Est $1,804,317 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,315 Sq Ft
8 Hawthorne Rd, Winchester, MA 01890

8 Hawthorne Rd, Winchester, MA 01890

/42
$3,699,000
- 7 Beds
- 7.5 Baths
- 7,982 Sq Ft
54 Johnson Rd, Winchester, MA 01890

This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master

Kim Covino Compass

54 Johnson Rd, Winchester, MA 01890
/39
$1,425,000 Sold Jun 25, 2025
- 2,496 Sq Ft
- $571/SF
- 6 Days On Market
- 4 Beds
- 3 Baths
- Built 1957
9 Thornberry Rd, Winchester, MA 01890

Nestled on a picturesque lot with lush landscaping and mature trees, 9 Thornberry Road offers a perfect blend of natural beauty and refined living. Sunlight pours into this thoughtfully designed home, featuring an open-concept layout ideal for comfortable living and entertaining. The main level includes a welcoming fireplace, hardwood floors, large living room, dining area, and an updated kitchen

Louise Coakley Better Homes and Gardens Real Estate - The Shanahan Group

9 Thornberry Rd, Winchester, MA 01890

/42
Est $2,403,779 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,473 Sq Ft
239 Ridge St, Winchester, MA 01890

239 Ridge St, Winchester, MA 01890

/2
$2,550,000
- 5 Beds
- 4.5 Baths
- 3,800 Sq Ft
19 Laurel Hill Ln, Winchester, MA 01890

Nestled on a quiet street in one of Winchester’s most coveted neighborhoods, 19 Laurel Hill Lane will offer refined living just minutes from Boston and top-rated schools. This latest Mark Stephen Development project will feature 4 bedrooms and 4.5 bathrooms, including a flexible first-floor suite perfect for a guest room or study. The heart of the home will be a spacious kitchen flowing into a

Mark Donnellan Advisors Living - Winchester

19 Laurel Hill Ln, Winchester, MA 01890
/34
$2,450,000 Sold Jun 24, 2025
- 5,218 Sq Ft
- $470/SF
- 19 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1999
31 Lawson Rd, Winchester, MA 01890

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 moldings along w/ a stunning kitchen that naturally flows into the living/dining area & family room,

Monte Marrocco Coldwell Banker Realty - Lexington

31 Lawson Rd, Winchester, MA 01890

/26
Est $1,172,349 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,826 Sq Ft
75 Dunster Ln, Winchester, MA 01890

75 Dunster Ln, Winchester, MA 01890

/41
$3,999,000 Open Sat 12PM - 1:30PM
- 6 Beds
- 4.5 Baths
- 6,367 Sq Ft
40 Foxcroft Rd, Winchester, MA 01890

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 large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

Monte Marrocco Coldwell Banker Realty - Lexington

40 Foxcroft Rd, Winchester, MA 01890
/39
$904,000 Sold Jun 23, 2025
- 1,528 Sq Ft
- $592/SF
- 5 Days On Market
- 2 Beds
- 1 Bath
- Built 1954
703 Washington St, Winchester, MA 01890

Delightful ranch, well maintained and located conveniently near the major routes. The kitchen is spacious and opens to the comfortable dining area with large built in hutch. It has been updated and features a tile backsplash, stainless steel appliances and recessed lighting. The living room is fireplaced and is nicely appointed with hardwood floors. Easy one level living with two first floor

Michael Barrett Barrett, Chris. J., REALTORS®

703 Washington St, Winchester, MA 01890

/42
Est $3,244,540 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 5,676 Sq Ft
222 High St, Winchester, MA 01890

222 High St, Winchester, MA 01890

/5
$2,899,000 New Construction
- 5 Beds
- 5.5 Baths
- 4,627 Sq Ft
11 Taft Dr, Winchester, MA 01890

Luxury and location converge in this stunning 5-bedroom, 5.5-bathroom home nestled in one of Winchester’s most coveted Westside neighborhoods. Beautifully rehabbed and thoughtfully expanded, this turnkey residence offers over 4,600 sq. ft. of refined living space, just steps from Ambrose School, one block from the Alewife bus stop, & a short ½-mile stroll to the commuter rail. Every detail has

Monte Marrocco Coldwell Banker Realty - Lexington

11 Taft Dr, Winchester, MA 01890
/16
$650,000 Sold Jun 23, 2025
- 1,007 Sq Ft
- $645/SF
- 7 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1900
27 Elm St, Winchester, MA 01890

Attention investors, contractors, and handy owner occupants looking to build sweat equity! This single family home is in need of major renovation and is the perfect opportunity for a contractor to make a profitable investment or an owner occupant to unlock instant sweat equity. Dream location just around the corner to Winchester Center's shops and restaurants, less than 0.3 miles to the top rated

Shao Realty Group RE/MAX Executive Realty

27 Elm St, Winchester, MA 01890

/27
Est $1,087,230 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,859 Sq Ft
46 Edward Dr, Winchester, MA 01890

46 Edward Dr, Winchester, MA 01890

/38
$2,499,000 Open Sun 12:30PM - 1:30PM
- 7 Beds
- 5.5 Baths
- 4,829 Sq Ft
89 Wildwood St, Winchester, MA 01890

Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

Monte Marrocco Coldwell Banker Realty - Lexington

89 Wildwood St, Winchester, MA 01890
/42
$1,890,000 Sold Jun 23, 2025
- 3,148 Sq Ft
- $600/SF
- 5 Days On Market
- 4 Beds
- 5 Baths
- Built 1993
15 Kendall St, Winchester, MA 01890

Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lot with slider to patio & expansive rear yard, this captivating home has an absolutely beautiful setting w/natural stone walls, raised planting beds w/flowering trees, perennials & a spectacular rose garden! Enjoy the lovely farmers porch & desirable layout w/sun-drenched kitchen

Kim Covino Compass

15 Kendall St, Winchester, MA 01890

Showing Results 121 - 160, Page 4 of 18

Massachusetts Middlesex County Winchester

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