Symmes Corner Homes

/36
$999,000 Pending
- 4 Beds
- 2.5 Baths
- 2,335 Sq Ft
163 Main St, Winchester, MA 01890

Charming multi-level home in close proximity to Winchester Center, public transit, Lincoln Elementary, and McCall. The main level offers an open floor plan with beautiful hardwood floors, bay windows, a skylit eat-in kitchen, and abundant natural light. Perfect for entertaining, the living and dining rooms flow seamlessly to a spacious yard, relaxing patio, and mature gardens. The top floor

Andersen Group Realty Keller Williams Realty Boston Northwest

163 Main St, Winchester, MA 01890
/36
$5,000 per month
- 3 Beds
- 1.5 Baths
- 2,364 Sq Ft
- House for Rent
27 Ledyard Rd Unit SF, Winchester, MA 01890

SHORT TERM RENTAL - Oversized cape with hardwood floors throughout. Large front to back living room with working fireplace, built in bookcases and cabinets and lots of natural light. Formal dining room with built in china cabinet and French door leading to spacious 3-season porch. Kitchen has all new stainless steel appliances and access to side porch for relaxing with morning coffee or

Diane Plunkett Plunkett Properties

27 Ledyard Rd Unit SF, 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

/42
Est $1,233,096 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,341 Sq Ft
30 Symmes Rd, Winchester, MA 01890

30 Symmes Rd, Winchester, MA 01890

/32
$1,199,000 Pending
- 3 Beds
- 2 Baths
- 1,978 Sq Ft
48 Winford Way, Winchester, MA 01890

Welcome to 48 Winford Way, a three bed, two bath Cape on a lovely level lot with a family room addition and a garage. A perfect starter home or downsizer with a full bath on each floor. Living room with large windows and a fireplace, dining room with an impressive chandelier and built-in china cabinet, eat-in kitchen with quartz countertops, tiled backsplash, and pantry closet. First floor family

Rebecca Brennan Better Homes and Gardens Real Estate - The Shanahan Group

48 Winford Way, 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

/39
Est $2,456,530 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,880 Sq Ft
3 Bacon St, Winchester, MA 01890

3 Bacon St, Winchester, MA 01890

/2
$999,999 Pending
- 2 Beds
- 1 Bath
- 1,666 Sq Ft
26 North Gateway, Winchester, MA 01890

LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or restoration All offers must be on attached OFFER TO PURCHASE form and prior to entering property the attached " Hold Harmless" agreement must be signed. All offers must include the OTP, Proof of funds and/or preapproval and copy of

Robert Dell Homes Unlimited

26 North Gateway, Winchester, MA 01890
/42
$1,475,000 Sold May 29, 2025
- 3,067 Sq Ft
- $481/SF
- 9 Days On Market
- 3 Beds
- 4 Baths
- Built 1961
36 Winford Way, Medford, MA 02155

Move right into this charming home in the heart of West Medford! Nestled in a prime location near Middlesex Fells and Playstead Park, this beautifully renovated home offers a perfect blend of modern upgrades & classic charm. Thoughtfully updated in 2018, with an additional renovation in 2020 that includes a spacious basement office suite, playroom, and ample storage space, this home is designed

Andersen Group Realty Keller Williams Realty Boston Northwest

36 Winford Way, Medford, MA 02155

/35
Est $1,383,628 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,441 Sq Ft
155 Main St, Winchester, MA 01890

155 Main St, Winchester, MA 01890

/42
$2,499,000 Sold May 19, 2025
- 4,270 Sq Ft
- $585/SF
- 0 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2024
50 Winford Way, Winchester, MA 01890

Just completed!! 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 living room, complete w/ a cozy fireplace, open dining leads to sitting room & out to a deck

Kim Covino Compass

50 Winford Way, Winchester, MA 01890

/39
Est $1,770,831 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,705 Sq Ft
17 Stowell Rd, Winchester, MA 01890

17 Stowell Rd, Winchester, MA 01890

/38
$2,850,000 Sold May 07, 2025
- 5,044 Sq Ft
- $565/SF
- 5 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2025
22 Standish Ln, Winchester, MA 01890

This distinguished residence, built by premier local developer, represents the pinnacle of elegant living! Soaring ~9' ceilings & pristine hardwood floors set an impressive tone in this meticulously crafted new construction offering 4 levels of refined living space. The eye-catching foyer ushers guests into a realm of sophisticated design, where premium finishes & high-end appliances elevate

Michaela Mahtani Leading Edge Real Estate

22 Standish Ln, Winchester, MA 01890

/34
Est $1,595,508 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,251 Sq Ft
9 Everell Rd, Winchester, MA 01890

9 Everell Rd, Winchester, MA 01890

/42
$1,815,000 Sold Apr 15, 2025
- 2,810 Sq Ft
- $646/SF
- 8 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1935
29 Allen Rd, Winchester, MA 01890

This expanded 4-bedroom, 2.5-bath colonial is a true gem in the heart of a serene Lincoln School neighborhood. Impeccably maintained by the same family for over 40 years, this home has been thoughtfully updated w/ modern comforts, incl. AC throughout. The 1st floor features a remodeled kitchen w/ stainless steel appliances, granite countertops & breakfast bar, flowing into a spacious family room

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

29 Allen Rd, Winchester, MA 01890

/34
Est $1,637,112 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,314 Sq Ft
20 Stowell Rd, Winchester, MA 01890

20 Stowell Rd, Winchester, MA 01890

/38
$2,199,000 Sold Jan 27, 2025
- 3,431 Sq Ft
- $641/SF
- 21 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2024
11 Alden Ln, Winchester, MA 01890

This stunning new 4 Bed 3.5 BA home in Winchester’s sought-after East Side is a must see! The first floor boasts a dramatic contemporary design with high ceilings and designer finishes with oversized windows drawing attention to the setting w/ large rear yard & oversized deck, great for entertaining and family enjoyment.The open airy layout features a great entry w/ mud room, high-end kitchen

Kim Covino Compass

11 Alden Ln, Winchester, MA 01890

/39
Est $2,218,198 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,588 Sq Ft
445 Highland Ave, Winchester, MA 01890

445 Highland Ave, Winchester, MA 01890

/30
$2,050,000 Sold Jan 24, 2025
- 3,450 Sq Ft
- $594/SF
- 89 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1953
9 South Gateway, Winchester, MA 01890

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 with en suite bath and an office/additional bedroom. Completing the first floor are a half bath

Mark Donnellan Advisors Living - Winchester

9 South Gateway, Winchester, MA 01890

/40
Est $1,112,405 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,589 Sq Ft
437 Highland Ave, Winchester, MA 01890

437 Highland Ave, Winchester, MA 01890

/36
$1,875,000 Sold Dec 23, 2024
- 3,376 Sq Ft
- $555/SF
- 28 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1925
10 Marshall Rd, Winchester, MA 01890

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 bathed in natural light. The chefs kitchen boasts high end appliances and flows seamlessly into a

Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

10 Marshall Rd, Winchester, MA 01890

/31
Est $2,124,977 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,380 Sq Ft
1 Marshall Rd, Winchester, MA 01890

1 Marshall Rd, Winchester, MA 01890

/40
$1,115,000 Sold Dec 05, 2024
- 3,364 Sq Ft
- $331/SF
- 82 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1935
708 Winthrop St, Medford, MA 02155

On A Lovely Corner Lot In West Medford And Right On The Winchester Line Sits This Stunning Four Bedroom Home. As You Step Into This Stately Residence You Are Captured By The Elegant Staircase And Abounding Natural Sunlight This Exquisite Space Has To Offer. You Are Met With Charm & Character At Every Turn. The Attached Garage Offers Parking And Additional Living Space. You Have A Rare Opportunity

Corey Mastrocola Welcome Home Properties, Inc.

708 Winthrop St, Medford, MA 02155

/28
Est $1,510,732 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,912 Sq Ft
11 Marshall Rd, Winchester, MA 01890

11 Marshall Rd, Winchester, MA 01890

/42
$2,250,000 Sold Nov 20, 2024
- 4,026 Sq Ft
- $559/SF
- 10 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2006
18 Town Way, Winchester, MA 01890

Stunning 2006 Colonial, meticulously maintained & decorator-perfect. A grand entry with high ceilings and elegant archways welcomes you into this sun-filled home. The charming living & dining rooms showcase custom details throughout. The gourmet granite kitchen features an oversized island with seating for four, dining area & high-end amenities. A mudroom with ample storage is conveniently

Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

18 Town Way, Winchester, MA 01890

/42
Est $1,872,988 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,866 Sq Ft
16 Marshall Rd, Winchester, MA 01890

16 Marshall Rd, Winchester, MA 01890

/38
$1,485,000 Sold Oct 25, 2024
- 3,028 Sq Ft
- $490/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1953
10 Robinson Rd, Medford, MA 02155

A beautifully done, full renovation on the Winchester/Medford line. An open concept first floor with a tremendous Great Room that features high ceilings, gas fireplace and sliding doors leading to a composite deck. The kitchen features a waterfall island with seating for three to four. Brand new cabinets, countertops and stainless steel appliances make this kitchen stand out. A sizable mud

Dave Beeching Advisors Living - Arlington

10 Robinson Rd, Medford, MA 02155

/38
Est $1,247,516 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 2,072 Sq Ft
428 Highland Ave, Winchester, MA 01890

428 Highland Ave, Winchester, MA 01890

/28
$2,357,000 Sold Oct 18, 2024
- 3,679 Sq Ft
- $641/SF
- 3 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2017
57 Winford Way, Winchester, MA 01890

Offer accepted,Open House cancel!Stunning custom-built colonial home from 2017! This property boasts an open floor plan with soaring ceilings, abundant natural light, and hardwood floors paired with recessed lighting throughout. The first floor features a spacious layout centered around a show-stopping kitchen, crafted by Bespoke of Winchester, equipped with BlueStar/Sub-Zero stainless steel

Dan Li Keller Williams Realty

57 Winford Way, Winchester, MA 01890

/33
Est $1,641,693 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,835 Sq Ft
4 Sargent Rd, Winchester, MA 01890

4 Sargent Rd, Winchester, MA 01890

/24
$1,070,000 Sold Sep 27, 2024
- 3,417 Sq Ft
- $313/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1960
21 Winford Way, Medford, MA 02155

REMARKABLE SERENITY is found in renovated Custom Built Ranch with over 3400sf of finished living space on two levels in desirable Colonial Village neighborhood on the Winchester line. Luxury upgrades include a NEW custom chef's kitchen, NEW custom tile bathroom, central air, new windows & new heating system. Mid-century home seekers will love the open, flowing space of this wide home. Large

Kelly Catallo Realty ONE Group Cosmopolitan

21 Winford Way, Medford, MA 02155

/34
Est $1,665,514 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,810 Sq Ft
26 Sargent Rd, Winchester, MA 01890

26 Sargent Rd, Winchester, MA 01890

/38
$1,380,000 Sold Sep 04, 2024
- 2,364 Sq Ft
- $584/SF
- 6 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1940
27 Ledyard Rd, Winchester, MA 01890

Discover the endless potential of this charming 3-bedroom, 1.5-bathroom home, perfectly positioned on a sought-after Winchester lot with excellent frontage and a generously sized yard. The finished lower level features a convenient walkout to a private backyard, creating additional living space and ample opportunities for outdoor enjoyment. This property presents a fantastic opportunity for a

Andersen Group Realty Keller Williams Realty Boston Northwest

27 Ledyard Rd, Winchester, MA 01890

/38
Est $1,404,997 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,664 Sq Ft
7 Perkins Rd, Winchester, MA 01890

7 Perkins Rd, Winchester, MA 01890

/3
$1,610,000 Sold Aug 15, 2024
- 2,212 Sq Ft
- $728/SF
- 6 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1920
12 Everell Rd, Winchester, MA 01890

Nestled in sought-after Symmes neighborhood this timeless home was renovated in 2019-2020 providing a refreshed layout and modern amenities while keeping the home's original charm. The gracious foyer leads to a front to back living room with fireplace, window seat and French doors opening to a new family room with a walkout to the patio and backyard. The dining room with bow window flows into the

Quinn Simpson Compass

12 Everell Rd, Winchester, MA 01890

/37
Est $1,611,846 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,623 Sq Ft
28 Pierrepont Rd, Winchester, MA 01890

28 Pierrepont Rd, Winchester, MA 01890

/35
$1,199,000 Sold Aug 06, 2024
- 2,332 Sq Ft
- $514/SF
- 11 Days On Market
- 5 Beds
- 1.5 Baths
- Built 1880
9 Bacon St, Winchester, MA 01890

Introducing this updated townhouse condo, with a single-family feel, in a top location. It has all the amenities that buyers desire, plus energy-efficient features such as solar panels, 2023 high-efficiency heating & A/C system, EV charger, and newer windows. Enjoy morning coffee on the spacious front porch, and gardening or hosting friends in the private backyard. Large sunlit rooms welcome you

Elena Langlois Compass

9 Bacon St, Winchester, MA 01890

/42
Est $3,191,363 Not Listed For Sale
- 6 Beds
- 5.5 Baths
- 5,970 Sq Ft
41 Franklin Rd, Winchester, MA 01890

41 Franklin Rd, Winchester, MA 01890

/17
$935,000 Sold Aug 05, 2024
- 1,946 Sq Ft
- $480/SF
- 10 Days On Market
- 3 Beds
- 1 Bath
- Built 1946
53 Winford Way, Winchester, MA 01890

Attention Investors and Visionaries! Discover the potential in this charming 3-bedroom, 1-bathroom property. Located in a sought-after Winchester lot, this home is surrounded by premier schools, convenient amenities and the Middlesex Fells Conservation area, making it a prime location for your next project. The existing structure offers a fantastic opportunity for a full renovation or teardown,

Andersen Group Realty Keller Williams Realty Boston Northwest

53 Winford Way, Winchester, MA 01890

/39
Est $1,720,118 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,688 Sq Ft
10 Clearwater Rd, Winchester, MA 01890

10 Clearwater Rd, Winchester, MA 01890

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