West Side Homes

/38
$1,650,000 Pending
- 4 Beds
- 3.5 Baths
- 2,755 Sq Ft
5 Thornton Rd, Winchester, MA 01890

This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

5 Thornton Rd, Winchester, MA 01890
/40
$1,877,000 Sold Jun 30, 2025
- 2,813 Sq Ft
- $667/SF
- 26 Days On Market
- 3 Beds
- 2 Baths
- Built 1930
20 Seneca Rd, Winchester, MA 01890

Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

20 Seneca Rd, Winchester, MA 01890

/40
Est $2,195,106 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,344 Sq Ft
3 Berkshire Dr, Winchester, MA 01890

3 Berkshire 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
/41
$1,500,000 Sold Jun 30, 2025
- 4,214 Sq Ft
- $356/SF
- 4 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1995
7 Wainwright Rd Unit 117, Winchester, MA 01890

Welcome to the largest unit at The Ledges! This stunning F unit boasts soaring ceilings and an expansive open floor plan, perfect for entertaining or relaxing in style. Custom decorated in a perfect, custom Palm Beach vibe, but easy to change if you don't love it. Sunlight floods the large formal living room, with an attached deck, bifurcated by a gas fireplace that leads to the dining room. A

Nancy Pallotta Advisors Living - Winchester

7 Wainwright Rd Unit 117, Winchester, MA 01890

/11
Est $1,321,101 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,218 Sq Ft
233 High St, Winchester, MA 01890

233 High 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
/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

/40
Est $1,320,746 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,430 Sq Ft
134 Johnson Rd, Winchester, MA 01890

134 Johnson Rd, Winchester, MA 01890

/33
$1,769,000 Pending
- 5 Beds
- 3.5 Baths
- 3,478 Sq Ft
10 Olde Lyme Rd, Winchester, MA 01890

Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state.

Darryl Brian RE/MAX Bentley's

10 Olde Lyme Rd, 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

/42
Est $2,008,563 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,361 Sq Ft
7 Wainwright Rd Unit 98, Winchester, MA 01890

7 Wainwright Rd Unit 98, Winchester, MA 01890

/40
$1,499,000 Pending
- 3 Beds
- 1.5 Baths
- 2,351 Sq Ft
19 Cox Rd, Winchester, MA 01890

Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w

Kim Covino Compass

19 Cox Rd, 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

/36
Est $1,361,804 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,823 Sq Ft
7 Wainwright Rd Unit 88, Winchester, MA 01890

7 Wainwright Rd Unit 88, 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

/33
Est $1,657,038 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,327 Sq Ft
7 Wainwright Rd Unit 72, Winchester, MA 01890

7 Wainwright Rd Unit 72, Winchester, MA 01890

/26
$1,140,000 Sold Jun 03, 2025
- 1,646 Sq Ft
- $693/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 1955
7 Indian Hill Rd, Winchester, MA 01890

This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood floors, a gas fireplace, and arched doorways add character and warmth to the space. The well-equipped kitchen features granite countertops, glass-front cabinetry and access to a side deck for al fresco dining. Three bright bedrooms and a

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

7 Indian Hill Rd, Winchester, MA 01890

/38
Est $1,572,062 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,368 Sq Ft
7 Wainwright Rd Unit 39, Winchester, MA 01890

7 Wainwright Rd Unit 39, Winchester, MA 01890

/37
$1,450,000 Sold May 30, 2025
- 3,763 Sq Ft
- $385/SF
- 34 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1988
7 Wainwright Rd Unit 8, Winchester, MA 01890

Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large

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

7 Wainwright Rd Unit 8, Winchester, MA 01890

/39
Est $1,726,241 Not Listed For Sale
- 2 Beds
- 4 Baths
- 3,655 Sq Ft
7 Wainwright Rd Unit 37, Winchester, MA 01890

7 Wainwright Rd Unit 37, Winchester, MA 01890

/25
$1,881,900 Sold May 30, 2025
- 3,488 Sq Ft
- $540/SF
- 34 Days On Market
- 4 Beds
- 4 Baths
- Built 1980
4 Olde Lyme Rd, Winchester, MA 01890

This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace and an open-concept design, this spacious home is bathed in natural beauty. The gourmet kitchen is pristine and boasts high-end appliances, quartz countertops, a prep sink and secondary dishwasher, and a large island—ideal for

Nancy Pallotta Advisors Living - Winchester

4 Olde Lyme Rd, Winchester, MA 01890

/42
Est $1,815,254 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,901 Sq Ft
7 Wainwright Rd Unit 5, Winchester, MA 01890

7 Wainwright Rd Unit 5, Winchester, MA 01890

/33
$1,785,000 Sold May 22, 2025
- 2,848 Sq Ft
- $627/SF
- 13 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1968
85 Thornberry Rd, Winchester, MA 01890

Welcome to the highly-coveted Westside of Winchester, MA. This meticulously maintained Colonial-style home is set on 20,000 sqft lot with professional landscaping. The living room features a charming wood-burning fireplace, while the sun-filled formal dining room is centered with an elegant chandelier. The kitchen has granite countertops, stainless steel appliances, and an adjacent eat-in area

Diane Basemera Coldwell Banker Realty - Newton

85 Thornberry Rd, Winchester, MA 01890

/41
Est $1,632,174 Not Listed For Sale
- 2 Beds
- 4 Baths
- 5,564 Sq Ft
7 Wainwright Rd Unit 41, Winchester, MA 01890

7 Wainwright Rd Unit 41, Winchester, MA 01890

/42
$4,065,000 Sold May 16, 2025
- 7,500 Sq Ft
- $542/SF
- 71 Days On Market
- 6 Beds
- 7.5 Baths
- Built 2025
6 Vinson Cir, Winchester, MA 01890

Nestled on a cul-de-sac in Winchester's desirable west side, this brand-new construction redefines modern luxury living. Spanning 7,500 sq. ft., this exquisite 6-bedroom, 7.5-bathroom home combines style, comfort, and functionality. Discover an open-concept floor plan bathed in natural light, perfect for entertaining and everyday living. The kitchen features top-of-the-line Wolf appliances,

Peter Kasseris Compass

6 Vinson Cir, Winchester, MA 01890

/42
Est $2,016,282 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,853 Sq Ft
40 Wainwright Rd, Winchester, MA 01890

40 Wainwright Rd, Winchester, MA 01890

/15
$1,088,000 Sold May 08, 2025
- 2,172 Sq Ft
- $501/SF
- 6 Days On Market
- 4 Beds
- 2 Baths
- Built 1985
322 Cambridge St, Winchester, MA 01890

Not your average Garrison Colonial! You might not expect the bright, open charm waiting within this inviting 8-room, 3-level home. The stunning main level living room, dining and kitchen area boasts cathedral ceilings, skylights, and a dramatic brick fireplace, creating a sense of space and light. This home features 2 full baths and 4 bedrooms, including 3 with brand-new hardwood floors and a

Joanne McDonnell RE/MAX Real Estate Center

322 Cambridge St, Winchester, MA 01890

/42
Est $2,917,639 Not Listed For Sale
- 5 Beds
- 6 Baths
- 5,678 Sq Ft
19 Socrates Way, Winchester, MA 01890

19 Socrates Way, Winchester, MA 01890

/42
$1,890,000 Sold Mar 28, 2025
- 4,318 Sq Ft
- $438/SF
- 7 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1956
19 Johnson Rd, Winchester, MA 01890

A DESIGNER DREAM! Welcome to 19 Johnson Road, a pristine 5-bedroom colonial-style home located in the highly sought-after Vinson Owen School district! As you enter the home, you are greeted by a stunning curved staircase adorned with molding and a statement-making light fixture. The first level boasts a fireplaced living room, a fireplaced family room, an updated kitchen, and a gorgeous formal

Philip Vita Compass

19 Johnson Rd, Winchester, MA 01890

/42
Est $2,662,831 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 5,713 Sq Ft
40 Amberwood Dr, Winchester, MA 01890

40 Amberwood Dr, Winchester, MA 01890

/31
$940,000 Sold Mar 14, 2025
- 2,418 Sq Ft
- $389/SF
- 8 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1985
60 Edward Dr Unit 60, Winchester, MA 01890

Welcome to this move in ready townhouse in Pepper Hill Estates! Enjoy easy living with this stunning open concept home boasting a newer eat-in kitchen, spacious dining room & oversized living room with a wood burning fireplace and floor to ceiling windows that are flooded w/natural light. This main floor also has great closet space, a half bath and a beautiful rear deck to enjoy. The 2nd level

Kim Covino Compass

60 Edward Dr Unit 60, Winchester, MA 01890

/38
Est $1,838,037 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 4,008 Sq Ft
45 Amberwood Dr, Winchester, MA 01890

45 Amberwood Dr, Winchester, MA 01890

/27
$1,200,000 Sold Feb 28, 2025
- 3,350 Sq Ft
- $358/SF
- 183 Days On Market
- 2 Beds
- 2.5 Baths
- Built 1989
7 Wainwright Rd Unit 22, Winchester, MA 01890

Now is the time to make a move! Step into a sophisticated lifestyle as you enter through a charming courtyard into this elegant condo. The beautifully updated kitchen is a standout, featuring granite countertops, cherry cabinetry, and premium new stainless steel appliances—a chef’s dream come true. The open-concept layout is perfect for modern living, with a dining area flowing into the inviting

DeWolfe Group Gibson Sotheby's International Realty

7 Wainwright Rd Unit 22, Winchester, MA 01890

/36
Est $2,288,320 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

/42
$2,025,000 Sold Feb 21, 2025
- 4,997 Sq Ft
- $405/SF
- 8 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1975
23 Olde Village Dr, Winchester, MA 01890

Welcome to this exceptional one floor living ranch-style home, a true haven for both luxury living and car enthusiasts. Nestled among towering trees, this expansive property offers the perfect balance of privacy and beauty, with a stunning 4-car garage designed to accommodate your prized vehicles, ample storage space, workshop, home gym or additional living space. With a grand, welcoming entrance

Andersen Group Realty Keller Williams Realty Boston Northwest

23 Olde Village Dr, Winchester, MA 01890

/38
Est $1,808,822 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,218 Sq Ft
27 Amberwood Dr, Winchester, MA 01890

27 Amberwood Dr, Winchester, MA 01890

/38
$1,650,000 Sold Jan 30, 2025
- 2,376 Sq Ft
- $694/SF
- 30 Days On Market
- 3 Beds
- 4 Baths
- Built 1927
36 Oneida Rd, Winchester, MA 01890

TOTAL RENOVATION! Thoughtfully crafted to create a warm and inviting abode. Step inside to discover the completely reimagined first floor with an open concept dining room, sitting room, and show-stopping brand new kitchen with a center island, and a slider leading to a patio, ideal for alfresco dining and entertaining. The first floor also hosts a versatile family room with access to a private

Philip Vita Compass

36 Oneida Rd, 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

/38
$1,900,000 Sold Jan 29, 2025
- 3,611 Sq Ft
- $526/SF
- 50 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1984
11 Plymouth Rd, Winchester, MA 01890

OPEN HOUSE SUNDAY 11/17 11:30-1:00pm. 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-appointed dining room with custom built-in China cabinet is perfect for large

Darryl Brian RE/MAX Bentley's

11 Plymouth Rd, Winchester, MA 01890

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