West Side Homes

/11
Est $1,333,096 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,218 Sq Ft
233 High St, Winchester, MA 01890

233 High St, Winchester, MA 01890

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/42
$1,729,000 Pending
- 4 Beds
- 5 Baths
- 5,361 Sq Ft
4 Aricia Ln, Winchester, MA 01890

Rare 5-car garage on a quiet, tree-lined cul-de-sac in one of Winchester’s most exclusive enclaves! Offering both serene privacy and seamless connectivity, 4 Aricia is perfectly positioned within walking distance to a coveted elementary school and Wright-Locke Farm, and minutes from the commuter rail and Routes 128 & 93. Set on nearly .5 acres of manicured grounds, the home’s exterior is framed

The McLaren D'Agostino Team Compass

4 Aricia Ln, Winchester, MA 01890
/42
$2,218,500 Sold Aug 29, 2025
- 3,940 Sq Ft
- $563/SF
- 74 Days On Market
- 5 Beds
- 5 Baths
- Built 1983
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

/40
Est $1,336,407 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

/41
$1,950,000 Pending
- 4 Beds
- 4.5 Baths
- 3,512 Sq Ft
7 Wainwright Rd Unit 72, Winchester, MA 01890

Extensively renovated and move-in ready, this stunning F-unit townhouse offers 4 bedrooms and 4.5 baths with impeccable detail and modern appeal throughout. The many windows, high ceilings, gleaming hardwood floors, and open design create a warm sun-filled home. You will enjoy the large kitchen and the ability to retreat to the dazzling first-floor primary suite, which provides single floor

Pirani & Wile Group Gibson Sotheby's International Realty

7 Wainwright Rd Unit 72, Winchester, MA 01890
/42
$2,500,000 Sold Aug 27, 2025
- 4,215 Sq Ft
- $593/SF
- 4 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1955
12 Olde Lyme Rd, Winchester, MA 01890

*** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates

Mary Beth McGillicuddy Engel & Völkers , South Shore

12 Olde Lyme Rd, Winchester, MA 01890

/42
Est $1,675,707 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

/42
$1,999,000 Pending
- 4 Beds
- 3.5 Baths
- 4,731 Sq Ft
6 Samoset Rd, Winchester, MA 01890

Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up

Anne Spry Barrett Sotheby's International Realty

6 Samoset Rd, Winchester, MA 01890
/33
$1,240,000 Sold Aug 20, 2025
- 2,570 Sq Ft
- $482/SF
- 9 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1966
3 Socrates Way, Winchester, MA 01890

Unlock the potential of this tri-level home in one of Winchester’s sought-after neighborhoods! Set on a 20,000 sq ft lot, this 4 bed, 2.5 bath, 1966-built home offers 2,116 sf of living space, a 2 car garage, & endless possibilities for renovation or redevelopment. The main level features a formal living room, dining room, & kitchen leading to a deck overlooking the backyard. A cozy family room

Pirani & Wile Group Gibson Sotheby's International Realty

3 Socrates Way, Winchester, MA 01890

/33
Est $1,901,935 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

/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
/19
$1,820,000 Sold Aug 19, 2025
- 3,784 Sq Ft
- $481/SF
- 5 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1974
109 Thornberry Rd, Winchester, MA 01890

Ideally located in one of Winchester’s most desirable neighborhoods, this classic Colonial blends timeless design with thoughtful updates. At the heart of the home, the beautifully updated kitchen features a generous center island, opening to a spacious family room with a slider leading to a large deck overlooking the expansive, level backyard - perfect for summer entertaining. Just off the

Andrew Martini Compass

109 Thornberry Rd, Winchester, MA 01890

/38
Est $1,614,216 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

/42
$1,775,000 Sold Aug 15, 2025
- 3,150 Sq Ft
- $563/SF
- 6 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1961
19 Pilgrim Dr, Winchester, MA 01890

Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –

Gorfinkle Group eXp Realty

19 Pilgrim Dr, Winchester, MA 01890

/39
Est $1,666,208 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

/38
$1,627,000 Sold Jul 31, 2025
- 2,853 Sq Ft
- $570/SF
- 7 Days On Market
- 5 Beds
- 4 Baths
- Built 1930
32 Oneida Rd, Winchester, MA 01890

Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

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

32 Oneida Rd, Winchester, MA 01890

/42
Est $1,757,606 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

/42
$1,650,000 Sold Jul 30, 2025
- 2,646 Sq Ft
- $624/SF
- 18 Days On Market
- 3 Beds
- 4 Baths
- Built 1957
50 Johnson Rd, Winchester, MA 01890

One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins.

Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

50 Johnson Rd, Winchester, MA 01890

/41
Est $1,579,732 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

/37
$1,390,000 Sold Jul 15, 2025
- 2,388 Sq Ft
- $582/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1963
26 Ridge St, Winchester, MA 01890

Set on a generous, beautifully landscaped lot, this meticulously maintained home showcases numerous recent upgrades, and offers both comfort and style. The newly renovated kitchen features upscale appliances and custom quartz countertops, perfect for everyday living and entertaining alike.Hardwood floors, two fireplaces, a sunlit living room, and a separate family room create inviting spaces

Dream Team Dreamega International Realty LLC

26 Ridge St, Winchester, MA 01890

/42
Est $1,962,870 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

/42
$1,540,000 Sold Jul 11, 2025
- 2,814 Sq Ft
- $547/SF
- 5 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1970
21 Johnson Rd, Winchester, MA 01890

This lovingly maintained Colonial home is ideally situated just a 1/2 mile from Vinson-Owen Elementary School. Featuring all 4 bedrooms on the second floor, the layout includes a spacious primary w/ an en-suite bath as well as a fully updated hall bath. The main level offers an elegant family room w/ soaring ceilings, a cozy fireplace, recessed lighting & a slider leading to the deck. The

Stefanie Clifford Keller Williams Realty Boston Northwest

21 Johnson Rd, Winchester, MA 01890

/42
Est $2,912,938 Not Listed For Sale
- 5 Beds
- 6 Baths
- 5,678 Sq Ft
19 Socrates Way, Winchester, MA 01890

19 Socrates Way, Winchester, MA 01890

/16
$1,050,000 Sold Jul 11, 2025
- 2,621 Sq Ft
- $401/SF
- 48 Days On Market
- 4 Beds
- 2 Baths
- Built 1952
61 Westland Ave, Winchester, MA 01890

Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

61 Westland Ave, Winchester, MA 01890

/42
Est $2,736,623 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

/39
$2,200,000 Sold Jun 30, 2025
- 3,818 Sq Ft
- $576/SF
- 0 Days On Market
- 4 Beds
- 4 Baths
- Built 1967
1 Saint Augustine Ct, Winchester, MA 01890

Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and gleaming hardwood floors throughout, it strikes the perfect balance between timeless charm and fresh, move-in-ready style. The front-to-back living room is flooded with natural light—ideal for everything from morning coffee to impromptu

Nancy Pallotta Gibson Sotheby's International Realty

1 Saint Augustine Ct, Winchester, MA 01890

/38
Est $1,869,213 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

/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

/36
Est $2,362,141 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

/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 Gibson Sotheby's International Realty

7 Wainwright Rd Unit 117, Winchester, MA 01890

/38
Est $1,838,847 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,218 Sq Ft
27 Amberwood Dr, Winchester, MA 01890

27 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

/42
Est $2,200,203 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

/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 $2,446,135 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,138 Sq Ft
5 Pilgrim Dr, Winchester, MA 01890

5 Pilgrim Dr, 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

/42
Est $2,020,403 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,256 Sq Ft
15 Pilgrim Dr, Winchester, MA 01890

15 Pilgrim Dr, 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

/40
Est $1,449,018 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,142 Sq Ft
16 Johnson Rd, Winchester, MA 01890

16 Johnson Rd, 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

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Massachusetts Middlesex County Winchester West Side

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