West Side Homes

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  /40

  $2,785,000

  • 4 Beds
  • 4 Baths
  • 5,674 Sq Ft

  10 Viking Rd, Winchester, MA 01890

  Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

  Anne Spry Barrett Sotheby's International Realty

  10 Viking Rd, Winchester, MA 01890
• Explore West Side

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  /20

  $2,358 - $20,886 per month plus fees

  Sanctuary Winchester West

  Studio - 3 Beds

  416 Cambridge St, Winchester, MA 01890

  The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

  416 Cambridge St, Winchester, MA 01890
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  /42

  $1,750,000 Sold Oct 31, 2025

  • 2,397 Sq Ft
  • $730/SF
  • 1 Day On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1937

  15 Westland Ave, Winchester, MA 01890

  OFFER ACCEPTED OH SUNDAY CANCELLED Taken down to the studs, this renovated and reimagined center entrance Colonial offers timeless elegance and modern comfort in one of Winchester’s most desirable neighborhoods. The gracious foyer gives way to a front-to-back living room anchored by a wood-burning fireplace with custom mantle. An adjacent sun-filled, south-facing room provides the perfect space

  Erica Carson Coldwell Banker Realty - Lexington

  15 Westland Ave, Winchester, MA 01890
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  /42

  Est $2,869,935 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 6,265 Sq Ft

  228 Ridge St, Winchester, MA 01890

  228 Ridge St, Winchester, MA 01890
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  /30

  $2,850,000

  • 6 Beds
  • 7 Baths
  • 6,968 Sq Ft

  14 Nassau Dr, Winchester, MA 01890

  Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New

  Weidong Li WINN Real Estate & Consulting

  14 Nassau Dr, Winchester, MA 01890
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  /41

  $6,900 total monthly price

  • 4 Beds
  • 4 Baths
  • 4,650 Sq Ft
  • House for Rent

  31 Coolidge Rd, Winchester, MA 01890

  A grand home with a perfect mix of serenity and entertaining spaces. The main level has endless possibilities with its ability to provide cozy living areas and also an open concept with great flow. Fully equipped modern kitchen with tons of storage and island, Formal dining room with custom built ins, french doors to separate or open up spaces, front to back fireplace between the massive family

  Sheri O'Connor Plunkett Properties

  31 Coolidge Rd, Winchester, MA 01890
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  /42

  $1,550,000 Sold Oct 31, 2025

  • 2,995 Sq Ft
  • $518/SF
  • 5 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1960

  205 Ridge St, Winchester, MA 01890

  Welcome to 205 Ridge Street, a stunning residence that blends timeless elegance with modern comfort, perfectly designed for today’s lifestyle. Nestled in one of Winchester’s most desirable neighborhoods, this five-bedroom, three-bath home offers the perfect balance of refined living and everyday convenience. From the moment you arrive, the property’s curb appeal and thoughtful details set the

  Debby Valdes eXp Realty

  205 Ridge St, Winchester, MA 01890
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  /40

  Est $1,375,352 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,529 Sq Ft

  15 Wincrest Dr, Winchester, MA 01890

  15 Wincrest Dr, Winchester, MA 01890
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  /42

  $3,299,000

  • 5 Beds
  • 7 Baths
  • 7,101 Sq Ft

  257 High St, Winchester, MA 01890

  Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

  Kim Covino Compass

  257 High St, Winchester, MA 01890
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  /29

  $3,200 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft
  • Apartment for Rent

  40 Dunster Ln Unit 1, Winchester, MA 01890

  Welcome to this charming, sun-filled 2-bed, 2-bath home in the heart of Winchester. With nearly 900 sq. ft. of living space, it blends classic New England charm with modern convenience. The house comes fully furnished—down to the silverware, linens, and decor—so you can simply unpack and relax. Enjoy hardwood floors, a bright living room, a modern kitchen with upgraded counters, and a private

  William Dynan Keller Williams Realty Evolution

  40 Dunster Ln Unit 1, Winchester, MA 01890
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  /38

  $2,000,000 Sold Oct 29, 2025

  • 5,000 Sq Ft
  • $400/SF
  • 3 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1968

  1 Fox Hunt Ln, Winchester, MA 01890

  Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office.

  Leigh Ventura Compass

  1 Fox Hunt Ln, Winchester, MA 01890
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  /33

  Est $1,525,632 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,034 Sq Ft

  10 Carriage Ln, Winchester, MA 01890

  10 Carriage Ln, Winchester, MA 01890
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  /36

  $3,600,000

  • 6 Beds
  • 7 Baths
  • 8,866 Sq Ft

  20 Amberwood Dr, Winchester, MA 01890

  Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

  Wei Wang WW Real Estate LLC

  20 Amberwood Dr, Winchester, MA 01890
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  /29

  $7,150 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 3,218 Sq Ft
  • House for Rent

  29 Wainwright Rd, Winchester, MA 01890

  Experience refined New England living in this elegant single-family home in Winchester, Massachusetts—an enclave of luxury just eight miles north of Boston and minutes to Cambridge. This light-filled, impeccably maintained residence blends sophistication and comfort with open living and entertaining spaces. The gourmet kitchen with stainless steel appliances and granite countertops flows into a

  Helen Stefan Gibson Sotheby's International Realty

  29 Wainwright Rd, Winchester, MA 01890
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  /24

  $2,155,000 Sold Oct 21, 2025

  • 3,186 Sq Ft
  • $676/SF
  • 1 Day On Market

  • 3 Beds
  • 4.5 Baths
  • Built 1988

  7 Wainwright Rd Unit 13, Winchester, MA 01890

  Stunning townhouse with 3 bedrooms and 4.5 bathrooms, meticulously renovated with high-end, designer finishes. The sun-drenched living room features 13 ft. ceilings, 5-in. oak floors, custom built-in book shelves, and a double-sided marble-surround fireplace that flows seamlessly to the brand-new gourmet chef’s kitchen. The kitchen is a showpiece with a Sub-Zero fridge, Thermador range, Acadia

  Isabella Bruno William Raveis R.E. & Home Services

  7 Wainwright Rd Unit 13, Winchester, MA 01890
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  /35

  Est $1,710,477 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,926 Sq Ft

  16 Nassau Dr, Winchester, MA 01890

  16 Nassau Dr, Winchester, MA 01890
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  /38

  $2,299,000

  • 5 Beds
  • 3.5 Baths
  • 5,006 Sq Ft

  276 High St, Winchester, MA 01890

  Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

  Kim Covino Compass

  276 High St, Winchester, MA 01890
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  $8,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  35 Thornberry Rd, Winchester, MA 01890

  No Broker Fee! Large Sun-filled Windows, Contemporary, Minimalist, and Modern Design. A truly rare opportunity to rent this magnificent single-family home in one of Winchester’s most desirable neighborhoods. The home was ground-up construction in 2010 with over 3,500 square feet of living space. Its open concept, large loft-style office / second living room area, four bedrooms, three and a half

  Frank Celeste Gibson Sotheby's International Realty

  35 Thornberry Rd, Winchester, MA 01890
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  /39

  $2,050,000 Sold Oct 15, 2025

  • 3,716 Sq Ft
  • $552/SF
  • 2 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1931

  64 Westland Ave, Winchester, MA 01890

  Open Houses Cancelled. Elegant 1930s Colonial boasts charming architectural features, 4 bedrooms, a recent addition & gorgeous top-of-the-line designer kitchen! The heart of the home is the open concept kitchen, which boasts Wolf & Sub-Zero appliances. The front foyer welcomes you to a grand living room with a fireplace, plus a pair of French doors opening to the most charming screen porch. The

  The Murphy Group Lexington William Raveis R.E. & Home Services

  64 Westland Ave, Winchester, MA 01890
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  /36

  Est $1,575,493 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,171 Sq Ft

  94 Johnson Rd, Winchester, MA 01890

  94 Johnson Rd, Winchester, MA 01890
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  /42

  $3,499,000

  • 7 Beds
  • 7.5 Baths
  • 7,982 Sq Ft

  54 Johnson Rd, Winchester, MA 01890

  This STUNNING newly constructed home facing Old Village Drive 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

  Kim Covino Compass

  54 Johnson Rd, Winchester, MA 01890
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  /24

  $1,165,000 Sold Oct 14, 2025

  • 2,458 Sq Ft
  • $474/SF
  • 43 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1958

  59 Johnson Rd, Winchester, MA 01890

  Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and

  Angela Zhang Greatland Real Estate LLC

  59 Johnson Rd, Winchester, MA 01890
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  /32

  Est $1,635,093 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  104 Thornberry Rd, Winchester, MA 01890

  104 Thornberry Rd, Winchester, MA 01890
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  /42

  $1,425,000

  • 3 Beds
  • 3.5 Baths
  • 3,350 Sq Ft

  7 Wainwright Rd Unit 29, Winchester, MA 01890

  Welcome to The Ledges, Winchester’s premier hilltop community offering refined, resort-style living with modern convenience. This sun-filled, beautifully updated home features an open layout with cathedral ceilings, hardwood floors, and newly landscaped courtyard space by Mahoney’s. The gourmet kitchen with premium appliances. Living Room opens to a private wooded deck, ideal for entertaining or

  Joanne Sexeny Coldwell Banker Realty - Lexington

  7 Wainwright Rd Unit 29, Winchester, MA 01890
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  /33

  $1,600,000 Sold Oct 10, 2025

  • 3,478 Sq Ft
  • $460/SF
  • 57 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1960

  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
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  /39

  Est $1,858,825 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,046 Sq Ft

  73 Thornberry Rd, Winchester, MA 01890

  73 Thornberry Rd, Winchester, MA 01890
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  /42

  $1,199,000

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  16 Ridge St, Winchester, MA 01890

  ATTENTION CONTRACTORS/BUILDERS & BUYERS LOOKING TO BUILD EQUITY~whether you do a light update/ expand or completely renovate; this well maintained 3 bedroom split entry home on a stunning 27k+ lot with a great layout and an oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning

  Kim Covino Compass

  16 Ridge St, Winchester, MA 01890
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  /28

  $1,713,000 Sold Sep 26, 2025

  • 3,002 Sq Ft
  • $571/SF
  • 53 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  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
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  /35

  Est $1,802,968 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,224 Sq Ft

  22 Berkshire Dr, Winchester, MA 01890

  22 Berkshire Dr, Winchester, MA 01890
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  /42

  $1,999,000

  • 5 Beds
  • 3.5 Baths
  • 6,232 Sq Ft

  5 Azalea Rd, Winchester, MA 01890

  NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and

  Anthony Marino The Marino Group Collection

  5 Azalea Rd, Winchester, MA 01890
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  /42

  $1,768,500 Sold Sep 25, 2025

  • 3,838 Sq Ft
  • $461/SF
  • 10 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1951

  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
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  /42

  Est $2,287,291 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,620 Sq Ft

  5 Partridge Ln, Winchester, MA 01890

  5 Partridge Ln, Winchester, MA 01890
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  /40

  $2,000,000

  • 6 Beds
  • 3.5 Baths
  • 4,696 Sq Ft

  5 Squire Rd, Winchester, MA 01890

  Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

  Alina Wang Coldwell Banker Realty - Lexington

  5 Squire Rd, Winchester, MA 01890
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  /36

  $1,950,000 Sold Sep 25, 2025

  • 4,378 Sq Ft
  • $445/SF
  • 40 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1987

  4 Fieldstone Dr, Winchester, MA 01890

  Nestled in a desirable Westside neighborhood, this stunning California contemporary/colonial home sits on a quiet cul-de-sac and offers 5 bedrooms, 3.5 baths, and over 20,000 sq ft of beautifully landscaped grounds. The sun-drenched interior features an open-concept kitchen and dining room with five fully opening doors leading to a bright four-seasons sunroom—perfect for gatherings year-round.

  Wenli Zheng Fairview Partners International LLC

  4 Fieldstone Dr, Winchester, MA 01890
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  /40

  Est $2,138,393 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 4,532 Sq Ft

  89 Thornberry Rd, Winchester, MA 01890

  89 Thornberry Rd, Winchester, MA 01890
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  /33

  $1,499,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,807 Sq Ft

  7 Wainwright Rd Unit 118, Winchester, MA 01890

  Exceptional 3 Bedroom 3 1/2 Bath Highly Desired End Unit Townhome at The Ledges! Main Level Features include: Inviting Sun-Filled Entry Foyer, Gleaming Hardwood Floors, Cathedral Ceilings, Granite/Stainless Chef's Kitchen w/Breakfast Room, Formal Dining Room, Living Room w/Gas Fireplace and Private Deck overlooking Tranquil Wooded Setting. Family Study w/ Custom Built-ins, Luxurious Primary

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Wainwright Rd Unit 118, Winchester, MA 01890
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  /42

  $1,725,000 Sold Sep 19, 2025

  • 2,541 Sq Ft
  • $679/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1960

  9 Pilgrim Dr, Winchester, MA 01890

  Welcome to this beautiful split-level home nestled on a desirable corner lot in Winchester’s sought after west side. Featuring gleaming hardwood floors throughout, this home offers a perfect blend of comfort and style. The main level boasts an open floor plan connecting the dining room, kitchen, and living room, and seamlessly flows into a stunning vaulted family room, perfect for both everyday

  McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

  9 Pilgrim Dr, Winchester, MA 01890
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  /40

  Est $2,116,906 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
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  /35

  $1,359,000 Pending

  • 5 Beds
  • 2 Baths
  • 3,033 Sq Ft

  7 Thornberry Rd, Winchester, MA 01890

  The land alone is worth this price!! 15Ksf lot & a newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level

  Kim Covino Compass

  7 Thornberry Rd, Winchester, MA 01890
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  /38

  $1,525,000 Sold Sep 12, 2025

  • 2,755 Sq Ft
  • $554/SF
  • 30 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1929

  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

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