West Side Homes

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  /38

  $2,350,000

  • 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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  /20

  $2,650 - $5,850 per month

  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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  /40

  $1,551,000 Sold Jul 15, 2025

  • 3,186 Sq Ft
  • $487/SF
  • 5 Days On Market

  • 3 Beds
  • 4.5 Baths
  • Built 1988

  7 Wainwright Rd Unit 13, Winchester, MA 01890

  Welcome to The Ledges, Winchester’s premier townhouse community! This extraordinary F Style corner unit is truly one of a kind with soaring ceilings, sun-filled spaces, and rare flat backyard space with two decks. A landscaped courtyard leads to a gracious foyer and transitions into an expansive open layout. The chef’s kitchen opens to the dining rm and features ss appliances, granite countertops

  Nancy Pallotta Advisors Living - Winchester

  7 Wainwright Rd Unit 13, Winchester, MA 01890
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  /42

  Est $2,874,660 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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  /39

  $1,900,000

  • 4 Beds
  • 5 Baths
  • 5,361 Sq Ft

  4 Aricia Ln, Winchester, MA 01890

  Tucked into the tree-lined enclave of Aricia Lane, this striking contemporary residence delivers bold architectural design, abundant light, and the seamless indoor-outdoor living today’s buyers crave. Set on nearly half an acre in one of Winchester’s most peaceful pockets, this home is a rare fusion of modern comfort, space, and convenience offering the rarest of features: a five-car garage. From

  The McLaren D'Agostino Team Compass

  4 Aricia Ln, Winchester, MA 01890
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  /26

  $9,500 per month

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

  35 Thornberry Rd, Winchester, MA 01890

  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 bathrooms,

  Frank Celeste Gibson Sotheby's International Realty

  35 Thornberry Rd, Winchester, MA 01890
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  /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
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  /30

  Est $2,087,183 Not Listed For Sale

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

  5 Squire Rd, Winchester, MA 01890

  5 Squire Rd, Winchester, MA 01890
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  /36

  $1,980,000 Open Sat 1PM - 2:30PM

  • 5 Beds
  • 3.5 Baths
  • 4,378 Sq Ft

  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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  /14

  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,836 Sq Ft
  • House for Rent

  3 Wainwright Rd Unit SFAM, Winchester, MA 01890

  Explore Sanctuary West's one-of-a-kind 1,836 square foot single family home! This 3-bedroom, 2.5 bathroom standalone home features luxury finishes with added historical touches such as exposed wood beams.

  Christine Ferris Ideal Real Estate Services, Inc.

  3 Wainwright Rd Unit SFAM, Winchester, MA 01890
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  /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
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  /40

  Est $1,368,810 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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  /41

  $2,250,000

  • 5 Beds
  • 5 Baths
  • 5,000 Sq Ft

  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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  /41

  $9,400 per month

  • 5 Beds
  • 4.5 Baths
  • 5,016 Sq Ft
  • House for Rent

  22 Amberwood Dr, Winchester, MA 01890

  Fabulous rental opportunity with full wing of an additional in-law suite for multi-generational living at its best. Beautiful designers’ grade high-end finishes throughout! Features separate side entry with inviting south-facing covered porch, a dramatic two-story foyer/ceiling, and the main kitchen that flows into an additional meal prep kitchen area with integrated appliances – Thermador

  Anita Lin Coldwell Banker Realty - Lexington

  22 Amberwood Dr, Winchester, MA 01890
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  /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 Advisors Living - Winchester

  1 Saint Augustine Ct, Winchester, MA 01890
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  /33

  Est $1,507,072 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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  /42

  $2,349,900

  • 5 Beds
  • 5 Baths
  • 3,940 Sq Ft

  17 Wagon Wheel Rd, Winchester, MA 01890

  Buyers' financing failed. 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

  Yifei Wang Dreamega International Realty LLC

  17 Wagon Wheel Rd, Winchester, MA 01890
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  /38

  $7,450 per month

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

  31 Coolidge Rd, Winchester, MA 01890

  Available now! Welcome to this beautifully renovated and maintained colonial at a very quiet street in a desirable neighborhood with easy commute to schools, Boston, highways and MBTA train stations. The 1st floor offers a foyer with formal dining room and living room in either sides. The kitchen, with island and full breakfast/dining area, flows into a family room that transitions to a private

  Carlos Xu Lexwin Realty

  31 Coolidge Rd, Winchester, MA 01890
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  /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
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  /42

  Est $1,461,452 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,125 Sq Ft

  47 Thornberry Rd, Winchester, MA 01890

  47 Thornberry Rd, Winchester, MA 01890
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  /39

  $2,299,000 Open Thu 4PM - 6PM

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

  5 Azalea Rd, Winchester, MA 01890

  NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Azalea Rd, Winchester, MA 01890
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  /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
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  /35

  Est $1,650,741 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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  /42

  $2,400,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,215 Sq Ft

  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
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  /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
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  /36

  Est $1,608,941 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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  /33

  $1,725,000 Open Thu 5PM - 6:30PM

  • 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 and awaits your personal touches. The living room features stunning woodwork, a wood-burning 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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  /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
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  /32

  Est $1,636,136 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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  /41

  $1,349,000

  • 3 Beds
  • 1.5 Baths
  • 3,335 Sq Ft

  10 Girard Rd, Winchester, MA 01890

  Unleash Your Vision in Winchester’s Coveted West Side! Don't miss this rare chance to transform this Mid-Century Modern ranch on a generous 15,024 square foot idyllic lot in one of Winchester’s most desirable neighborhoods. Whether you renovate, expand, or enjoy this home as it is, this 3-bed, 1.5-bath home offers endless potential. Nestled on a quiet, tree-lined street abutting conservation land

  Joanne Sexeny Coldwell Banker Realty - Lexington

  10 Girard Rd, Winchester, MA 01890
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  /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
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  /34

  Est $2,068,389 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,000 Sq Ft

  133 Johnson Rd, Winchester, MA 01890

  133 Johnson Rd, Winchester, MA 01890
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  /28

  $1,765,300

  • 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
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  /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
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  /39

  Est $1,919,199 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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  /41

  $2,899,000 Open Sun 1:30PM - 2:30PM

  • 5 Beds
  • 4.5 Baths
  • 6,904 Sq Ft

  11 Fieldstone Dr, Winchester, MA 01890

  Stunning 5BD/4.5BA contemporary estate on a private cul-de-sac in Winchester’s most coveted neighborhood. Modern design with soaring two-story ceilings, skylights, wide-plank hardwoods, and a dramatic stone fireplace. Gourmet chef’s kitchen with all-white waterfall island, Sub-Zero appliances, and butler’s pantry. Luxe primary suite with dual walk-in closet, spa bath, and private terrace. Fully

  Andersen Group Realty Keller Williams Realty Boston Northwest

  11 Fieldstone Dr, Winchester, MA 01890
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  /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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  /35

  Est $1,821,153 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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  /34

  $1,449,900

  • 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
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  /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

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