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Recently Sold West Side Homes

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  • 5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    /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
  • 17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, 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
  • 12 Olde Lyme Rd, Winchester, MA 01890
    12 Olde Lyme Rd, Winchester, MA 01890
    12 Olde Lyme Rd, 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
  • 3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, 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 Advisors Living - Winchester

    3 Socrates Way, Winchester, MA 01890
  • 109 Thornberry Rd, Winchester, MA 01890
    109 Thornberry Rd, Winchester, MA 01890
    109 Thornberry 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
  • 19 Pilgrim Dr, Winchester, MA 01890
    19 Pilgrim Dr, Winchester, MA 01890
    19 Pilgrim Dr, 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
  • 32 Oneida Rd, Winchester, MA 01890
    32 Oneida Rd, Winchester, MA 01890
    32 Oneida Rd, 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
  • 50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, 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
  • 7 Wainwright Rd Unit 13, Winchester, MA 01890
    7 Wainwright Rd Unit 13, Winchester, MA 01890
    7 Wainwright Rd Unit 13, Winchester, MA 01890
    /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
  • 26 Ridge St, Winchester, MA 01890
    26 Ridge St, Winchester, MA 01890
    26 Ridge St, 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
  • 21 Johnson Rd, Winchester, MA 01890
    21 Johnson Rd, Winchester, MA 01890
    21 Johnson 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
  • 61 Westland Ave, Winchester, MA 01890
    61 Westland Ave, Winchester, MA 01890
    61 Westland Ave, 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
  • 1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, Winchester, MA 01890
    1 Saint Augustine Ct, 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 Advisors Living - Winchester

    1 Saint Augustine Ct, Winchester, MA 01890
  • 20 Seneca Rd, Winchester, MA 01890
    20 Seneca Rd, Winchester, MA 01890
    20 Seneca 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
  • 7 Wainwright Rd Unit 117, Winchester, MA 01890
    7 Wainwright Rd Unit 117, Winchester, MA 01890
    7 Wainwright Rd Unit 117, 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
  • 9 Thornberry Rd, Winchester, MA 01890
    9 Thornberry Rd, Winchester, MA 01890
    9 Thornberry Rd, 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
  • 65 Thornberry Rd, Winchester, MA 01890
    65 Thornberry Rd, Winchester, MA 01890
    65 Thornberry 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
  • 7 Hutchinson Rd, Winchester, MA 01890
    7 Hutchinson Rd, Winchester, MA 01890
    7 Hutchinson 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
  • 34 Coolidge Rd, Winchester, MA 01890
    34 Coolidge Rd, Winchester, MA 01890
    34 Coolidge Rd, 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
  • 7 Indian Hill Rd, Winchester, MA 01890
    7 Indian Hill Rd, Winchester, MA 01890
    7 Indian Hill 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
  • 7 Wainwright Rd Unit 8, Winchester, MA 01890
    7 Wainwright Rd Unit 8, Winchester, MA 01890
    7 Wainwright Rd Unit 8, 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
  • 4 Olde Lyme Rd, Winchester, MA 01890
    4 Olde Lyme Rd, Winchester, MA 01890
    4 Olde Lyme Rd, 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
  • 85 Thornberry Rd, Winchester, MA 01890
    85 Thornberry Rd, Winchester, MA 01890
    85 Thornberry Rd, 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
  • 6 Vinson Cir, Winchester, MA 01890
    6 Vinson Cir, Winchester, MA 01890
    6 Vinson Cir, 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
  • 322 Cambridge St, Winchester, MA 01890
    322 Cambridge St, Winchester, MA 01890
    322 Cambridge St, 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
  • 31 Coolidge Rd, Winchester, MA 01890
    31 Coolidge Rd, Winchester, MA 01890
    31 Coolidge Rd, Winchester, MA 01890
    /41

    $2,000,000 Sold Apr 15, 2025

    • 4,650 Sq Ft
    • $430/SF
    • 11 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1980

    31 Coolidge Rd, Winchester, MA 01890

    Set against a serene woodland backdrop, this beautifully maintained colonial blends formal spaces with open, airy rooms designed for both grand entertaining and cozy everyday living. In the foyer, a staircase is flanked by the dining and living rooms on either sides. The kitchen, with center island and full dining area, flows into a showstopping family room that transitions to a private office

    Nancy Pallotta Advisors Living - Winchester

    31 Coolidge Rd, Winchester, MA 01890
  • 19 Johnson Rd, Winchester, MA 01890
    19 Johnson Rd, Winchester, MA 01890
    19 Johnson Rd, 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
  • 60 Edward Dr Unit 60, Winchester, MA 01890
    60 Edward Dr Unit 60, Winchester, MA 01890
    60 Edward Dr Unit 60, 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
  • 7 Wainwright Rd Unit 22, Winchester, MA 01890
    7 Wainwright Rd Unit 22, Winchester, MA 01890
    7 Wainwright Rd Unit 22, 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
  • 23 Olde Village Dr, Winchester, MA 01890
    23 Olde Village Dr, Winchester, MA 01890
    23 Olde Village 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
  • 36 Oneida Rd, Winchester, MA 01890
    36 Oneida Rd, Winchester, MA 01890
    36 Oneida Rd, 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
  • 11 Plymouth Rd, Winchester, MA 01890
    11 Plymouth Rd, Winchester, MA 01890
    11 Plymouth Rd, 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
  • 14 Henry St, Winchester, MA 01890
    14 Henry St, Winchester, MA 01890
    14 Henry St, Winchester, MA 01890
    /42

    $1,517,500 Sold Jan 09, 2025

    • 3,091 Sq Ft
    • $491/SF
    • 7 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1957

    14 Henry St, Winchester, MA 01890

    Incredible value! Don’t miss this 6 BR, 3 full bathroom expanded colonial w/ over 3,000 square feet of living space tucked away in a charming Vinson Owen School neighborhood. This expansive home features an open concept, eat-in kitchen/family room w/ granite countertops, double ovens, large island, recessed lighting & cozy family room. The sunny kitchen also opens to a private backyard w/ stone

    Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

    14 Henry St, Winchester, MA 01890
  • 28 Thornberry Rd, Winchester, MA 01890
    28 Thornberry Rd, Winchester, MA 01890
    28 Thornberry Rd, Winchester, MA 01890
    /29

    $1,335,000 Sold Dec 27, 2024

    • 2,245 Sq Ft
    • $595/SF
    • 117 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1959

    28 Thornberry Rd, Winchester, MA 01890

    Welcome to 28 Thornberry! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining,

    Shaundize Moosavizadeh Coldwell Banker Realty - Boston

    28 Thornberry Rd, Winchester, MA 01890
  • 15 Westland Ave, Winchester, MA 01890
    15 Westland Ave, Winchester, MA 01890
    15 Westland Ave, Winchester, MA 01890
    /25

    $1,000,000 Sold Dec 19, 2024

    • 1,840 Sq Ft
    • $543/SF
    • 8 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1937

    15 Westland Ave, Winchester, MA 01890

    A dIamond in the rough!!! Are you a contractor or handy end user looking for a project in sought after WInchester? Look no further than this 1937, 4 bedroom Colonial brimming with potential. The charm of yesteryear shows through with custom built-ins, crown moldings, hardwood flooring and so much more. Full walk out unfinished basement with double soapstone sink and a full walk up attic lends

    Libby Rankin Hamill Berkshire Hathaway HomeServices Stephan Real Estate

    15 Westland Ave, Winchester, MA 01890
  • 31 Girard Rd, Winchester, MA 01890
    31 Girard Rd, Winchester, MA 01890
    31 Girard Rd, Winchester, MA 01890
    /38

    $1,650,000 Sold Dec 11, 2024

    • 3,158 Sq Ft
    • $522/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1975

    31 Girard Rd, Winchester, MA 01890

    Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you’ll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen, seamlessly connected to a bright and airy dining area. This space is perfect for hosting

    Philip Vita Compass

    31 Girard Rd, Winchester, MA 01890
  • 7 Wainwright Rd Unit 29, Winchester, MA 01890
    7 Wainwright Rd Unit 29, Winchester, MA 01890
    7 Wainwright Rd Unit 29, Winchester, MA 01890
    /40

    $1,225,000 Sold Dec 09, 2024

    • 3,350 Sq Ft
    • $366/SF
    • 27 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1988

    7 Wainwright Rd Unit 29, Winchester, MA 01890

    Imagine arriving home to peace & serenity at The Ledges, a hilltop oasis on Winchester's West side. This tranquil retreat offers carefree living & your private sanctuary. Relax in the fireplace living room, sliders to your private deck & expansive views. The main bedroom en suite, is conveniently located on the first floor. Second level finds a loft, skylit bonus room perfect for a home office,

    Joanne Sexeny Coldwell Banker Realty - Lexington

    7 Wainwright Rd Unit 29, Winchester, MA 01890
  • 62 Edward Dr, Winchester, MA 01890
    62 Edward Dr, Winchester, MA 01890
    62 Edward Dr, Winchester, MA 01890
    /30

    $900,000 Sold Nov 21, 2024

    • 1,857 Sq Ft
    • $485/SF
    • 6 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1985

    62 Edward Dr, Winchester, MA 01890

    Welcome to 62 Edward Drive in the sought-after Pepper Hill Estates. This spacious townhouse-style condo features two bedrooms and a versatile bonus room on the lower level, perfect for a home office, guest space, or playroom. The well-maintained home boasts an open living and dining area filled with natural light and a beautiful fireplace. The updated kitchen includes granite countertops, newer

    Melissa Perrone Better Homes and Gardens Real Estate - The Shanahan Group

    62 Edward Dr, Winchester, MA 01890
  • 43 Emerson Rd, Winchester, MA 01890
    43 Emerson Rd, Winchester, MA 01890
    43 Emerson Rd, Winchester, MA 01890
    /42

    $2,035,000 Sold Nov 19, 2024

    • 4,730 Sq Ft
    • $430/SF
    • 12 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1953

    43 Emerson Rd, Winchester, MA 01890

    See it to believe it! Don’t miss this sprawling 5 bed, 4 full bath Cape-style home in an idyllic Ambrose school neighborhood. 1st floor features mudroom w/entry from attached garage, laundry room w/sink, living room w/fireplace, bedroom, full bath, & dining area w/French doors to a deck. But the jewel of this floor is the recent addition of a stunning eat-in kitchen & sun-filled primary suite.

    Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

    43 Emerson Rd, Winchester, MA 01890
  • 5 Thoreau Cir, Winchester, MA 01890
    5 Thoreau Cir, Winchester, MA 01890
    /2

    $1,910,000 Sold Nov 04, 2024

    • 5,287 Sq Ft
    • $361/SF
    • 9 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1977

    5 Thoreau Cir, Winchester, MA 01890

    Welcome to this custom-built oversized ranch, cherished & meticulously maintained by the current owners. This idyllic property is situated on a large lot at the end of a cul-de-sac, abutting peaceful conservation land. The main level features grand scale rooms including a spacious eat in kitchen, 2 beautiful living rooms w/ wood burning fireplaces, a stunning dining room for holidays & dinner

    Kim Covino Compass

    5 Thoreau Cir, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Massachusetts Middlesex County Winchester West Side

Recently Sold Real Estate & Homes in West Side, Winchester

Learn more about living in West Side

Frequently Asked Questions

What is the average time to sell a house in West Side, MA?
The houses for sale in West Side, MA spend an average of 26 days on the market.
What is the number of active homes for sale in West Side, MA?
There are 10 active homes for sale in West Side, MA.

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 26 days on the market compared to the national average of 52 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,589,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,589,000
Median Single Family Sale Price
$1,771,049
Median 2 Bedroom Sale Price
$1,070,000
Average Price Per Sq Ft
$500
Number of Homes for Sale
10
Last 12 months Home Sales
52
Months of Supply
2.30
Median List Price
$1,697,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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