Recently Sold Homes near Winchester High School

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  /35

  $1,750,000 Sold Jun 17, 2025

  • 2,597 Sq Ft
  • $674/SF
  • 2 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1925

  18 Englewood Rd, Winchester, MA 01890

  OFFER ACCEPTED - Open Houses CANCELED This stunning, sun-filled home welcomes you with a front porch facing southwest for sunset views! Move right in and enjoy so many updates - new windows, new kitchen, new shared bath, new heating and cooling systems, new exercise/mudroom, new landscaping and so much more!!! With fabulous detail and a focus on energy efficiency, this home will win your heart

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  18 Englewood Rd, Winchester, MA 01890
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  /42

  $2,350,000 Sold Jun 16, 2025

  • 4,212 Sq Ft
  • $558/SF
  • 15 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1880

  19 Yale St, Winchester, MA 01890

  Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom

  Nancy Pallotta Advisors Living - Winchester

  19 Yale St, Winchester, MA 01890
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  /36

  $749,900 Sold Jun 13, 2025

  • 1,545 Sq Ft
  • $485/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1999

  7 Conant Rd Unit 34, Winchester, MA 01890

  Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of

  Melanie Lentini Leading Edge Real Estate

  7 Conant Rd Unit 34, Winchester, MA 01890
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  /40

  $3,025,000 Sold Jun 13, 2025

  • 5,198 Sq Ft
  • $582/SF
  • 50 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 1910

  21 Sheffield W, Winchester, MA 01890

  Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

  Kim Covino Compass

  21 Sheffield W, 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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  /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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  /23

  $1,182,000 Sold Jun 09, 2025

  • 1,520 Sq Ft
  • $778/SF
  • 24 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1929

  10 Allen Rd, Winchester, MA 01890

  Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the

  Sally Baldwin Coldwell Banker Realty - Lexington

  10 Allen Rd, Winchester, MA 01890
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  /41

  $2,850,000 Sold Jun 09, 2025

  • 4,325 Sq Ft
  • $659/SF
  • 8 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1953

  45 Brooks St, Winchester, MA 01890

  Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4BD 4 BA home offering a classic exterior with a stunning "must see" interior; featuring formal spaces great for entertaining blended w/casual living areas both inside & out w/ walls of floor to ceiling windows capturing the elements of

  Kim Covino Compass

  45 Brooks St, Winchester, MA 01890
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  /19

  $690,000 Sold Jun 06, 2025

  • 1,634 Sq Ft
  • $422/SF
  • 20 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1999

  7 Conant Rd Unit 60, Winchester, MA 01890

  OPEN HOUSE Sunday, May 18: 1-3:30PM. Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and

  Irene Novia Loka Matahari Real Estate LLC

  7 Conant Rd Unit 60, 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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  /38

  $1,475,000 Sold Jun 05, 2025

  • 2,897 Sq Ft
  • $509/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1934

  195 Mystic Valley Pkwy, Winchester, MA 01890

  Lovely brick home just up the road from EVERYTHING!!! Commuter Rail, Library, Schools, Shopping, Restaurants, Town Hall. Less than 9 miles to Boston! So close to the Middlesex Fells and the Tri-Community Greenway. Location, location, location - CHECK! Now the structure...classic brick home built to stand the test of time with BIG IMPROVEMENTS. Grand front to back living room with fireplace leads

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  195 Mystic Valley Pkwy, Winchester, MA 01890
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  /42

  $2,111,000 Sold Jun 05, 2025

  • 4,744 Sq Ft
  • $445/SF
  • 6 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1922

  14 Grove St, Winchester, MA 01890

  Located just outside the town center near Brooks neighborhood & the train to Boston! This spacious home has it all! Situated on a lovely level lot w/ 2 car garage & private yard, this updated move in ready home boasts an abundance of space w/ideal layout & large sun drenched eat in kitchen with skylights & bay window, adjacent family room, living room w/ fplc, formal dining, office, laundry & 2

  Kim Covino Compass

  14 Grove St, Winchester, MA 01890
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  /11

  $1,269,000 Sold Jun 04, 2025

  • 2,136 Sq Ft
  • $594/SF
  • 1 Day On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2025

  158 Swanton St Unit 160, Winchester, MA 01890

  Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

  Monte Marrocco Coldwell Banker Realty - Lexington

  158 Swanton St Unit 160, Winchester, MA 01890
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  /24

  $1,084,000 Sold Jun 04, 2025

  • 2,290 Sq Ft
  • $473/SF
  • 30 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2025

  160 Swanton St Unit 160, Winchester, MA 01890

  Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

  Monte Marrocco Coldwell Banker Realty - Lexington

  160 Swanton St Unit 160, 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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  /34

  $2,000,000 Sold Jun 02, 2025

  • 3,039 Sq Ft
  • $658/SF
  • 7 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1927

  11 Chesterford Rd E, Winchester, MA 01890

  Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly

  Joseph Pollack Redfin Corp.

  11 Chesterford Rd E, Winchester, MA 01890
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  /33

  $699,900 Sold May 30, 2025

  • 1,326 Sq Ft
  • $528/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1890

  32 Clark St, Winchester, MA 01890

  A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

  Rodrigo Serrano Leading Edge Real Estate

  32 Clark St, Winchester, MA 01890
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  /42

  $1,350,000 Sold May 30, 2025

  • 3,351 Sq Ft
  • $403/SF
  • 38 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1946

  34 Fells Rd, Winchester, MA 01890

  Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

  Andersen Group Realty Keller Williams Realty Boston Northwest

  34 Fells 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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  /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
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  /42

  $1,558,000 Sold May 29, 2025

  • 2,792 Sq Ft
  • $558/SF
  • 9 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1993

  24 Eugene Dr, Winchester, MA 01890

  Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layout plus amenities like central air, 1st floor laundry room, direct indoor access to a 2-car garage, and delightful wooded back yard are more outstanding details. The kitchen & family room at the back of the house will be everyone’s favorite gathering spot. The eat-in kitchen

  Andrea O'Reilly Keller Williams Realty Evolution

  24 Eugene Dr, Winchester, MA 01890
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  /42

  $1,475,000 Sold May 29, 2025

  • 3,067 Sq Ft
  • $481/SF
  • 9 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1961

  36 Winford Way, Medford, MA 02155

  Move right into this charming home in the heart of West Medford! Nestled in a prime location near Middlesex Fells and Playstead Park, this beautifully renovated home offers a perfect blend of modern upgrades & classic charm. Thoughtfully updated in 2018, with an additional renovation in 2020 that includes a spacious basement office suite, playroom, and ample storage space, this home is designed

  Andersen Group Realty Keller Williams Realty Boston Northwest

  36 Winford Way, Medford, MA 02155
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  /31

  $948,000 Sold May 29, 2025

  • 1,469 Sq Ft
  • $645/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1928

  79 Sylvester Ave, Winchester, MA 01890

  Discover where form meets function in this beautifully maintained home, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a quintessential location. Thoughtfully updated, the kitchen, exterior, and bedrooms reflect pride of ownership, showcasing care and attention

  Anne Spry Barrett Sotheby's International Realty

  79 Sylvester Ave, Winchester, MA 01890
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  /31

  $380,000 Sold May 23, 2025

  • 613 Sq Ft
  • $620/SF
  • 15 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1966

  200 Swanton St Unit 722, Winchester, MA 01890

  Top-Floor Penthouse Condo with Scenic Views at Parkview Condominiums Move right into this beautifully updated 1-bedroom, 1-bath top-floor unit at the highly desirable Parkview Condominiums in Winchester. Centrally located on the 7th floor, this penthouse offers stunning treetop and pond views from your private balcony—perfect for enjoying peaceful moments all year round. Inside, you'll find a

  Yang Liu Weston Realty LLC

  200 Swanton St Unit 722, Winchester, MA 01890
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  /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
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  /42

  $2,750,000 Sold May 19, 2025

  • 5,263 Sq Ft
  • $523/SF
  • 12 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1920

  35 Lawson Rd, Winchester, MA 01890

  Welcome 35 Lawson where elegance meets modern luxury in this exquisite 6-bedroom 4F, 2H bathroom residence. A stunning marble mudroom welcomes you into the home w/ heated floors leading into fabulous new custom kitchen featuring a large dining island, inset cabinets, Wolf/Sub-Zero appliances (2 dishwashers, 2 ovens/ steam oven, 2 fridge drawers) a sleek gas fireplace, built-in banquette & direct

  Kim Covino Compass

  35 Lawson Rd, Winchester, MA 01890
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  /42

  $2,499,000 Sold May 19, 2025

  • 4,270 Sq Ft
  • $585/SF
  • 0 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2024

  50 Winford Way, Winchester, MA 01890

  Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace, open dining leads to sitting room & out to a deck

  Kim Covino Compass

  50 Winford Way, Winchester, MA 01890
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  /38

  $2,600,000 Sold May 19, 2025

  • 4,060 Sq Ft
  • $640/SF
  • 88 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1912

  3 Lagrange St, Winchester, MA 01890

  Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting foyer welcomes you from a wrap-around porch into an open yet intimate layout connecting the kitchen, dining, and family rooms. A mudroom with marble checkered flooring and a walk-in pantry with a beverage fridge add practical luxury.

  Mark Donnellan Advisors Living - Winchester

  3 Lagrange St, Winchester, MA 01890
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  /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 Coldwell Banker Realty - Lexington

  6 Vinson Cir, Winchester, MA 01890
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  /13

  $680,000 Sold May 15, 2025

  • 968 Sq Ft
  • $702/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1963

  15 Charles Rd, Winchester, MA 01890

  Rarely available 2 bedrooms 2 bathrooms townhouse at The Residences in Winchester! Here is your chance to move into a wonderful community. This unit has a private level large back yard, where you can have your own garden area. First floor features a living room-dining room and kitchen. Second floor has two bedrooms and two baths ( Master bedroom has a 3/4 bath). Recently renovated and freshly

  Beiping Zhao Jack Gately Real Estate, LLC

  15 Charles Rd, Winchester, MA 01890
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  /42

  $2,200,000 Sold May 09, 2025

  • 4,097 Sq Ft
  • $537/SF
  • 24 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1939

  88 Arlington St, Winchester, MA 01890

  Welcome to this warm & inviting home nestled amidst the serene landscapes of the Winchester Country Club. A Royal Barry Wills design, showcasing 5-beds, 3.5-baths, w/4 fireplaces & attached direct entry 2 car garage! This home has w/ an abundance of charm in every room; the spacious living areas are warm and inviting & flooded with natural light, showcasing original woodwork & oversized wood

  Kim Covino Compass

  88 Arlington St, Winchester, MA 01890
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  /39

  $3,199,000 Sold May 09, 2025

  • 6,694 Sq Ft
  • $478/SF
  • 9 Days On Market

  • 7 Beds
  • 5 Baths
  • Built 1880

  12 Prospect St, Winchester, MA 01890

  Exuding elegant luxury, this fully renovated Victorian boasts a carriage house and extraordinary grounds, in one of Winchester’s most coveted neighborhoods! A show-stopping chef's kitchen boasts state-of-the-art Thermador appliances, wine tower, 42'' fridge, a 6-burner gas range, a quartzite island with seating for 4, & a breakfast nook overlooking a beautifully landscaped large yard with rock

  Nancy Pallotta Advisors Living - Winchester

  12 Prospect 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
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  /38

  $2,850,000 Sold May 07, 2025

  • 5,044 Sq Ft
  • $565/SF
  • 5 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2025

  22 Standish Ln, Winchester, MA 01890

  This distinguished residence, built by premier local developer, represents the pinnacle of elegant living! Soaring ~9' ceilings & pristine hardwood floors set an impressive tone in this meticulously crafted new construction offering 4 levels of refined living space. The eye-catching foyer ushers guests into a realm of sophisticated design, where premium finishes & high-end appliances elevate

  Michaela Mahtani Leading Edge Real Estate

  22 Standish Ln, Winchester, MA 01890
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  /27

  $975,000 Sold May 07, 2025

  • 2,873 Sq Ft
  • $339/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  18 Pine Grove Park, Winchester, MA 01890

  Beautifully maintained one owner Cape, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a terrific location. Three bedrooms, two full baths, with a bonus room offer flexibility and space to make it your own. Gleaming hardwood floors throughout, with built-ins in

  Michele Forester EXIT Premier Real Estate

  18 Pine Grove Park, Winchester, MA 01890
• 

  

  /20

  $2,398,000 Sold May 06, 2025

  • 4,468 Sq Ft
  • $537/SF
  • 26 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1937

  74 Hillcrest Pkwy, Winchester, MA 01890

  Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fells Reservation on one of Winchester's most picturesque streets! First floor seamlessly blends living, dining, & kitchen areas. Living room has wood burning fireplace & custom built-in shelves. Dining room offers delightful space for cozy gatherings and the spacious eat-in kitchen

  Ann Hogstadius RE/MAX Real Estate Center

  74 Hillcrest Pkwy, Winchester, MA 01890
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  /36

  $730,000 Sold May 01, 2025

  • 1,393 Sq Ft
  • $524/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1890

  21 Shepard Ct, Winchester, MA 01890

  Welcome to 21 Shepard Court, a beautifully renovated townhouse nestled in a quiet cul-de-sac. This 2+ bedroom, 1-bathroom home offers four levels of living space with modern upgrades & timeless charm. Renovated features: The main level boasts a high-end kitchen with new quartz countertops stainless steel appliances, custom cabinetry, & eat in island. The bathroom has been fully upgraded with

  Abe Guillen Encore Realty

  21 Shepard Ct, Winchester, MA 01890
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  /39

  $4,650,000 Sold May 01, 2025

  • 7,779 Sq Ft
  • $598/SF
  • 5 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 1915

  19 Rangeley Rd, Winchester, MA 01890

  A treasure. That's how this residence is viewed, throughout town, throughout the decades. One family had the vision to bring this cherished home back to life with a renovation that bestowed the best of everything. On Rangeley Road, gentle rolling lawns fold softly into a private, winding road. Gorgeous architecture graces every lot and ancient oaks stand sentry. Located just steps to the town

  Nancy Pallotta Advisors Living - Winchester

  19 Rangeley Rd, Winchester, MA 01890
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  /36

  $1,600,000 Sold Apr 30, 2025

  • 2,809 Sq Ft
  • $570/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2004

  24 Water St, Winchester, MA 01890

  Discover the warmth and charm of this inviting New England Colonial, newly built in 2004. This sun-filled home features three bedrooms, 3.5 bathrooms, and a flexible floor plan. First floor features a large family room, dining room, updated kitchen with SS appliances, abundant custom cabinetry, a half bath, mudroom, and a separate living room. Second floor offers a sizable primary suite with a

  Domingo Medina Coldwell Banker Realty - Lexington

  24 Water St, Winchester, MA 01890
• 

  

  /30

  $1,200,000 Sold Apr 30, 2025

  • 2,060 Sq Ft
  • $583/SF
  • 8 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1926

  36 Lebanon St, Winchester, MA 01890

  Nicely updated home in desirable Muraco district! This home has been meticulously maintained & features many recent updates including newer windows, central air conditioning & updated systems. Enjoy the sun drenched spaces from the spacious living room w/ fplc & bay window to the charming dining room w/ china cabinet, sunny eat-in kitchen, office, plus 3 season porch & 1/2 bath complete the first

  Kim Covino Compass

  36 Lebanon St, Winchester, MA 01890

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