Winchester, MA Homes

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  /37

  Est $1,380,571 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,597 Sq Ft

  22 Albamont Rd, Winchester, MA 01890

  22 Albamont Rd, Winchester, MA 01890
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  /36

  $1,599,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,279 Sq Ft

  73 Grove St, Winchester, MA 01890

  This stunning 4-bedroom Center Entrance Colonial in the desirable Ambrose School District has been beautifully updated for modern living. A complete first-floor renovation features a reimagined layout with a custom-designed kitchen boasting Thermador and Bosch appliances, marble and quartzite counters, walk-in pantry, and a bar w/ beverage fridge. Spacious, light-filled rooms showcase gleaming

  Monte Marrocco Coldwell Banker Realty - Lexington

  73 Grove St, Winchester, MA 01890
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  /39

  $1,149,000 Sold Jul 31, 2025

  • 2,300 Sq Ft
  • $500/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2017

  83 Canal St Unit 85, Winchester, MA 01890

  This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary

  Mary O'Hagan Barrett Sotheby's International Realty

  83 Canal St Unit 85, Winchester, MA 01890
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  /31

  Est $1,146,237 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,321 Sq Ft

  23 New Meadows Rd, Winchester, MA 01890

  23 New Meadows Rd, Winchester, MA 01890
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  /42

  $1,729,000 Pending

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

  4 Aricia Ln, Winchester, MA 01890

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

  The McLaren D'Agostino Team Compass

  4 Aricia Ln, Winchester, MA 01890
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  /42

  $2,635,000 Sold Jul 31, 2025

  • 5,354 Sq Ft
  • $492/SF
  • 117 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1850

  8 Chestnut St, Winchester, MA 01890

  Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and

  The McLaren D'Agostino Team Compass

  8 Chestnut St, Winchester, MA 01890
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  /37

  Est $1,429,278 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,386 Sq Ft

  15 New Meadows Rd, Winchester, MA 01890

  15 New Meadows Rd, Winchester, MA 01890
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  /37

  $1,649,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,508 Sq Ft

  166 Forest St, Winchester, MA 01890

  The buyer got cold feet. Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading

  Ning Sun United Real Estate, LLC

  166 Forest St, Winchester, MA 01890
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  /29

  $1,300,000 Sold Jul 30, 2025

  • 2,238 Sq Ft
  • $581/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1905

  49 Lincoln St, Winchester, MA 01890

  Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking

  Vantage Point Team William Raveis R.E. & Home Services

  49 Lincoln St, Winchester, MA 01890
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  /25

  Est $1,604,312 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,139 Sq Ft

  11 New Meadows Rd, Winchester, MA 01890

  11 New Meadows Rd, Winchester, MA 01890
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  /41

  $1,125,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  89 Main St, Winchester, MA 01890

  Welcome to this charming Cape on a spacious corner lot in Winchester. The main level offers hardwood floors, a front-to-back living room with fireplace and built-ins, a dining room with corner hutch, and a half bath. The kitchen features granite counters, stainless steel appliances, abundant cabinetry, and a breakfast island that opens to the cathedral-ceiling family room. A side entry with

  Andersen Group Realty Keller Williams Realty Boston Northwest

  89 Main St, Winchester, MA 01890
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  /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
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  /36

  Est $1,824,106 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,432 Sq Ft

  21 Westland Ave, Winchester, MA 01890

  21 Westland Ave, Winchester, MA 01890
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  /39

  $3,599,000 Pending

  • 6 Beds
  • 4.5 Baths
  • 5,876 Sq Ft

  5 Stratford Rd, Winchester, MA 01890

  This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

  Kim Covino Compass

  5 Stratford Rd, Winchester, MA 01890
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  /42

  $2,690,000 Sold Jul 30, 2025

  • 4,704 Sq Ft
  • $572/SF
  • 6 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1954

  34 Swan Rd, Winchester, MA 01890

  Situated in the prestigious Myopia Hill neighborhood, this exceptional sprawling ranch offers a rare combination of timeless elegance & modern comfort. Set on a lush, private acre, offering nearly 4,500 sq ft of beautifully maintained living space designed for both everyday living & grand-scale entertaining. Exquisite custom woodwork, built-ins & moldings lend sophistication throughout.

  Laurie Cappuccio Classified Realty Group

  34 Swan Rd, Winchester, MA 01890
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  /40

  Est $1,702,069 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,414 Sq Ft

  23 Westland Ave, Winchester, MA 01890

  23 Westland Ave, Winchester, MA 01890
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  /12

  $795,000 Pending

  • Land
  • 0.44 Acre
  • $1,806,818 per Acre

  14 Cross St, Woburn, MA 01801

  ATTENTION developers, contractors, investors and future homeowners – recently reconfigured 14 Cross Street located immediately over the WINCHESTER line is an attractive sized residential lot consisting of 19,277 square feet of land (see attached recorded plan, Lot 1) Lot is zoned R-2 (Per Building Department - single or 2 family structure permitted.) Currently situated on the lot is a building

  Donna Bozza Barrett Sotheby's International Realty

  14 Cross St, Woburn, MA 01801
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  /30

  $1,207,500 Sold Jul 24, 2025

  • 1,573 Sq Ft
  • $768/SF
  • 20 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1910

  18 Brookside Ave, Winchester, MA 01890

  Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to a bright bow front living room w/ high ceilings, that flows into the dining room & beautifully updated kitchen w/ stainless appliances & custom cabinetry w/ generous counter space. Off the kitchen, there’s a half bath and a bonus room—great as an office, playroom, or casual

  Kim Covino Compass

  18 Brookside Ave, Winchester, MA 01890
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  /41

  Est $2,798,258 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,100 Sq Ft

  14 Seneca Rd, Winchester, MA 01890

  14 Seneca Rd, Winchester, MA 01890
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  /32

  $715,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,596 Sq Ft

  171 Swanton St Unit 73, Winchester, MA 01890

  Welcome to The Village in Winchester! This picturesque 80-unit condominium community is set along conservation land and the Aberjona River. Unit 73 is a spacious, 2-bedroom, 2.5-bath end-unit townhouse with rare offering of a first floor bonus room; den, home office, bedroom, you decide! The first floor also offers a living room with skylight and fireplace, kitchen, dining room, half bath and

  John and Maria Reilly JMR Real Estate Group LLC

  171 Swanton St Unit 73, Winchester, MA 01890
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  /39

  $950,000 Sold Jul 17, 2025

  • 1,540 Sq Ft
  • $617/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1875

  6 Francis Circuit Unit 6, Winchester, MA 01890

  Submerge yourself in historic elegance in this meticulously detailed Victorian home, brimming with classic design. Located on one of Winchester’s most serene and desirable cul-de-sacs, this stunning gem overflows with rich architectural details. Inside, you'll find three stately fireplaces, two oversized pocket doors, exquisite antique leaded light fixtures, stained glass, gleaming hardwood

  Katherine Waters-Clark Compass

  6 Francis Circuit Unit 6, Winchester, MA 01890
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  /40

  Est $1,873,456 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,158 Sq Ft

  49 Westland Ave, Winchester, MA 01890

  49 Westland Ave, Winchester, MA 01890
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  /42

  $3,750,000 Pending

  • 6 Beds
  • 3.5 Baths
  • 4,484 Sq Ft

  9 Lakeview Terrace, Winchester, MA 01890

  LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

  Kim Covino Compass

  9 Lakeview Terrace, Winchester, MA 01890
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  /34

  $680,000 Sold Jul 17, 2025

  • 1,160 Sq Ft
  • $586/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  7 Conant Rd Unit 23, Winchester, MA 01890

  Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts’ top-rated school districts. Located in the desirable Lynch Elementary district, which will open a brand-new school building this fall. This move-in ready home has just been freshly painted, with brand-new kitchen appliances and new carpeting throughout. The open-concept living and dining area

  Xin Cui Hooli Homes Boston

  7 Conant Rd Unit 23, Winchester, MA 01890
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  /42

  Est $2,802,164 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,315 Sq Ft

  6 Agawam Rd, Winchester, MA 01890

  6 Agawam Rd, Winchester, MA 01890
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  /37

  $679,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft

  7 Conant Rd Unit 20, Winchester, MA 01890

  Rarely available and beautifully renovated first-floor unit at The Willows designed with everyday functionality in mind. This one-story unit offers stair-free access and living, along with easy accessibility from the adjacent one-car garage with an attic and a tandem parking spot. Upon entry, you’ll find an inviting open concept living and dining area with freshly installed hardwood flooring, a

  Brian Woods Woods Properties Inc.

  7 Conant Rd Unit 20, Winchester, MA 01890
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  /32

  $1,280,000 Sold Jul 16, 2025

  • 2,137 Sq Ft
  • $599/SF
  • 21 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2015

  18 Hemingway St, Winchester, MA 01890

  This COMPLETEDLY GUTTED AND REBUILT IN 2015 5B3.5B colonia-preserving a portion of original foundation, is located in a quiet neighborhood yet just minutes to Town Center, Elementary & High School, Town beach, Horn Pond, Fells Reservation, commuter rail station/Bus 134 to Wellington T. The architect-designed home features hardwood flooring throughout, high ceiling & abundant natural light. 1st

  Julia Xie Keller Williams Realty-Merrimack

  18 Hemingway St, Winchester, MA 01890
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  /39

  Est $1,604,351 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,428 Sq Ft

  21 Samoset Rd, Winchester, MA 01890

  21 Samoset Rd, Winchester, MA 01890
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  /40

  $1,499,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,351 Sq Ft

  19 Cox Rd, Winchester, MA 01890

  Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w

  Kim Covino Compass

  19 Cox Rd, Winchester, MA 01890
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  /25

  $1,226,000 Sold Jul 15, 2025

  • 2,534 Sq Ft
  • $484/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1980

  8 Ware Rd, Winchester, MA 01890

  Tucked into the desirable Winchester Highlands and abutting the Middlesex Fells, 8 Ware Road offers space, comfort, and a flexible footprint. This well-maintained ranch features 3 bedrooms on the main level, including a primary suite with full bath, plus a finished basement with a spacious family room, walk-out sliding patio door, large flex space, & bonus 4th bedroom. The kitchen includes modern

  Alex Navarro Coldwell Banker Realty - Beverly

  8 Ware Rd, Winchester, MA 01890
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  /28

  Est $1,792,628 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,800 Sq Ft

  5 Manomet Rd, Winchester, MA 01890

  5 Manomet Rd, Winchester, MA 01890
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  /40

  $1,600,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,331 Sq Ft

  149 Horn Pond Brook Rd, Winchester, MA 01890

  Picture perfect cape style home across from the Lynch Elementary School. This beautiful home on a corner lot checks all the boxes with 4/5 bedrooms on 2 floors and 2 full baths. Extra bonus space in lower level for home office or gym. Huge, beautiful yard that is perfect for outdoor recreation. Pretty eat in kitchen has direct entry to deck. This custom built home has been lovingly maintained

  Nancy McLaughlin Redfin Corp.

  149 Horn Pond Brook Rd, Winchester, MA 01890
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  /32

  $1,115,000 Sold Jul 15, 2025

  • 1,978 Sq Ft
  • $564/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1951

  48 Winford Way, Winchester, MA 01890

  Welcome to 48 Winford Way, a three bed, two bath Cape on a lovely level lot with a family room addition and a garage. A perfect starter home or downsizer with a full bath on each floor. Living room with large windows and a fireplace, dining room with an impressive chandelier and built-in china cabinet, eat-in kitchen with quartz countertops, tiled backsplash, and pantry closet. First floor family

  Rebecca Brennan Better Homes and Gardens Real Estate - The Shanahan Group

  48 Winford Way, Winchester, MA 01890
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  /36

  Est $2,246,862 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,871 Sq Ft

  111 Arlington St, Winchester, MA 01890

  111 Arlington St, Winchester, MA 01890
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  /35

  $1,060,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,849 Sq Ft

  62 Richardson St, Winchester, MA 01890

  Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly situated on a large corner lot. Venture into Unit 1 through the all seasons porch. The kitchen offers ample cabinet space, center island, & breakfast nook. Two bedrooms on level 1, both w/ ample closet storage. Full bath w/

  Frank Ventresca Strategy Street

  62 Richardson St, Winchester, MA 01890
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  /32

  $1,280,000 Sold Jul 15, 2025

  • 2,349 Sq Ft
  • $545/SF
  • 6 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1948

  25 Canterbury Rd, Winchester, MA 01890

  Don't miss your opportunity to own on Canterbury Road! This sun-drenched, 4-bedroom home with hardwood flooring offers an open and classic layout. Enjoy the spacious living room with built-ins, four, second floor bedrooms, and an expansive .37 acre lot. The versatile family room provides flexible space for a home office, playroom, or guest space! Imagine evenings on the covered porch or patio,

  Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

  25 Canterbury Rd, Winchester, MA 01890
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  /41

  Est $2,728,264 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,830 Sq Ft

  108 Arlington St, Winchester, MA 01890

  108 Arlington St, Winchester, MA 01890
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  /2

  $999,999 Pending

  • 2 Beds
  • 1 Bath
  • 1,666 Sq Ft

  26 North Gateway, Winchester, MA 01890

  LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or restoration All offers must be on attached OFFER TO PURCHASE form and prior to entering property the attached " Hold Harmless" agreement must be signed. All offers must include the OTP, Proof of funds and/or preapproval and copy of

  Robert Dell Homes Unlimited

  26 North Gateway, Winchester, MA 01890
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  /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
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  /42

  Est $2,198,525 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft

  20 Westland Ave, Winchester, MA 01890

  20 Westland Ave, Winchester, MA 01890

Showing Results 241 - 280, Page 7 of 18