Winchester, MA Homes

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  /31

  $3,390,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,847 Sq Ft

  25 Myopia Rd, Winchester, MA 01890

  A timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering tranquil views of lush gardens and rolling hills. Thoughtful architectural details enrich every space, while multiple patios and wrap-around porch create an effortless flow between indoor& outdoor. The gracious main level unfolds into beautifully connected living spaces, featuring an office, elegant dining

  Wenjun Cao Engel & Volkers Boston

  25 Myopia Rd, Winchester, MA 01890
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  /23

  $2,550 Per Month

  • 2 Beds
  • 1 Bath
  • 1,195 Sq Ft
  • Apartment for Rent

  26 Lebanon St Unit 26, Winchester, MA 01890

  This great second floor 2 bedroom is bright and spacious. The office leads to a three-season room. The entry hall leads to living room, dining room, and office. The full bath is flanked by 2 bedrooms. Eat in kitchen with pantry is spacious enough to have a dining table. Available immediately to qualified tenant.

  Anne Spry Barrett Sotheby's International Realty

  26 Lebanon St Unit 26, Winchester, MA 01890
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  /13

  $680,000 Sold May 15, 2025

  15 Charles Rd, Winchester, MA 01890

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Above List Price
  • $702/SF
  • 12 Days On Market

  Current Estimated Value $648,900

  Last Listing Agent Beiping Zhao Jack Gately Real Estate, LLC

  15 Charles Rd, Winchester, MA 01890
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  /42

  Est $2,937,617 Not Listed For Sale

  19 Socrates Way, Winchester, MA 01890

  • 5 Beds
  • 6 Baths
  • 5,678 Sq Ft
  • Built 1994

  19 Socrates Way, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $467/SF
  • 12 Days On Market

  • Last Sold Price $2,650,000
  • Jun 03, 2024

  Last Listing Agent Lucille Murray Gibson Sotheby's International Realty
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  /42

  $3,450,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 5,128 Sq Ft

  50 Oxford St, Winchester, MA 01890

  **OFFER ACCEPTED OPEN HOUSE CANCELED** Set on an oversized lot w/ a stunning in-ground pool, jacuzzi, pool house & expansive level lawn, this exceptional home blends luxury, privacy, & modern living. Expanded & extensively renovated top-to-bottom, the home features an open layout w/ designer kitchen, spacious family room & oversized attached 2-car garage. Walls of windows & French doors overlook

  Kim Covino Compass

  50 Oxford St, Winchester, MA 01890
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  /22

  $8,000 Per Month

  • 3 Beds
  • 2 Baths
  • 3,500 Sq Ft
  • House for Rent

  31 Fells Rd, Winchester, MA 01890

  Available for short term rental through October 2025 with flexible lease options. Prime location on desirable Fells Road with easy access to Middlesex Fells trails and conservation land. This charming home sits on a beautiful lot and offers a spacious first floor featuring a large family room, updated kitchen, and a den or optional first floor bedroom. Enjoy the screened porch overlooking the

  Kim Covino Compass

  31 Fells Rd, Winchester, MA 01890
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  /23

  $950,000 Sold Dec 04, 2025

  16 Park Ave Unit 1, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft
  • Built 1915

  Last Sold Summary

  • 5% Below List Price
  • $619/SF
  • 26 Days On Market

  Current Estimated Value $952,320

  Last Listing Agent Andrea Mackey The Agency Boston

  16 Park Ave Unit 1, Winchester, MA 01890
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  /42

  Est $2,707,511 Not Listed For Sale

  40 Amberwood Dr, Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 5,713 Sq Ft
  • Built 1983

  40 Amberwood Dr, Winchester, MA 01890

  Last Sold Summary

  • 18% Above List Price
  • $403/SF
  • 8 Days On Market

  • Last Sold Price $2,300,000
  • Jul 21, 2023

  Last Listing Agent Kim Covino Compass
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  /42

  $4,449,000

  • 5 Beds
  • 5.5 Baths
  • 6,526 Sq Ft

  4 Dartmouth St, Winchester, MA 01890

  Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully maintained and updated, blending classic architecture with modern comfort. This 5 bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and

  Nancy Pallotta Gibson Sotheby's International Realty

  4 Dartmouth St, Winchester, MA 01890
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  /29

  $8,000 Per Month

  • 5 Beds
  • 3.5 Baths
  • 3,369 Sq Ft
  • House for Rent

  54 Spruce St, Winchester, MA 01890

  Well maintained 5 bedroom, 3.5-bath single-family home built in 2004, ideally located within walking distance to the town center, schools, shopping, and the commuter rail. This spacious home features hardwood floors, central AC, and a thoughtfully designed layout perfect for everyday living and entertaining. The bright kitchen flows into generous living and dining spaces, while the finished

  Dylan Archambault Archambault Real Estate

  54 Spruce St, Winchester, MA 01890
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  /42

  $2,650,000 Sold Apr 21, 2026

  45 Bacon St, Winchester, MA 01890

  • 7 Beds
  • 8 Baths
  • 7,043 Sq Ft
  • Built 2011

  Last Sold Summary

  • 11% Below List Price
  • $376/SF
  • 29 Days On Market

  Current Estimated Value $2,948,019

  Last Listing Agent Kim Covino Compass

  45 Bacon St, Winchester, MA 01890
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  /38

  Est $1,878,528 Not Listed For Sale

  45 Amberwood Dr, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 4,008 Sq Ft
  • Built 1983

  45 Amberwood Dr, Winchester, MA 01890

  Last Sold Summary

  • 21% Above List Price
  • $387/SF
  • 3 Days On Market

  • Last Sold Price $1,550,000
  • Jun 02, 2023

  Last Listing Agent Kim Covino Compass
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  /35

  $2,395,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 4,087 Sq Ft

  15 Gershon Way Unit 15, Winchester, MA 01890

  Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual

  Moira Lown Coldwell Banker Realty - Wellesley

  15 Gershon Way Unit 15, Winchester, MA 01890
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  /18

  $5,900 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Apartment for Rent

  44 Spruce St Unit 2, Winchester, MA 01890

  Spacious 4-bedroom, 2.5-bath townhouse ideally located within walking distance to the town center, schools, and commuter rail. This well-maintained home features beautiful hardwood flooring throughout, a bright and functional layout, and generous living space perfect for everyday living and entertaining. Enjoy outdoor living with a private deck and a fenced-in yard. Additional highlights include

  Dylan Archambault Archambault Real Estate

  44 Spruce St Unit 2, Winchester, MA 01890
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  /42

  $1,700,000 Sold May 01, 2026

  114 Johnson Rd, Winchester, MA 01890

  • 3 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 1880

  Last Sold Summary

  • 5% Below List Price
  • $534/SF
  • 22 Days On Market

  Current Estimated Value $1,760,520

  Last Listing Agent Rosemary Kelleher LAER Realty Partners

  114 Johnson Rd, Winchester, MA 01890
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  /36

  Est $2,191,333 Not Listed For Sale

  9 Amberwood Dr, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,257 Sq Ft
  • Built 2021

  9 Amberwood Dr, Winchester, MA 01890

  Last Sold Summary

  • 14% Above List Price
  • $451/SF
  • 195 Days On Market

  • Last Sold Price $1,920,000
  • Nov 01, 2023

  Last Listing Agent Nicholas Gatto Better Homes and Gardens Real Estate - The Shanahan Group
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  /42

  $2,999,000

  • 5 Beds
  • 4 Baths
  • 4,028 Sq Ft

  10 Dartmouth St, Winchester, MA 01890

  Winchester's premiere location! This stunning waterfront gem is perfectly situated on Winter Pond, offering over 80 feet of direct water frontage with expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this property presents a rare opportunity to enjoy water activities such as kayaking, paddleboarding, fishing, ice skating and hockey all

  Kim Covino Compass

  10 Dartmouth St, Winchester, MA 01890
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  /8

  $4,100 Per Month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  63 Holland St Unit 63, Winchester, MA 01890

  Welcome to 63 Holland St in Winchester! A beautifully renovated 2-bedroom, 1-bath apartment offering a perfect mix of charm and modern updates. This bright and inviting first-floor unit features hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom includes a walk-in tiled

  Issam Dib Skyline Realty

  63 Holland St Unit 63, Winchester, MA 01890
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  /42

  $1,830,000 Sold Feb 26, 2026

  35 Glen Green, Winchester, MA 01890

  • 4 Beds
  • 2 Baths
  • 3,509 Sq Ft
  • Built 1934

  Last Sold Summary

  • 8% Below List Price
  • $522/SF
  • 36 Days On Market

  Current Estimated Value $1,873,301

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

  35 Glen Green, Winchester, MA 01890
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  /42

  Est $2,388,816 Not Listed For Sale

  5 Pilgrim Dr, Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 4,138 Sq Ft
  • Built 1962

  5 Pilgrim Dr, Winchester, MA 01890

  Last Sold Summary

  • $580/SF
  • 5 Days On Market

  • Last Sold Price $2,400,000
  • Oct 28, 2024

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  /42

  $3,099,000

  • 5 Beds
  • 4.5 Baths
  • 5,406 Sq Ft

  10 Rangeley Rd, Winchester, MA 01890

  Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a

  Karima Alami Compass

  10 Rangeley Rd, Winchester, MA 01890
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  /20

  $4,850 Per Month

  • 4 Beds
  • 1.5 Baths
  • 1,700 Sq Ft
  • House for Rent

  488 Washington St, Winchester, MA 01890

  Charming, updated Colonial filled with character. This beautiful home features an updated kitchen that is bright and open and offers granite counter tops, stainless steel appliances, frameless maple cabinets & recessed lights. Updated bathrooms. Hardwood floors throughout the 1st & 2nd floors. Access the stone and granite patio through French doors in the dining room. The patio is fenced in and

  Matthew Pierce True North Realty

  488 Washington St, Winchester, MA 01890
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  /15

  $930,000 Sold Jun 20, 2025

  48 Tremont St, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,333 Sq Ft
  • Built 1959

  Last Sold Summary

  • 7% Below List Price
  • $399/SF
  • 25 Days On Market

  Current Estimated Value $991,932

  Last Listing Agent Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

  48 Tremont St, Winchester, MA 01890
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  /42

  Est $1,996,548 Not Listed For Sale

  15 Pilgrim Dr, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 4,256 Sq Ft
  • Built 1959

  15 Pilgrim Dr, Winchester, MA 01890

  Last Sold Summary

  • 6% Above List Price
  • $441/SF
  • 13 Days On Market

  • Last Sold Price $1,875,000
  • May 31, 2023

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  /23

  $688,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  666 Main St Unit 315, Winchester, MA 01890

  Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry, assigned parking,

  Jing Chen Peace of Mind Realty

  666 Main St Unit 315, Winchester, MA 01890
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  /15

  $2,675 Per Month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  200 Swanton St Unit T37, Winchester, MA 01890

  ALL UTILITIES INCLUDED!!!! Ground Level with Private Entrance. NO STAIRS! Lovely terrace level unit at Parkview available 5/1 This immaculate and well cared for home includes dishwasher, on site laundry, parking,Situated in a very convenient location, near everything! Enjoy the beautifully landscaped common area with pool, cabana and picnic table. Super Value with ALL UTILITIES INCLUDED make this

  Mary Doyle Berkshire Hathaway HomeServices Commonwealth Real Estate

  200 Swanton St Unit T37, Winchester, MA 01890
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  /42

  $1,330,000 Sold Apr 14, 2026

  40 Pickering St, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,454 Sq Ft
  • Built 1870

  Last Sold Summary

  • 6% Above List Price
  • $542/SF
  • 0 Days On Market

  Current Estimated Value $1,232,664

  Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

  40 Pickering St, Winchester, MA 01890
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  /40

  Est $1,410,454 Not Listed For Sale

  16 Johnson Rd, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 3,142 Sq Ft
  • Built 1958

  16 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 1% Below List Price
  • $452/SF
  • 6 Days On Market

  • Last Sold Price $1,420,000
  • Apr 17, 2024

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty
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  /36

  $2,000,000

  • 6 Beds
  • 5 Baths
  • 3,403 Sq Ft

  6 Ivy Cir, Winchester, MA 01890

  Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

  Valerie Post Engel & Volkers Boston

  6 Ivy Cir, Winchester, MA 01890
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  /35

  $1,750,000 Sold Jun 17, 2025

  18 Englewood Rd, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 2,597 Sq Ft
  • Built 1925

  Last Sold Summary

  • 6% Above List Price
  • $674/SF
  • 2 Days On Market

  Current Estimated Value $1,661,866

  Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  18 Englewood Rd, Winchester, MA 01890
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  /42

  Est $1,876,739 Not Listed For Sale

  19 Johnson Rd, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 4,318 Sq Ft
  • Built 1956

  19 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 1% Below List Price
  • $438/SF
  • 7 Days On Market

  • Last Sold Price $1,890,000
  • Mar 28, 2025

  Last Listing Agent Philip Vita Compass
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  /13

  $259,000

  • 1 Bath
  • 394 Sq Ft

  200 Swanton St Unit 538, Winchester, MA 01890

  Michael Masci North Atlantic Realty Group

  200 Swanton St Unit 538, Winchester, MA 01890
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  /42

  $2,890,000 Sold Aug 14, 2025

  21 Fernway, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 5,386 Sq Ft
  • Built 1963

  Last Sold Summary

  • $537/SF
  • 9 Days On Market

  Current Estimated Value $2,899,664

  Last Listing Agent Kim Covino Compass

  21 Fernway, Winchester, MA 01890
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  /33

  Est $1,909,493 Not Listed For Sale

  8 Olde Lyme Rd, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 4,603 Sq Ft
  • Built 1960

  8 Olde Lyme Rd, Winchester, MA 01890

  Last Sold Summary

  • 5% Above List Price
  • $396/SF
  • 2 Days On Market

  • Last Sold Price $1,825,000
  • May 23, 2024

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty
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  /40

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,605 Sq Ft

  7 Sherman Place, Winchester, MA 01890

  Welcome to this sun-drenched newer construction & freshly updated 4 Bed 2.5 Bath luxury townhome, set on a quiet cul-de-sac with a private, professionally landscaped yard & secret garden. This spacious home lives like a free standing house with a thoughtful layout designed for both everyday living and entertaining. Highlights include soaring 9-foot ceilings, oversized windows & high efficiency

  Kim Covino Compass

  7 Sherman Place, Winchester, MA 01890
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  /30

  $900,000 Sold Oct 20, 2025

  171 Swanton St Unit 5, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 1,843 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Above List Price
  • $488/SF
  • 8 Days On Market

  Current Estimated Value $910,308

  Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

  171 Swanton St Unit 5, Winchester, MA 01890
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  /42

  Est $1,769,581 Not Listed For Sale

  8 Hawthorne Rd, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 3,315 Sq Ft
  • Built 1959

  8 Hawthorne Rd, Winchester, MA 01890

  Last Sold Summary

  • 4% Above List Price
  • $513/SF
  • 4 Days On Market

  • Last Sold Price $1,700,000
  • Aug 01, 2024

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty
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  /34

  $1,799,000 Pending

  • 5 Beds
  • 4 Baths
  • 4,334 Sq Ft

  237 Swanton St, Winchester, MA 01890

  **Unbelievable deal!! **NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring

  Kim Covino Compass

  237 Swanton St, Winchester, MA 01890
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  /32

  $868,000 Sold Sep 04, 2025

  235 Cross St, Winchester, MA 01890

  • 3 Beds
  • 1.5 Baths
  • 1,931 Sq Ft
  • Built 1956

  Last Sold Summary

  • 16% Above List Price
  • $450/SF
  • 8 Days On Market

  Current Estimated Value $905,695

  Last Listing Agent Melanie Lentini Leading Edge Real Estate

  235 Cross St, Winchester, MA 01890
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  /42

  Est $2,322,759 Not Listed For Sale

  239 Ridge St, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,473 Sq Ft
  • Built 2018

  239 Ridge St, Winchester, MA 01890

  Last Sold Summary

  • 3% Above List Price
  • $506/SF
  • 5 Days On Market

  • Last Sold Price $2,265,000
  • Jul 13, 2023

  Last Listing Agent Kim Covino Compass

Showing Results 121 - 160, Page 4 of 18