Winchester, MA Homes

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  $1,700,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,500 Sq Ft

  307 Cross St, Winchester, MA 01890

  Thoughtfully reimagined & expanded in 2019, this sophisticated colonial offers 5-6 bedrooms & 5 baths with a beautiful open floor plan - perfect for a growing family or multi-generational living. A striking granite kitchen with crisp white cabinetry, premium stainless appliances & oversized island flows seamlessly into the dining area - ideal for everyday living & refined entertaining. A

  Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

  307 Cross St, Winchester, MA 01890
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  /13

  $3,400

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Townhouse for Rent

  2 George Rd, Winchester, MA 01890

  Short-term lease is also available.Discover refined living in Winchester, Massachusetts - one of Boston's most desirable suburban communities. This 3-bedroom, 2-bathroom condo offers 1,232 square feet of well-designed living space. Whether you're relocating for work, on a professional assignment, or seeking a high-quality long-term rental in a neighborhood with top schools, this home

  2 George Rd, Winchester, MA 01890
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  /25

  $715,000 Sold Jun 27, 2025

  7 Conant Rd Unit 37, Winchester, MA 01890

  • 2 Beds
  • 2.5 Baths
  • 1,539 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $465/SF
  • 33 Days On Market

  Current Estimated Value $725,799

  Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Conant Rd Unit 37, Winchester, MA 01890
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  /42

  Est $2,179,464 Not Listed For Sale

  5 Partridge Ln, Winchester, MA 01890

  • 5 Beds
  • 4 Baths
  • 4,620 Sq Ft
  • Built 1967

  5 Partridge Ln, Winchester, MA 01890

  Last Sold Summary

  • 10% Above List Price
  • $428/SF
  • 6 Days On Market

  • Last Sold Price $1,977,000
  • Jun 30, 2023

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  /24

  $727,000

  • 2 Beds
  • 1 Bath
  • 1,029 Sq Ft

  115 Washington St Unit 2A, Winchester, MA 01890

  Newly Renovated! 2 Bd at Church Place in Winchester Center! This stunning corner unit renovation was just completed & is ideally located in the heart of the center. Perfect for down-sizers or anyone seeking easy living w/ access to the train, restaurants, shops & top-rated schools - all the conveniences right outside your door! This bright & airy unit offers an open floor plan w/ beautiful arched

  Kim Covino Compass

  115 Washington St Unit 2A, Winchester, MA 01890
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  /16

  $3,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

  9 Mount Vernon St Unit A, Winchester, MA 01890

  Beautiful, modern 3-bedroom, 2-bathroom unit located in the town's center! Steps to the commuter rail, shops and restaurants nearby. The unit ison the second floor, featuring an open floor plan with the kitchen (full stainless steel appliances) overseeing the dining area and living room, highceilings, large windows- great natural lighting, gleaming hardwood floors throughout, two full bathrooms,

  Anna Mean AC Realty

  9 Mount Vernon St Unit A, Winchester, MA 01890
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  /19

  $690,000 Sold Jun 06, 2025

  7 Conant Rd Unit 60, Winchester, MA 01890

  • 2 Beds
  • 2.5 Baths
  • 1,634 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $422/SF
  • 20 Days On Market

  Current Estimated Value $733,937

  Last Listing Agent Irene Novia Loka Matahari Real Estate LLC

  7 Conant Rd Unit 60, Winchester, MA 01890
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  /40

  Est $2,022,789 Not Listed For Sale

  89 Thornberry Rd, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 4,532 Sq Ft
  • Built 1964

  89 Thornberry Rd, Winchester, MA 01890

  Last Sold Summary

  • 12% Above List Price
  • $397/SF
  • 12 Days On Market

  • Last Sold Price $1,799,000
  • Jul 18, 2023

  Last Listing Agent Kim Covino Compass
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  /35

  $3,399,000

  • 7 Beds
  • 7.5 Baths
  • 7,226 Sq Ft

  1 Plymouth Rd, Winchester, MA 01890

  Discover a beautifully reimagined home in one of Winchester’s most sought-after neighborhoods, offering exceptional space, comfort, and convenience in a truly prime location. With 7 bedrooms, 7 full baths, and 1 half bath, 1 Plymouth has been thoughtfully expanded and rebuilt with high-end finishes throughout to suit today’s lifestyle. At the heart of the home is a stunning fireplaced family room

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  1 Plymouth Rd, Winchester, MA 01890
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  $15,000 Per Month

  • 5 Beds
  • 4.5 Baths
  • 5,820 Sq Ft
  • House for Rent

  186 Ridge St, Winchester, MA 01890

  Flexible rental options available - property can be delivered fully furnished or unfurnished, depending on tenant preference. Beautiful new construction home located on the West Side of Town and proudly situated on over an acre lot with gorgeous views! 5 bedroom 4.5 bath, 5,820SF custom built colonial with three-car attached garage with side entrance into oversized mudroom. Main level features

  Anzor Sidamonidze Skylight Real Estate, LLC

  186 Ridge St, Winchester, MA 01890
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  /38

  $1,525,000 Sold Sep 12, 2025

  5 Thornton Rd, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 2,755 Sq Ft
  • Built 1929

  Last Sold Summary

  • 12% Below List Price
  • $554/SF
  • 30 Days On Market

  Current Estimated Value $1,760,461

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

  5 Thornton Rd, Winchester, MA 01890
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  /40

  Est $1,943,267 Not Listed For Sale

  3 Berkshire Dr, Winchester, MA 01890

  • 5 Beds
  • 2.5 Baths
  • 3,344 Sq Ft
  • Built 1967

  3 Berkshire Dr, Winchester, MA 01890

  Last Sold Summary

  • 9% Below List Price
  • $635/SF
  • 4 Days On Market

  • Last Sold Price $2,125,000
  • Jul 15, 2024

  Last Listing Agent Allison Shannon Berkshire Hathaway HomeServices Robert Paul Properties
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  /39

  $1,299,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,030 Sq Ft

  12 Hancock St, Winchester, MA 01890

  This beautifully maintained home blends timeless craftsmanship with thoughtful modern updates. Architectural details, including stunning stained-glass windows, add warmth and personality throughout, and pair beautifully with the updated kitchen and baths. Spacious rooms, oversized windows, 9-foot ceilings, and a desirable layout create an airy, expansive feeling that lives larger than the square

  Elena Langlois Compass

  12 Hancock St, Winchester, MA 01890
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  /6

  $2,200 Per Month

  • 1 Bed
  • 1 Bath
  • 602 Sq Ft
  • Condo for Rent

  200 Swanton St Unit L12, Winchester, MA 01890

  Recently renovated one bedroom, one bath condominium available in downtown Winchester. Bright and sunny unit with an open floor plan and amazing park & water views from private balcony. Rent includes all utilities - heat/hot water, air conditioning, electricity, and parking for 1 car. Incredible location walkable to shops, town center, and train to Boston. *Pets not allowed.*

  Noha Soliman Leading Edge Real Estate

  200 Swanton St Unit L12, Winchester, MA 01890
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  /42

  $1,540,000 Sold Jul 11, 2025

  21 Johnson Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,814 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Above List Price
  • $547/SF
  • 5 Days On Market

  Current Estimated Value $1,540,767

  Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

  21 Johnson Rd, Winchester, MA 01890
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  /11

  Est $1,254,065 Not Listed For Sale

  233 High St, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 2,218 Sq Ft
  • Built 1952

  233 High St, Winchester, MA 01890

  Last Sold Summary

  • 8% Above List Price
  • $523/SF
  • 7 Days On Market

  • Last Sold Price $1,161,000
  • Jan 18, 2024

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  /31

  $1,250,000

  • 5 Beds
  • 1.5 Baths
  • 2,688 Sq Ft

  6 Hancock St, Winchester, MA 01890

  Classic turn-of-the-century Victorian filled with charm and character, ready for its next owner. 5 total bedrooms; 4 on the second floor and 1 on the 3rd floor, plus 3rd floor office. 1.5 baths, this well-maintained home awaits your finishing touches and features hardwood floors throughout, showcasing its timeless architectural details. Enjoy warm summer evenings on the inviting screened front

  Pirani & Wile Group Gibson Sotheby's International Realty

  6 Hancock St, Winchester, MA 01890
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  /26

  $6,500 Per Month

  • 4 Beds
  • 4 Baths
  • 3,436 Sq Ft
  • House for Rent

  37 Emerson Rd, Winchester, MA 01890

  This sunlit, upgraded Winchester single-family home offers a perfect blend of comfort and elegance. The versatile 4-bedrooms & 4-Bathrooms layout features a convenient 1st-floor full bath alongside a formal living room, dining room, office, and spacious family room. The primary suite is located on the 2nd floor with a private ensuite. Skylights brighten the living areas, which open to a wide

  Hao Wang Dreamega International Realty LLC

  37 Emerson Rd, Winchester, MA 01890
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  /42

  $1,558,000 Sold May 29, 2025

  24 Eugene Dr, Winchester, MA 01890

  • 3 Beds
  • 3.5 Baths
  • 2,792 Sq Ft
  • Built 1993

  Last Sold Summary

  • 18% Above List Price
  • $558/SF
  • 9 Days On Market

  Current Estimated Value $1,545,960

  Last Listing Agent Andrea O'Reilly Keller Williams Realty Evolution

  24 Eugene Dr, Winchester, MA 01890
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  /40

  Est $1,308,441 Not Listed For Sale

  134 Johnson Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,430 Sq Ft
  • Built 1977

  134 Johnson Rd, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $484/SF
  • 3 Days On Market

  • Last Sold Price $1,175,000
  • Jun 27, 2024

  Last Listing Agent Steve Savarese Senne
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  /41

  $2,200,000

  • 6 Beds
  • 4.5 Baths
  • 6,900 Sq Ft

  16 Glenwood Ave, Winchester, MA 01890

  Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr

  Kim Covino Compass

  16 Glenwood Ave, Winchester, MA 01890
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  /14

  $7,900 Per Month

  • 4 Beds
  • 2.5 Baths
  • 4,300 Sq Ft
  • House for Rent

  18 Grant Rd, Winchester, MA 01890

  An exceptional 4-bedroom, 2.5 bath home offers both comfort and versatility. The expansive family room, located just off the kitchen, creates a welcoming setting for entertaining or relaxing. The kitchen is equipped with modern appliances and features a slider that opens to the back deck. A first-floor laundry room and a conveniently located bedroom/office enhance the home’s practicality. The

  Jill Shanley CJL Rentals & Property Management Co., Inc.

  18 Grant Rd, Winchester, MA 01890
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  /42

  $1,850,000 Sold Jan 15, 2026

  77A Brooks St, Winchester, MA 01890

  • 6 Beds
  • 3.5 Baths
  • 4,122 Sq Ft
  • Built 1890

  Last Sold Summary

  • 19% Below List Price
  • $449/SF
  • 35 Days On Market

  Current Estimated Value $1,918,259

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  77A Brooks St, Winchester, MA 01890
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  /42

  Est $1,765,522 Not Listed For Sale

  7 Wainwright Rd Unit 98, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,361 Sq Ft
  • Built 1995

  7 Wainwright Rd Unit 98, Winchester, MA 01890

  Last Sold Summary

  • 12% Below List Price
  • $595/SF
  • 6 Days On Market

  • Last Sold Price $2,000,000
  • Jun 24, 2024

  Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group
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  /35

  $2,975,000

  • 7 Beds
  • 6 Baths
  • 5,888 Sq Ft

  115 Church St, Winchester, MA 01890

  Distinguished Colonial Revival located in the desirable “Flats" neighborhood offering 5,888 SF with 7 bedrooms and 6 baths across three finished levels. Period details include a quartered oak foyer and staircase, bay windows, pocket doors, and decorative millwork. Chef's kitchen features a Viking gas range, Thermador refrigerator, and granite countertops. Family room has a wood-burning fireplace

  Jennifer Ryer Better Homes and Gardens Real Estate - The Shanahan Group

  115 Church St, Winchester, MA 01890
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  /30

  $4,150 Per Month

  • 4 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Apartment for Rent

  10-12 Webster St Unit 1, Winchester, MA 01890

  Amazing 4 bed 2 bath available 2/1/26 located within close proximity of Winchester Center! This spacious apartment takes up the first floor and lower level of a 2 family, but it has a single-family feel to it! Inside on the first floor, you'll find hardwood floors throughout, a living room, a dining room, two spacious bedrooms, and a great eat-in kitchen featuring a new dishwasher and

  Ryan Kelly Real Broker MA, LLC

  10-12 Webster St Unit 1, Winchester, MA 01890
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  /24

  $2,155,000 Sold Oct 21, 2025

  7 Wainwright Rd Unit 13, Winchester, MA 01890

  • 3 Beds
  • 4.5 Baths
  • 3,186 Sq Ft
  • Built 1988

  Last Sold Summary

  • $676/SF
  • 1 Day On Market

  Current Estimated Value $1,923,907

  Last Listing Agent Isabella Bruno William Raveis R.E. & Home Services

  7 Wainwright Rd Unit 13, Winchester, MA 01890
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  /39

  Est $1,754,274 Not Listed For Sale

  7 Wainwright Rd Unit 37, Winchester, MA 01890

  • 2 Beds
  • 4 Baths
  • 3,655 Sq Ft
  • Built 1988

  7 Wainwright Rd Unit 37, Winchester, MA 01890

  Last Sold Summary

  • 11% Above List Price
  • $431/SF
  • 6 Days On Market

  • Last Sold Price $1,575,000
  • Aug 03, 2023

  Last Listing Agent Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group
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  /31

  $1,299,000

  • 3 Beds
  • 3.5 Baths
  • 2,420 Sq Ft

  129 Washington St Unit 131, Winchester, MA 01890

  Just moments from Winchester Center, this townhouse-style condo lives like a single-family, offering space, flow, and flexibility across four finished levels. The main living area is designed for how you actually live, with an open layout that brings the kitchen, dining, and living spaces together seamlessly. Coffered ceilings, wainscoting, and thoughtful updates add character, while the recently

  The Mary Scimemi Team Leading Edge Real Estate

  129 Washington St Unit 131, Winchester, MA 01890
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  /39

  $13,000 Per Month

  • 6 Beds
  • 5.5 Baths
  • 6,400 Sq Ft
  • House for Rent

  52 N Border Rd, Winchester, MA 01890

  Grand and masterfully crafted, this exceptional residence sits on a private road abutting the Fells conservation land, offering rare privacy and natural surroundings. The spacious home features 6 bedrooms and 6 bathrooms, beginning with a stunning foyer that opens to a sprawling first floor. Sun-filled rooms showcase exquisite custom craftsmanship throughout. The gourmet kitchen is equipped with

  Dylan Archambault Archambault Real Estate

  52 N Border Rd, Winchester, MA 01890
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  /40

  $1,160,000 Sold Aug 14, 2025

  518 Washington St, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,302 Sq Ft
  • Built 1915

  Last Sold Summary

  • 3% Below List Price
  • $504/SF
  • 22 Days On Market

  Current Estimated Value $1,212,020

  Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

  518 Washington St, Winchester, MA 01890
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  /42

  Est $1,801,676 Not Listed For Sale

  7 Wainwright Rd Unit 5, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 3,901 Sq Ft
  • Built 1988

  7 Wainwright Rd Unit 5, Winchester, MA 01890

  Last Sold Summary

  • 3% Above List Price
  • $449/SF
  • 7 Days On Market

  • Last Sold Price $1,750,000
  • Mar 28, 2024

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  $3,549,000

  • 6 Beds
  • 4.5 Baths
  • 6,460 Sq Ft

  40 Foxcroft Rd, Winchester, MA 01890

  40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows.

  The Boston ONE Team Serhant

  40 Foxcroft Rd, Winchester, MA 01890
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  /38

  $4,500 Per Month

  • 2 Beds
  • 2 Baths
  • 1,811 Sq Ft
  • Condo for Rent

  8 Richardson St Unit 2, Winchester, MA 01890

  Beautiful, high end two story condo for rent; close to everything Winchester has to offer! This unique penthouse dulpex condo offers all the space of a single family home with an open concept floor plan featuring high end finishes and hardwood floors throughout. Enjoy a private entrance, a stunning living room w/ high ceilings, a beautiful gas fireplace and high end buit ins; chefs kitchen

  Kim Covino Compass

  8 Richardson St Unit 2, Winchester, MA 01890
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  /41

  $2,425,000 Sold Jul 31, 2025

  15 Churchill Rd, Winchester, MA 01890

  • 4 Beds
  • 4.5 Baths
  • 5,501 Sq Ft
  • Built 2025

  Last Sold Summary

  • 7% Below List Price
  • $441/SF
  • 61 Days On Market

  Current Estimated Value $2,428,084

  Last Listing Agent Kim Covino Compass

  15 Churchill Rd, Winchester, MA 01890
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  /41

  Est $1,579,265 Not Listed For Sale

  7 Wainwright Rd Unit 41, Winchester, MA 01890

  • 2 Beds
  • 4 Baths
  • 5,564 Sq Ft
  • Built 1988

  7 Wainwright Rd Unit 41, Winchester, MA 01890

  Last Sold Summary

  • 5% Above List Price
  • $270/SF
  • 7 Days On Market

  • Last Sold Price $1,500,000
  • Jun 21, 2024

  Last Listing Agent Jill Citrano Leading Edge Real Estate
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  $1,100,000

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  83 Church St Unit 15, Winchester, MA 01890

  Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal

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

  83 Church St Unit 15, Winchester, MA 01890
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  /39

  $12,000 Per Month

  • 7 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • House for Rent

  34 Glen Rd, Winchester, MA 01890

  TOP location! Beautifully renovated single family colonial in Ambrose elementary district, situated on a gorgeous lot with oversized new 2 car garage, This 6-7 bedroom 3.5 bath home has been tastefully updated & redesigned offering desirable open concept living w/ central air & all new systems. This home features a welcoming front porch, spacious foyer, beautiful custom chefs kitchen w/

  Kim Covino Compass

  34 Glen Rd, Winchester, MA 01890
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  /42

  $2,499,000 Sold May 19, 2025

  50 Winford Way, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,270 Sq Ft
  • Built 2024

  Last Sold Summary

  • $585/SF
  • 0 Days On Market

  Current Estimated Value $2,447,889

  Last Listing Agent Kim Covino Compass

  50 Winford Way, Winchester, MA 01890
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  /42

  Est $1,929,994 Not Listed For Sale

  40 Wainwright Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,853 Sq Ft
  • Built 1992

  40 Wainwright Rd, Winchester, MA 01890

  Last Sold Summary

  • 1% Above List Price
  • $669/SF
  • 7 Days On Market

  • Last Sold Price $1,910,000
  • May 29, 2024

  Last Listing Agent Kim Covino Compass

Showing Results 81 - 120, Page 3 of 18