Winchester, MA Homes

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  /42

  $2,900,000 Sold Mar 07, 2025

  64 Wildwood St, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 4,400 Sq Ft
  • Built 1917

  Last Sold Summary

  • 3% Below List Price
  • $659/SF
  • 67 Days On Market

  Current Estimated Value $2,879,641

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

  64 Wildwood St, Winchester, MA 01890
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  /40

  Est $1,402,170 Not Listed For Sale

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

  16 Johnson Rd, Winchester, MA 01890

  16 Johnson Rd, Winchester, MA 01890
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  /42

  $1,899,000 Open Sat 12PM - 1PM

  • 6 Beds
  • 3.5 Baths
  • 4,696 Sq Ft

  5 Squire Rd, Winchester, MA 01890

  Designed for modern living and effortless entertaining, this home’s exceptional open-concept main level sets it apart from the moment you enter. Anchored by a chef’s kitchen with stone countertops, an oversized island, and premium Viking appliances, the space flows seamlessly into the family room with a striking shiplap fireplace and direct access to a spacious composite deck. Set in a desirable

  Andersen Group Realty Keller Williams Realty Boston Northwest

  5 Squire 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

  Last Listing Agent Andrea Mackey The Agency Boston

  16 Park Ave Unit 1, Winchester, MA 01890
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  /33

  Est $1,977,966 Not Listed For Sale

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

  8 Olde Lyme Rd, Winchester, MA 01890

  8 Olde Lyme Rd, Winchester, MA 01890
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  /30

  $1,025,000 Pending

  • 6 Beds
  • 2 Baths
  • 2,605 Sq Ft

  353-355 Washington St, Winchester, MA 01890

  Investor alert! About one mile from an array of shops, restaurants, & the commuter rail to Boston, this Winchester multi-family is a rare opportunity waiting to be redesigned! Held by the same family for many years, the property offers substantial square footage & endless potential for those ready to roll up their sleeves. While it requires significant renovation, the reward will be well worth

  Julie Gibson Gibson Sotheby's International Realty

  353-355 Washington St, Winchester, MA 01890
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  /39

  $4,650,000 Sold May 01, 2025

  19 Rangeley Rd, Winchester, MA 01890

  • 5 Beds
  • 7 Baths
  • 7,779 Sq Ft
  • Built 1915

  Last Sold Summary

  • 3% Below List Price
  • $598/SF
  • 5 Days On Market

  Current Estimated Value $4,492,812

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  19 Rangeley Rd, Winchester, MA 01890
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  /42

  Est $1,781,215 Not Listed For Sale

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

  8 Hawthorne Rd, Winchester, MA 01890

  8 Hawthorne 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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  /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 $969,062

  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 $2,479,038 Not Listed For Sale

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

  239 Ridge St, Winchester, MA 01890

  239 Ridge St, Winchester, MA 01890
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  /42

  $1,350,000 Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2.5 Baths
  • 2,153 Sq Ft

  6 Marchant Rd, Winchester, MA 01890

  Updated / move in ready 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, train & Boston. The first floor offers an ideal layout w gleaming hardwood floors, updated kitchen w/stainless steel appliances & island seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc & dining room.

  Kim Covino Compass

  6 Marchant Rd, Winchester, MA 01890
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  /2

  $2,222,500 Sold Mar 27, 2025

  41 Foxcroft Rd, Winchester, MA 01890

  • 4 Beds
  • 3.5 Baths
  • 2,900 Sq Ft
  • Built 1932

  Last Sold Summary

  • 1% Above List Price
  • $766/SF
  • 0 Days On Market

  Current Estimated Value $2,135,026

  Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  41 Foxcroft Rd, Winchester, MA 01890
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  /26

  Est $1,151,055 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,826 Sq Ft

  75 Dunster Ln, Winchester, MA 01890

  75 Dunster Ln, Winchester, MA 01890
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  /41

  $1,460,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,316 Sq Ft

  26 Berkshire Dr, Winchester, MA 01890

  Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

  DANIEL BEIRNE OpenDoor Brokerage LLC

  26 Berkshire Dr, 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 $1,699,649

  Last Listing Agent Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  18 Englewood Rd, Winchester, MA 01890
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  /42

  Est $3,200,078 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,676 Sq Ft

  222 High St, Winchester, MA 01890

  222 High St, Winchester, MA 01890
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  /24

  $969,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  139 High St, Winchester, MA 01890

  This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

  Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

  139 High St, 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 $2,879,825

  Last Listing Agent Kim Covino Compass

  21 Fernway, Winchester, MA 01890
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  /30

  Est $927,880 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,857 Sq Ft

  62 Edward Dr, Winchester, MA 01890

  62 Edward Dr, Winchester, MA 01890
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  /2

  $359,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  20 Arthur St, Winchester, MA 01890

  Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

  Dan O'Connell LAER Realty Partners

  20 Arthur St, 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 $886,300

  Last Listing Agent Jonathan Radford Coldwell Banker Realty - Boston

  171 Swanton St Unit 5, Winchester, MA 01890
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  /27

  Est $1,085,960 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,859 Sq Ft

  46 Edward Dr, Winchester, MA 01890

  46 Edward Dr, Winchester, MA 01890
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  /42

  $1,649,000

  • 4 Beds
  • 4 Baths
  • 3,343 Sq Ft

  263 Highland Ave, Winchester, MA 01890

  Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home

  Seeme Moreira Coldwell Banker Realty - Lexington

  263 Highland Ave, 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 $854,738

  Last Listing Agent Melanie Lentini Leading Edge Real Estate

  235 Cross St, Winchester, MA 01890
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  /36

  Est $1,045,399 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,568 Sq Ft

  55 Edward Dr, Winchester, MA 01890

  55 Edward Dr, Winchester, MA 01890
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  /33

  $699,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,532 Sq Ft

  7 Conant Rd Unit 33, Winchester, MA 01890

  Rarely available ground-floor townhouse at The Willows with easy access to a private garage. This bright and sunny 2-bedroom, 2-bath condo offers the convenience and comfort today’s buyers are seeking. Open concept kitchen with a breakfast bar, and an adjacent dining area—perfect for everyday living or entertaining. The expansive living room is highlighted by a gas fireplace and slider that opens

  Pirani & Wile Group Gibson Sotheby's International Realty

  7 Conant Rd Unit 33, Winchester, MA 01890
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  /39

  $1,425,000 Sold Dec 01, 2025

  102 Hillcrest Pkwy, Winchester, MA 01890

  • 4 Beds
  • 2 Baths
  • 1,755 Sq Ft
  • Built 1939

  Last Sold Summary

  • 19% Above List Price
  • $812/SF
  • 4 Days On Market

  Last Listing Agent Curtis Howe Howe Realty Group

  102 Hillcrest Pkwy, Winchester, MA 01890
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  /42

  Est $1,039,651 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,738 Sq Ft

  41 Edward Dr, Winchester, MA 01890

  41 Edward Dr, 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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  /42

  $1,550,000 Sold Oct 31, 2025

  205 Ridge St, Winchester, MA 01890

  • 5 Beds
  • 3 Baths
  • 2,995 Sq Ft
  • Built 1960

  Last Sold Summary

  • $518/SF
  • 5 Days On Market

  Current Estimated Value $1,559,841

  Last Listing Agent Debby Valdes eXp Realty

  205 Ridge St, Winchester, MA 01890
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  /38

  Est $1,057,516 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,754 Sq Ft

  34 Edward Dr, Winchester, MA 01890

  34 Edward Dr, Winchester, MA 01890
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  /32

  $722,500 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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  /36

  $519,000 Sold Oct 08, 2025

  115 Washington St Unit 3D, Winchester, MA 01890

  • 1 Bed
  • 1.5 Baths
  • 769 Sq Ft
  • Built 1988

  Last Sold Summary

  • $675/SF
  • 5 Days On Market

  Current Estimated Value $516,223

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

  115 Washington St Unit 3D, Winchester, MA 01890
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  /37

  Est $902,002 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft

  47 Edward Dr, Winchester, MA 01890

  47 Edward Dr, Winchester, MA 01890
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  /42

  $3,470,000 Pending

  • 5 Beds
  • 6 Baths
  • 6,127 Sq Ft

  10 Sheffield W, Winchester, MA 01890

  Exceptional Colonial Revival in one of Winchester’s most sought-after Sheffield neighborhoods, known for its tree-lined streets and a shared community green. Timeless architecture meets modern livability across four finished levels. The chef’s kitchen features a large island, walk-in pantry, wet bar, and custom cabinetry, opening to a spacious family room with gas fireplace. Formal living and

  Jay Noble Lamacchia Realty, Inc.

  10 Sheffield W, Winchester, MA 01890
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  /41

  $2,350,000 Sold Apr 15, 2025

  5 Pine St, Winchester, MA 01890

  • 5 Beds
  • 3.5 Baths
  • 4,273 Sq Ft
  • Built 1910

  Last Sold Summary

  • 4% Above List Price
  • $550/SF
  • 7 Days On Market

  Current Estimated Value $2,344,735

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

  5 Pine St, Winchester, MA 01890
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  /31

  Est $1,895,156 Not Listed For Sale

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

  56 Ridge St, Winchester, MA 01890

  56 Ridge St, Winchester, MA 01890
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  /35

  $1,375,000 Sold Jan 23, 2026

  32 Oak St, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,652 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Above List Price
  • $518/SF
  • 6 Days On Market

  Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

  32 Oak St, Winchester, MA 01890
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  /42

  Est $957,827 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,890 Sq Ft

  25 Henry St, Winchester, MA 01890

  25 Henry St, Winchester, MA 01890

Showing Results 121 - 160, Page 4 of 18