Winchester, MA Homes

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  /29

  $949,999

  • 4 Beds
  • 2 Baths
  • 2,326 Sq Ft

  96 Loring Ave, Winchester, MA 01890

  Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens

  

  Jeremy Smith

  StartPoint Realty

  96 Loring Ave, Winchester, MA 01890
• Explore Winchester

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  /16

  $1,750 Per Month

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

  200 Swanton St Unit 240, Winchester, MA 01890

  AVAILABLE NOW! Bright and inviting second-floor studio at Parkview Condominiums! Rent includes heat, hot water, electricity, and air conditioning. Additional amenities include storage, an outdoor swimming pool, on-site laundry, and one parking space. An additional parking pass may be purchased. Tenant is responsible for obtaining renters insurance. First month’s rent, last month’s rent, security

  

  Joan Powell

  REMAX Andrew Realty Services

  200 Swanton St Unit 240, Winchester, MA 01890
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  /30

  $729,000

  Sold Aug 12, 2026

  171 Swanton St Unit 7, Winchester, MA 01890

  • 2 Beds
  • 2.5 Baths
  • 1,431 Sq Ft
  • Built 1984

  Last Sold Summary

  • $509/SF
  • 19 Days On Market

  Current Estimated Value $738,713

  Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

  171 Swanton St Unit 7, Winchester, MA 01890
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  /42

  Est $1,696,280

  Not Listed For Sale

  9 Pilgrim Dr, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,541 Sq Ft
  • Built 1960

  9 Pilgrim Dr, Winchester, MA 01890

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate
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  /34

  $974,900

  • 3 Beds
  • 2.5 Baths
  • 1,719 Sq Ft

  258 Cross St, Winchester, MA 01890

  A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with

  

  Justin Blankenship

  Fiv Realty Co

  258 Cross St, Winchester, MA 01890
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  /20

  Starting at $2,568

  Total Monthly Price

  • Studio - 3 Beds

  416 Cambridge St, Winchester, MA 01890

  The Sanctuary at Winchester West is crafted to elevate every moment of your day—from morning workouts in the fully equipped fitness center to productive afternoons in private work-from-home pods and inviting gathering spaces. Whether you're entertaining in the chef-inspired kitchen and lounge, relaxing by the fire with neighbors, or enjoying the convenience of Whole Foods and local shops just

  Sanctuary Winchester West

  

  416 Cambridge St, Winchester, MA 01890
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  /42

  $1,055,000

  Sold May 15, 2026

  15 Edward Dr Unit 15, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,082 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Above List Price
  • $507/SF
  • 5 Days On Market

  Last Listing Agent Alina Wang Coldwell Banker Realty - Lexington

  15 Edward Dr Unit 15, Winchester, MA 01890
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  /14

  Est $291,016

  Not Listed For Sale

  200 Swanton St Unit 402, Winchester, MA 01890

  • 1 Bed
  • 1 Bath
  • 388 Sq Ft
  • Built 1966

  200 Swanton St Unit 402, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Michael Masci North Atlantic Realty Group
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  /42

  $1,925,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  15 Fieldstone Dr, Winchester, MA 01890

  Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless

  Anne Spry Barrett Sotheby's International Realty

  15 Fieldstone Dr, Winchester, MA 01890
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  /9

  $3,200 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! This beautifully renovated 2-bedroom, 1-bath townhome offers the perfect blend of classic charm and modern updates, featuring hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom showcases a walk-in tiled shower with a custom glass

  

  Issam Dib

  Skyline Realty

  63 Holland St Unit 63, Winchester, MA 01890
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  /31

  $1,240,000

  Sold Apr 27, 2026

  12 Thornberry Rd, Winchester, MA 01890

  • 3 Beds
  • 2 Baths
  • 2,087 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $594/SF
  • 6 Days On Market

  Current Estimated Value $1,238,250

  Last Listing Agent Kim Covino Compass

  12 Thornberry Rd, Winchester, MA 01890
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  /32

  Est $518,058

  Not Listed For Sale

  200 Swanton St Unit 239, Winchester, MA 01890

  • 2 Beds
  • 1 Bath
  • 822 Sq Ft
  • Built 1966

  200 Swanton St Unit 239, Winchester, MA 01890

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Joan Powell REMAX Andrew Realty Services
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  /39

  $1,529,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,956 Sq Ft

  20 Sargent Rd, Winchester, MA 01890

  Classic East Hill center-entrance Colonial offered for the first time in decades, blending timeless character with gracious everyday living. The front-to-back living room features a beamed ceiling and gas fireplace, creating a warm and inviting gathering space. The dining room is accented by built-in china cabinets, while the eat-in kitchen offers stone counters, stainless steel appliances,

  Anne Spry Barrett Sotheby's International Realty

  20 Sargent Rd, Winchester, MA 01890
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  /24

  Starting at $2,817

  Total Monthly Price

  • 1 - 3 Beds

  25-35 River St, Winchester, MA 01890

  The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and

  Sanctuary Winchester North

  

  25-35 River St, Winchester, MA 01890
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  /35

  $1,379,000

  Sold Jan 05, 2026

  6 Wyman Ct Unit 6, Winchester, MA 01890

  • 3 Beds
  • 4.5 Baths
  • 2,722 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $507/SF
  • 15 Days On Market

  Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington

  6 Wyman Ct Unit 6, Winchester, MA 01890
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  /31

  Est $1,541,374

  Not Listed For Sale

  6 Highland Ave, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,506 Sq Ft
  • Built 1974

  6 Highland Ave, Winchester, MA 01890

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Peter Rooney Compass
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  /23

  $630,000

  $99K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,494 Sq Ft

  247 Washington St Unit 11, Winchester, MA 01890

  Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for

  Heejeong Joo Coldwell Banker Realty - Lexington

  247 Washington St Unit 11, Winchester, MA 01890
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  /13

  $2,150 Per Month

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

  200 Swanton St Unit 313, Winchester, MA 01890

  Available now at desirable Parkview Condominiums in Winchester! This bright and spacious third-floor one-bedroom condo features sliders leading to a private balcony overlooking the beautifully landscaped grounds and pond. Enjoy a well-maintained kitchen and bath, generous closet space, and one parking spot included, with an additional parking pass available for purchase. Community amenities

  

  Joan Powell

  REMAX Andrew Realty Services

  200 Swanton St Unit 313, Winchester, MA 01890
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  /42

  $1,255,000

  Sold Jan 07, 2026

  104 Church St, Winchester, MA 01890

  • 4 Beds
  • 1.5 Baths
  • 2,696 Sq Ft
  • Built 1897

  Last Sold Summary

  • 10% Below List Price
  • $466/SF
  • 46 Days On Market

  Current Estimated Value $1,397,049

  Last Listing Agent Kim Covino Compass

  104 Church St, Winchester, MA 01890
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  /36

  Est $1,916,269

  Not Listed For Sale

  20 Grayson Rd, Winchester, MA 01890

  • 5 Beds
  • 4.5 Baths
  • 3,825 Sq Ft
  • Built 2025

  20 Grayson Rd, Winchester, MA 01890

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Monte Marrocco Coldwell Banker Realty - Lexington
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  /40

  $1,099,000

  Open Sat 1PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,411 Sq Ft

  24 Richardson St, Winchester, MA 01890

  Tucked on a quiet side street just north of Main Street, this circa-1853 antique pairs the character of a classic Winchester home with the space of a beautiful, sun-filled addition (completed in 2003): A lovely farmer's porch welcomes you and, once inside, hardwood and tile floors run through the main living spaces. Front rooms include a quaint sitting room and private office. A gas fireplace

  Andersen Group Realty Keller Williams Realty Boston Northwest

  24 Richardson St, Winchester, MA 01890
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  /11

  $2,293 Plus Fees

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

  3 Wainwright Rd Unit 212, Winchester, MA 01890

  With common spaces designed with you in mind, The Sanctuary at Winchester West invites you to live an inspired life. Gather around the fireplace in the Great Room, create a culinary masterpiece in the Chef’s Kitchen, or reflect and recharge in one of many curated outdoor living spaces. At The Sanctuary, there’s space for all your pursuits. Each apartment home at The Sanctuary at Winchester West

  3 Wainwright Rd Unit 212, Winchester, MA 01890
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  /17

  $330,000

  Sold Jul 28, 2026

  200 Swanton St Unit 228, Winchester, MA 01890

  • 1 Bed
  • 1 Bath
  • 606 Sq Ft
  • Built 1966

  Last Sold Summary

  • 17% Below List Price
  • $545/SF
  • 199 Days On Market

  Current Estimated Value $370,419

  Last Listing Agent Joan Powell REMAX Andrew Realty Services

  200 Swanton St Unit 228, Winchester, MA 01890
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  /39

  Est $2,348,551

  Not Listed For Sale

  38 Winthrop Street Extension, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 4,539 Sq Ft
  • Built 2020

  38 Winthrop Street Extension, Winchester, MA 01890

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Ryan Wilson Keller Williams Realty
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  /24

  $495,000

  • 2 Beds
  • 1 Bath
  • 822 Sq Ft

  200 Swanton St Unit 303, Winchester, MA 01890

  Enjoy the best of Winchester living in this beautifully updated two-bedroom condo at Parkview, just minutes from Winchester Center, local shops, dining, parks, and commuter access. A bright, open-concept layout creates an inviting flow for everyday living and entertaining. The modern kitchen features stainless steel appliances, while fresh paint throughout adds a crisp, contemporary feel. Both

  Joseph Pollack Redfin Corp.

  200 Swanton St Unit 303, Winchester, MA 01890
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  /16

  $1,878 Per Month

  • 1 Bath
  • 397 Sq Ft
  • Apartment for Rent

  200 Swanton St Unit 708, Winchester, MA 01890

  Sunny top-level studio apartment available now at desirable Parkview Condominiums in Winchester! This bright and open studio features a spacious layout with sliders to a balcony overlooking the beautifully landscaped grounds and pond. Enjoy a well-maintained kitchen and bath, ample closet space, and one assigned parking spot (extra spot can be rented). The community offers a pool, picnic area,

  

  Joan Powell

  REMAX Andrew Realty Services

  200 Swanton St Unit 708, Winchester, MA 01890
• 

  $2,575,000

  Sold Jun 16, 2026

  2 Edgewater Place, Winchester, MA 01890

  • 4 Beds
  • 4.5 Baths
  • 3,945 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $653/SF
  • 34 Days On Market

  Current Estimated Value $2,624,187

  Last Listing Agent Nancy Pallotta Gibson Sotheby's International Realty

  2 Edgewater Place, Winchester, MA 01890
• 

  

  /34

  Est $846,698

  Not Listed For Sale

  897 Main St Unit 1, Winchester, MA 01890

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 2014

  897 Main St Unit 1, Winchester, MA 01890

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest
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  /33

  $2,849,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 5,058 Sq Ft

  7 Viking Rd, Winchester, MA 01890

  Tucked on a quiet cul-de-sac in the sought-after Vinson Owen school district, this completely renovated 5-bedroom, 4.5-bath Colonial offers an exceptional blend of comfort and elevated design. Massive columns in classic revival style create stunning curb appeal, offering a striking introduction to the transformation inside. A spectacular chef's kitchen anchors the main level, featuring an

  Andersen Group Realty Keller Williams Realty Boston Northwest

  7 Viking Rd, Winchester, MA 01890
• 

  

  /11

  $2,769 Plus Fees

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft
  • Condo for Rent

  3 Wainwright Rd Unit 525, Winchester, MA 01890

  With common spaces designed with you in mind, The Sanctuary at Winchester West invites you to live an inspired life. Gather around the fireplace in the Great Room, create a culinary masterpiece in the Chef’s Kitchen, or reflect and recharge in one of many curated outdoor living spaces. At The Sanctuary, there’s space for all your pursuits. Each apartment home at The Sanctuary at Winchester West

  3 Wainwright Rd Unit 525, Winchester, MA 01890
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  /39

  $1,560,000

  Sold Apr 30, 2026

  17 Cranston Rd, Winchester, MA 01890

  • 4 Beds
  • 2.5 Baths
  • 2,578 Sq Ft
  • Built 1950

  Last Sold Summary

  • $605/SF
  • 5 Days On Market

  Current Estimated Value $1,558,066

  Last Listing Agent Anne Spry Barrett Sotheby's International Realty

  17 Cranston Rd, Winchester, MA 01890
• 

  

  /41

  Est $1,488,325

  Not Listed For Sale

  23 Elmwood Ave Unit C, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,189 Sq Ft
  • Built 2017

  23 Elmwood Ave Unit C, Winchester, MA 01890

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Kim Covino Compass
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  /40

  $2,199,000

  • 4 Beds
  • 3.5 Baths
  • 3,570 Sq Ft

  19 Hancock St, Winchester, MA 01890

  Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor

  Philip Vita Compass

  19 Hancock St, Winchester, MA 01890
• 

  

  /20

  $3,450 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,924 Sq Ft
  • Townhouse for Rent

  60 Lake St, Winchester, MA 01890

  Welcome to this spacious 2-bedroom, 2.5-bath townhome in a highly desirable Winchester location with beautiful views of Wedge Pond. Offering multiple levels of living space, this home provides plenty of room to spread out, work from home, and relax.The main level features an open kitchen and dining area, creating a comfortable and functional space for everyday living and entertaining. Step

  60 Lake St, Winchester, MA 01890
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  /42

  $1,055,000

  Sold Feb 26, 2026

  7 Trinity Rd, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1963

  Last Sold Summary

  • 11% Below List Price
  • $495/SF
  • 24 Days On Market

  Current Estimated Value $1,191,098

  Last Listing Agent Gayle Winters Compass

  7 Trinity Rd, Winchester, MA 01890
• 

  

  /28

  Est $1,353,660

  Not Listed For Sale

  261 Cambridge St Unit 261 G, Winchester, MA 01890

  • 3 Beds
  • 2.5 Baths
  • 2,705 Sq Ft
  • Built 1885

  261 Cambridge St Unit 261 G, Winchester, MA 01890

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group
• 

  

  /41

  $1,749,000

  $50K PRICE DROP Pending

  • 3 Beds
  • 3.5 Baths
  • 3,010 Sq Ft

  1 Town Way, Winchester, MA 01890

  Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing

  Philip Vita Compass

  1 Town Way, Winchester, MA 01890
• 

  

  /11

  $2,293 Plus Fees

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

  3 Wainwright Rd Unit 203, Winchester, MA 01890

  With common spaces designed with you in mind, The Sanctuary at Winchester West invites you to live an inspired life. Gather around the fireplace in the Great Room, create a culinary masterpiece in the Chef’s Kitchen, or reflect and recharge in one of many curated outdoor living spaces. At The Sanctuary, there’s space for all your pursuits. Each apartment home at The Sanctuary at Winchester West

  3 Wainwright Rd Unit 203, Winchester, MA 01890
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  /42

  $1,750,000

  Sold Jul 09, 2026

  24 Hinds Rd, Winchester, MA 01890

  • 4 Beds
  • 3 Baths
  • 2,814 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Below List Price
  • $622/SF
  • 7 Days On Market

  Current Estimated Value $1,747,039

  Last Listing Agent Kim Covino Compass

  24 Hinds Rd, Winchester, MA 01890
• 

  

  /42

  Est $3,598,589

  Not Listed For Sale

  6 Vinson Cir, Winchester, MA 01890

  • 6 Beds
  • 7.5 Baths
  • 7,500 Sq Ft
  • Built 2025

  6 Vinson Cir, Winchester, MA 01890

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Peter Kasseris Serhant

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