Middlesex, MA Homes

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  /42

  $1,899,000 Open Sat 11:30AM - 12:30PM

  • 5 Beds
  • 3.5 Baths
  • 3,294 Sq Ft

  20 Grove Place, Winchester, MA 01890

  From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Cafe appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

  Andersen Group Realty Keller Williams Realty Boston Northwest

  20 Grove Place, Winchester, MA 01890
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  Explore Grove Street

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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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  /40

  Est $2,899,053 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,822 Sq Ft

  31 Brooks St, Winchester, MA 01890

  31 Brooks St, Winchester, MA 01890
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  /26

  $2,239,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 4,798 Sq Ft

  61 Grove St, Winchester, MA 01890

  STUNNING CUSTOM-BUILT HOME, Welcome to this easy living, maintenance free sophisticated residence. Completely rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in shower & soaking tub. An exquisite kitchen with granite island, counters and back splash, All Bosch appliances,

  Dorothea Feffer Coldwell Banker Realty - Lexington

  61 Grove St, Winchester, MA 01890
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  /26

  $2,160,000 Sold Jul 14, 2025

  • 4,023 Sq Ft
  • $537/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1998

  19 Sussex Rd, Winchester, MA 01890

  Ideally located in a very desirable neighborhood that abuts the town forest and surrounded by cul-de-sacs, this elegant well-designed 4-bedroom, 3.5-bathroom colonial home has been meticulously maintained by the original owners and features a spacious layout with ample room for comfortable living. The floorplan is thoughtfully designed, with a nice flow from one room to the next. The family room

  Ida Bianco Coldwell Banker Realty - Lexington

  19 Sussex Rd, Winchester, MA 01890
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  /42

  Est $2,728,838 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,650 Sq Ft

  27 Brooks St, Winchester, MA 01890

  27 Brooks St, Winchester, MA 01890
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  /42

  $3,249,000 Pending

  • 6 Beds
  • 5 Baths
  • 7,005 Sq Ft

  18 Wickham Rd, Winchester, MA 01890

  Just 3 years young, this pristine masterpiece is nestled in a sought-after neighborhood just footsteps from the Town Forest and within walking distance of Wedgemere Station and Downtown Winchester. Step into the first floor and be captivated by the soaring ceilings. The showstopping kitchen features a SubZero fridge, a Bertazzoni 48” range, and a full eat-in area. This space flows into the family

  Philip Vita Compass

  18 Wickham Rd, Winchester, MA 01890
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  /38

  $1,924,000 Sold Jul 10, 2025

  • 4,195 Sq Ft
  • $459/SF
  • 4 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1995

  5 Hastings Rd, Winchester, MA 01890

  Rare opportunity on a peaceful cul-de-sac. This extraordinary 4-bedroom, 4-bathroom home is nestled in one of Winchester's most sought-after neighborhoods. For the first time ever, this meticulously maintained residence is available on a street where properties rarely change hands. Bathed in abundant natural light, the thoughtfully designed floor plan showcases generously sized living spaces that

  Nancy Pallotta Advisors Living - Winchester

  5 Hastings Rd, Winchester, MA 01890
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  /14

  Est $765,747 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  22 Grove Place Unit 29, Winchester, MA 01890

  22 Grove Place Unit 29, Winchester, MA 01890
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  /37

  $859,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,123 Sq Ft

  22 Grove Place Unit 4, Winchester, MA 01890

  Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect opportunity to enjoy the lovely town of Winchester and keep costs down. Near Symmes corner, downtown Winchester & Wedgemere train station, this wonderful 2 bedroom, 1 bathroom end unit lives and feels like a single home with windows on all three sides. The kitchen offers a

  Kim Covino Compass

  22 Grove Place Unit 4, Winchester, MA 01890
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  /41

  $2,850,000 Sold Jun 09, 2025

  • 4,325 Sq Ft
  • $659/SF
  • 8 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1953

  45 Brooks St, Winchester, MA 01890

  Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4BD 4 BA home offering a classic exterior with a stunning "must see" interior; featuring formal spaces great for entertaining blended w/casual living areas both inside & out w/ walls of floor to ceiling windows capturing the elements of

  Kim Covino Compass

  45 Brooks St, Winchester, MA 01890
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  /39

  Est $1,154,532 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 3,045 Sq Ft

  22 Grove Place Unit 26, Winchester, MA 01890

  22 Grove Place Unit 26, Winchester, MA 01890
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  /42

  $2,111,000 Sold Jun 05, 2025

  • 4,744 Sq Ft
  • $445/SF
  • 6 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1922

  14 Grove St, Winchester, MA 01890

  Located just outside the town center near Brooks neighborhood & the train to Boston! This spacious home has it all! Situated on a lovely level lot w/ 2 car garage & private yard, this updated move in ready home boasts an abundance of space w/ideal layout & large sun drenched eat in kitchen with skylights & bay window, adjacent family room, living room w/ fplc, formal dining, office, laundry & 2

  Kim Covino Compass

  14 Grove St, Winchester, MA 01890
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  /42

  Est $3,008,924 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,208 Sq Ft

  11 Brooks St, Winchester, MA 01890

  11 Brooks St, Winchester, MA 01890
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  /42

  $2,825,000 Sold Feb 25, 2025

  • 5,850 Sq Ft
  • $483/SF
  • 8 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 2018

  16 Wickham Rd, Winchester, MA 01890

  Tucked away on a quiet sought after neighborhood, just steps away from the Wedgemere Station and Winchester Center, this meticulously maintained 5-bedroom home built in 2018 perfectly blends modern design with refined details, including beautiful coffered ceilings, wainscoting, chair rails, and crown moulding. The 1st floor offers a formal living room, a spacious family room with a fireplace, a

  Rodrigo Serrano Leading Edge Real Estate

  16 Wickham Rd, Winchester, MA 01890
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  /42

  Est $1,537,463 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,898 Sq Ft

  25 York Rd, Winchester, MA 01890

  25 York Rd, Winchester, MA 01890
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  /36

  $1,025,000 Sold Dec 23, 2024

  • 3,045 Sq Ft
  • $337/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1986

  22 Grove Place Unit 30, Winchester, MA 01890

  Welcome to 22 Grove Place Unit 30, a 3-bedroom, 3-bathroom townhouse in Winchester, MA, that combines single-family privacy with the ease of townhouse living. This home just had the walls and ceilings freshly painted, along with new light fixtures that add a modern touch. The main level offers a spacious living room with high ceilings, a cozy double sided gas fireplace, a home office, first floor

  Peter Kasseris Compass

  22 Grove Place Unit 30, Winchester, MA 01890
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  /35

  Est $1,770,080 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,527 Sq Ft

  37 Canterbury Rd, Winchester, MA 01890

  37 Canterbury Rd, Winchester, MA 01890
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  /42

  $3,005,000 Sold Oct 25, 2024

  • 5,896 Sq Ft
  • $510/SF
  • 8 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2024

  15 W Chardon Rd, Winchester, MA 01890

  Elegance meets modern luxury in this stunning new construction home located at 15 W Chardon Road, Winchester. Nestled in a sought after neighborhood, this 5/6-bedroom, 5.5-bathroom residence offers a timeless appeal and an array of upscale amenities. The primary suite is a sanctuary of indulgence, featuring an oversized deck, offering a serene retreat for relaxation and enjoyment. For those with

  Philip Vita Compass

  15 W Chardon Rd, Winchester, MA 01890
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  /42

  Est $2,647,027 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,635 Sq Ft

  47 Grove St, Winchester, MA 01890

  47 Grove St, Winchester, MA 01890
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  /42

  $2,355,000 Sold Oct 03, 2024

  • 4,278 Sq Ft
  • $550/SF
  • 35 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1992

  9 Brooks St, Winchester, MA 01890

  Stunning home in wonderful Brooks neighborhood convenient to Commuter Rail, town center, walking trails and Fells. All living space is above grade with huge potential to finish basement as your heart desires. Kitchen, bathrooms RENOVATED by current owners with attention to details. You'll love how the kitchen eating area is the perfect spot to hang out adjacent to the family room with fireplace

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  9 Brooks St, Winchester, MA 01890
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  /37

  Est $1,543,275 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,946 Sq Ft

  74 Grove St, Winchester, MA 01890

  74 Grove St, Winchester, MA 01890
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  /40

  $1,890,000 Sold Aug 30, 2024

  • 2,809 Sq Ft
  • $673/SF
  • 3 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1910

  6 Fenwick Rd, Winchester, MA 01890

  Welcome to this beautifully renovated home seamlessly blending original old world charm with modern day design. A gorgeous farmers porch welcomes you into this spacious 5 bed 3.5 bath home w/ a rear addition nicely expanding the original design. Featuring a large open concept kitchen w/ ample prep space & peninsula seating w/ adjacent dining area or family room showcasing walls of windows

  Kim Covino Compass

  6 Fenwick Rd, Winchester, MA 01890
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  /39

  Est $2,468,230 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,778 Sq Ft

  3 Wellington Rd, Winchester, MA 01890

  3 Wellington Rd, Winchester, MA 01890
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  /41

  $2,725,000 Sold Aug 26, 2024

  • 5,171 Sq Ft
  • $527/SF
  • 0 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1998

  10 Briarwood Ln, Winchester, MA 01890

  Experience the perfect blend of nature and luxury in this custom-built Colonial! Private home with a resort like backyard abuts Brooks Parkhurst Town Forest. This stunning 6-bedroom home offers a dramatic layout and design that's sure to impress. A elegant & captivating buttress staircase greets you upon entry. The heart of the home is an updated open-concept kitchen, complete with pantry & half

  Monte Marrocco Coldwell Banker Realty - Lexington

  10 Briarwood Ln, Winchester, MA 01890
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  /30

  Est $2,971,087 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,750 Sq Ft

  11 Wickham Rd, Winchester, MA 01890

  11 Wickham Rd, Winchester, MA 01890
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  /37

  Est $2,162,269 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,248 Sq Ft

  6 Wickham Rd, Winchester, MA 01890

  6 Wickham Rd, Winchester, MA 01890
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  /40

  Est $1,605,019 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,922 Sq Ft

  19 W Chardon Rd, Winchester, MA 01890

  19 W Chardon Rd, Winchester, MA 01890
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  /40

  Est $1,970,517 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,324 Sq Ft

  22 Grove St, Winchester, MA 01890

  22 Grove St, Winchester, MA 01890
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  /39

  Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,206 Sq Ft

  20 Bacon St Unit A, Winchester, MA 01890

  20 Bacon St Unit A, Winchester, MA 01890
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  /42

  Est $3,171,632 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 5,265 Sq Ft

  15 & 17 Brooks St, Winchester, MA 01890

  15 & 17 Brooks St, Winchester, MA 01890
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  /29

  Est $1,006,053 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,898 Sq Ft

  22 Grove Place Unit 35, Winchester, MA 01890

  22 Grove Place Unit 35, Winchester, MA 01890
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  /41

  Est $2,806,390 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 5,423 Sq Ft

  13 Briarwood Ln, Winchester, MA 01890

  13 Briarwood Ln, Winchester, MA 01890
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  /23

  Est $2,495,835 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,036 Sq Ft

  2 Hastings Rd, Winchester, MA 01890

  2 Hastings Rd, Winchester, MA 01890
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  /26

  Est $923,875 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,130 Sq Ft

  22 Grove Place Unit 20, Winchester, MA 01890

  22 Grove Place Unit 20, Winchester, MA 01890
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  /31

  Est $1,977,772 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,296 Sq Ft

  1 Sussex Rd, Winchester, MA 01890

  1 Sussex Rd, Winchester, MA 01890
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  /20

  Est $1,763,962 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,790 Sq Ft

  94 Grove St, Winchester, MA 01890

  94 Grove St, Winchester, MA 01890
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  /33

  Est $1,520,421 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft

  33 Canterbury Rd, Winchester, MA 01890

  33 Canterbury Rd, Winchester, MA 01890
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  /33

  Est $1,667,370 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,092 Sq Ft

  31 Canterbury Rd, Winchester, MA 01890

  31 Canterbury Rd, Winchester, MA 01890
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  /36

  Est $1,964,965 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,999 Sq Ft

  79 Grove St, Winchester, MA 01890

  79 Grove St, Winchester, MA 01890

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