Middlesex, MA Homes

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  $499,800

  • 2 Beds
  • 1 Bath
  • 822 Sq Ft

  200 Swanton St Unit 239, Winchester, MA 01890

  Sunny second-floor 2-bedroom unit overlooking a serene duck pond. This home features an open layout with hardwood floors, an updated granite and stainless-steel kitchen, and a modern bath with a sleek barn door. Each bedroom offers two closets, plus three additional hallway closets for exceptional storage. Enjoy a private enclosed balcony with serene views. The HOA fee includes heat, hot water,

  

  Joan Powell

  Advisors Living - Merrimac

  (781) 488-1546

  200 Swanton St Unit 239, Winchester, MA 01890
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  Explore Winchester

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  $3,195 - $4,350 per month

  Sanctuary Winchester North

  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

  25-35 River St, Winchester, MA 01890
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  $1,627,000 Sold Jul 31, 2025

  • 2,853 Sq Ft
  • $570/SF
  • 7 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1930

  32 Oneida Rd, Winchester, MA 01890

  Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

  Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

  32 Oneida Rd, Winchester, MA 01890
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  /39

  Est $2,357,027 Not Listed For Sale

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

  38 Winthrop Street Extension, Winchester, MA 01890

  38 Winthrop Street Extension, Winchester, MA 01890
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  $1,990,000

  • 4 Beds
  • 4.5 Baths
  • 4,474 Sq Ft

  4 Chestnut St, Winchester, MA 01890

  Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blue cabinetry, copper accents, and bold designer touches. One bedroom opens to a composite deck

  

  Tyson Lynch

  The Proper Nest Real Estate

  (781) 633-6582

  4 Chestnut St, Winchester, MA 01890
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  /42

  $6,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,516 Sq Ft
  • Apartment for Rent

  192 Cross St, Winchester, MA 01890

  Discover elegant living in this stunning Winchester duplex offering exceptional space and comfort across four thoughtfully designed levels. Ideal for both relaxation and entertaining, the home boasts an expansive kitchen flowing seamlessly into inviting dining and spacious family areas. Retreat upstairs to generously sized bedrooms, each designed for restful privacy, including the ensuite primary

  Anne Spry Barrett Sotheby's International Realty

  192 Cross St, Winchester, MA 01890
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  /41

  $2,425,000 Sold Jul 31, 2025

  • 5,501 Sq Ft
  • $441/SF
  • 61 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  15 Churchill Rd, Winchester, MA 01890

  Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor

  Kim Covino Compass

  15 Churchill Rd, Winchester, MA 01890
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  /33

  Est $1,722,294 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,254 Sq Ft

  20 Graystone Cir Unit 20, Winchester, MA 01890

  20 Graystone Cir Unit 20, Winchester, MA 01890
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  /42

  $2,750,000

  • 6 Beds
  • 5.5 Baths
  • 4,563 Sq Ft

  382 S Border Rd, Winchester, MA 01890

  GORGEOUS NEW CONSTRUCTION - 12 Rooms - 6 BD's - 5.5 BA's You will be captivated by the grand entrance - attention to detail - high coffered 10' ceilings and excellent flow that leads you to the magnificent Open Floor Plan - custom-designed Kitchen which is the heart of this home. no expense was spared, w/custom Cabinets, Thermador appliances, oversized Center Island; Living Rm/Great Rm, w/FP,

  Lucille Murray Advisors Living - Winchester

  382 S Border Rd, Winchester, MA 01890
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  /20

  $3,220 - $4,250 per month

  Sanctuary Winchester West

  Studio - 3 Beds

  416 Cambridge St, Winchester, MA 01890

  The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

  416 Cambridge St, Winchester, MA 01890
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  /39

  $1,149,000 Sold Jul 31, 2025

  • 2,300 Sq Ft
  • $500/SF
  • 4 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2017

  83 Canal St Unit 85, Winchester, MA 01890

  This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary

  Mary O'Hagan Barrett Sotheby's International Realty

  83 Canal St Unit 85, Winchester, MA 01890
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  /42

  Est $2,853,598 Not Listed For Sale

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

  228 Ridge St, Winchester, MA 01890

  228 Ridge St, Winchester, MA 01890
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  $1,999,000

  • 7 Beds
  • 2.5 Baths
  • 3,413 Sq Ft

  2 Lagrange St, Winchester, MA 01890

  EXQUISITE 12 ROOM, 7 BEDROOMS, 2 STUNNING FIREPLACES, 2.5 BATH QUEEN ANNE VICTORIAN! Easy Stroll to Center of Town. Hear the Church Bells Strike the Hour. Delightfully Quiet Street with a Family Orientated Community. Beautiful Morning and Evening Sun. During the Day the Huge Sun Deck off the Kitchen with a SPACIOUS AWNING is both Shady and Warm. Multi Outdoor Opportunities for Living including a

  Alison Lules-Cuccio Don Baker Real Estate

  2 Lagrange St, Winchester, MA 01890
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  $7,750 per month

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  10 Farrow St, Winchester, MA 01890

  Single Family Home rental in Winchester. NO BROKERS FEE. Available 8/5, 8/15, 9/1. Completely rebuilt from ground up in 2019 w/Attached 1 Car Garage. 4 Beds, 3.5 baths & 3500SF w/ 2 dedicated home offices. Modern kitchen w/Quartz Countertops, Stainless Steel Appliances & Venting for cooking. Open concept has an Island connecting dining & living spaces. Sundrenched Living Room offers a wood

  Collin Bray Century 21 Cityside

  10 Farrow St, Winchester, MA 01890
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  /29

  $1,300,000 Sold Jul 30, 2025

  • 2,238 Sq Ft
  • $581/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1905

  49 Lincoln St, Winchester, MA 01890

  Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking

  Vantage Point Team William Raveis R.E. & Home Services

  49 Lincoln St, Winchester, MA 01890
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  /30

  Est $2,087,183 Not Listed For Sale

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

  5 Squire Rd, Winchester, MA 01890

  5 Squire Rd, Winchester, MA 01890
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  /4

  $1,890,000

  • 5 Beds
  • 5 Baths
  • 3,301 Sq Ft

  166 Forest St, Winchester, MA 01890

  Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A

  Ning Sun United Real Estate, LLC

  166 Forest St, Winchester, MA 01890
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  /15

  $1,700 per month

  • Studio
  • 1 Bath
  • 350 Sq Ft
  • Condo for Rent

  200 Swanton St, Winchester, MA 01890

  Studio apartment on the 7th floor in Winchester with a private balcony overlooking Duck Pond. Heat, hot water, AC, and electricity included. Building amenities include an elevator, outdoor swimming pool, visitor parking, and 1 free parking pass (additional parking available at extra cost to HOA). Convenient location close to shopping, restaurants, and major highways. Enjoy comfortable and

  200 Swanton St, Winchester, MA 01890
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  $1,650,000 Sold Jul 30, 2025

  • 2,646 Sq Ft
  • $624/SF
  • 18 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1957

  50 Johnson Rd, Winchester, MA 01890

  One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins.

  Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

  50 Johnson Rd, Winchester, MA 01890
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  /40

  Est $1,368,810 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,529 Sq Ft

  15 Wincrest Dr, Winchester, MA 01890

  15 Wincrest Dr, Winchester, MA 01890
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  $3,199,000

  • 6 Beds
  • 6.5 Baths
  • 8,463 Sq Ft

  26 Swan Rd, Winchester, MA 01890

  Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end

  Kim Covino Compass

  26 Swan Rd, Winchester, MA 01890
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  /18

  $2,000 per month

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

  200 Swanton St Unit L25, Winchester, MA 01890

  The sought after Parkview Condominium! Prime Winchester Location ! All newly PAINTED ! Living room with glass sliders to balcony overlooking a calming and picturesque landscaped wildlife garden and pond with ducks & swans. Rent includes ALL utilities - heat, cold & hot water, electricity and 1 gated parking space! Amenities: swimming pool and on-site laundry facilities! No pets. No smoking of

  Ai Cheng Goh Z. Realty

  200 Swanton St Unit L25, Winchester, MA 01890
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  $2,690,000 Sold Jul 30, 2025

  • 4,704 Sq Ft
  • $572/SF
  • 6 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1954

  34 Swan Rd, Winchester, MA 01890

  Situated in the prestigious Myopia Hill neighborhood, this exceptional sprawling ranch offers a rare combination of timeless elegance & modern comfort. Set on a lush, private acre, offering nearly 4,500 sq ft of beautifully maintained living space designed for both everyday living & grand-scale entertaining. Exquisite custom woodwork, built-ins & moldings lend sophistication throughout.

  Laurie Cappuccio Classified Realty Group

  34 Swan Rd, Winchester, MA 01890
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  /33

  Est $1,549,030 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,034 Sq Ft

  10 Carriage Ln, Winchester, MA 01890

  10 Carriage Ln, Winchester, MA 01890
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  $2,350,000

  • 5 Beds
  • 3.5 Baths
  • 5,006 Sq Ft

  276 High St, Winchester, MA 01890

  Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

  Kim Covino Compass

  276 High St, Winchester, MA 01890
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  /4

  $1,750 per month

  • Studio
  • 1 Bath
  • Condo for Rent

  2 Elmwood Ave Unit 14, Winchester, MA 01890

  This nice Studio 1 Bath place in the WINCHESTER area is available for 09-05-2025.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was

  2 Elmwood Ave Unit 14, Winchester, MA 01890
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  $1,207,500 Sold Jul 24, 2025

  • 1,573 Sq Ft
  • $768/SF
  • 20 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1910

  18 Brookside Ave, Winchester, MA 01890

  Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to a bright bow front living room w/ high ceilings, that flows into the dining room & beautifully updated kitchen w/ stainless appliances & custom cabinetry w/ generous counter space. Off the kitchen, there’s a half bath and a bonus room—great as an office, playroom, or casual

  Kim Covino Compass

  18 Brookside Ave, Winchester, MA 01890
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  Est $1,469,914 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,125 Sq Ft

  47 Thornberry Rd, Winchester, MA 01890

  47 Thornberry Rd, Winchester, MA 01890
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  /42

  $1,899,000 Open Sat 1:30PM - 2:30PM

  • 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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  $4,100 per month

  • 3 Beds
  • 1.5 Baths
  • 1,542 Sq Ft
  • House for Rent

  104 Wendell St, Winchester, MA 01890

  3-Bedroom single colonial house in Winchester for rent. Situated at a quiet neighborhood, this 3-bedroom and 1.5 bathroom single family house has a nice floor plan with a good kitchen. Hardwood floor throughout. The first floor has a spacious living room, an open concept kitchen and dining area. Kitchen is equipped with stainless appliances, granite counter tops and a slider that leads to the

  Weidong Li WINN Real Estate & Consulting

  104 Wendell St, Winchester, MA 01890
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  /39

  $950,000 Sold Jul 17, 2025

  • 1,540 Sq Ft
  • $617/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1875

  6 Francis Circuit Unit 6, Winchester, MA 01890

  Submerge yourself in historic elegance in this meticulously detailed Victorian home, brimming with classic design. Located on one of Winchester’s most serene and desirable cul-de-sacs, this stunning gem overflows with rich architectural details. Inside, you'll find three stately fireplaces, two oversized pocket doors, exquisite antique leaded light fixtures, stained glass, gleaming hardwood

  Katherine Waters-Clark Compass

  6 Francis Circuit Unit 6, Winchester, MA 01890
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  /35

  Est $1,650,741 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,926 Sq Ft

  16 Nassau Dr, Winchester, MA 01890

  16 Nassau Dr, Winchester, MA 01890
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  $2,239,000

  • 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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  /30

  $2,750 per month

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

  6 Skillings Rd Unit 2j, Winchester, MA 01890

  Two bedroom one bath unit located right out of Winchester Center. Open loft style living room and kitchen. Two good size bedrooms and full bath with w/d in unit. Hardwood floors throughout unit. Lots of natural sun light, gas heat and gas cooking, central ac, attic storage, 1 or 2 car parking. Walk to many shops, restaurants, commuter rail, duck pond, library, etc. Close to Winchester Hospital.

  6 Skillings Rd Unit 2j, Winchester, MA 01890
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  $680,000 Sold Jul 17, 2025

  • 1,160 Sq Ft
  • $586/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  7 Conant Rd Unit 23, Winchester, MA 01890

  Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts’ top-rated school districts. Located in the desirable Lynch Elementary district, which will open a brand-new school building this fall. This move-in ready home has just been freshly painted, with brand-new kitchen appliances and new carpeting throughout. The open-concept living and dining area

  Xin Cui Hooli Homes Boston

  7 Conant Rd Unit 23, Winchester, MA 01890
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  Est $1,594,158 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,171 Sq Ft

  94 Johnson Rd, Winchester, MA 01890

  94 Johnson Rd, Winchester, MA 01890
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  /42

  $2,499,000 Open Thu 5:30PM - 7PM

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  14 Grant Rd, Winchester, MA 01890

  Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space

  Monte Marrocco Coldwell Banker Realty - Lexington

  14 Grant Rd, Winchester, MA 01890
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  /20

  $2,950 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  37-39 Spruce St Unit 37, Winchester, MA 01890

  Welcome to this beautifully home in a prime Winchester location! Recently gut renovated and in pristine condition, this unit is truly move-in ready.The open floor plan features gleaming hardwood floors, a spacious living area, and a stunning chef’s kitchen with granite countertops, stainless steel appliances, new cabinetry, and a charming breakfast nook with wet bar. Enjoy the convenience of

  Kim Covino Compass

  37-39 Spruce St Unit 37, Winchester, MA 01890
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  /32

  $1,280,000 Sold Jul 16, 2025

  • 2,137 Sq Ft
  • $599/SF
  • 21 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2015

  18 Hemingway St, Winchester, MA 01890

  This COMPLETEDLY GUTTED AND REBUILT IN 2015 5B3.5B colonia-preserving a portion of original foundation, is located in a quiet neighborhood yet just minutes to Town Center, Elementary & High School, Town beach, Horn Pond, Fells Reservation, commuter rail station/Bus 134 to Wellington T. The architect-designed home features hardwood flooring throughout, high ceiling & abundant natural light. 1st

  Julia Xie Keller Williams Realty-Merrimack

  18 Hemingway St, Winchester, MA 01890
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  /32

  Est $1,618,198 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,622 Sq Ft

  104 Thornberry Rd, Winchester, MA 01890

  104 Thornberry Rd, Winchester, MA 01890

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