Middlesex, MA Homes

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  $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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  Explore Winchester Highlands

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  /45

  $2,810 - $5,235 per month

  The Mave

  1 - 2 Beds

  225 Fallon Rd, Stoneham, MA 02180

  Here, smart design imbues modern comforts with alfresco joys. Quartz countertops, glass-enclosed showers, and quality stainless steel appliances add to your quality of life. Energy-efficient windows stream in sunlight while wood-style flooring inspires your next jaunt outside. But with thoughtful features like our enhanced fitness center and cyber studio, you won't have to wander far to activate

  225 Fallon Rd, Stoneham, MA 02180
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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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  /42

  Est $1,367,064 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,365 Sq Ft

  18 Forest St, Winchester, MA 01890

  18 Forest St, Winchester, MA 01890
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  /42

  $2,499,000 Open Sun 1PM - 2PM

  • 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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  /16

  $4,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Apartment for Rent

  24 Clematis St Unit 2, Winchester, MA 01890

  Welcome to Winchester! Discover this stylishly renovated home perfect for comfortable living. Features include a modern kitchen with white cabinets and butcher block counters, a cozy living room with a sectional sofa and floor lamp, an elegant dining area, a sleek bathroom with marble tiles, and a chic staircase. Enjoy a private living near Winchester Hospital and the town center. Enjoy a

  The North Star Group Keller Williams Realty Evolution

  24 Clematis St Unit 2, Winchester, MA 01890
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  /30

  $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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  /42

  Est $1,394,935 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,381 Sq Ft

  24 Brookside Ave, Winchester, MA 01890

  24 Brookside Ave, Winchester, MA 01890
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  /2

  $2,550,000

  • 5 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  19 Laurel Hill Ln, Winchester, MA 01890

  Nestled on a quiet street in one of Winchester’s most coveted neighborhoods, 19 Laurel Hill Lane will offer refined living just minutes from Boston and top-rated schools. This latest Mark Stephen Development project will feature 4 bedrooms and 4.5 bathrooms, including a flexible first-floor suite perfect for a guest room or study. The heart of the home will be a spacious kitchen flowing into a

  Mark Donnellan Advisors Living - Winchester

  19 Laurel Hill Ln, Winchester, MA 01890
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  /10

  $2,600 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  343 Washington St, Winchester, MA 01890

  343 Washington St, Winchester, MA 01890
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  /25

  $1,226,000 Sold Jul 15, 2025

  • 2,534 Sq Ft
  • $484/SF
  • 6 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1980

  8 Ware Rd, Winchester, MA 01890

  Tucked into the desirable Winchester Highlands and abutting the Middlesex Fells, 8 Ware Road offers space, comfort, and a flexible footprint. This well-maintained ranch features 3 bedrooms on the main level, including a primary suite with full bath, plus a finished basement with a spacious family room, walk-out sliding patio door, large flex space, & bonus 4th bedroom. The kitchen includes modern

  Alex Navarro Coldwell Banker Realty - Beverly

  8 Ware Rd, Winchester, MA 01890
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  /29

  Est $1,037,148 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,380 Sq Ft

  88 Forest St, Winchester, MA 01890

  88 Forest St, Winchester, MA 01890
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  /36

  $1,899,000 Pending

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

  20 Grayson Rd, Winchester, MA 01890

  Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear

  Monte Marrocco Coldwell Banker Realty - Lexington

  20 Grayson Rd, Winchester, MA 01890
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  /11

  $3,500 per month

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Apartment for Rent

  534 Washington St Unit 2, Winchester, MA 01890

  Welcome to this 3-bedroom spacious and bright apartment near the North Reservoir and Middlesex Fells Reservation!!! With many windows, the unit is flooded with natural light. The open-concept living space features a hardwood floor and recessed lighting. Cook with joy in a kitchen that includes granite countertops, a 5-burner stainless steel gas cooktop, and abundant cabinetry. All 3 bedrooms

  Mena Boone Keller Williams Realty Boston Northwest

  534 Washington St Unit 2, Winchester, MA 01890
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  /32

  $1,250,000 Sold Jun 30, 2025

  • 2,759 Sq Ft
  • $453/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  80 Harvard St, Winchester, MA 01890

  Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3 bedrooms and a bathroom.

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

  80 Harvard St, Winchester, MA 01890
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  /41

  Est $1,163,817 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,696 Sq Ft

  28 Garfield Ave, Winchester, MA 01890

  28 Garfield Ave, Winchester, MA 01890
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  /31

  $1,500,000 Pending

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

  6 Highland Ave, Winchester, MA 01890

  4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is

  Peter Rooney Compass

  6 Highland Ave, Winchester, MA 01890
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  /23

  $3,600 per month

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Condo for Rent

  40 Florence St Unit 2, Winchester, MA 01890

  (All is just repainted, brand new kitchen floor and countertops - Ready to rent out) 3-Bed / 2 Full-bath apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this three-bedroom and two-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless

  40 Florence St Unit 2, Winchester, MA 01890
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  /39

  $904,000 Sold Jun 23, 2025

  • 1,528 Sq Ft
  • $592/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1954

  703 Washington St, Winchester, MA 01890

  Delightful ranch, well maintained and located conveniently near the major routes. The kitchen is spacious and opens to the comfortable dining area with large built in hutch. It has been updated and features a tile backsplash, stainless steel appliances and recessed lighting. The living room is fireplaced and is nicely appointed with hardwood floors. Easy one level living with two first floor

  Michael Barrett Barrett, Chris. J., REALTORS®

  703 Washington St, Winchester, MA 01890
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  /41

  Est $1,259,264 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,302 Sq Ft

  39 Forest St, Winchester, MA 01890

  39 Forest St, Winchester, MA 01890
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  /33

  $1,250,000

  • 4 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  162 Forest St, Winchester, MA 01890

  Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining

  Paul Cirignano The Synergy Group

  162 Forest St, Winchester, MA 01890
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  /18

  $3,200 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  40 Florence St Unit 40, Winchester, MA 01890

  2-Bedroom apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this two-bedroom and one-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless appliances, granite counter tops and a side door that leads to the big and bright backyard. Two bright

  Weidong Li WINN Real Estate & Consulting

  40 Florence St Unit 40, Winchester, MA 01890
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  /42

  $1,187,000 Sold Jun 18, 2025

  • 1,906 Sq Ft
  • $623/SF
  • 12 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1926

  44 Forest St, Winchester, MA 01890

  This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living

  Kim Covino Compass

  44 Forest St, Winchester, MA 01890
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  /41

  Est $1,175,251 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,281 Sq Ft

  502 Washington St, Winchester, MA 01890

  502 Washington St, Winchester, MA 01890
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  /16

  $1,225,000

  • 4 Beds
  • 3 Baths
  • 1,860 Sq Ft

  60 Harvard St, Winchester, MA 01890

  Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while

  Mark Krasnyansky eXp Realty

  60 Harvard St, Winchester, MA 01890
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  /12

  $3,200 per month

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

  65 Highland Ave Unit 1, Winchester, MA 01890

  1 bed and 1 bath located in Winchester Highlands. Easy access to downtown and public transportation!

  65 Highland Ave Unit 1, Winchester, MA 01890
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  /35

  $1,750,000 Sold Jun 17, 2025

  • 2,597 Sq Ft
  • $674/SF
  • 2 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1925

  18 Englewood Rd, Winchester, MA 01890

  OFFER ACCEPTED - Open Houses CANCELED This stunning, sun-filled home welcomes you with a front porch facing southwest for sunset views! Move right in and enjoy so many updates - new windows, new kitchen, new shared bath, new heating and cooling systems, new exercise/mudroom, new landscaping and so much more!!! With fabulous detail and a focus on energy efficiency, this home will win your heart

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  18 Englewood Rd, Winchester, MA 01890
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  /33

  Est $1,242,906 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,490 Sq Ft

  17 Cross St, Winchester, MA 01890

  17 Cross St, Winchester, MA 01890
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  /36

  $1,349,900 Open Sun 11:30AM - 1PM

  • 5 Beds
  • 2 Baths
  • 1,706 Sq Ft

  35 Harvard St, Winchester, MA 01890

  Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

  Joanne Mulkerin J. Mulkerin Realty

  35 Harvard St, Winchester, MA 01890
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  /12

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Apartment for Rent

  17 Irving St Unit 3, Winchester, MA 01890

  Great opportunity to live close to Winchester Center.Available June 1st this 2nd floor unit features a large deck before entering kitchen. Kitchen has been completely done over new floors, cabinets and all new appliances, living room, bedroom and full bath. Next level, has two bedrooms, bath with shower. All hardwood floors and many windows. Tenant is responsible for Gas, Electric and Cable.

  Robin Griffiths J. Mulkerin Realty

  17 Irving St Unit 3, Winchester, MA 01890
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  /42

  $1,350,000 Sold May 30, 2025

  • 3,351 Sq Ft
  • $403/SF
  • 38 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1946

  34 Fells Rd, Winchester, MA 01890

  Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

  Andersen Group Realty Keller Williams Realty Boston Northwest

  34 Fells Rd, Winchester, MA 01890
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  /42

  Est $2,114,531 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,350 Sq Ft

  7 Nathaniel Rd, Winchester, MA 01890

  7 Nathaniel Rd, Winchester, MA 01890
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  /37

  $1,299,000 Open Sun 11AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft

  147 Highland Ave, Winchester, MA 01890

  Call for a private showing anytime! Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you w/ a spacious living room w fplc that flows seamlessly into a sun-drenched updated

  Kim Covino Compass

  147 Highland Ave, Winchester, MA 01890
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  /36

  $11,000 per month

  • 6 Beds
  • 4.5 Baths
  • 6,500 Sq Ft
  • House for Rent

  52 N Border Rd, Winchester, MA 01890

  Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home has 6 bedrooms, and 5 bathrooms. The stunning foyer welcomes you to the sprawling first floor. The custom work throughout each sun filled room is exquisite. Gourmet kitchen with top of the line appliances. Generous sized rooms to entertain guests. A private home office with built

  Julia Marino Archambault Real Estate

  52 N Border Rd, Winchester, MA 01890
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  /42

  $1,558,000 Sold May 29, 2025

  • 2,792 Sq Ft
  • $558/SF
  • 9 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1993

  24 Eugene Dr, Winchester, MA 01890

  Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layout plus amenities like central air, 1st floor laundry room, direct indoor access to a 2-car garage, and delightful wooded back yard are more outstanding details. The kitchen & family room at the back of the house will be everyone’s favorite gathering spot. The eat-in kitchen

  Andrea O'Reilly Keller Williams Realty Evolution

  24 Eugene Dr, Winchester, MA 01890
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  /38

  Est $1,347,368 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,799 Sq Ft

  39 Nathaniel Rd, Winchester, MA 01890

  39 Nathaniel Rd, Winchester, MA 01890
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  /6

  $1,100,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,060 Sq Ft

  540-542 Washington St, Winchester, MA 01890

  Great Two-Family Home in a Desirable Location! This well-maintained two-family property features a total of 4 bedrooms and 2 full bathrooms, with beautiful hardwood floors throughout. Each unit offers spacious living areas filled with natural light. The basement includes laundry hookups with washer and dryer included. Enjoy the convenience of 6 off-street parking spaces—a rare find! Situated just

  Wei Wang WW Real Estate LLC

  540-542 Washington St, Winchester, MA 01890
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  /20

  $2,398,000 Sold May 06, 2025

  • 4,468 Sq Ft
  • $537/SF
  • 26 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1937

  74 Hillcrest Pkwy, Winchester, MA 01890

  Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fells Reservation on one of Winchester's most picturesque streets! First floor seamlessly blends living, dining, & kitchen areas. Living room has wood burning fireplace & custom built-in shelves. Dining room offers delightful space for cozy gatherings and the spacious eat-in kitchen

  Ann Hogstadius RE/MAX Real Estate Center

  74 Hillcrest Pkwy, Winchester, MA 01890
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  /38

  Est $1,243,034 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,681 Sq Ft

  32 Nathaniel Rd, Winchester, MA 01890

  32 Nathaniel Rd, Winchester, MA 01890
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  /38

  $1,099,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  8 Garfield Ave, Winchester, MA 01890

  Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a custom built free standing office/cottage/gym/ movie house, blends timeless charm w/ modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace w/ built ins, the dining room is perfect

  Kim Covino Compass

  8 Garfield Ave, Winchester, MA 01890

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