The Flats Homes

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  $2,275,000

  • 6 Beds
  • 2.5 Baths
  • 4,104 Sq Ft

  15 Wildwood St, Winchester, MA 01890

  Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized

  Kim Covino Compass

  15 Wildwood St, Winchester, MA 01890
• Explore The Flats

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  /13

  $3,795 total monthly price

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

  7 Lewis Rd Unit 2, Winchester, MA 01890

  Wonderful opportunity to rent in Winchester, less than a half mile from the town common. Rarely available First floor unit with hardwood floors throughout, 2 bedrooms and one full tiled bath. Additional storage space in lower level that is wired to your specific unit...could be used for office space, home gym, craft room, etc. Carefree living with Heat, basic cable tv and all exterior maintenance

  

  Catherine Albiani

  Better Homes and Gardens Real Estate - The Shanahan Group

  (781) 404-8664

  7 Lewis Rd Unit 2, Winchester, MA 01890
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  $2,030,000 Sold Dec 01, 2025

  • 5,791 Sq Ft
  • $351/SF
  • 8 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1925

  58 Bacon St, Winchester, MA 01890

  Welcome to 58 Bacon Street—a perfect blend of classic charm and modern comforts. The main level features a front-to-back fireplaced living room, sunroom, formal dining room, and a stunning 2024 kitchen renovation with custom cabinetry, quartz island, and high-end stainless appliances, opening to a bright family room. Upstairs offers flexible space with dual primary suite options (one with

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

  58 Bacon St, Winchester, MA 01890
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  Est $1,704,114 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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  $3,099,000 Open Sun 12PM - 1PM

  • 6 Beds
  • 6.5 Baths
  • 6,028 Sq Ft

  44 Cabot St, Winchester, MA 01890

  Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

  Andersen Group Realty Keller Williams Realty Boston Northwest

  44 Cabot St, Winchester, MA 01890
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  /4

  $3,000 per month plus fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  45 Church St Unit 3, Winchester, MA 01890

  Property Id: 2254146Sunny spacious center of town ; 2 mantels, high ceilings, Victorian apartment. Walk to stores, restaurants, bank and commuter rail. Convenient to Boston and art. 95.Heated, with washer dryer in unit. Off street parking.

  45 Church St Unit 3, Winchester, MA 01890
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  /39

  $2,600,000 Sold Nov 21, 2025

  • 4,779 Sq Ft
  • $544/SF
  • 44 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1938

  48 Salisbury St, Winchester, MA 01890

  Thoughtfully renovated & meticulously maintained, this classic colonial home in the Flats invites with timeless charm & modern conveniences. Through the center entrance be welcomed into the fireplaced living room & dining room- both refreshed in 2025 with new lighting, paint & wallpaper. The open-plan custom kitchen with marble counters, stainless appliances, and a butler’s pantry with sink,

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

  48 Salisbury St, Winchester, MA 01890
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  Est $1,968,720 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,011 Sq Ft

  67 Wildwood St, Winchester, MA 01890

  67 Wildwood St, Winchester, MA 01890
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  /41

  $2,799,000 Pending

  • 7 Beds
  • 5.5 Baths
  • 5,864 Sq Ft

  10 Sheffield Rd, Winchester, MA 01890

  This stunning Colonial Revival home, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master suite with walk-in closets and a Jacuzzi bath, along with

  Andersen Group Realty Keller Williams Realty Boston Northwest

  10 Sheffield Rd, Winchester, MA 01890
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  $3,700 total monthly price

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • Apartment for Rent

  11 Elmwood Ave Unit 11, Winchester, MA 01890

  Welcome to 11 Elmwood, just steps from Winchester Center. You’ll love being able to stroll to your morning coffee, grab dinner with friends, browse the local shops, or catch the commuter rail without ever needing your car. Inside, this home offers three levels of comfortable living space plus a finished basement that works beautifully as a quiet office, a cozy hangout spot, or simply extra

  Melanie Lentini Leading Edge Real Estate

  11 Elmwood Ave Unit 11, Winchester, MA 01890
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  $3,599,000 Sold Nov 20, 2025

  • 5,876 Sq Ft
  • $612/SF
  • 27 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1870

  5 Stratford Rd, Winchester, MA 01890

  This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

  Kim Covino Compass

  5 Stratford Rd, Winchester, MA 01890
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  /41

  Est $2,557,946 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,676 Sq Ft

  79 Yale St, Winchester, MA 01890

  79 Yale St, Winchester, MA 01890
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  /40

  $2,250,000 Pending

  • 6 Beds
  • 5 Baths
  • 3,728 Sq Ft

  6 Ivy Cir, Winchester, MA 01890

  Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large

  Rose Hall Blue Ocean Realty, LLC

  6 Ivy Cir, Winchester, MA 01890
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  /6

  $1,950 per month plus fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  2 Elmwood Ave Unit 52, Winchester, MA 01890

  This nice 1 Bedroom 1 Bath place in the WINCHESTER area is available for Now.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 obtained.

  2 Elmwood Ave Unit 52, Winchester, MA 01890
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  $4,450,000 Sold Oct 24, 2025

  • 7,679 Sq Ft
  • $580/SF
  • 1 Day On Market

  • 5 Beds
  • 7 Baths
  • Built 1937

  20 Foxcroft Rd, Winchester, MA 01890

  A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over 1⁄2 acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for

  Carolyn Walsh Better Homes and Gardens Real Estate - The Shanahan Group

  20 Foxcroft Rd, Winchester, MA 01890
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  Est $2,539,943 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,775 Sq Ft

  76 Yale St, Winchester, MA 01890

  76 Yale St, Winchester, MA 01890
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  $2,299,000 Pre-Foreclosure

  • 7 Beds
  • 5.5 Baths
  • 4,929 Sq Ft

  89 Wildwood St, Winchester, MA 01890

  Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  89 Wildwood St, Winchester, MA 01890
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  /23

  $5,750 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,948 Sq Ft
  • House for Rent

  113 Cambridge St, Winchester, MA 01890

  Ideally located near Winchester Center, this beautifully updated home combines modern design with classic New England charm. 113 Cambridge Street features a fully renovated kitchen with custom cabinetry, quartz counters, and premium appliances, opening to bright, inviting living spaces. The newly finished basement adds incredible versatility, ideal for a playroom, gym, or guest suite. With four

  Ryan Clunan Campion & Company Fine Homes Real Estate

  113 Cambridge St, Winchester, MA 01890
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  /40

  $3,242,250 Sold Oct 17, 2025

  • 5,250 Sq Ft
  • $618/SF
  • 25 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1870

  4 Norwood St, Winchester, MA 01890

  Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor

  Mark Donnellan Gibson Sotheby's International Realty

  4 Norwood St, Winchester, MA 01890
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  Est $2,051,472 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,003 Sq Ft

  12 Woodside Rd, Winchester, MA 01890

  12 Woodside Rd, Winchester, MA 01890
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  /31

  $1,999,000 Open Thu 5PM - 6PM

  • 4 Beds
  • 3.5 Baths
  • 3,475 Sq Ft

  46 Church St, Winchester, MA 01890

  Welcome to 46 Church Street. This spacious, beautifully maintained, Paul Whitney built home is just outside the heart of Winchester center with easy access to the commuter rail, schools, restaurants, and shopping. Offering flexible living areas and abundant room throughout, the residence features four bedrooms, three and a half bathrooms, two dedicated home offices, and a generously sized bonus

  Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

  46 Church St, Winchester, MA 01890
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  /7

  $1,950 per month plus fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  2 Elmwood Ave Unit 11, Winchester, MA 01890

  This nice 1 Bedroom 1 Bath place in the WINCHESTER area is available for Now.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 obtained.

  2 Elmwood Ave Unit 11, Winchester, MA 01890
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  $1,900,000 Sold Oct 17, 2025

  • 3,413 Sq Ft
  • $557/SF
  • 12 Days On Market

  • 7 Beds
  • 2.5 Baths
  • Built 1890

  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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  Est $3,338,103 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,550 Sq Ft

  47 Wedgemere Ave, Winchester, MA 01890

  47 Wedgemere Ave, Winchester, MA 01890
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  /41

  $4,174,000

  • 7 Beds
  • 6 Baths
  • 7,043 Sq Ft

  2 Everett Ave, Winchester, MA 01890

  Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end

  Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

  2 Everett Ave, Winchester, MA 01890
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  $5,700 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,575 Sq Ft
  • Condo for Rent

  2 Rangeley Rd Unit 2, Winchester, MA 01890

  Location, Location, Location!! This beautifully updated 2 bedroom 2.5 bath conveniently located in Winchester Center. Recently renovated, this unit boasts a stunning kitchen with farmer sink, high end stainless appliances, custom cabinetry and pantry. First floor offers living room w/ fireplace and large dining room with hardwood throughout. 2 spacious bedrooms and 1.5 baths complete the second

  Kim Covino Compass

  2 Rangeley Rd Unit 2, Winchester, MA 01890
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  $2,862,500 Sold Oct 10, 2025

  • 5,238 Sq Ft
  • $546/SF
  • 6 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1915

  54 Wedgemere Ave, Winchester, MA 01890

  Exceptional value, prime living in this stunning home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive backyard featuring gorgeous

  Kim Covino Compass

  54 Wedgemere Ave, Winchester, MA 01890
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  Est $2,260,380 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,605 Sq Ft

  61 Oxford St, Winchester, MA 01890

  61 Oxford St, Winchester, MA 01890
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  $1,399,000 Open Sat 11AM - 12:30PM

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

  6 Wyman Ct Unit 6, Winchester, MA 01890

  Another Tree Top Group masterpiece –Welcome to 6 Wyman Court! New full gut renovation townhome with 2,722 sq. ft., 3 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center

  Monte Marrocco Coldwell Banker Realty - Lexington

  6 Wyman Ct Unit 6, Winchester, MA 01890
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  /20

  $1,850 per month plus fees

  • 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 Now.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 obtained. We

  2 Elmwood Ave Unit 14, Winchester, MA 01890
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  /39

  $1,475,000 Sold Sep 26, 2025

  • 1,947 Sq Ft
  • $758/SF
  • 7 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2011

  60 Graystone Cir Unit 60, Winchester, MA 01890

  Meticulously maintained, 2-bedroom, 2.5-bath townhome with 2 car garage. The kitchen features custom cabinets, granite countertops, high-end stainless steel appliances and gleaming hardwood floors. The living/dining room combo features hardwood floors, gas fireplace, cathedral ceilings along with french doors that open to a private patio with gas grill. Spacious first floor primary suite boasts a

  Pirani & Wile Group Gibson Sotheby's International Realty

  60 Graystone Cir Unit 60, Winchester, MA 01890
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  Est $2,728,569 Not Listed For Sale

  • 7 Beds
  • 3.5 Baths
  • 5,616 Sq Ft

  49 Oxford St, Winchester, MA 01890

  49 Oxford St, Winchester, MA 01890
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  $1,399,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 2,500 Sq Ft

  4 Wyman Ct Unit 4, Winchester, MA 01890

  Another Tree Top Group masterpiece –Welcome to 4 Wyman Court! New full gut renovation townhome with 2,500 sq. ft., 4 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center

  Monte Marrocco Coldwell Banker Realty - Lexington

  4 Wyman Ct Unit 4, Winchester, MA 01890
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  $3,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,900 Sq Ft
  • Townhouse for Rent

  112 Church St, Winchester, MA 01890

  Winchesters finest neighborhood among beautiful homes and surroundings. 2 bed townhouse with separate basement area and laundry and private porches. Lease flexible short or long term, be the first to rent this home from new buyer.2 private rooms upstairs for office (or 2 more bedrooms). Available now.

  112 Church St, Winchester, MA 01890
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  $2,350,000 Sold Aug 29, 2025

  • 5,824 Sq Ft
  • $404/SF
  • 60 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1911

  107 Cambridge St, Winchester, MA 01890

  Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz

  Stephen Stratford William Raveis R.E. & Home Services

  107 Cambridge St, Winchester, MA 01890
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  Est $2,328,557 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,516 Sq Ft

  38 Cabot St, Winchester, MA 01890

  38 Cabot St, Winchester, MA 01890
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  $1,725,000 Pending

  • 7 Beds
  • 2.5 Baths
  • 2,998 Sq Ft

  1 Copley St, Winchester, MA 01890

  Gracious Center Entrance colonial situated in top Flats location on a desirable corner lot. This home has all the charm of yesteryear and has many custom features including a beautiful front staircase with window seats, hardwood floors and sunny rooms. Attractive cherry cabinet kitchen with granite island. Large front to back living room has fireplace and is situated next to enclosed porch.

  Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

  1 Copley St, Winchester, MA 01890
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  /2

  $720,000 Sold Aug 26, 2025

  • 1,300 Sq Ft
  • $554/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1980

  29 Vine St Unit 7, Winchester, MA 01890

  Immerse yourself in the vibrant heart of Winchester Center with this exquisite 2-bedroom, 1.5-bathroom condominium! Step into the open-concept living and dining area, where a modern touch meets downtown flair. A rare freestanding wood-burning fireplace accentuates the space, offering warmth and a touch of classic charm. Delight in the recently renovated kitchen, designed for both style and

  Philip Vita Compass

  29 Vine St Unit 7, Winchester, MA 01890
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  Est $1,791,878 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,131 Sq Ft

  39 Wildwood St, Winchester, MA 01890

  39 Wildwood St, Winchester, MA 01890
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  /34

  $1,499,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,865 Sq Ft

  53 Bacon St, Winchester, MA 01890

  Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering

  Taleen Chiofaro Leading Edge Real Estate

  53 Bacon St, Winchester, MA 01890

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