The Flats Homes

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  /42

  $4,250,000

  • 5 Beds
  • 3.5 Baths
  • 4,484 Sq Ft

  9 Lakeview Terrace, Winchester, MA 01890

  LAKEFRONT! Nestled on the serene shore of Mystic Lake just 7 miles from Boston, this extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room! Located in one of Winchester’s most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and

  Kim Covino Compass

  9 Lakeview Terrace, Winchester, MA 01890
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• 

  

  

  /7

  $2,050 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  2 Elmwood Ave Unit 1, Winchester, MA 01890

  This nice 1 Bed 1 Bath place in the WINCHESTER area is available for Now. Included Features are: Laundry in Basement.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

  2 Elmwood Ave Unit 1, Winchester, MA 01890
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  /42

  $2,350,000 Sold Jun 16, 2025

  • 4,212 Sq Ft
  • $558/SF
  • 15 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1880

  19 Yale St, Winchester, MA 01890

  Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom

  Nancy Pallotta Advisors Living - Winchester

  19 Yale St, Winchester, MA 01890
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  /33

  Est $1,745,337 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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  /39

  $3,599,000

  • 6 Beds
  • 4.5 Baths
  • 5,876 Sq Ft

  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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  /13

  $3,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,331 Sq Ft
  • Condo for Rent

  29 Vine St Unit 3, Winchester, MA 01890

  Two-level apartment with two bedrooms, two baths, and a parking space. Possible second parking space - negotiable. Large kitchen space with stainless steel appliances. Spacious off-living room, fenced porch. In-unit laundry. Walk-in closet. Dream location: t-station, shops, bike path, cafes, and much more, all within a 5-minute walk. Beautiful views of the Fells. First month and security deposit.

  Jasmina Cesic Danehy Realty Corp.

  29 Vine St Unit 3, Winchester, MA 01890
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  /40

  $3,025,000 Sold Jun 13, 2025

  • 5,198 Sq Ft
  • $582/SF
  • 50 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 1910

  21 Sheffield W, Winchester, MA 01890

  Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

  Kim Covino Compass

  21 Sheffield W, Winchester, MA 01890
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  /41

  Est $2,073,231 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  73 Pond St, Winchester, MA 01890

  73 Pond St, Winchester, MA 01890
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  /42

  $2,899,000 Open Sun 12PM - 1PM

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

  10 Sheffield Rd, Winchester, MA 01890

  This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, 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

  Andersen Group Realty Keller Williams Realty Boston Northwest

  10 Sheffield Rd, Winchester, MA 01890
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  /11

  $1,895 per month

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  75 Church St Unit R, Winchester, MA 01890

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

  75 Church St Unit R, Winchester, MA 01890
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  /38

  $2,600,000 Sold May 19, 2025

  • 4,060 Sq Ft
  • $640/SF
  • 88 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1912

  3 Lagrange St, Winchester, MA 01890

  Nestled in a sought-after neighborhood, this stunningly reimagined home combines timeless charm and modern comfort, just a short walk to downtown. The inviting foyer welcomes you from a wrap-around porch into an open yet intimate layout connecting the kitchen, dining, and family rooms. A mudroom with marble checkered flooring and a walk-in pantry with a beverage fridge add practical luxury.

  Mark Donnellan Advisors Living - Winchester

  3 Lagrange St, Winchester, MA 01890
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  /42

  Est $2,466,480 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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  /38

  $3,249,000 Open Sun 11:30AM - 12:30PM

  • 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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  /25

  $4,300 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  67 Church St, Winchester, MA 01890

  Enjoy this beautiful renovated home right outside Winchester center! Direct entry unit completely updated all new with gorgeous kitchen & bath, hardwood floors, new heating system with central air, new windows, electric, very high ceilings, washer & dryer in unit, 2 car parking driveway in rear, exclusive patio area great for grilling! beautifully finished lower level offers a large room/

  Kim Covino Compass

  67 Church St, Winchester, MA 01890
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  /39

  $4,650,000 Sold May 01, 2025

  • 7,779 Sq Ft
  • $598/SF
  • 5 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 1915

  19 Rangeley Rd, Winchester, MA 01890

  A treasure. That's how this residence is viewed, throughout town, throughout the decades. One family had the vision to bring this cherished home back to life with a renovation that bestowed the best of everything. On Rangeley Road, gentle rolling lawns fold softly into a private, winding road. Gorgeous architecture graces every lot and ancient oaks stand sentry. Located just steps to the town

  Nancy Pallotta Advisors Living - Winchester

  19 Rangeley Rd, Winchester, MA 01890
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  /36

  Est $3,669,782 Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 6,073 Sq Ft

  25 Dartmouth St, Winchester, MA 01890

  25 Dartmouth St, Winchester, MA 01890
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  /42

  $3,099,000

  • 6 Beds
  • 3.5 Baths
  • 5,238 Sq Ft

  54 Wedgemere Ave, Winchester, MA 01890

  Exceptional living in this stunning Wedgemere Ave 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 back yard featuring

  Kim Covino Compass

  54 Wedgemere Ave, Winchester, MA 01890
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  /39

  $10,000 per month

  • 7 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • House for Rent

  34 Glen Rd, Winchester, MA 01890

  TOP location! Beautifully renovated single family colonial in Ambrose elementary district, situated on a gorgeous lot with oversized new 2 car garage, This 6-7 bedroom 3.5 bath home has been tastefully updated & redesigned offering desirable open concept living w/ central air & all new systems. This home features a welcoming front porch, spacious foyer, beautiful custom chefs kitchen w/

  Kim Covino Compass

  34 Glen Rd, Winchester, MA 01890
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  /42

  $2,420,000 Sold Apr 25, 2025

  • 4,173 Sq Ft
  • $580/SF
  • 8 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1914

  48 Wedgemere Ave, Winchester, MA 01890

  This elegant 1914 Revival home combines timeless charm w/ exceptional architectural details. Located on a highly sought-after, picturesque street in "The Flats," this 5-bedroom, 4 1/2 half-bath residence offers spacious living throughout. The main floor boasts a formal living room w/ built-in bookcases & fireplace, a grand dining room, & a kitchen w/ two impressive butler’s pantries. Inviting

  Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

  48 Wedgemere Ave, Winchester, MA 01890
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  /32

  Est $1,878,458 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  57 Wildwood St, Winchester, MA 01890

  57 Wildwood St, Winchester, MA 01890
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  /5

  $3,999,000 New Construction

  • 6 Beds
  • 4.5 Baths
  • 6,367 Sq Ft

  40 Foxcroft Rd, Winchester, MA 01890

  An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

  Monte Marrocco Coldwell Banker Realty - Lexington

  40 Foxcroft Rd, Winchester, MA 01890
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  /42

  $2,500,000 Sold Apr 18, 2025

  • 3,851 Sq Ft
  • $649/SF
  • 4 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1936

  7 Rangeley Rd, Winchester, MA 01890

  **OFFER ACCEPTED/ OH CANCELED* Delightful home in Rangeley Estates, just outside Winchester Center! Featuring 5 bedrooms & 4.5 baths; 2 primary bedroom options w/ en-suite baths. A unique layout w/ a California vibe w/open airy spaces perfect for modern day living & just steps from the vibrant downtown. Enjoy easy access to Train, schools, shops, coffee, dining & more, while being tucked away in

  Kim Covino Compass

  7 Rangeley Rd, Winchester, MA 01890
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  /42

  Est $1,997,801 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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  /42

  $3,895,000 Pending

  • 7 Beds
  • 8 Baths
  • 7,587 Sq Ft

  25 Wedgemere Ave, Winchester, MA 01890

  Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7

  Prestige Homes Realty Team Prestige Homes Real Estate, LLC

  25 Wedgemere Ave, Winchester, MA 01890
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  /41

  $2,350,000 Sold Apr 15, 2025

  • 4,273 Sq Ft
  • $550/SF
  • 7 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1910

  5 Pine St, Winchester, MA 01890

  This recently renovated Victorian blends historic charm with modern luxury in a prime in-town location-minutes to the shops, Common, train and Wedge Pond. Step into the central hall showcasing elegant woodwork, high ceilings, and gleaming floors. The new kitchen features high-end appliances, a butler’s pantry, and dining banquette. Entertain in the sun-drenched dining room with a marble fireplace

  Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

  5 Pine St, Winchester, MA 01890
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  /42

  Est $3,341,227 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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  /42

  $3,199,000 Pending

  • 5 Beds
  • 5 Baths
  • 4,279 Sq Ft

  51 Wedgemere Ave, Winchester, MA 01890

  Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-placed foyer welcomes you into the home, enhanced by a new chefs kitchen w/ 10' island, custom cabinetry, & adjacent family room overlooking yard. With four floors of beautifully finished spaces, there's room for every lifestyle need. Enjoy

  Kim Covino Compass

  51 Wedgemere Ave, Winchester, MA 01890
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  /39

  $2,224,000 Sold Apr 11, 2025

  • 3,487 Sq Ft
  • $638/SF
  • 8 Days On Market

  • 6 Beds
  • 2.5 Baths
  • Built 1910

  5 Woodside Rd, Winchester, MA 01890

  Introducing a captivating waterside home on a gorgeous 34,000 sf lot, located in a top location w/ expansive frontage on Little Winter Pond. This 6-bedroom, 2.5-bathroom home offers unparalleled access to the picturesque pond for activities such as ice skating, fishing, kayaking, & more. The home’s interior is highlighted by high ceilings, hardwood floors & an original fireplace for cozy winter

  Kim Covino Compass

  5 Woodside Rd, Winchester, MA 01890
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  /37

  Est $2,216,760 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,696 Sq Ft

  21 Foxcroft Rd, Winchester, MA 01890

  21 Foxcroft Rd, Winchester, MA 01890
• 

  

  /7

  $3,450,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,800 Sq Ft

  58 Wedgemere Ave, Winchester, MA 01890

  Experience the timeless charm of this stunning English Tudor in Winchester’s coveted Flats neighborhood. Set on an oversized lot with mature landscaping, this home is undergoing a full renovation and expansion by Mark Stephen Development, blending classic elegance with modern luxury. The reimagined design features two fireplaces, an expansive family room, living room, dining room, first- and

  Mark Donnellan Advisors Living - Winchester

  58 Wedgemere Ave, Winchester, MA 01890
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  /42

  $3,665,000 Sold Mar 27, 2025

  • 5,768 Sq Ft
  • $635/SF
  • 1 Day On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1895

  6 Lakeview Rd, Winchester, MA 01890

  Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town’s most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Reconstructed and designed by RENEW, a company committed to blending historical integrity with modern amenities, paying meticulous attention to every

  Kim Covino Compass

  6 Lakeview Rd, Winchester, MA 01890
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  /39

  Est $2,106,642 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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  /40

  $2,295,000 Open Sun 12PM - 1:30PM

  • 6 Beds
  • 5.5 Baths
  • 5,791 Sq Ft

  58 Bacon St, Winchester, MA 01890

  Timeless elegance & contemporary comfort span four meticulously finished levels.This stately residence boasts 15 rooms, including six bedrooms and five-and-a-half bathrooms(2 en-suite). An inviting living room, anchored by a distinguished fireplace, flows seamlessly into an adjacent sunroom, offering a perfect retreat. The formal dining room opens to a covered porch, complete with a gas line for

  Real Estate Advisors Group Coldwell Banker Realty - Belmont

  58 Bacon St, Winchester, MA 01890
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  /42

  $2,350,000 Sold Mar 24, 2025

  • 3,059 Sq Ft
  • $768/SF
  • 6 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1940

  17 Dix St, Winchester, MA 01890

  Prime Waterfront home in downtown Winchester!! Take advantage of this unique opportunity to customize, renovate, expand or rebuild your dream home on this heavenly 1/2 acre lot with gorgeous grounds and expansive frontage on Wedge Pond. The current home was custom built and enjoyed by one family who made unforgettable memories here including skating, swimming, canoeing & sledding right in their

  Kim Covino Compass

  17 Dix St, Winchester, MA 01890
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  /42

  Est $2,683,291 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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  /35

  $2,499,000 Open Sun 1:30PM - 3PM

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

  6 Ivy Cir, Winchester, MA 01890

  Stunning new construction Colonial tucked away at the end of a quiet cul-de-sac in "The Flats", offering the ideal combination of luxury, comfort, and convenience. Just minutes from Winchester Center, this beautifully crafted home places top-rated schools, boutique shopping, and vibrant dining right at your doorstep. Meticulously designed with high-end finishes throughout. Features include an

  Monte Marrocco Coldwell Banker Realty - Lexington

  6 Ivy Cir, Winchester, MA 01890
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  /42

  $3,250,000 Sold Mar 18, 2025

  • 4,714 Sq Ft
  • $689/SF
  • 9 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1909

  23 Everett Ave, Winchester, MA 01890

  Talk about curb appeal! This fabulous Colonial home beckons with an amazing front porch overlooking an expansive front yard, proudly perched on a quiet corner in one of the most coveted neighborhoods in town. Well-tended gardens and plants mesh with giant overhanging oak trees making your heart sing. Inside, delight in the quarter-sawn oak walls and floors, huge sunny family room and a dining

  Nancy Pallotta Advisors Living - Winchester

  23 Everett Ave, Winchester, MA 01890
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  /24

  Est $2,163,359 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
• 

  

  /42

  $2,599,000

  • 6 Beds
  • 4.5 Baths
  • 5,824 Sq Ft

  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

  Maija Sawyer Puleo William Raveis R.E. & Home Services

  107 Cambridge St, Winchester, MA 01890
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  /42

  $2,900,000 Sold Mar 07, 2025

  • 4,400 Sq Ft
  • $659/SF
  • 67 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1917

  64 Wildwood St, Winchester, MA 01890

  Exquisitely restored brick Colonial situated in the sought-after Flats neighborhood of Winchester. Boasting refinished hardwood floors, beautiful moldings and trim, and high ceilings throughout, no detail has been overlooked in this meticulous renovation. The gourmet kitchen, featuring high end appliances, is perfect for culinary enthusiasts, while the formal dining room, complete w/ wood-burning

  McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

  64 Wildwood St, Winchester, MA 01890

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