Winchester, MA Homes

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  /41

  $2,599,000

  • 4 Beds
  • 4.5 Baths
  • 5,501 Sq Ft

  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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  /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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  /37

  Est $868,803 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft

  47 Edward Dr, Winchester, MA 01890

  47 Edward Dr, Winchester, MA 01890
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  /34

  $1,449,900

  • 5 Beds
  • 2 Baths
  • 3,033 Sq Ft

  7 Thornberry Rd, Winchester, MA 01890

  Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighborhood. 15 minutes to Downtown Boston. 5 bedrooms, 2 full baths, Living, Dining PLUS family room & 2nd finished room ( play or office) ground level room heated & A/C walk access to outdoor deck & fire pit. Open concept kitchen area. Hardwood floors, 2 fireplace, 2 garage space,

  salim chowdhury TAJ Mahal Realty LLC

  7 Thornberry Rd, Winchester, MA 01890
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  /42

  $1,815,000 Sold Apr 15, 2025

  • 2,810 Sq Ft
  • $646/SF
  • 8 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1935

  29 Allen Rd, Winchester, MA 01890

  This expanded 4-bedroom, 2.5-bath colonial is a true gem in the heart of a serene Lincoln School neighborhood. Impeccably maintained by the same family for over 40 years, this home has been thoughtfully updated w/ modern comforts, incl. AC throughout. The 1st floor features a remodeled kitchen w/ stainless steel appliances, granite countertops & breakfast bar, flowing into a spacious family room

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

  29 Allen Rd, Winchester, MA 01890
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  /31

  Est $1,890,297 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,028 Sq Ft

  56 Ridge St, Winchester, MA 01890

  56 Ridge St, Winchester, MA 01890
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  /42

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

  • 3 Beds
  • 2.5 Baths
  • 2,605 Sq Ft

  14 Hillside Ave, Winchester, MA 01890

  Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps from Town Center! This property has been lovingly owned & maintained by the same family for 70+ years and is now ready for new owners. Prepare to fall in love with the charm and period details of this circa 1870 historic home, the first house built on Hillside Ave. The 1st floor

  Seeme Moreira Coldwell Banker Realty - Lexington

  14 Hillside 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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  /23

  Est $1,013,872 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft

  12 James St, Winchester, MA 01890

  12 James St, Winchester, MA 01890
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  /42

  $2,850,000

  • 6 Beds
  • 7 Baths
  • 6,968 Sq Ft

  14 Nassau Dr, Winchester, MA 01890

  (Price Improved) Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical

  Weidong Li WINN Real Estate & Consulting

  14 Nassau Dr, 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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  /38

  Est $1,269,530 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,827 Sq Ft

  10 James St, Winchester, MA 01890

  10 James St, Winchester, MA 01890
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  /34

  $2,349,000

  • 4 Beds
  • 3.5 Baths
  • 4,959 Sq Ft

  5 Azalea Rd, Winchester, MA 01890

  Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Azalea Rd, Winchester, MA 01890
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  /38

  $2,600,000 Sold Apr 08, 2025

  • 4,323 Sq Ft
  • $601/SF
  • 7 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1929

  30 Swan Rd, Winchester, MA 01890

  Discover the prestige of owning a home at 30 Swan Road, a distinguished Tudor-style residence on one of Winchester's most esteemed streets. Offering magnificent grounds and an impressive brick exterior complemented by a slate roof, this property sets the tone for the elegance within. It's perfect for a buyer looking to add sweat equity or a contractor seeking a rewarding project. Upon entering,

  Jay Noble Compass

  30 Swan Rd, Winchester, MA 01890
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  /42

  Est $945,922 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,890 Sq Ft

  25 Henry St, Winchester, MA 01890

  25 Henry St, Winchester, MA 01890
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  /4

  $3,799,900

  • 7 Beds
  • 7.5 Baths
  • 7,429 Sq Ft

  11 Viking Rd, Winchester, MA 01890

  Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

  The McLaren D'Agostino Team Compass

  11 Viking Rd, Winchester, MA 01890
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  /42

  $1,890,000 Sold Mar 28, 2025

  • 4,318 Sq Ft
  • $438/SF
  • 7 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1956

  19 Johnson Rd, Winchester, MA 01890

  A DESIGNER DREAM! Welcome to 19 Johnson Road, a pristine 5-bedroom colonial-style home located in the highly sought-after Vinson Owen School district! As you enter the home, you are greeted by a stunning curved staircase adorned with molding and a statement-making light fixture. The first level boasts a fireplaced living room, a fireplaced family room, an updated kitchen, and a gorgeous formal

  Philip Vita Compass

  19 Johnson Rd, Winchester, MA 01890
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  /26

  Est $857,390 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,279 Sq Ft

  28 Henry St, Winchester, MA 01890

  28 Henry St, Winchester, MA 01890
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  /22

  $1,295,000

  • 4 Beds
  • 1.5 Baths
  • 2,202 Sq Ft

  71 Woodside Rd, Winchester, MA 01890

  Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of living space on a 7,126-square-foot lot. Built in 1927, the home exudes timeless character with its spacious rooms, abundant natural light, and original architectural details. Perfect for homeowners and developers alike, the property offers endless potential for renovation,

  Jorge Rodriguez Carlton's Wharf & Co.

  71 Woodside Rd, Winchester, MA 01890
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  /42

  $682,000 Sold Mar 28, 2025

  • 1,196 Sq Ft
  • $570/SF
  • 68 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  7 Conant Rd Unit 24, Winchester, MA 01890

  A rare opportunity to live at the Willows in Winchester. Fabulous corner unit on 2nd floor w/ open concept living and dining area features gorgeous hardwood floors. You will be impressed w/ the updated kitchen featuring solid granite counters, stainless steel sink and appliances, new carpeting and paint added in the bedrooms 1 year ago. New paint in dining room and closets. Gas fireplace for the

  Paul Bettencourt Beaudoin & Associates, REALTOR®

  7 Conant Rd Unit 24, Winchester, MA 01890
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  /20

  Est $1,101,233 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft

  14 Locke St, Winchester, MA 01890

  14 Locke St, Winchester, MA 01890
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  /42

  $2,650,000

  • 4 Beds
  • 3 Baths
  • 4,276 Sq Ft

  8 Tanglewood Ln, Winchester, MA 01890

  This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard.

  Kim Covino Compass

  8 Tanglewood Ln, 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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  /17

  Est $2,111,163 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,578 Sq Ft

  21 Dunster Ln, Winchester, MA 01890

  21 Dunster Ln, Winchester, MA 01890
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  /34

  $3,698,000

  • 6 Beds
  • 7 Baths
  • 8,866 Sq Ft

  20 Amberwood Dr, Winchester, MA 01890

  Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

  Dan Li Keller Williams Realty

  20 Amberwood Dr, 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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  /37

  Est $2,133,374 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,346 Sq Ft

  6 Ridge St, Winchester, MA 01890

  6 Ridge St, Winchester, MA 01890
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  /42

  $3,989,000

  • 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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  /33

  $615,000 Sold Mar 24, 2025

  • 1,452 Sq Ft
  • $424/SF
  • 5 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1960

  299 Cross St Unit 299, Winchester, MA 01890

  Welcome to The Residences at Winchester! A perfect move-in ready single-family alternative without the hassle of yard work. Fantastic chance to own this 2 bedroom 1.5 bathroom gem with beautiful hardwood floors, open concept living/dining/kitchen in Winchester at a budget-friendly price. Why rent when you can own? The finished lower level adds over 400 square feet of extra living area.

  Patricia Nunez Redfin Corp.

  299 Cross St Unit 299, Winchester, MA 01890
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  /38

  Est $1,246,936 Not Listed For Sale

  • 5 Beds
  • 1.5 Baths
  • 2,383 Sq Ft

  18 Ridge St, Winchester, MA 01890

  18 Ridge St, Winchester, MA 01890
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  /37

  $679,900 Open Sun 1PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft

  7 Conant Rd Unit 20, Winchester, MA 01890

  Rarely available and beautifully renovated first-floor unit at The Willows designed with everyday functionality in mind. This one-story unit offers stair-free access and living, along with easy accessibility from the adjacent one-car garage with an attic and a tandem parking spot. Upon entry, you’ll find an inviting open concept living and dining area with freshly installed hardwood flooring, a

  Brian Woods Woods Properties Inc.

  7 Conant Rd Unit 20, Winchester, MA 01890
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  /2

  $1,650,000 Sold Mar 19, 2025

  • 3,381 Sq Ft
  • $488/SF
  • 14 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1938

  5 Alben St, Winchester, MA 01890

  Welcome to this charming Colonial, thoughtfully maintained by its owners! Nestled on a peaceful, tree-lined street, this beautifully updated colonial home exudes warmth and character. Featuring a recently updated roof (2022), new triple pane energy efficient windows with transferable lifetime warranty (2018), and fresh interior and exterior paint, this home is move-in ready and full of charm.

  Andersen Group Realty Keller Williams Realty Boston Northwest

  5 Alben St, Winchester, MA 01890
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  /41

  Est $2,086,683 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,730 Sq Ft

  2 Tanglewood Ln, Winchester, MA 01890

  2 Tanglewood Ln, Winchester, MA 01890
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  /42

  $3,699,000 Open Sun 11AM - 12PM

  • 7 Beds
  • 7.5 Baths
  • 7,982 Sq Ft

  54 Johnson Rd, Winchester, MA 01890

  This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master

  Kim Covino Compass

  54 Johnson Rd, 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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  /34

  Est $2,789,795 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 7,235 Sq Ft

  25 Olde Village Dr, Winchester, MA 01890

  25 Olde Village Dr, 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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  /42

  $1,670,000 Sold Mar 18, 2025

  • 3,224 Sq Ft
  • $518/SF
  • 59 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1945

  9 Robinson Park, Winchester, MA 01890

  Classic Colonial 4 bedroom 3+1/2 bath on quiet street overlooking the Mystic Lake. Awaits buyers with vision prepared to renovate. Freshly painted interior gleaming hardwood floors. Gracious front to back fireplaced living room w/custom shelves & built-ins & picture windows. Formal dining room w/2 china closets adjacent to large open eat-in light filled kitchen. French doors to back deck.

  Paul Reardon William Raveis R.E. & Home Services

  9 Robinson Park, Winchester, MA 01890
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  /22

  Est $2,617,623 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,333 Sq Ft

  18 Olde Village Dr, Winchester, MA 01890

  18 Olde Village Dr, 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

Showing Results 161 - 200, Page 5 of 18