Middlesex, MA Homes

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  /42

  $3,750,000

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

  9 Lakeview Terrace, Winchester, MA 01890

  LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

  Kim Covino Compass

  9 Lakeview Terrace, Winchester, MA 01890
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  Explore The Flats

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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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  /39

  $1,400,000 Sold Jul 14, 2025

  • 2,282 Sq Ft
  • $613/SF
  • 38 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  20 Fletcher St Unit 20, Winchester, MA 01890

  Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication

  Kim Covino Compass

  20 Fletcher St Unit 20, 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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  /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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  /42

  $2,500,000 Sold Jul 14, 2025

  • 3,719 Sq Ft
  • $672/SF
  • 7 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1952

  17 Harrison St, Winchester, MA 01890

  Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized

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

  17 Harrison St, Winchester, MA 01890
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  /41

  Est $2,068,254 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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  /41

  $2,899,000

  • 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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  /23

  $4,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • Condo for Rent

  41 Church St Unit 1, Winchester, MA 01890

  2 bed and 2.5 bath located in Winchester. Easy access to downtown and public transportation!

  41 Church St Unit 1, Winchester, MA 01890
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  /28

  $1,260,000 Sold Jun 30, 2025

  • 2,705 Sq Ft
  • $466/SF
  • 41 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1885

  261 Cambridge St Unit 261 G, Winchester, MA 01890

  Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms,

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

  261 Cambridge St Unit 261 G, Winchester, MA 01890
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  /41

  Est $1,824,086 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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  /39

  $3,249,000

  • 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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  /35

  $1,100,000 Sold Jun 27, 2025

  • 3,157 Sq Ft
  • $348/SF
  • 20 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1866

  63 Church St, Winchester, MA 01890

  Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

  Nancy McLaughlin Redfin Corp.

  63 Church St, Winchester, MA 01890
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  /41

  Est $2,488,810 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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  /42

  $2,975,000

  • 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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  /22

  $4,200,000 Sold Jun 26, 2025

  • 5,208 Sq Ft
  • $806/SF
  • 4 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2025

  3 Foxcroft Rd, Winchester, MA 01890

  Nearing completion! Welcome to this exquisite 6-bedroom, 5-1/2 bath residence nestled in one of Winchesters most prestigious neighborhoods. This completely rebuilt, expanded & tastefully renovated home is one of a kind, offering a perfect blend of elegance & modern sophistication for a lifestyle of luxury & comfort. Step inside to discover a beautifully designed interior that exudes charm & style

  Kim Covino Compass

  3 Foxcroft Rd, Winchester, MA 01890
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  /42

  Est $2,450,896 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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  /40

  $3,399,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,250 Sq Ft

  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 Advisors Living - Winchester

  4 Norwood St, Winchester, MA 01890
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  /42

  $2,950,000 Sold Jun 23, 2025

  • 4,279 Sq Ft
  • $689/SF
  • 23 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1914

  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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  /36

  Est $3,621,355 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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  /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

  $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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  /32

  Est $1,950,508 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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  /42

  $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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  /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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  /42

  Est $2,007,191 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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  /40

  $2,195,000

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

  58 Bacon St, Winchester, MA 01890

  Timeless elegance spans four meticulously finished levels with 15 rooms, 6 bedrooms and 5+ bathrooms(2 en-suite). Living room flows seamlessly into a sunroom for a perfect retreat. The dining room opens to a covered porch with a gas line for the grill. New, top shelf, chef’s kitchen with all the bells & whistles and open to the family room. Thoughtfully designed for convenience, an elevator from

  Real Estate Advisors Group Coldwell Banker Realty - Belmont

  58 Bacon St, 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 $3,237,940 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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  /35

  $2,399,000

  • 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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  /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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  /37

  Est $2,274,129 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
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  /42

  $2,499,000

  • 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

  $2,420,000 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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  /39

  Est $2,261,004 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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  /41

  $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 $2,721,938 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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  /38

  $2,499,000 New Construction

  • 7 Beds
  • 5.5 Baths
  • 4,829 Sq Ft

  89 Wildwood St, Winchester, MA 01890

  Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

  Monte Marrocco Coldwell Banker Realty - Lexington

  89 Wildwood St, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18