Winchester, MA Homes

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  /42

  $1,549,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,587 Sq Ft

  32 Woodside Rd, Winchester, MA 01890

  Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc..along with serenity and privacy so hard to find. This home offers ample living

  Kim Covino Compass

  32 Woodside Rd, Winchester, MA 01890
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  /42

  $3,174,500 Sold Sep 02, 2025

  • 7,005 Sq Ft
  • $453/SF
  • 9 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 2022

  18 Wickham Rd, Winchester, MA 01890

  Just 3 years young, this pristine masterpiece is nestled in a sought-after neighborhood just footsteps from the Town Forest and within walking distance of Wedgemere Station and Downtown Winchester. Step into the first floor and be captivated by the soaring ceilings. The showstopping kitchen features a SubZero fridge, a Bertazzoni 48” range, and a full eat-in area. This space flows into the family

  Philip Vita Compass

  18 Wickham Rd, Winchester, MA 01890
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  /38

  Est $1,250,372 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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  /29

  $1,200,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,004 Sq Ft

  50 Lincoln St, Winchester, MA 01890

  This beautiful Victorian home, featuring an inviting front porch, stunning period detail including wainscoting, original tin ceilings, custom built-ins, and three fireplaces is not to be missed! Maple hardwood floors flow through an open-concept layout to a spacious eat-in kitchen with a lovely exposed brick wall. The second floor has three bedrooms and a full bath plus a sweet window seat and an

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

  50 Lincoln St, Winchester, MA 01890
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  /16

  $825,000 Sold Aug 29, 2025

  • 1,825 Sq Ft
  • $452/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1985

  171 Swanton St Unit 64, Winchester, MA 01890

  Turn-key end-unit townhouse in Winchester’s sought-after community! Sun-filled open layout with wood floors, quartz kitchen countertops, modern cabinets, and stainless appliances. Two renovated baths feature designer tile and sleek fixtures. Enjoy high-efficiency HVAC with Energy Recovery Ventilation, radiant-heated floors, water filtration, and in-unit laundry. Step outside to a private patio

  Xiaoli Xie JKS Boston Realty LLC

  171 Swanton St Unit 64, Winchester, MA 01890
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  /42

  Est $944,501 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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  /13

  $3,199,000 Pending

  • 6 Beds
  • 7 Baths
  • 5,709 Sq Ft

  39 Town Way, Winchester, MA 01890

  Discover all this gorgeous new construction home in top East Side location will offer! Designed with today’s lifestyle in mind, this home features a flexible open floor plan perfect for entertaining & everyday living / A great opportunity for you to customize the finishes & bring your vision to life! First floor offers a mudroom, half bath, office/living room, bedroom w/ full bath & a stunning

  Kim Covino Compass

  39 Town Way, Winchester, MA 01890
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  /42

  $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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  /26

  Est $838,577 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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  /11

  $299,000 Pending

  • 1 Bed
  • 1 Bath
  • 394 Sq Ft

  200 Swanton St Unit 636, Winchester, MA 01890

  Immaculate, studio condominium within the desirable Parkview Condominiums in Winchester. The large private balcony overlooks a beautiful wildlife pond, and the grounds are meticulously landscaped. The kitchen features tile flooring, updated granite countertops, and a breakfast bar. The Condominium amenities include: in-ground swimming pool, barbecue area, large parking area with plenty of

  Michael Masci North Atlantic Realty Group

  200 Swanton St Unit 636, Winchester, MA 01890
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  /42

  $2,218,500 Sold Aug 29, 2025

  • 3,940 Sq Ft
  • $563/SF
  • 74 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1983

  17 Wagon Wheel Rd, Winchester, MA 01890

  Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends

  Yifei Wang Dreamega International Realty LLC

  17 Wagon Wheel Rd, Winchester, MA 01890
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  /20

  Est $1,064,140 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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  /39

  $1,199,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,755 Sq Ft

  102 Hillcrest Pkwy, Winchester, MA 01890

  Attention renovators and investors! This Cape-style home in need of significant renovation offers 7 rooms, 4 bedrooms, and 2 full baths. Features include a fireplace living room, dining room, and hardwood flooring throughout. Enjoy a private yard for outdoor enjoyment. Prime location directly across from the Middlesex Fells Reservation and minutes to Winchester Center, schools, shops, and

  Curtis Howe Howe Realty Group

  102 Hillcrest Pkwy, Winchester, MA 01890
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  /40

  $1,200,000 Sold Aug 27, 2025

  • 2,566 Sq Ft
  • $468/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1930

  70 Woodside Rd, Winchester, MA 01890

  Have you ever dreamed of owning a house with a white picket fence? Here it is! Eight rooms, four bedrooms, 2.5 baths. Corner lot with backyard patio, shed and one car garage. The large living room with many windows and a fireplace opens to the dining room. French doors from the dining room lead to a room that can be used as a family room, play room for the kids, or another bedroom. The

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

  70 Woodside Rd, Winchester, MA 01890
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  /17

  Est $2,163,979 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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  /33

  $1,499,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,807 Sq Ft

  7 Wainwright Rd Unit 118, Winchester, MA 01890

  Exceptional 3 Bedroom 3 1/2 Bath Highly Desired End Unit Townhome at The Ledges! Main Level Features include: Inviting Sun-Filled Entry Foyer, Gleaming Hardwood Floors, Cathedral Ceilings, Granite/Stainless Chef's Kitchen w/Breakfast Room, Formal Dining Room, Living Room w/Gas Fireplace and Private Deck overlooking Tranquil Wooded Setting. Family Study w/ Custom Built-ins, Luxurious Primary

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Wainwright Rd Unit 118, Winchester, MA 01890
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  /42

  $2,500,000 Sold Aug 27, 2025

  • 4,215 Sq Ft
  • $593/SF
  • 4 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1955

  12 Olde Lyme Rd, Winchester, MA 01890

  *** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates

  Mary Beth McGillicuddy Engel & Völkers , South Shore

  12 Olde Lyme Rd, Winchester, MA 01890
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  /38

  Est $1,238,423 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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  /40

  $2,349,000 Pending

  • 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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  /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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  /40

  Est $2,557,739 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 6,259 Sq Ft

  280 High St, Winchester, MA 01890

  280 High St, Winchester, MA 01890
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  /35

  $1,359,000 Pending

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

  7 Thornberry Rd, Winchester, MA 01890

  The land alone is worth this price!! 15Ksf lot & a newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level

  Kim Covino Compass

  7 Thornberry Rd, Winchester, MA 01890
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  /38

  $1,062,350 Sold Aug 22, 2025

  • 1,536 Sq Ft
  • $692/SF
  • 42 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1940

  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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  /41

  Est $2,120,665 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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  /34

  $999,999 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,001 Sq Ft

  9 Sylvester Ct, Winchester, MA 01890

  Tucked away on a private cul-de-sac in one of Winchester’s most desirable neighborhoods, this adorable 4-bedroom, 1.5-bath single-family cape style home with full rear dormer offers a rare opportunity to renovate, expand, and build equity in a prime location. Set in the brand new **Lynch School District**, this property is ideal for homeowners, investors, or builders looking to customize and add

  Kim Covino Compass

  9 Sylvester Ct, Winchester, MA 01890
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  /42

  $1,330,000 Sold Aug 21, 2025

  • 2,605 Sq Ft
  • $511/SF
  • 73 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1870

  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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  /40

  Est $2,228,283 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,567 Sq Ft

  99 Ridge St, Winchester, MA 01890

  99 Ridge St, Winchester, MA 01890
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  /32

  $949,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  16 Park Ave Unit 2, Winchester, MA 01890

  Experience luxury living just steps from vibrant Winchester Center in this beautifully renovated 2016 condo. High ceilings & gleaming HW floors flow throughout this spacious, light-filled home, w/an open floor plan that features fireplaced living & dining area adjoining a chef’s eat-in kitchen, outfitted w/ SS appliances & granite countertops.The home offers 3 generously sized bedrooms & 2 full

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

  16 Park Ave Unit 2, Winchester, MA 01890
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  /28

  $785,500 Sold Aug 20, 2025

  • 1,435 Sq Ft
  • $547/SF
  • 8 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  171 Swanton St Unit 12, Winchester, MA 01890

  Welcome to The Village in Winchester! This picturesque 80-unit condominium community is set along conservation land and the Aberjona River. Unit 12 is a spacious, renovated 2-bedroom, 2.5-bath townhouse offering a bright living room with skylight and gas fireplace, updated kitchen, dining room, and private outdoor patio. The second floor features a large primary suite with ample closet space and

  John and Maria Reilly JMR Real Estate Group LLC

  171 Swanton St Unit 12, Winchester, MA 01890
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  /42

  Est $1,263,153 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,542 Sq Ft

  119 Ridge St, Winchester, MA 01890

  119 Ridge St, Winchester, MA 01890
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  /37

  $1,299,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,492 Sq Ft

  40 Sargent Rd, Winchester, MA 01890

  Nestled in Winchester’s coveted Lincoln School district, this classic Colonial offers timeless charm, modern comfort, and unbeatable curb appeal! Situated on a beautiful corner lot, the property features a detached 2-car garage and welcoming exterior that sets the tone for what awaits inside. The main level boasts a warm and inviting living room with a wood-burning fireplace, perfect for cozy

  Philip Vita Compass

  40 Sargent Rd, Winchester, MA 01890
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  /33

  $1,240,000 Sold Aug 20, 2025

  • 2,570 Sq Ft
  • $482/SF
  • 9 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1966

  3 Socrates Way, Winchester, MA 01890

  Unlock the potential of this tri-level home in one of Winchester’s sought-after neighborhoods! Set on a 20,000 sq ft lot, this 4 bed, 2.5 bath, 1966-built home offers 2,116 sf of living space, a 2 car garage, & endless possibilities for renovation or redevelopment. The main level features a formal living room, dining room, & kitchen leading to a deck overlooking the backyard. A cozy family room

  Pirani & Wile Group Gibson Sotheby's International Realty

  3 Socrates Way, Winchester, MA 01890
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  /41

  Est $3,719,266 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,322 Sq Ft

  11 Viking Rd, Winchester, MA 01890

  11 Viking Rd, Winchester, MA 01890
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  /33

  $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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  /19

  $1,820,000 Sold Aug 19, 2025

  • 3,784 Sq Ft
  • $481/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1974

  109 Thornberry Rd, Winchester, MA 01890

  Ideally located in one of Winchester’s most desirable neighborhoods, this classic Colonial blends timeless design with thoughtful updates. At the heart of the home, the beautifully updated kitchen features a generous center island, opening to a spacious family room with a slider leading to a large deck overlooking the expansive, level backyard - perfect for summer entertaining. Just off the

  Andrew Martini Compass

  109 Thornberry Rd, Winchester, MA 01890
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  /40

  Est $1,395,339 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  25 Lockeland Rd, Winchester, MA 01890

  25 Lockeland Rd, 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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  /42

  $2,700,000 Sold Aug 18, 2025

  • 3,708 Sq Ft
  • $728/SF
  • 2 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1929

  34 Rangeley Rd, Winchester, MA 01890

  Welcome to this truly distinctive home nestled on a lush landscaped lot in historic & highly sought after Rangeley Estates neighborhood. Just moments from downtown Winchester, this hidden gem offers a unique blend of privacy and convenience! This stunning home boasts 5 bedrooms & 4 full baths, seamlessly blending original charm with modern amenities. Step inside to discover sun-filled rooms and a

  Kim Covino Compass

  34 Rangeley Rd, Winchester, MA 01890
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  /37

  Est $2,234,992 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,209 Sq Ft

  4 Mayflower Rd, Winchester, MA 01890

  4 Mayflower Rd, Winchester, MA 01890
• 

  

  /42

  $1,199,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,459 Sq Ft

  162 Swanton St Unit 162, Winchester, MA 01890

  NEW CONSTRUCTION!! Welcome to this meticulously crafted, modern townhouse END UNIT offering over 2,100 sq ft of thoughtfully designed living space. The open-concept main level features gorgeous mill work, gleaming hardwood floors, a cozy fireplace & sleek chef-inspired kitchen w/ stainless appliances, large center island & an adjacent mudroom w/ half bath perfect for today’s lifestyle. The 2nd

  Kim Covino Compass

  162 Swanton St Unit 162, Winchester, MA 01890

Showing Results 161 - 200, Page 5 of 18