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Newest Homes for Sale in Winchester, MA

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  • 77A Brooks St, Winchester, MA 01890
    77A Brooks St, Winchester, MA 01890
    77A Brooks St, Winchester, MA 01890
    /42

    $2,275,000 Open Sat 11AM - 12:30PM

    • 6 Beds
    • 3.5 Baths
    • 4,122 Sq Ft

    77A Brooks St, Winchester, MA 01890

    This stately Victorian offers an exceptional blend of preserved character and modern functionality across its generous, well-appointed layout. Sunlit rooms highlight hardwood floors, detailed millwork, bay windows, and a graceful fireplace, creating a warm and elegant flow throughout the main level. The expansive kitchen features stone counters, a central island, French doors, and direct access

    Anne Spry Barrett Sotheby's International Realty

    77A Brooks St, Winchester, MA 01890
  • 29 Shepard Ct, Winchester, MA 01890
    29 Shepard Ct, Winchester, MA 01890
    29 Shepard Ct, Winchester, MA 01890
    /40

    $2,399,000 Open Sat 12PM - 1:30PM

    • 6 Beds
    • 5 Baths
    • 4,594 Sq Ft

    29 Shepard Ct, Winchester, MA 01890

    With 6 bedrooms & 5 full baths, this beautifully crafted new construction located at the end of a cul-de-sac delivers refined style, a modern layout & effortless living. The open layout showcases a chef’s kitchen with an oversized island, quartz counters & Thermador appliances, seamlessly connecting to the dining & living rooms, both with their own gas fireplace. Detailed millwork, coffered

    Pirani & Wile Group Gibson Sotheby's International Realty

    29 Shepard Ct, Winchester, MA 01890
  • 200 Swanton St Unit 234, Winchester, MA 01890
    200 Swanton St Unit 234, Winchester, MA 01890
    200 Swanton St Unit 234, Winchester, MA 01890
    /17

    $269,000

    • 1 Bath
    • 388 Sq Ft

    200 Swanton St Unit 234, Winchester, MA 01890

    Sunny studio unit overlooking the pond and courtyard at Parkview Condos in Winchester. Unit features include large private balcony with large sliding door that lets in lots of natural sun light. New LVP flooring in the living room/bedroom area and hallway. Freshly painted all throughout. Kitchen has granite countertops and a new refrigerator and electric range. The condominium amenities include

    Devin Caglayan All County Select Property Management

    200 Swanton St Unit 234, Winchester, MA 01890
  • 19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    /42

    $2,999,000 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 5.5 Baths
    • 5,257 Sq Ft

    19 Town Way, Winchester, MA 01890

    Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive

    Philip Vita Compass

    19 Town Way, Winchester, MA 01890
  • 20 Grove Place, Winchester, MA 01890
    20 Grove Place, Winchester, MA 01890
    20 Grove Place, Winchester, MA 01890
    /40

    $1,869,000 Open Sat 1PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 3,294 Sq Ft

    20 Grove Place, Winchester, MA 01890

    From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

    Andersen Group Realty Keller Williams Realty Boston Northwest

    20 Grove Place, Winchester, MA 01890
  • 30 Prospect St, Winchester, MA 01890
    30 Prospect St, Winchester, MA 01890
    30 Prospect St, Winchester, MA 01890
    /42

    $2,099,000

    • 4 Beds
    • 3 Baths
    • 2,519 Sq Ft

    30 Prospect St, Winchester, MA 01890

    One of Winchester’s most beloved neighborhoods sets the tone for 30 Prospect Street, a beautifully reimagined home transformed by an extensive remodel less than five years ago. A spectacular, fully renovated Chef's kitchen anchors the main level with high-end finishes and a seamless flow for living and entertaining. The living room is sunny and inviting, featuring an impressive fireplace,

    Karima Alami Compass

    30 Prospect St, Winchester, MA 01890
  • 89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    /37

    $2,299,000 Open Sat 12PM - 1:30PM

    • 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
  • 4 Wyman Ct Unit 4, Winchester, MA 01890
    4 Wyman Ct Unit 4, Winchester, MA 01890
    4 Wyman Ct Unit 4, Winchester, MA 01890
    /27

    $1,399,000 Open Sat 11AM - 12PM

    • 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
  • 41 Squire Rd, Winchester, MA 01890
    41 Squire Rd, Winchester, MA 01890
    41 Squire Rd, Winchester, MA 01890
    /25

    $989,000

    • 4 Beds
    • 1.5 Baths
    • 2,162 Sq Ft

    41 Squire Rd, Winchester, MA 01890

    Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest

    William Cordts Charlesgate Realty Group, llc

    41 Squire Rd, Winchester, MA 01890
  • 139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    /24

    $999,000 Open Sat 12PM - 1:30PM

    • 3 Beds
    • 1.5 Baths
    • 1,302 Sq Ft

    139 High St, Winchester, MA 01890

    This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

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

    139 High St, Winchester, MA 01890
  • 8 Felsdale Close, Winchester, MA 01890
    8 Felsdale Close, Winchester, MA 01890
    8 Felsdale Close, Winchester, MA 01890
    /42

    $2,075,000 Open Sat 1:30PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 3,658 Sq Ft

    8 Felsdale Close, Winchester, MA 01890

    Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells' scenic trails, the setting is both serene and convenient. Designed by renowned architect Harry M.

    Anne Spry Barrett Sotheby's International Realty

    8 Felsdale Close, Winchester, MA 01890
  • 19 Gershon Way Unit 1, Winchester, MA 01890
    19 Gershon Way Unit 1, Winchester, MA 01890
    19 Gershon Way Unit 1, Winchester, MA 01890
    /42

    $2,299,000 Open Sun 11:30AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 3,953 Sq Ft

    19 Gershon Way Unit 1, Winchester, MA 01890

    Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

    Philip Vita Compass

    19 Gershon Way Unit 1, Winchester, MA 01890
  • 19 Gershon Way, Winchester, MA 01890
    19 Gershon Way, Winchester, MA 01890
    19 Gershon Way, Winchester, MA 01890
    /42

    $2,299,000 Open Sun 11:30AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 3,953 Sq Ft

    19 Gershon Way, Winchester, MA 01890

    Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

    Philip Vita Compass

    19 Gershon Way, Winchester, MA 01890
  • 666 Main St Unit 312, Winchester, MA 01890
    666 Main St Unit 312, Winchester, MA 01890
    666 Main St Unit 312, Winchester, MA 01890
    /16

    $799,999

    • 2 Beds
    • 2 Baths
    • 1,240 Sq Ft

    666 Main St Unit 312, Winchester, MA 01890

    Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry hook-ups, garage parking,

    Walace Nogueira

    666 Main St Unit 312, Winchester, MA 01890
  • 6 Marchant Rd, Winchester, MA 01890
    6 Marchant Rd, Winchester, MA 01890
    6 Marchant Rd, Winchester, MA 01890
    /42

    $1,350,000

    • 3 Beds
    • 2.5 Baths
    • 2,153 Sq Ft

    6 Marchant Rd, Winchester, MA 01890

    Updated 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, the train, and route to Boston. The first floor offers an ideal layout with an updated kitchen, stainless steel appliances & island w seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc and dining room. A 3 season

    Kim Covino Compass

    6 Marchant Rd, Winchester, MA 01890
  • 237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    /35

    $2,149,000 Open Sat 11AM - 12:30PM

    • 5 Beds
    • 4 Baths
    • 4,334 Sq Ft

    237 Swanton St, Winchester, MA 01890

    NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas

    Kim Covino Compass

    237 Swanton St, Winchester, MA 01890
  • 26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    /41

    $1,475,000

    • 3 Beds
    • 2.5 Baths
    • 2,316 Sq Ft

    26 Berkshire Dr, Winchester, MA 01890

    Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

    DANIEL BEIRNE OpenDoor Brokerage LLC

    26 Berkshire Dr, Winchester, MA 01890
  • 18 Raymond Place, Winchester, MA 01890
    18 Raymond Place, Winchester, MA 01890
    18 Raymond Place, Winchester, MA 01890
    /16

    $899,900

    • Land
    • 0.23 Acre
    • $3,912,609 per Acre

    18 Raymond Place, Winchester, MA 01890

    An opportunity awaits at 18 Raymond Place! This property offers a nearly 10,000 sq/ft lot, ample parking, and a large structure in a quaint, idyllic neighborhood. This freestanding building offers over 2 levels of space with direct exterior lower access for separate quarters. High ceilings, and lots of natural sunlight, this property awaits your customization. Each floor has 2 bathrooms, and the

    Kim Covino Compass

    18 Raymond Place, Winchester, MA 01890
  • 273 Cambridge Rd Unit 202, Woburn, MA 01801
    273 Cambridge Rd Unit 202, Woburn, MA 01801
    273 Cambridge Rd Unit 202, Woburn, MA 01801
    /38

    $499,900

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

    273 Cambridge Rd Unit 202, Woburn, MA 01801

    Spacious 2-bedroom, 2-bath condo at Crescent Park offering 1,168 square feet of one-level living. This bright unit features an open-concept living and dining area with direct access to a private balcony. The kitchen includes ample cabinetry and a separate pantry. The primary bedroom offers a walk-in closet and en-suite bathroom. While the unit could benefit from some cosmetic updates, it presents

    Brian Hermann Better Living Real Estate, LLC

    273 Cambridge Rd Unit 202, Woburn, MA 01801
  • 200 Swanton St Unit T28, Winchester, MA 01890
    200 Swanton St Unit T28, Winchester, MA 01890
    200 Swanton St Unit T28, Winchester, MA 01890
    /29

    $385,000 Open Sat 1:30PM - 3PM

    • 1 Bed
    • 1 Bath
    • 634 Sq Ft

    200 Swanton St Unit T28, Winchester, MA 01890

    Beautiful terrace-level 1-bedroom condo at Parkview Condos in Winchester! This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (781) 384-5553

    200 Swanton St Unit T28, Winchester, MA 01890
  • 10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    /39

    $2,695,000 Open Sat 1:30PM - 3PM

    • 4 Beds
    • 4 Baths
    • 5,674 Sq Ft

    10 Viking Rd, Winchester, MA 01890

    Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

    Anne Spry Barrett Sotheby's International Realty

    10 Viking Rd, Winchester, MA 01890
  • 19 Mason Way Unit 75, Woburn, MA 01801
    19 Mason Way Unit 75, Woburn, MA 01801
    19 Mason Way Unit 75, Woburn, MA 01801
    /30

    $1,349,999 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,909 Sq Ft

    19 Mason Way Unit 75, Woburn, MA 01801

    New Construction at Highland at Vale in Woburn! The Jackson floor plan offers over 2,900 sq. ft. of living space, including a finished basement. The bright kitchen features abundant cabinetry, stainless steel appliances, and a large island that opens to a spacious gathering room and a distinctive octagon-shaped dining area with bay window. Enjoy wooded views from your private deck—perfect for

    Erin Sullivan Pulte Homes of New England

    19 Mason Way Unit 75, Woburn, MA 01801
  • 2 Mason Way Unit 6524, Woburn, MA 01801
    2 Mason Way Unit 6524, Woburn, MA 01801
    2 Mason Way Unit 6524, Woburn, MA 01801
    /30

    $1,299,999 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,909 Sq Ft

    2 Mason Way Unit 6524, Woburn, MA 01801

    This stunning new construction end-unit townhome offers 3 bedrooms, 3.5 bathrooms, and a finished basement with full bath—perfect for flexible living or guest space. The chef’s kitchen boasts stainless steel appliances, a large center island, and abundant cabinetry, opening seamlessly to the spacious living room and private deck. A formal dining room with a charming bay window adds warmth and

    Erin Sullivan Pulte Homes of New England

    2 Mason Way Unit 6524, Woburn, MA 01801
  • 6 Mason Way Unit 6324, Woburn, MA 01801
    6 Mason Way Unit 6324, Woburn, MA 01801
    6 Mason Way Unit 6324, Woburn, MA 01801
    /30

    $1,149,999 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,143 Sq Ft

    6 Mason Way Unit 6324, Woburn, MA 01801

    New Construction Move- In Ready Townhome at Highland at Vale in Woburn! The Jackson floor plan offers over 2,100 sq. ft. of thoughtfully designed living space with 3 spacious bedrooms and 2.5 baths. The main level features a bright kitchen with stainless steel appliances, abundant cabinetry, and a large center island, flowing into an oversized gathering room and an octagon-shaped dining room with

    Erin Sullivan Pulte Homes of New England

    6 Mason Way Unit 6324, Woburn, MA 01801
  • 8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    /5

    $3,250,000

    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    8 Priscilla Ln, Winchester, MA 01890

    Welcome to 8 Priscilla Ln, Winchester—a brand-new 5 bed, 5.5 bath luxury home designed by Salt & Stone Co where elevated craftsmanship meets everyday comfort. Spanning 6,500 ± sq ft, this home features a chef’s kitchen with custom cabinetry, premium appliances, and an oversized center island flowing into a dramatic two-story living room with fireplace and glass slider to the backyard. The

    The Pezzano Group Rise Signature Homes

    8 Priscilla Ln, Winchester, MA 01890
  • 53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    /37

    $2,799,000

    • 5 Beds
    • 4 Baths
    • 5,083 Sq Ft

    53 Winford Way, Winchester, MA 01890

    Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

    Andersen Group Realty Keller Williams Realty Boston Northwest

    53 Winford Way, Winchester, MA 01890
  • 15 Wildwood St, Winchester, MA 01890
    15 Wildwood St, Winchester, MA 01890
    15 Wildwood St, Winchester, MA 01890
    /42

    $2,275,000 Open Sat 11:30AM - 1PM

    • 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
  • 53 Bacon St, Winchester, MA 01890
    53 Bacon St, Winchester, MA 01890
    53 Bacon St, Winchester, MA 01890
    /34

    $1,499,000

    • 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
  • 16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    /42

    $1,149,000 Open Sat 1:30PM - 2:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft

    16 Ridge St, Winchester, MA 01890

    27,000 SF lot!!! Set far back from the street~ Don't miss this opportunity! Whether looking to lightly update/ expand or completely renovate; this well maintained 3 bedroom split entry home with a stunning oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning fireplace, a

    Kim Covino Compass

    16 Ridge St, Winchester, MA 01890
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /42

    $1,999,000

    • 5 Beds
    • 3.5 Baths
    • 6,232 Sq Ft

    5 Azalea Rd, Winchester, MA 01890

    NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and

    Anthony Marino The Marino Group Collection

    5 Azalea Rd, Winchester, MA 01890
  • 22 Oldham Rd, Arlington, MA 02474
    22 Oldham Rd, Arlington, MA 02474
    22 Oldham Rd, Arlington, MA 02474
    /41

    $3,380,000

    • 5 Beds
    • 5.5 Baths
    • 5,737 Sq Ft

    22 Oldham Rd, Arlington, MA 02474

    Elegantly sited on Morningside Hill, this home is a luxury-built masterpiece. Thoughtfully designed & artfully crafted, it exudes opulence & cozy comfort. A gracious entry hall welcomes you into sophisticated living, highlighted by a breathtaking two-story living room adorned with countless windows. The chef's kitchen, a culinary haven, is equipped with state-of-the-art Thermador appliances,

    Suzanne Koller Compass

    22 Oldham Rd, Arlington, MA 02474
  • 40 Foxcroft Rd, Winchester, MA 01890
    40 Foxcroft Rd, Winchester, MA 01890
    40 Foxcroft Rd, Winchester, MA 01890
    /42

    $3,799,000 Open Sat 12:30PM - 1:30PM

    • 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
  • 80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    /37

    $3,099,000 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 3.5 Baths
    • 5,632 Sq Ft

    80 Arlington St, Winchester, MA 01890

    New roof. New landscaping. New exterior paint. New price! With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved home offers 11 rooms, 5 bedrooms and 3.5 baths. Enjoy views from the sun-splashed eat-in kitchen w/

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

    80 Arlington St, Winchester, MA 01890
  • 44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    /39

    $3,099,000 Open Sat 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
  • 14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    /30

    $2,850,000

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

    14 Nassau Dr, Winchester, MA 01890

    Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. 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 New

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, Winchester, MA 01890
  • 380 Cross St, Winchester, MA 01890
    380 Cross St, Winchester, MA 01890
    380 Cross St, Winchester, MA 01890
    /23

    $949,000

    • 4 Beds
    • 2 Baths
    • 1,938 Sq Ft

    380 Cross St, Winchester, MA 01890

    This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a favorite place for family to congregate and get

    Pavan Patel Realty ONE Group Nest

    380 Cross St, Winchester, MA 01890
  • 571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    /35

    $898,000 Open Fri 12PM - 1:30PM

    • 3 Beds
    • 1 Bath
    • 1,425 Sq Ft

    571 Washington St, Winchester, MA 01890

    Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for

    Ryan Wilson Keller Williams Realty

    571 Washington St, Winchester, MA 01890
  • 2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    /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
  • 257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    /42

    $3,299,000

    • 5 Beds
    • 7 Baths
    • 7,101 Sq Ft

    257 High St, Winchester, MA 01890

    Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

    Kim Covino Compass

    257 High St, Winchester, MA 01890
  • 20 Arthur St, Winchester, MA 01890
    20 Arthur St, Winchester, MA 01890
    /2

    $389,900

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    20 Arthur St, Winchester, MA 01890

    Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

    Dan O'Connell LAER Realty Partners

    20 Arthur St, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Massachusetts Middlesex County Winchester

Newest Listings for Sale in Winchester, MA

Frequently Asked Questions

What is the average home price in Winchester, MA?
Homes for sale in Winchester, MA have an average home price of $1,956,925.
How many homes have sold over the last 12 months in Winchester, MA?
165 homes have sold in Winchester, MA over the last 12 months.
Is Winchester, MA a safe city?
In general, the safest neighborhoods in Winchester, MA with lower crime scores are West Side, The Flats, Grove Street, Winchester Highlands and Symmes Corner.
What are the most popular zip codes in Winchester, MA?
The most popular zip codes in Winchester, MA include 01890, 01801, 02155, 02474 and 02420.
What are the most popular neighborhoods in Winchester, MA?
The most popular neighborhoods in Winchester, MA with the most homes for sale are West Side, The Flats, Grove Street, Winchester Highlands and Symmes Corner.
How much do you need to make to afford a house in Winchester?
The median home price in Winchester is $1,749,900. If you put a 20% down payment of $350,000 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $8,630 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $370K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Winchester, MA?
Winchester, MA has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Lexington High School, Arlington High School and Jonas Clarke Middle School. The neighborhoods in Winchester with the highest rated schools are West Side, North Main and The Flats. Browse all the schools in Winchester, MA to learn more.

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 21 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,651,000, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,651,000
Median Single Family Sale Price
$1,877,000
Median Townhouse Sale Price
$1,462,500
Median 2 Bedroom Sale Price
$920,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$562
Number of Homes for Sale
28
Last 12 months Home Sales
165
Months of Supply
2.00
Median List Price
$1,749,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
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