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Newest Homes for Sale in Winchester, MA

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  • 112 Highland Ave, Winchester, MA 01890
    112 Highland Ave, Winchester, MA 01890
    112 Highland Ave, Winchester, MA 01890
    /41

    $2,495,000 Open Sat 11AM - 12:30PM

    • 6 Beds
    • 3.5 Baths
    • 5,121 Sq Ft

    112 Highland Ave, Winchester, MA 01890

    Timeless Victorian grandeur meets modern living in this iconic Winchester home situated on the corner of Wilson Street w/ easy access to Fells trails! This recently renovated sun-filled 6 BR 4 BA home offers nearly 5000 ft.2 of beautifully scaled living spaces filled w/ extraordinary architectural charm & elegant details featuring a brand new state of the art gorgeous kitchen w/ Wolf & Sub Zero

    Kim Covino Compass

    112 Highland Ave, Winchester, MA 01890
  • 50 Oxford St, Winchester, MA 01890
    50 Oxford St, Winchester, MA 01890
    50 Oxford St, Winchester, MA 01890
    /42

    $3,450,000 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 3.5 Baths
    • 5,128 Sq Ft

    50 Oxford St, Winchester, MA 01890

    Rare opportunity in a prime Flats location! Set on an oversized lot w/ a stunning in-ground pool, jacuzzi, pool house & expansive level lawn, this exceptional home blends luxury, privacy, & modern living. Expanded & extensively renovated top-to-bottom, the home features an open layout w/ designer kitchen, spacious family room & oversized attached 2-car garage. Walls of windows & French doors

    Kim Covino Compass

    50 Oxford St, Winchester, MA 01890
  • 7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    /40

    $1,495,000 Open Sat 10:30AM - 11:30AM

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

    7 Sherman Place, Winchester, MA 01890

    Welcome to this sun-drenched newer construction & freshly updated 4 Bed 2.5 Bath luxury townhome, set on a quiet cul-de-sac with a private, professionally landscaped yard & secret garden. This spacious home lives like a free standing house with a thoughtful layout designed for both everyday living and entertaining. Highlights include soaring 9-foot ceilings, oversized windows & high efficiency

    Kim Covino Compass

    7 Sherman Place, Winchester, MA 01890
  • 200 Swanton St Unit 318, Winchester, MA 01890
    200 Swanton St Unit 318, Winchester, MA 01890
    200 Swanton St Unit 318, Winchester, MA 01890
    /9

    $379,900 Open Sat 11AM - 12PM

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 318, Winchester, MA 01890

    Beautifully renovated oversized one-bedroom condo at Parkview Condominium featuring an open floor plan and private balcony overlooking a serene Japanese garden and duck pond. Spacious primary bedroom offers room for a king-size bed and includes a walk-in closet. Updated kitchen, bathroom, and flooring provide years of low-maintenance living. Amenities include swimming pool, cabana, picnic

    Mike Huang Lewis & Joyce Real Estate

    200 Swanton St Unit 318, Winchester, MA 01890
  • 8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    /35

    $3,250,000 Open Sat 12PM - 2PM

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

    8 Priscilla Ln, Winchester, MA 01890

    Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef’s kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and

    The Pezzano Group Rise Signature Homes

    8 Priscilla Ln, Winchester, MA 01890
  • 68 Dothan St, Arlington, MA 02474
    68 Dothan St, Arlington, MA 02474
    68 Dothan St, Arlington, MA 02474
    /36

    $1,249,000 Open Fri 4:30PM - 6:30PM

    • 3 Beds
    • 2 Baths
    • 1,986 Sq Ft

    68 Dothan St, Arlington, MA 02474

    A peaceful retreat offering privacy, serenity, and a beautiful yard and garden made for slow mornings and quiet weekends. Tucked into Arlington's coveted Turkey Hill neighborhood, this updated raised ranch sits on a private wooded lot just steps from McClennen Park, with Whipple Hill Conservation Land, the Arlington Reservoir, and Wright-Locke Farm all close by. The main level features vaulted

    Jason Jeon Compass

    68 Dothan St, Arlington, MA 02474
  • 129 Washington St Unit 131, Winchester, MA 01890
    129 Washington St Unit 131, Winchester, MA 01890
    129 Washington St Unit 131, Winchester, MA 01890
    /31

    $1,299,000 Open Fri 5PM - 7PM

    • 3 Beds
    • 3.5 Baths
    • 2,420 Sq Ft

    129 Washington St Unit 131, Winchester, MA 01890

    Just moments from Winchester Center, this townhouse-style condo lives like a single-family, offering space, flow, and flexibility across four finished levels. The main living area is designed for how you actually live, with an open layout that brings the kitchen, dining, and living spaces together seamlessly. Coffered ceilings, wainscoting, and thoughtful updates add character, while the recently

    The Mary Scimemi Team Leading Edge Real Estate

    129 Washington St Unit 131, Winchester, MA 01890
  • 38 Salem St Unit 40, Winchester, MA 01890
    38 Salem St Unit 40, Winchester, MA 01890
    38 Salem St Unit 40, Winchester, MA 01890
    /39

    $1,500,000 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 3.5 Baths
    • 3,362 Sq Ft

    38 Salem St Unit 40, Winchester, MA 01890

    A rare opportunity to enjoy easy, yet refined living in Winchester, this well-maintained newer construction home offers 4-5 bedrooms and 3 1⁄2 baths with a thoughtfully designed open floor plan. The main level features a spacious living area, eat-in kitchen with granite countertops, stainless steel appliances and pantry, along with a 1⁄2 bath and practical mudroom for everyday ease. Upstairs,

    Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

    38 Salem St Unit 40, Winchester, MA 01890
  • 115 Church St, Winchester, MA 01890
    115 Church St, Winchester, MA 01890
    115 Church St, Winchester, MA 01890
    /35

    $2,975,000 Open Sat 11:30AM - 1PM

    • 7 Beds
    • 6 Baths
    • 5,888 Sq Ft

    115 Church St, Winchester, MA 01890

    Distinguished Colonial Revival located in the desirable “Flats" neighborhood offering 5,888 SF with 7 bedrooms and 6 baths across three finished levels. Period details include a quartered oak foyer and staircase, bay windows, pocket doors, and decorative millwork. Chef's kitchen features a Viking gas range, Thermador refrigerator, and granite countertops. Family room has a wood-burning fireplace

    Jennifer Ryer Better Homes and Gardens Real Estate - The Shanahan Group

    115 Church St, Winchester, MA 01890
  • 12 Cox Rd, Winchester, MA 01890
    12 Cox Rd, Winchester, MA 01890
    12 Cox Rd, Winchester, MA 01890
    /41

    $1,799,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,818 Sq Ft

    12 Cox Rd, Winchester, MA 01890

    SHOWINGS BEGIN AT OPEN HOUSE THURSDAY MAY 7th 5:00-6:30pm. Fabulous 11 room, 4 bedroom Colonial set on a beautiful lot on Winchester’s west side. The first floor offers a bright and sunny, open concept kitchen and family room which creates the perfect space for everyday living and entertaining which leads to a mud room, laundry, and home offic . Completing the first floor is half bath off

    Darryl Brian RE/MAX Bentley's

    12 Cox Rd, Winchester, MA 01890
  • 10 Rangeley Rd, Winchester, MA 01890
    10 Rangeley Rd, Winchester, MA 01890
    10 Rangeley Rd, Winchester, MA 01890
    /42

    $3,099,000

    • 5 Beds
    • 4.5 Baths
    • 5,406 Sq Ft

    10 Rangeley Rd, Winchester, MA 01890

    Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a

    Karima Alami Compass

    10 Rangeley Rd, Winchester, MA 01890
  • 50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    /42

    $2,595,000 Open Sat 12:30PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 4,403 Sq Ft

    50 Brooks St, Winchester, MA 01890

    Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home &

    Kim Covino Compass

    50 Brooks St, Winchester, MA 01890
  • 6 Hancock St, Winchester, MA 01890
    6 Hancock St, Winchester, MA 01890
    6 Hancock St, Winchester, MA 01890
    /31

    $1,250,000 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 1.5 Baths
    • 2,688 Sq Ft

    6 Hancock St, Winchester, MA 01890

    Classic turn-of-the-century Victorian filled with charm and character, ready for its next owner. 5 total bedrooms; 4 on the second floor and 1 on the 3rd floor, plus 3rd floor office. 1.5 baths, this well-maintained home awaits your finishing touches and features hardwood floors throughout, showcasing its timeless architectural details. Enjoy warm summer evenings on the inviting screened front

    Pirani & Wile Group Gibson Sotheby's International Realty

    6 Hancock St, Winchester, MA 01890
  • 6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    /36

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

    • 6 Beds
    • 5 Baths
    • 3,403 Sq Ft

    6 Ivy Cir, Winchester, MA 01890

    Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

    Valerie Post Engel & Volkers Boston

    6 Ivy Cir, Winchester, MA 01890
  • 2 Stratton Dr Unit 307, Woburn, MA 01801
    2 Stratton Dr Unit 307, Woburn, MA 01801
    2 Stratton Dr Unit 307, Woburn, MA 01801
    /21

    $625,000

    • 1 Bed
    • 1 Bath
    • 985 Sq Ft

    2 Stratton Dr Unit 307, Woburn, MA 01801

    2024-built 1 bedroom condo at Highland at Vale offering easy single-level living! This bright, open-concept home features an airy, contemporary layout ideal for both everyday living and entertaining. The stylish white kitchen showcases stainless steel appliances, ample storage, and a center island, seamlessly flowing into the dining and living areas. Sliders from the living room lead to a private

    Kim Covino Compass

    2 Stratton Dr Unit 307, Woburn, MA 01801
  • 144 Marble St Unit 403, Stoneham, MA 02180
    144 Marble St Unit 403, Stoneham, MA 02180
    144 Marble St Unit 403, Stoneham, MA 02180
    /29

    $485,000 Open Sat 11:30AM - 12:30PM

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft

    144 Marble St Unit 403, Stoneham, MA 02180

    Welcome to The Gates of Stoneham, a desirable and well-maintained condo community on the Winchester/Stoneham line. This bright 2-bed, 2 bath home offers 1,295 sq ft of move-in-ready space with elevator access and assigned parking. The open-concept layout includes a generously sized kitchen and separate dining area, perfect for everyday living and entertaining. Sunlight pours in through glass

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

    144 Marble St Unit 403, Stoneham, MA 02180
  • 16 Glenwood Ave, Winchester, MA 01890
    16 Glenwood Ave, Winchester, MA 01890
    16 Glenwood Ave, Winchester, MA 01890
    /41

    $2,200,000 Open Sat 1PM - 2PM

    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    16 Glenwood Ave, Winchester, MA 01890

    Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr

    Kim Covino Compass

    16 Glenwood Ave, Winchester, MA 01890
  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /40

    $3,379,000 Open Sat 1PM - 2PM

    • 7 Beds
    • 7.5 Baths
    • 8,540 Sq Ft

    37 Mayflower Rd, Winchester, MA 01890

    Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

    Kim Covino Compass

    37 Mayflower Rd, Winchester, MA 01890
  • 14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    /36

    $2,799,000 Open Sat 12:30PM - 2PM

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

    14 Nassau Dr, Winchester, MA 01890

    Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. 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 England

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, Winchester, MA 01890
  • 200 Swanton St Unit 717, Winchester, MA 01890
    200 Swanton St Unit 717, Winchester, MA 01890
    200 Swanton St Unit 717, Winchester, MA 01890
    /30

    $364,900

    • 1 Bed
    • 1 Bath
    • 613 Sq Ft

    200 Swanton St Unit 717, Winchester, MA 01890

    Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for

    Cameron Moniz Coldwell Banker Realty - Lexington

    200 Swanton St Unit 717, Winchester, MA 01890
  • 2 Edgewater Place, Winchester, MA 01890
    2 Edgewater Place, Winchester, MA 01890
    2 Edgewater Place, Winchester, MA 01890
    /32

    $2,700,000 Open Sat 12:30PM - 1:30PM

    • 4 Beds
    • 4.5 Baths
    • 3,945 Sq Ft

    2 Edgewater Place, Winchester, MA 01890

    A quiet cul-de-sac near the Mystic Lakes sets the stage for this exceptional Royal Barry Wills residence, masterfully reimagined. Every inch reflects elevated craftsmanship and a refined sense of luxury, with bespoke finishes and thoughtfully curated amenities throughout. The main level unfolds with effortless elegance, anchored by a state-of-the-art chef’s kitchen featuring custom cabinetry,

    Nancy Pallotta Gibson Sotheby's International Realty

    2 Edgewater Place, Winchester, MA 01890
  • 74 Wedgemere Ave, Winchester, MA 01890
    74 Wedgemere Ave, Winchester, MA 01890
    74 Wedgemere Ave, Winchester, MA 01890
    /42

    $2,950,000 Open Sat 11AM - 12PM

    • 5 Beds
    • 4.5 Baths
    • 5,202 Sq Ft

    74 Wedgemere Ave, Winchester, MA 01890

    The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and

    Kim Covino Compass

    74 Wedgemere Ave, Winchester, MA 01890
  • 1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    /35

    $3,399,000 Open Sat 1PM - 2PM

    • 7 Beds
    • 7.5 Baths
    • 7,226 Sq Ft

    1 Plymouth Rd, Winchester, MA 01890

    Discover a beautifully reimagined home in one of Winchester’s most sought-after neighborhoods, offering exceptional space, comfort, and convenience in a truly prime location. With 7 bedrooms, 7 full baths, and 1 half bath, 1 Plymouth has been thoughtfully expanded and rebuilt with high-end finishes throughout to suit today’s lifestyle. At the heart of the home is a stunning fireplaced family room

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    1 Plymouth Rd, Winchester, MA 01890
  • 83 Church St Unit 15, Winchester, MA 01890
    83 Church St Unit 15, Winchester, MA 01890
    83 Church St Unit 15, Winchester, MA 01890
    /34

    $1,100,000

    • 2 Beds
    • 1.5 Baths
    • 1,365 Sq Ft

    83 Church St Unit 15, Winchester, MA 01890

    Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal

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

    83 Church St Unit 15, Winchester, MA 01890
  • 94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    /41

    $1,849,999 Open Sat 12PM - 1:30PM

    • 4 Beds
    • 3 Baths
    • 3,512 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    This quintessential Colonial blends timeless charm with modern updates, offering a truly move-in ready home in a unique location! Directly across the street, the Winchester Swim and Tennis Club presents a rare opportunity for immediate membership—enjoy your own private club lifestyle just in time for summer! Just a few doors from Vinson-Owen Elementary, morning drop-offs couldn’t be easier.

    Philip Vita Compass

    94 Johnson Rd, Winchester, MA 01890
  • 380 Cross St, Winchester, MA 01890
    380 Cross St, Winchester, MA 01890
    380 Cross St, Winchester, MA 01890
    /41

    $929,900 Open Sat 12PM - 1:30PM

    • 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 nice place for family to congregate and get to

    Rajive Dogra Coldwell Banker Realty - Lexington

    380 Cross St, Winchester, MA 01890
  • 4 Stratton Dr Unit 308, Woburn, MA 01801
    4 Stratton Dr Unit 308, Woburn, MA 01801
    4 Stratton Dr Unit 308, Woburn, MA 01801
    /24

    $889,000

    • 3 Beds
    • 2 Baths
    • 1,370 Sq Ft

    4 Stratton Dr Unit 308, Woburn, MA 01801

    Commuter-friendly, thoughtfully designed newer construction condo at Highland at Vale offering a refined take on low-maintenance living in Woburn. Positioned on the 3rd floor with high ceilings, this single-level home features scenic sunset views from a private balcony with a hilltop vantage and seamless indoor-outdoor flow. The layout is effortlessly arranged for privacy with 2 spacious

    Erika Tarlow Coldwell Banker Realty - Boston

    4 Stratton Dr Unit 308, Woburn, MA 01801
  • 200 Swanton St Unit T35, Winchester, MA 01890
    200 Swanton St Unit T35, Winchester, MA 01890
    200 Swanton St Unit T35, Winchester, MA 01890
    /39

    $400,000

    • 2 Beds
    • 1 Bath
    • 810 Sq Ft

    200 Swanton St Unit T35, Winchester, MA 01890

    SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of

    Nuri Tirana Tirana Real Estate Group

    200 Swanton St Unit T35, Winchester, MA 01890
  • 115 Washington St Unit 2A, Winchester, MA 01890
    115 Washington St Unit 2A, Winchester, MA 01890
    115 Washington St Unit 2A, Winchester, MA 01890
    /24

    $727,000 Open Sat 1PM - 2PM

    • 2 Beds
    • 1 Bath
    • 1,029 Sq Ft

    115 Washington St Unit 2A, Winchester, MA 01890

    Newly Renovated! 2 Bd at Church Place in Winchester Center! This stunning corner unit renovation was just completed & is ideally located in the heart of the center. Perfect for down-sizers or anyone seeking easy living w/ access to the train, restaurants, shops & top-rated schools - all the conveniences right outside your door! This bright & airy unit offers an open floor plan w/ beautiful arched

    Kim Covino Compass

    115 Washington St Unit 2A, Winchester, MA 01890
  • 10 Dartmouth St, Winchester, MA 01890
    10 Dartmouth St, Winchester, MA 01890
    10 Dartmouth St, Winchester, MA 01890
    /42

    $2,999,000 Open Sat 11AM - 12:30PM

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

    10 Dartmouth St, Winchester, MA 01890

    Winchester's premiere location! This stunning waterfront gem is perfectly situated on Winter Pond, offering over 80 feet of direct water frontage with expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this property presents a rare opportunity to enjoy water activities such as kayaking, paddleboarding, fishing, ice skating and hockey all

    Kim Covino Compass

    10 Dartmouth St, Winchester, MA 01890
  • 276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    /38

    $2,299,000 Open Sat 11AM - 12PM

    • 5 Beds
    • 3.5 Baths
    • 5,006 Sq Ft

    276 High St, Winchester, MA 01890

    Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

    Kim Covino Compass

    276 High St, Winchester, MA 01890
  • 200 Swanton St Unit 538, Winchester, MA 01890
    200 Swanton St Unit 538, Winchester, MA 01890
    200 Swanton St Unit 538, Winchester, MA 01890
    /13

    $259,000

    • 1 Bath
    • 394 Sq Ft

    200 Swanton St Unit 538, Winchester, MA 01890

    Michael Masci North Atlantic Realty Group

    200 Swanton St Unit 538, Winchester, MA 01890
  • 6 Mason Way Unit 63, Woburn, MA 01801
    6 Mason Way Unit 63, Woburn, MA 01801
    6 Mason Way Unit 63, Woburn, MA 01801
    /33

    $1,299,995 New Construction

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

    6 Mason Way Unit 63, 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 63, Woburn, MA 01801
  • 2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    /41

    $3,747,000

    • 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
  • 40 Foxcroft Rd, Winchester, MA 01890
    40 Foxcroft Rd, Winchester, MA 01890
    40 Foxcroft Rd, Winchester, MA 01890
    /42

    $3,650,000 Open Sat 11AM - 12:30PM

    • 6 Beds
    • 4.5 Baths
    • 6,460 Sq Ft

    40 Foxcroft Rd, Winchester, MA 01890

    40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows.

    The Boston ONE Team Serhant

    40 Foxcroft Rd, Winchester, MA 01890
  • 666 Main St Unit 315, Winchester, MA 01890
    666 Main St Unit 315, Winchester, MA 01890
    666 Main St Unit 315, Winchester, MA 01890
    /23

    $688,000

    • 2 Beds
    • 2 Baths
    • 1,025 Sq Ft

    666 Main St Unit 315, 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, assigned parking,

    Jing Chen Peace of Mind Realty

    666 Main St Unit 315, Winchester, MA 01890
  • 4 Dartmouth St, Winchester, MA 01890
    4 Dartmouth St, Winchester, MA 01890
    4 Dartmouth St, Winchester, MA 01890
    /42

    $4,449,000

    • 5 Beds
    • 5.5 Baths
    • 6,526 Sq Ft

    4 Dartmouth St, Winchester, MA 01890

    Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully maintained and updated, blending classic architecture with modern comfort. This 5 bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and

    Nancy Pallotta Gibson Sotheby's International Realty

    4 Dartmouth St, Winchester, MA 01890
  • 9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    /10

    $3,400,000

    • 6 Beds
    • 5.5 Baths
    • 6,100 Sq Ft

    9 Albamont Rd, Winchester, MA 01890

    Brand new high end construction in prime Winchester location! Currently under construction w/ completion expected late spring 2026. A thoughtfully designed home with immense curb appeal showcasing stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer

    Kim Covino Compass

    9 Albamont Rd, Winchester, MA 01890
  • 53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    /16

    $2,799,000 Open Sat 12PM - 1PM

    • 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
  • 27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    /39

    $3,290,000

    • 6 Beds
    • 5.5 Baths
    • 7,431 Sq Ft

    27 Everett Ave, Winchester, MA 01890

    This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are

    Nancy Pallotta Gibson Sotheby's International Realty

    27 Everett Ave, 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 $1,895,642.
Are home prices dropping in Winchester?
Yes, home prices in Winchester are down 3% in the last 12 months.
How many homes have sold over the last 12 months in Winchester, MA?
178 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 The Flats, West Side, 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, 02474, 02420 and 02155.
What are the most popular neighborhoods in Winchester, MA?
The most popular neighborhoods in Winchester, MA with the most homes for sale are The Flats, West Side, 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 $1,649,000. If you put a 20% down payment of $329,800 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $8,230 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $353K 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 Greater Boston Academy, Lexington Christian Academy and Lexington High School. The neighborhoods in Winchester with the highest rated schools are North Main, The Flats and West Side. Browse all the schools in Winchester, MA to learn more.

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 22 days on the market compared to the national average of 57 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,554,500, down 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,554,500
Median Single Family Sale Price
$1,750,000
Median Townhouse Sale Price
$1,475,000
Median 2 Bedroom Sale Price
$935,000
Average Price Per Sq Ft
$560
Number of Homes for Sale
29
Last 12 months Home Sales
178
Months of Supply
2.00
Median List Price
$1,649,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-8%
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