59

Winchester, MA Homes for Sale

Section Image Section Image
  • 200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    /17

    $375,000

    Open Sat 1:30PM - 2:30PM $24K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 228, Winchester, MA 01890

    Welcome to Parkview Condos! This one bed one bath, bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with new flooring and excellent closet space, freshly

    Agent Photo

    Joan Powell

    REMAX Andrew Realty Services

    (781) 417-5122

    200 Swanton St Unit 228, Winchester, MA 01890
  • 200 Swanton St Unit 303, Winchester, MA 01890
    200 Swanton St Unit 303, Winchester, MA 01890
    200 Swanton St Unit 303, Winchester, MA 01890
    /19

    $505,000

    • 2 Beds
    • 1 Bath
    • 822 Sq Ft

    200 Swanton St Unit 303, Winchester, MA 01890

    Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and

    Agent Photo

    Joan Powell

    REMAX Andrew Realty Services

    (781) 562-4157

    200 Swanton St Unit 303, Winchester, MA 01890
  • 15 Fieldstone Dr, Winchester, MA 01890
    15 Fieldstone Dr, Winchester, MA 01890
    15 Fieldstone Dr, Winchester, MA 01890
    /42

    $1,999,900

    Open Sat 11AM - 12:30PM
    • 4 Beds
    • 3.5 Baths
    • 3,286 Sq Ft

    15 Fieldstone Dr, Winchester, MA 01890

    Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless

    Anne Spry Barrett Sotheby's International Realty

    15 Fieldstone Dr, Winchester, MA 01890
  • 10 Farrow St, Winchester, MA 01890
    10 Farrow St, Winchester, MA 01890
    10 Farrow St, Winchester, MA 01890
    /35

    $1,649,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 3.5 Baths
    • 2,768 Sq Ft

    10 Farrow St, Winchester, MA 01890

    Winchester Single Family Home with Attached Garage. Completely rebuilt in 2019, 4 Bedrooms + 2 Home Offices & 3.5 Bathrooms across 2,750+ SF! Two "WFH Offices" with Door & Window for privacy. Open-Concept Kitchen: Quartz Island/Countertops & Stainless Steel Appliances. Induction cooking & Hood Venting. Open-Concept Flows into the Connected Dining Room & Sundrenched Living Room with Wood Burning

    Collin Bray Century 21 Cityside

    10 Farrow St, Winchester, MA 01890
  • 1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    /40

    $1,799,000

    $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    1 Town Way, Winchester, MA 01890

    Welcome home to this completely renovated gem, ideally situated on a corner lot in the highly sought-after Lincoln Elementary School district. Warm, inviting, and truly move-in ready, this home offers the open-concept first floor buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy

    Philip Vita Compass

    1 Town Way, Winchester, MA 01890
  • 171 Swanton St Unit 7, Winchester, MA 01890
    171 Swanton St Unit 7, Winchester, MA 01890
    171 Swanton St Unit 7, Winchester, MA 01890
    /30

    $729,000

    Open Sat 12PM - 1:30PM
    • 2 Beds
    • 2.5 Baths
    • 1,431 Sq Ft

    171 Swanton St Unit 7, Winchester, MA 01890

    Easy living awaits at The Village, where this well-maintained, freshly painted, townhouse offers a functional layout, desirable amenities, and a convenient Winchester location. The main level features hardwood floors, an oversized living room with gas fireplace, an open dining area, and kitchen with direct access to a private patio overlooking the beautifully landscaped grounds. A half bath and

    Pirani & Wile Group Gibson Sotheby's International Realty

    171 Swanton St Unit 7, 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

    • 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
  • 23 Shepard Ct Unit U23, Winchester, MA 01890
    23 Shepard Ct Unit U23, Winchester, MA 01890
    23 Shepard Ct Unit U23, Winchester, MA 01890
    /41

    $699,900

    Open Sat 2:30PM - 4PM $49K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,380 Sq Ft

    23 Shepard Ct Unit U23, Winchester, MA 01890

    Huge Price Drop – Best Value in the Winchester School District! Beautifully maintained townhouse-style condex offering 3 levels of living in a prime Winchester location. This sun-filled home features 3 bedrooms, 2 full baths, 2 half baths, and a flexible third-floor suite perfect as a primary bedroom, guest space, or home office. Recent updates include a 2019 high-efficiency gas boiler, 2019

    Nancy Zhang Zhenning Fairview Partners International LLC

    23 Shepard Ct Unit U23, Winchester, MA 01890
  • 2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    2 Everett Ave, Winchester, MA 01890
    /41

    $3,475,000

    $272K PRICE DROP
    • 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
  • 117 Highland Ave, Winchester, MA 01890
    117 Highland Ave, Winchester, MA 01890
    117 Highland Ave, Winchester, MA 01890
    /41

    $1,725,000

    Open Fri 11:30AM - 12:30PM
    • 5 Beds
    • 3.5 Baths
    • 3,722 Sq Ft

    117 Highland Ave, Winchester, MA 01890

    Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and

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

    117 Highland Ave, Winchester, MA 01890
  • 94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    /40

    $1,799,000

    Open Sat 12:30PM - 2PM
    • 4 Beds
    • 3 Baths
    • 3,366 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated

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

    94 Johnson Rd, Winchester, MA 01890
  • 9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    /10

    $3,200,000

    $200K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 6,100 Sq Ft

    9 Albamont Rd, Winchester, MA 01890

    Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases 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

    Kim Covino Compass

    9 Albamont Rd, Winchester, MA 01890
  • 16 Glenwood Ave, Winchester, MA 01890
    16 Glenwood Ave, Winchester, MA 01890
    16 Glenwood Ave, Winchester, MA 01890
    /41

    $2,099,000

    Open Sun 10AM - 11AM $101K PRICE DROP
    • 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
  • 50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    50 Brooks St, Winchester, MA 01890
    /42

    $2,450,000

    Open Sat 1PM - 2:30PM $145K PRICE DROP
    • 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
  • 18 Middlesex St, Winchester, MA 01890
    18 Middlesex St, Winchester, MA 01890
    18 Middlesex St, Winchester, MA 01890
    /32

    $2,795,000

    • 4 Beds
    • 4.5 Baths
    • 5,233 Sq Ft

    18 Middlesex St, Winchester, MA 01890

    This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the

    Tina Natale Luxury Living Real Estate

    18 Middlesex St, Winchester, MA 01890
  • 8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    8 Priscilla Ln, Winchester, MA 01890
    /35

    $3,149,000

    Open Sat 11AM - 12PM $101K PRICE DROP
    • 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
  • 1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    /35

    $3,299,000

    Open Sat 2PM - 3:30PM $100K PRICE DROP
    • 7 Beds
    • 7.5 Baths
    • 7,226 Sq Ft

    1 Plymouth Rd, Winchester, MA 01890

    Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    1 Plymouth 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

    $51K PRICE DROP
    • 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
  • 11 Carriage Ln, Winchester, MA 01890
    11 Carriage Ln, Winchester, MA 01890
    11 Carriage Ln, Winchester, MA 01890
    /38

    $1,699,000

    Open Fri 12:30PM - 1:30PM
    • 4 Beds
    • 3 Baths
    • 2,707 Sq Ft

    11 Carriage Ln, Winchester, MA 01890

    15K LOT!! Move right into this beautifully updated 4 BR 3 BA open concept home w/stunning rear addition/primary bedroom suite! This impeccably maintained, nicely updated home has a bright & airy open layout w/ abundant natural light streaming through oversized windows. The main living area flows seamlessly from the spacious living room w/beautiful fireplace into the dining room & kitchen. The

    Kim Covino Compass

    11 Carriage Ln, Winchester, MA 01890
  • 9 Wilson St, Winchester, MA 01890
    9 Wilson St, Winchester, MA 01890
    9 Wilson St, Winchester, MA 01890
    /38

    $1,900,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3.5 Baths
    • 2,943 Sq Ft

    9 Wilson St, Winchester, MA 01890

    Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a

    Elena Langlois Compass

    9 Wilson St, Winchester, MA 01890
  • 16 & 16A Glenwood Ave, Winchester, MA 01890
    16 & 16A Glenwood Ave, Winchester, MA 01890
    16 & 16A Glenwood Ave, Winchester, MA 01890
    /41

    $2,099,000

    Open Sun 10AM - 11AM $101K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    16 & 16A Glenwood Ave, Winchester, MA 01890

    Must see! sprawling 2-3 family beautifully renovated & expanded home 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,

    Kim Covino Compass

    16 & 16A Glenwood Ave, Winchester, MA 01890
  • 53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    53 Winford Way, Winchester, MA 01890
    /12

    $2,599,000

    Open Sat 1:30PM - 2:30PM $200K PRICE DROP
    • 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
  • 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

    $1,199,000

    Open Sat 10AM - 12PM $100K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,420 Sq Ft

    129 Washington St Unit 131, Winchester, MA 01890

    Prime Winchester location just moments from Winchester Center, within walking distance to elementary, middle, high school, downtown and commuter rail. Ideal for commuters and locals alike. 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

    The Mary Scimemi Team Leading Edge Real Estate

    129 Washington St Unit 131, Winchester, MA 01890
  • 2 York Rd, Winchester, MA 01890
    2 York Rd, Winchester, MA 01890
    2 York Rd, Winchester, MA 01890
    /39

    $1,949,000

    Open Sat 12PM - 1:30PM
    • 4 Beds
    • 3.5 Baths
    • 3,494 Sq Ft

    2 York Rd, Winchester, MA 01890

    Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized

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

    2 York 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
  • 18 Bradford Rd, Winchester, MA 01890
    18 Bradford Rd, Winchester, MA 01890
    18 Bradford Rd, Winchester, MA 01890
    /28

    $659,000

    • 3 Beds
    • 1.5 Baths
    • 1,331 Sq Ft

    18 Bradford Rd, Winchester, MA 01890

    Welcome to this beautifully updated 3-bedroom,1.5-bath townhouse with a large flat Exclusive to use backyard (0.18 acres) located in Residences at Winchester, the highly desirable new Lynch School district with low condo fees. The spacious sun-filled living room offers large windows, abundant natural light, and gleaming hardwood floors throughout the home. The renovated kitchen features quartz

    Wei Wenny Fu Phoenix Real Estate

    18 Bradford Rd, Winchester, MA 01890
  • 339-341 Washington St, Winchester, MA 01890
    339-341 Washington St, Winchester, MA 01890
    339-341 Washington St, Winchester, MA 01890
    /36

    $999,000

    Open Sun 12PM - 1:30PM $100K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 2,160 Sq Ft

    339-341 Washington St, Winchester, MA 01890

    Exceptional opportunity for investors, owner-occupants, or multigenerational living in this two-family home conveniently located near Winchester Center, restaurants, shopping, commuter rail, and major routes. The first floor has 2 bedrooms plus an office, while the second floor includes a third bedroom. Both units are filled with natural light and share nearly identical layouts with enclosed

    Nancy Pallotta Gibson Sotheby's International Realty

    339-341 Washington St, Winchester, MA 01890
  • 4 Dartmouth St, Winchester, MA 01890
    4 Dartmouth St, Winchester, MA 01890
    4 Dartmouth St, Winchester, MA 01890
    /41

    $4,449,000

    $250K PRICE DROP
    • 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
  • 10 Rangeley Rd, Winchester, MA 01890
    10 Rangeley Rd, Winchester, MA 01890
    10 Rangeley Rd, Winchester, MA 01890
    /42

    $3,199,000

    • 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
  • 211 Forest St, Winchester, MA 01890
    211 Forest St, Winchester, MA 01890
    211 Forest St, Winchester, MA 01890
    /41

    $2,199,000

    Open Sat 11AM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 3,474 Sq Ft

    211 Forest St, Winchester, MA 01890

    Welcomed by a convenient horseshoe driveway surrounded by thoughtfully designed gardens, 211 Forest has undergone a completely reimagined renovation. This curated family residence shows refined attention to detail and a designer’s eye at every turn. From the custom kitchen with bespoke cabinetry and premium hardware, AGA cast-iron range and Liebherr refrigerator to the sunporch filled with

    Michael Gilbert Stuart St James, Inc.

    211 Forest St, Winchester, MA 01890
  • 22 Arthur St, Winchester, MA 01890
    22 Arthur St, Winchester, MA 01890
    22 Arthur St, Winchester, MA 01890
    /13

    $414,500

    • 2 Beds
    • 1 Bath
    • 1,121 Sq Ft

    22 Arthur St, Winchester, MA 01890

    This property is available to and priced for Income Eligible families in 100% of the moderate-income range. See attached application for eligibility requirements. Throughout the tenure of the current homeowner many upgrades have been made to this property. Roof, new porch, updated Electrical, kitchen cabinets, Gas furnace, DE leading, new brick chimney. The exterior of the home is being prepped

    Karen Morand MCO Realty Service, LLC

    22 Arthur St, Winchester, MA 01890
  • 26 N Gateway, Winchester, MA 01890
    26 N Gateway, Winchester, MA 01890
    26 N Gateway, Winchester, MA 01890
    /36

    $2,199,000

    Open Fri 11AM - 12PM
    • 4 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    26 N Gateway, Winchester, MA 01890

    Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the

    Pirani & Wile Group Gibson Sotheby's International Realty

    26 N Gateway, Winchester, MA 01890
  • 8 Hawthorne Rd, Winchester, MA 01890
    8 Hawthorne Rd, Winchester, MA 01890
    8 Hawthorne Rd, Winchester, MA 01890
    /27

    $1,885,000

    Open Sat 11AM - 12:30PM $40K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,315 Sq Ft

    8 Hawthorne Rd, Winchester, MA 01890

    Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees.

    Elaine Song Coldwell Banker Realty - Lexington

    8 Hawthorne Rd, Winchester, MA 01890
  • 21 Willowdale Rd, Winchester, MA 01890
    21 Willowdale Rd, Winchester, MA 01890
    21 Willowdale Rd, Winchester, MA 01890
    /42

    $2,400,000

    Open Sat 1PM - 2PM
    • 5 Beds
    • 3.5 Baths
    • 4,591 Sq Ft

    21 Willowdale Rd, Winchester, MA 01890

    New construction 2019, this impressive 4-5-bedroom, 4.5-bath custom built East side colonial offers exceptional space and a highly sought-after floor plan. The chef's eat-in kitchen features a large center island, abundant cabinetry & sunny dining area that seamlessly blends w/ the spacious family room w built ins & fireplace. Sun-filled living and dining rooms are connected by a double-sided

    Kim Covino Compass

    21 Willowdale Rd, Winchester, MA 01890
  • 38 Robinhood Rd, Winchester, MA 01890
    38 Robinhood Rd, Winchester, MA 01890
    38 Robinhood Rd, Winchester, MA 01890
    /32

    $1,225,000

    Open Sat 11:30AM - 1:30PM
    • 3 Beds
    • 3 Baths
    • 1,736 Sq Ft

    38 Robinhood Rd, Winchester, MA 01890

    Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open

    Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

    38 Robinhood Rd, 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

    • 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
  • 7 Wainwright Rd Unit 47, Winchester, MA 01890
    7 Wainwright Rd Unit 47, Winchester, MA 01890
    7 Wainwright Rd Unit 47, Winchester, MA 01890
    /32

    $1,330,000

    Open Sat 11:30AM - 1PM
    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft

    7 Wainwright Rd Unit 47, Winchester, MA 01890

    Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub.

    Felicity Tuttle Better Homes and Gardens Real Estate - The Shanahan Group

    7 Wainwright Rd Unit 47, Winchester, MA 01890
  • 2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    2 Atherton Rd, Winchester, MA 01890
    /38

    $3,600,000

    Open Sat 12:30PM - 1:45PM
    • 6 Beds
    • 6.5 Baths
    • 7,400 Sq Ft

    2 Atherton Rd, Winchester, MA 01890

    This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is

    Brooke Zarbano Regatta Realty

    2 Atherton Rd, Winchester, MA 01890
  • 14 Rangeley Ridge, Winchester, MA 01890
    14 Rangeley Ridge, Winchester, MA 01890
    14 Rangeley Ridge, Winchester, MA 01890
    /39

    $1,498,000

    Open Sat 11AM - 2PM
    • 3 Beds
    • 2 Baths
    • 2,387 Sq Ft

    14 Rangeley Ridge, Winchester, MA 01890

    Located in the highly desirable Rangeley Estates - a location that puts everyday conveniences close with comfortable living. The main level is designed for everyday living & entertaining with a spacious fireplaced living room with built-in bookcase, separate family room with large closets, dining room opens to deck for easy indoor/outdoor entertaining, kitchen with island seating & stainless

    Peter Rooney Compass

    14 Rangeley Ridge, Winchester, MA 01890
  • 7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    7 Ridge St, Winchester, MA 01890
    /39

    $1,499,000

    $51K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 3,360 Sq Ft

    7 Ridge St, Winchester, MA 01890

    Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds

    Paul Cirignano The Synergy Group

    7 Ridge St, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Massachusetts Middlesex County Winchester

Real Estate & Homes for Sale in Winchester, MA

Why Live in Winchester

Winchester, MA, a peaceful Greater Boston suburb, has evolved from a rural farming community to a primarily residential town with a population of nearly 23,000. Located 8 miles north of Boston, Winchester is known for its grand New England homes, ranging from historic Colonial Revivals to modern Cape Cods and ranch styles. The town boasts one of the best school districts in the state, with Winchester Public Schools serving over 4,300 students and receiving high ratings. The private Acera School also offers quality education. Outdoor enthusiasts can enjoy Mystic Lakes State Park, Middlesex Fells Reservation, and the Tri-Community Greenway, which connects Winchester with Woburn and Stoneham. The town's downtown area, bordered by Wedge and Mill Ponds, features a variety of markets, restaurants, boutiques, and service shops. Community events such as Winchester Town Day, PRIDEFest, and summer concerts at Town Common foster a strong sense of community. Wright-Locke Farm, a 383-year-old sustainable conservancy, provides fresh organic produce and nature-based activities. Winchester is accessible via U.S. Route 3 and Interstates 93 and 95, with public transit options including the MBTA bus and commuter rail. Logan International Airport is about 11 miles away. The town has a lower crime risk compared to the national average, with recent data indicating a decrease in violent crimes.

Learn more about living in Winchester

Frequently Asked Questions

What is the average home price in Winchester, MA?
Homes for sale in Winchester, MA have an average home price of $1,871,994.
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.
What is the average household income in Winchester, MA?
The average household income in Winchester, MA is $206K.
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, 02155 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 North Main, The Flats, West Side, 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 $1,669,444. If you put a 20% down payment of $333,900 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $8,460 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $363K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $206K.
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 Prices in Winchester, MA

The median home sale price in Winchester, MA is $1,554,600, down 9% year-over-year. Homes in Winchester sell in 23 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$1,554,600
Median Single Family Sale Price
$1,750,000
Median Townhouse Sale Price
$1,350,000
Median 2 Bedroom Sale Price
$940,000
Average Price Per Sq Ft
$560
Number of Homes for Sale
36
Last 12 months Home Sales
178
Months of Supply
2.40
Median List Price
$1,669,444
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-9%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group