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Winchester, MA Homes for Sale

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  • 200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    /26

    $379,000

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 228, Winchester, MA 01890

    Welcome to Parkview Condominiums in Winchester. This 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

    RE/MAX Andrew Realty Services

    (781) 417-5122

    200 Swanton St Unit 228, Winchester, MA 01890
  • 20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    /36

    $3,600,000 Open Sat 1:30PM - 2:30PM

    • 6 Beds
    • 7 Baths
    • 8,866 Sq Ft

    20 Amberwood Dr, Winchester, MA 01890

    Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    (781) 678-8050

    20 Amberwood Dr, Winchester, MA 01890
  • 15 Edward Dr Unit 15, Winchester, MA 01890
    15 Edward Dr Unit 15, Winchester, MA 01890
    15 Edward Dr Unit 15, Winchester, MA 01890
    /42

    $958,000

    • 3 Beds
    • 2.5 Baths
    • 2,082 Sq Ft

    15 Edward Dr Unit 15, Winchester, MA 01890

    Welcome to the highly sought-after Pepper Hill Estates, ideally situated on a quiet street near Vinson-Owen Elementary School and within walking distance to Wright-Locke Farm and McClennen Park. This Colonial-style home offers a highly desirable and functional layout. The first floor features an open-concept design with a spacious living room, dining area, and a custom-built kitchen by Schrock

    Agent Photo

    Alina Wang

    Coldwell Banker Realty - Lexington

    (781) 512-7277

    15 Edward Dr Unit 15, Winchester, MA 01890
  • 1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    /40

    $1,899,000

    • 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
  • 10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    /42

    $2,499,000

    • 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
  • 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
  • 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
  • 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
  • 2 Abby Rd, Winchester, MA 01890
    2 Abby Rd, Winchester, MA 01890
    2 Abby Rd, Winchester, MA 01890
    /35

    $2,649,000 Open Sat 1PM - 2:30PM

    • 4 Beds
    • 4.5 Baths
    • 5,614 Sq Ft

    2 Abby Rd, Winchester, MA 01890

    Tucked on a quiet cul-de-sac within an exclusive enclave of homes, this newer residence offers a harmony of refined living and natural beauty. Just moments from the trails and vistas of the Middlesex Fells Reservation, this home is ideally positioned for those who value serenity and effortless access to the outdoors. Thoughtfully designed, it unfolds with an airy, open-concept where a sunlit

    Nancy Pallotta Gibson Sotheby's International Realty

    2 Abby Rd, Winchester, MA 01890
  • 15 Mayflower Rd, Winchester, MA 01890
    15 Mayflower Rd, Winchester, MA 01890
    15 Mayflower Rd, Winchester, MA 01890
    /39

    $3,425,000 Open Sat 12PM - 1:30PM

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

    15 Mayflower Rd, Winchester, MA 01890

    Discover a stunningly reimagined home nestled in one of Winchester’s most sought after neighborhoods—an exceptional opportunity to own a beautifully crafted, completely transformed residence. Expanded and rebuilt with intention, 15 Mayflower delivers the space, layout, and flexibility today’s lifestyle demands, with a thoughtful floor plan that balances open concept living and well defined

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    15 Mayflower Rd, 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 11:30AM - 1PM

    • 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
  • 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
  • 29 Pilgrim Dr, Winchester, MA 01890
    29 Pilgrim Dr, Winchester, MA 01890
    29 Pilgrim Dr, Winchester, MA 01890
    /42

    $1,749,000 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 3 Baths
    • 3,271 Sq Ft

    29 Pilgrim Dr, Winchester, MA 01890

    Beautifully updated home offers generous living spaces and a seamless, open flow. Sun-filled living and dining areas feature hardwood floors, elegant detailing, and a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, and large island that opens to the dining area, which flows into the

    Anne Spry Barrett Sotheby's International Realty

    29 Pilgrim Dr, Winchester, MA 01890
  • 25 Myopia Rd, Winchester, MA 01890
    25 Myopia Rd, Winchester, MA 01890
    25 Myopia Rd, Winchester, MA 01890
    /31

    $3,390,000

    • 4 Beds
    • 3.5 Baths
    • 4,847 Sq Ft

    25 Myopia Rd, Winchester, MA 01890

    A timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering tranquil views of lush gardens and rolling hills. Thoughtful architectural details enrich every space, while multiple patios and wrap-around porch create an effortless flow between indoor& outdoor. The gracious main level unfolds into beautifully connected living spaces, featuring an office, elegant dining

    Wenjun Cao Engel & Volkers Boston

    25 Myopia Rd, Winchester, MA 01890
  • 4 Dartmouth St, Winchester, MA 01890
    4 Dartmouth St, Winchester, MA 01890
    4 Dartmouth St, Winchester, MA 01890
    /42

    $4,699,000

    • 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
  • 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

    $699,000

    • 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
  • 237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    237 Swanton St, Winchester, MA 01890
    /35

    $1,945,000 Open Sat 11:30AM - 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
  • 54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    /42

    $3,499,000 Open Sat 11AM - 12PM

    • 5 Beds
    • 7.5 Baths
    • 6,899 Sq Ft

    54 Johnson Rd, Winchester, MA 01890

    This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the

    Kim Covino Compass

    54 Johnson Rd, Winchester, MA 01890
  • 15 East St, Winchester, MA 01890
    15 East St, Winchester, MA 01890
    15 East St, Winchester, MA 01890
    /39

    $1,199,000 Open Sat 1PM - 2:30PM

    • 3 Beds
    • 1.5 Baths
    • 1,973 Sq Ft

    15 East St, Winchester, MA 01890

    Move in ready & nicely remodeled ranch on a fabulous 10K fenced lot! This 3-4bedroom, 2 full bath home w/full lower level including office, family room/bedroom & full bath offers a sunny, functional layout w/ tasteful updates throughout.The main living spaces flow seamlessly, highlighted by a newer eat-in kitchen w/ access to deck & great yard; perfect for indoor/outdoor living & entertaining.

    Kim Covino Compass

    15 East St, Winchester, MA 01890
  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /42

    $3,537,000

    • 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
  • 15 Gershon Way Unit 15, Winchester, MA 01890
    15 Gershon Way Unit 15, Winchester, MA 01890
    15 Gershon Way Unit 15, Winchester, MA 01890
    /35

    $2,395,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3.5 Baths
    • 4,087 Sq Ft

    15 Gershon Way Unit 15, Winchester, MA 01890

    Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual

    Moira Lown Coldwell Banker Realty - Wellesley

    15 Gershon Way Unit 15, Winchester, MA 01890
  • 65 High St, Winchester, MA 01890
    65 High St, Winchester, MA 01890
    65 High St, Winchester, MA 01890
    /26

    $1,499,999

    • 6 Beds
    • 3 Baths
    • 2,658 Sq Ft

    65 High St, Winchester, MA 01890

    Fantastic! The best value in Winchester in a desired neighborhood. The sunny first floor flows nicely from room to room, with hardwood floors in the living areas and a hallway leading to the 3 original bedrooms. Ideal for an office, guests, or visiting in-laws. A screen porch and patio off the dining room ideal for al fresco dining. The generous second-floor renovation features a full bath with

    Anna Jung K Stadium Realty INC

    65 High St, Winchester, MA 01890
  • 34 Robinhood Rd, Winchester, MA 01890
    34 Robinhood Rd, Winchester, MA 01890
    34 Robinhood Rd, Winchester, MA 01890
    /37

    $1,524,000 Open Sat 1PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 3,380 Sq Ft

    34 Robinhood Rd, Winchester, MA 01890

    This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main

    Janet Halloran RE/MAX Real Estate Center

    34 Robinhood Rd, Winchester, MA 01890
  • 10 Dartmouth St, Winchester, MA 01890
    10 Dartmouth St, Winchester, MA 01890
    10 Dartmouth St, Winchester, MA 01890
    /42

    $3,299,000 Open Sat 12:30PM - 1:30PM

    • 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
  • 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

    $1,300,468 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
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 $1,904,255.
How many homes have sold over the last 12 months in Winchester, MA?
174 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 $1,649,500. If you put a 20% down payment of $329,900 and had a 30-year fixed mortgage with an interest rate of 6.46%, your estimated principal and interest payment would be $8,310 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $356K 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 55 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,600,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,600,000
Median Single Family Sale Price
$1,737,000
Median Townhouse Sale Price
$1,412,500
Median 2 Bedroom Sale Price
$770,000
Average Price Per Sq Ft
$564
Number of Homes for Sale
19
Last 12 months Home Sales
174
Months of Supply
1.30
Median List Price
$1,649,500
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-3%
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