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Winchester, MA Homes for Sale

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  • 4 Chestnut St, Winchester, MA 01890
    4 Chestnut St, Winchester, MA 01890
    4 Chestnut St, Winchester, MA 01890
    /41

    $1,990,000

    • 4 Beds
    • 4.5 Baths
    • 4,474 Sq Ft

    4 Chestnut St, Winchester, MA 01890

    Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blue cabinetry, copper accents, and bold designer touches. One bedroom opens to a composite deck

    Agent Photo

    Tyson Lynch

    The Proper Nest Real Estate

    (781) 633-6582

    4 Chestnut St, Winchester, MA 01890
  • 9 Washington Ave, Woburn, MA 01801
    9 Washington Ave, Woburn, MA 01801
    9 Washington Ave, Woburn, MA 01801
    /40

    $1,575,000 Open Sat 11:30AM - 1PM

    • 5 Beds
    • 4 Baths
    • 4,578 Sq Ft

    9 Washington Ave, Woburn, MA 01801

    On the Winchester line! This custom-built 2014 home offers nine-foot ceilings and an open, spacious layout. A grand entryway leads to a formal dining room and an oversized chef’s kitchen with granite island, repurposed oak table extension, prep sink, high-end appliances, wine refrigerator, and pantry. The kitchen flows seamlessly into a fireplaced family room with built-in media storage and a

    Agent Photo

    Beverlee Vidoli

    RE/MAX Realty Experts

    (339) 217-7648

    9 Washington Ave, Woburn, MA 01801
  • 18 Blueberry Ln, Lexington, MA 02420
    18 Blueberry Ln, Lexington, MA 02420
    18 Blueberry Ln, Lexington, MA 02420
    /40

    $4,200,000 Open Sun 12:30PM - 2PM

    • 6 Beds
    • 6.5 Baths
    • 7,705 Sq Ft

    18 Blueberry Ln, Lexington, MA 02420

    This 2021 architectural showpiece offers 7,700+ sq. ft. of inspired living on nearly an acre in one of Lexington’s most sought-after neighborhoods. Soaring ceilings, expansive walls of glass, and custom finishes create light-filled, luxurious spaces. The chef’s kitchen—anchored by a striking oversized island—features top of the line cabinetry and appliances, a wet bar, and opens to a dramatic

    Agent Photo

    Kelty Agnew

    RE/MAX Innovative Properties

    (339) 333-7832

    18 Blueberry Ln, Lexington, MA 02420
  • 6 Abby Rd, Winchester, MA 01890
    6 Abby Rd, Winchester, MA 01890
    6 Abby Rd, Winchester, MA 01890
    /40

    $2,999,999

    • 5 Beds
    • 4.5 Baths
    • 5,716 Sq Ft

    6 Abby Rd, Winchester, MA 01890

    Here's a rare opportunity to own a spectacular new construction home by a premier local builder on a BRAND-NEW road. This property stands prominently on its lot, overlooking a lush wooded area with close proximity to “The Fells”. The first floor is designed for both entertaining and everyday living, featuring formal dining, a designer kitchen with a butler's pantry, and a fireplaced family room

    Philip Vita Compass

    6 Abby Rd, Winchester, MA 01890
  • 20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    /33

    $3,600,000 Open Sat 12:30PM - 2:30PM

    • 6 Beds
    • 7.5 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

    Wei Wang WW Real Estate LLC

    20 Amberwood Dr, Winchester, MA 01890
  • 5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    /39

    $3,599,000

    • 6 Beds
    • 4.5 Baths
    • 5,876 Sq Ft

    5 Stratford Rd, Winchester, MA 01890

    This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

    Kim Covino Compass

    5 Stratford Rd, Winchester, MA 01890
  • 48 Salisbury St, Winchester, MA 01890
    48 Salisbury St, Winchester, MA 01890
    48 Salisbury St, Winchester, MA 01890
    /39

    $2,750,000

    • 5 Beds
    • 3.5 Baths
    • 4,779 Sq Ft

    48 Salisbury St, Winchester, MA 01890

    Thoughtfully renovated & meticulously maintained, this classic colonial home in the Flats invites with timeless charm & modern conveniences. Through the center entrance be welcomed into the fireplaced living room & dining room- both refreshed in 2025 with new lighting, paint & wallpaper. The open-plan custom kitchen with marble counters, stainless appliances, and a butler’s pantry with sink,

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

    48 Salisbury St, Winchester, MA 01890
  • 11 Taft Dr, Winchester, MA 01890
    11 Taft Dr, Winchester, MA 01890
    11 Taft Dr, Winchester, MA 01890
    /18

    $2,849,000

    • 5 Beds
    • 5.5 Baths
    • 4,627 Sq Ft

    11 Taft Dr, Winchester, MA 01890

    Luxury, location, and lifestyle come together in this beautiful new 5-bed, 5.5-bath home in Winchester’s sought-after Westside. Just steps to Ambrose School, one block from the Alewife bus stop, a short stroll to the commuter rail, and right down the street from the Winchester Boat Club, this home offers unmatched convenience and charm. Inside, enjoy over 4,600 sq. ft. of thoughtfully designed

    Rose Hall Blue Ocean Realty, LLC

    11 Taft Dr, Winchester, MA 01890
  • 6 Ledgewood Rd, Winchester, MA 01890
    6 Ledgewood Rd, Winchester, MA 01890
    6 Ledgewood Rd, Winchester, MA 01890
    /42

    $3,989,000

    • 6 Beds
    • 7.5 Baths
    • 7,330 Sq Ft

    6 Ledgewood Rd, Winchester, MA 01890

    Majestic 6 BR, 7.5 BA w/ 3 car garage! Custom home in one of Winchesters most sought after neighborhoods. From the moment you step inside, you will feel the unsurpassed quality of this grand home built by top local builder. A welcoming wrap-around front porch & foyer flow into the formal dining room & into the beautiful oversized family room. The stunning eat in kitchen boasts custom cabinetry,

    Kim Covino Compass

    6 Ledgewood Rd, Winchester, MA 01890
  • 162 Swanton St Unit 162, Winchester, MA 01890
    162 Swanton St Unit 162, Winchester, MA 01890
    162 Swanton St Unit 162, Winchester, MA 01890
    /42

    $1,275,000

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

    162 Swanton St Unit 162, Winchester, MA 01890

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

    Kim Covino Compass

    162 Swanton St Unit 162, Winchester, MA 01890
  • 382 S Border Rd, Winchester, MA 01890
    382 S Border Rd, Winchester, MA 01890
    382 S Border Rd, Winchester, MA 01890
    /42

    $2,689,000 Open Thu 5PM - 6:30PM

    • 6 Beds
    • 5.5 Baths
    • 4,563 Sq Ft

    382 S Border Rd, Winchester, MA 01890

    NEW HIGH-END CONSTRUCTION - 12 Rms - 6 BD's - 5.5 BA's You will be captivated by the grand entrance - attention to detail - high coffered 10' ceilings and excellent flow that leads you to the magnificent Open Floor Plan - custom-designed Kitchen which is the heart of this home. no expense was spared; custom Cabinets, Thermador appliances, oversized Center Island; Living Rm/Great Rm w/FP, Dining

    Lucille Murray Advisors Living - Winchester

    382 S Border Rd, Winchester, MA 01890
  • 7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    /30

    $1,500,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 2,765 Sq Ft

    7 Sherman Place, Winchester, MA 01890

    Welcome to a sun-filled, newly renovated 4-bedroom,2.5-bath luxury residence nestled on a cul-de-sac w/ private garden! This is a 2,760 SF townhome, living like a free-standing home & offering a thoughtful layout ideal for living & entertaining. Standout features: 9-ft ceilings, oversized windows & a state-of-the-art, eco-conscious, high-efficiency heat pump system. The first level: open concept

    Ides Figueiredo Coldwell Banker Realty - Brookline

    7 Sherman Place, Winchester, MA 01890
  • 19 Laurel Hill Ln, Winchester, MA 01890
    19 Laurel Hill Ln, Winchester, MA 01890
    /2

    $2,550,000

    • 5 Beds
    • 4.5 Baths
    • 3,800 Sq Ft

    19 Laurel Hill Ln, Winchester, MA 01890

    Nestled on a quiet street in one of Winchester’s most coveted neighborhoods, 19 Laurel Hill Lane will offer refined living just minutes from Boston and top-rated schools. This latest Mark Stephen Development project will feature 4 bedrooms and 4.5 bathrooms, including a flexible first-floor suite perfect for a guest room or study. The heart of the home will be a spacious kitchen flowing into a

    Mark Donnellan Advisors Living - Winchester

    19 Laurel Hill Ln, Winchester, MA 01890
  • 10 Mason Way Unit 61, Woburn, MA 01801
    10 Mason Way Unit 61, Woburn, MA 01801
    10 Mason Way Unit 61, Woburn, MA 01801
    /28

    $1,274,995 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    10 Mason Way Unit 61, Woburn, MA 01801

    Discover new construction at Highland at Vale in Woburn! The Southbrook is a stunning townhome featuring open-concept living and abundant natural light throughout. The spacious kitchen flows seamlessly into the gathering room and private deck—ideal for entertaining. Enjoy the ease of a first-floor Owner’s Suite complete with a spa-like bath for the perfect retreat. Upstairs, a generous loft is

    Erin Sullivan Pulte Homes of New England

    10 Mason Way Unit 61, Woburn, MA 01801
  • 115 Washington St Unit 3D, Winchester, MA 01890
    115 Washington St Unit 3D, Winchester, MA 01890
    115 Washington St Unit 3D, Winchester, MA 01890
    /36

    $519,000

    • 1 Bed
    • 1.5 Baths
    • 769 Sq Ft

    115 Washington St Unit 3D, Winchester, MA 01890

    Welcome to Church Place in Winchester. This light-filled one-bedroom condo offers a unique two-level layout with beautiful windows that frame picturesque views of the town. The main level features an airy, open-concept living and dining area, highlighted by a cathedral ceiling in the living room making it perfect for entertaining or enjoying a quiet evening at home. Upstairs, you’ll find a cozy

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    115 Washington St Unit 3D, Winchester, MA 01890
  • 62 Vine St Unit 62, Winchester, MA 01890
    62 Vine St Unit 62, Winchester, MA 01890
    62 Vine St Unit 62, Winchester, MA 01890
    /39

    $799,900 Open Sat 1PM - 2:30PM

    • 2 Beds
    • 2 Baths
    • 1,545 Sq Ft

    62 Vine St Unit 62, Winchester, MA 01890

    Bright & Airy Cottage at Desirable Wedgewood Place in the heart of Winchester! This charming 2-level, 2-bed, 2-bath “cottage” style condo offers convenience of condo living w/ the feel of a single-family home. Sun-filled layout features a wood-burning fireplace w/ brick hearth, built-ins, hardwood floors, and an updated kitchen with new lighting, flooring, stainless fridge, dishwasher, cooktop &

    David Shorey Real Broker MA, LLC

    62 Vine St Unit 62, Winchester, MA 01890
  • 14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    /42

    $2,399,000 Open Thu 4:30PM - 6PM

    • 6 Beds
    • 4.5 Baths
    • 4,200 Sq Ft

    14 Grant Rd, Winchester, MA 01890

    Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space

    Monte Marrocco Coldwell Banker Realty - Lexington

    14 Grant Rd, Winchester, MA 01890
  • 36 Elmwood Ave Unit 4, Winchester, MA 01890
    36 Elmwood Ave Unit 4, Winchester, MA 01890
    36 Elmwood Ave Unit 4, Winchester, MA 01890
    /31

    $1,049,000

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft

    36 Elmwood Ave Unit 4, Winchester, MA 01890

    Welcome to this stunning 2-bedroom, 2-bathroom condo, built in 2021 and being offered by its original owner. Perfectly situated in the center of Winchester, this home is designed for effortless one-level living and offers the best of modern convenience and timeless style with an open and airy floor plan with oversized windows which fill the space with natural light. The gourmet kitchen flows

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

    36 Elmwood Ave Unit 4, Winchester, MA 01890
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /40

    $2,199,000

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

    5 Azalea Rd, Winchester, MA 01890

    NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials

    Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    5 Azalea Rd, Winchester, MA 01890
  • 171 Swanton St Unit 60, Winchester, MA 01890
    171 Swanton St Unit 60, Winchester, MA 01890
    171 Swanton St Unit 60, Winchester, MA 01890
    /27

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 1,824 Sq Ft

    171 Swanton St Unit 60, Winchester, MA 01890

    Well kept, end-unit townhouse at The Village offering a blank slate for new owners to update or renovate to their precise desire! End unit means you have more windows, more natural light and 3 parking spots (1 garage spot w direct access into the home & EVSE charging unit, 1 spot in front of your garage AND 1 spot adjacent)! Kitchen has an opening to the dining room that has fabulous, vaulted

    Michaela Hellman Redfin Corp.

    171 Swanton St Unit 60, Winchester, MA 01890
  • 2 George Rd Unit 2, Winchester, MA 01890
    2 George Rd Unit 2, Winchester, MA 01890
    2 George Rd Unit 2, Winchester, MA 01890
    /25

    $662,500

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    2 George Rd Unit 2, Winchester, MA 01890

    Presenting a charming 3- Bedrooms ,2 - Baths home at The Residences at Winchester featuring gleaming hardwood floors, freshly painted interior and updated lower level with brand new flooring. This move-in-ready has comfort , and functionality across all levels. The first floor includes bright Living room ,a dedicated dining room and an updated kitchen with granite countertops and stainless

    Rajive Dogra Coldwell Banker Realty - Lexington

    2 George Rd Unit 2, Winchester, MA 01890
  • 19 Glengarry Rd, Winchester, MA 01890
    19 Glengarry Rd, Winchester, MA 01890
    19 Glengarry Rd, Winchester, MA 01890
    /42

    $2,099,000

    • 6 Beds
    • 3.5 Baths
    • 3,521 Sq Ft

    19 Glengarry Rd, Winchester, MA 01890

    A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic

    Kim Covino Compass

    19 Glengarry Rd, Winchester, MA 01890
  • 7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    /35

    $1,379,000

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

    7 Thornberry Rd, Winchester, MA 01890

    Priced to SELL this newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept

    Kim Covino Compass

    7 Thornberry Rd, Winchester, MA 01890
  • 59 Johnson Rd, Winchester, MA 01890
    59 Johnson Rd, Winchester, MA 01890
    59 Johnson Rd, Winchester, MA 01890
    /24

    $1,249,900

    • 3 Beds
    • 2.5 Baths
    • 2,458 Sq Ft

    59 Johnson Rd, Winchester, MA 01890

    Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and

    Angela Zhang Greatland Real Estate LLC

    59 Johnson Rd, Winchester, MA 01890
  • 5 Bacon St, Winchester, MA 01890
    5 Bacon St, Winchester, MA 01890
    5 Bacon St, Winchester, MA 01890
    /42

    $2,299,900 Open Sun 1:30PM - 3PM

    • 6 Beds
    • 4 Baths
    • 4,385 Sq Ft

    5 Bacon St, Winchester, MA 01890

    This meticulously updated home blends timeless character with modern comfort, offering flexibility as a two-family or multi-generational single-family residence. Prior owners embraced multi-generational living, appreciating the spacious layout and exquisite built-ins that grace both living and dining rooms with elegance and timeless appeal. A grand central staircase links all 3 levels, while

    Anne Spry Barrett Sotheby's International Realty

    5 Bacon St, Winchester, MA 01890
  • 26 Swan Rd, Winchester, MA 01890
    26 Swan Rd, Winchester, MA 01890
    26 Swan Rd, Winchester, MA 01890
    /42

    $3,199,000

    • 6 Beds
    • 6.5 Baths
    • 8,463 Sq Ft

    26 Swan Rd, Winchester, MA 01890

    Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end

    Kim Covino Compass

    26 Swan Rd, Winchester, MA 01890
  • 276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    /38

    $2,350,000

    • 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
  • 60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    /16

    $1,075,000

    • 4 Beds
    • 3 Baths
    • 1,860 Sq Ft

    60 Harvard St, Winchester, MA 01890

    Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while

    Mark Krasnyansky eXp Realty

    60 Harvard St, Winchester, MA 01890
  • 20 Grove Place, Winchester, MA 01890
    20 Grove Place, Winchester, MA 01890
    20 Grove Place, Winchester, MA 01890
    /42

    $1,879,000 Open Sat 12:30PM - 1:30PM

    • 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 Cafe 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
  • 61 Grove St, Winchester, MA 01890
    61 Grove St, Winchester, MA 01890
    61 Grove St, Winchester, MA 01890
    /27

    $2,239,000 Open Sat 11AM - 12:30PM

    • 5 Beds
    • 4.5 Baths
    • 4,798 Sq Ft

    61 Grove St, Winchester, MA 01890

    - 2017 - STUNNING CUSTOM- BUILT HOME, COMPLETELY rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. Welcome to this easy living, maintenance free sophisticated residence. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in shower & soaking tub. An exquisite kitchen with granite island, counters and back splash, All Bosch

    Dorothea Feffer Coldwell Banker Realty - Lexington

    61 Grove St, Winchester, MA 01890
  • 4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    /41

    $1,900,000 Open Sat 1PM - 2:30PM

    • 4 Beds
    • 5 Baths
    • 5,361 Sq Ft

    4 Aricia Ln, Winchester, MA 01890

    Rare 5-car garage on a quiet, tree-lined cul-de-sac in one of Winchester’s most exclusive enclaves! Offering both serene privacy and seamless connectivity, 4 Aricia is perfectly positioned within walking distance to a coveted elementary school and Wright-Locke Farm, and minutes from the commuter rail and Routes 128 & 93. Set on nearly .5 acres of manicured grounds, the home’s exterior is framed

    The McLaren D'Agostino Team Compass

    4 Aricia Ln, Winchester, MA 01890
  • 58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    /40

    $2,195,000 Open Sun 12PM - 1:30PM

    • 6 Beds
    • 5.5 Baths
    • 5,791 Sq Ft

    58 Bacon St, Winchester, MA 01890

    Timeless elegance spans four meticulously finished levels with 15 rooms, 6 bedrooms and 5+ bathrooms(2 en-suite). Living room flows seamlessly into a sunroom for a perfect retreat. The dining room opens to a covered porch with a gas line for the grill. New, top shelf, chef’s kitchen with all the bells & whistles and open to the family room. Thoughtfully designed for convenience, an elevator from

    Real Estate Advisors Group Coldwell Banker Realty - Belmont

    58 Bacon St, Winchester, MA 01890
  • 35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    /36

    $1,349,900

    • 5 Beds
    • 2 Baths
    • 1,706 Sq Ft

    35 Harvard St, Winchester, MA 01890

    Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

    Joanne Mulkerin J. Mulkerin Realty

    35 Harvard St, Winchester, MA 01890
  • 44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    /39

    $3,249,000 Open Sat 2PM - 3PM

    • 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
  • 5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    /40

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

    • 6 Beds
    • 3.5 Baths
    • 4,696 Sq Ft

    5 Squire Rd, Winchester, MA 01890

    Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

    Alina Wang Coldwell Banker Realty - Lexington

    5 Squire Rd, Winchester, MA 01890
  • 11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    /42

    $3,799,900

    • 7 Beds
    • 7.5 Baths
    • 7,429 Sq Ft

    11 Viking Rd, Winchester, MA 01890

    Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

    The McLaren D'Agostino Team Compass

    11 Viking Rd, Winchester, MA 01890
  • 54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    /42

    $3,699,000

    • 7 Beds
    • 7.5 Baths
    • 7,982 Sq Ft

    54 Johnson Rd, Winchester, MA 01890

    This newly constructed home faces Old Village Dr. & 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 master

    Kim Covino Compass

    54 Johnson Rd, 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
    /32

    $1,399,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 2,722 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 2,722 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
  • 89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    /38

    $2,399,000 Open Sun 11AM - 12PM

    • 7 Beds
    • 5.5 Baths
    • 4,829 Sq Ft

    89 Wildwood St, Winchester, MA 01890

    Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

    Monte Marrocco Coldwell Banker Realty - Lexington

    89 Wildwood St, Winchester, MA 01890
  • 6 Wyman Ct Unit 6, Winchester, MA 01890
    6 Wyman Ct Unit 6, Winchester, MA 01890
    6 Wyman Ct Unit 6, Winchester, MA 01890
    /34

    $1,399,000 New Construction

    • 3 Beds
    • 4.5 Baths
    • 2,722 Sq Ft

    6 Wyman Ct Unit 6, Winchester, MA 01890

    Another Tree Top Group masterpiece –Welcome to 4 Wyman Court! New full gut renovation townhome with 2,722 sq. ft., 3 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

    6 Wyman Ct Unit 6, 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 $1,934,545.
How many homes have sold over the last 12 months in Winchester, MA?
163 homes have sold in Winchester, MA over the last 12 months.
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 $1,712,450. If you put a 20% down payment of $342,500 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $8,710 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $373K a year to afford the median home price in Winchester.
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, Jonas Clarke Middle School and Vinson-Owen Elementary 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 20 days on the market compared to the national average of 52 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,670,000, up 14% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,670,000
Median Single Family Sale Price
$1,910,000
Median Townhouse Sale Price
$1,542,500
Median 2 Bedroom Sale Price
$940,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$550
Number of Homes for Sale
26
Last 12 months Home Sales
163
Months of Supply
1.90
Median List Price
$1,712,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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