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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
  • 60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    60 Graystone Cir Unit 60, Winchester, MA 01890
    /39

    $1,499,000 Open Fri 10:30AM - 11:30AM

    • 2 Beds
    • 2.5 Baths
    • 1,947 Sq Ft

    60 Graystone Cir Unit 60, Winchester, MA 01890

    Meticulously maintained, 2-bedroom, 2.5-bath townhome with 2 car garage. The kitchen features custom cabinets, granite countertops, high-end stainless steel appliances and gleaming hardwood floors. The living/dining room combo features hardwood floors, gas fireplace, cathedral ceilings along with french doors that open to a private patio with gas grill. Spacious first floor primary suite boasts a

    Pirani & Wile Group Advisors Living - Winchester

    60 Graystone Cir Unit 60, 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 Open Thu 4PM - 5PM

    • 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

    $2,750,000

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

    382 S Border Rd, Winchester, MA 01890

    GORGEOUS NEW CONSTRUCTION - 12 Rooms - 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, w/custom Cabinets, Thermador appliances, oversized Center Island; Living Rm/Great Rm, w/FP,

    Lucille Murray Advisors Living - Winchester

    382 S Border Rd, 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
  • 14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    /42

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

    • 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
  • 6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    /35

    $2,299,000 Open Thu 5:30PM - 7PM

    • 6 Beds
    • 5 Baths
    • 3,728 Sq Ft

    6 Ivy Cir, Winchester, MA 01890

    Stunning new construction Colonial tucked away at the end of a quiet cul-de-sac in "The Flats", offering the ideal combination of luxury, comfort, and convenience. Just minutes from Winchester Center, this beautifully crafted home places top-rated schools, boutique shopping, and vibrant dining right at your doorstep. Meticulously designed with high-end finishes throughout. Features include an

    Monte Marrocco Coldwell Banker Realty - Lexington

    6 Ivy Cir, Winchester, MA 01890
  • 9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    /42

    $3,750,000

    • 6 Beds
    • 3.5 Baths
    • 4,484 Sq Ft

    9 Lakeview Terrace, Winchester, MA 01890

    LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

    Kim Covino Compass

    9 Lakeview Terrace, 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
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /42

    $2,299,000

    • 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
  • 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
  • 89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    /38

    $2,399,000 Open Thu 5:30PM - 7PM

    • 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 Mason Way Unit 63, Woburn, MA 01801
    6 Mason Way Unit 63, Woburn, MA 01801
    6 Mason Way Unit 63, Woburn, MA 01801
    /30

    $1,304,855 New Construction

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

    6 Mason Way Unit 63, Woburn, MA 01801

    New Construction 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 a bay

    Erin Sullivan Pulte Homes of New England

    6 Mason Way Unit 63, Woburn, MA 01801
  • 15 Mason Way Unit 73, Woburn, MA 01801
    15 Mason Way Unit 73, Woburn, MA 01801
    15 Mason Way Unit 73, Woburn, MA 01801
    /19

    $1,199,999 New Construction

    • 3 Beds
    • 3.5 Baths
    • 1,921 Sq Ft

    15 Mason Way Unit 73, Woburn, MA 01801

    New construction townhome at Highland at Vale in Woburn! The Wheaton floor plan offers 1,921 sq. ft. across two thoughtfully designed levels. The bright, open kitchen features stainless steel appliances, ample cabinetry, and a large island—perfect for everyday living or entertaining. An expansive gathering room and optional bay window in the dining area bring in abundant natural light, with

    Erin Sullivan Pulte Homes of New England

    15 Mason Way Unit 73, Woburn, MA 01801
  • 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
  • 13 Mason Way Unit 72, Woburn, MA 01801
    13 Mason Way Unit 72, Woburn, MA 01801
    13 Mason Way Unit 72, Woburn, MA 01801
    /30

    $1,299,995 New Construction

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

    13 Mason Way Unit 72, Woburn, MA 01801

    Welcome to Highland at Vale in Woburn! This new construction Jackson townhome offers 2,143 square feet of thoughtfully designed living space across two levels. The open-concept kitchen is a chef’s dream with stainless steel appliances, abundant cabinetry, and a large center island. A bright gathering room and dining area with optional bay window lead to a private outdoor deck—perfect for

    Erin Sullivan Pulte Homes of New England

    13 Mason Way Unit 72, Woburn, MA 01801
  • 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
  • 6 Samoset Rd, Winchester, MA 01890
    6 Samoset Rd, Winchester, MA 01890
    6 Samoset Rd, Winchester, MA 01890
    /42

    $1,999,000 Open Sun 2PM - 3:30PM

    • 4 Beds
    • 3.5 Baths
    • 4,731 Sq Ft

    6 Samoset Rd, Winchester, MA 01890

    Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up

    Anne Spry Barrett Sotheby's International Realty

    6 Samoset Rd, Winchester, MA 01890
  • 9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, Winchester, MA 01890
    9 Pilgrim Dr, Winchester, MA 01890
    /42

    $1,599,000 Open Sat 11:30AM - 1:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,541 Sq Ft

    9 Pilgrim Dr, Winchester, MA 01890

    Welcome to this beautiful split-level home nestled on a desirable corner lot in Winchester’s sought after west side. Featuring gleaming hardwood floors throughout, this home offers a perfect blend of comfort and style. The main level boasts an open floor plan connecting the dining room, kitchen, and living room, and seamlessly flows into a stunning vaulted family room, perfect for both everyday

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    9 Pilgrim Dr, Winchester, MA 01890
  • 15 Governors Ave Unit 1, Winchester, MA 01890
    15 Governors Ave Unit 1, Winchester, MA 01890
    15 Governors Ave Unit 1, Winchester, MA 01890
    /32

    $689,000 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 1 Bath
    • 1,358 Sq Ft

    15 Governors Ave Unit 1, Winchester, MA 01890

    Turn-key 3-bed condo offers effortless living just moments from downtown Winchester, Muraco School, & Middlesex Fells—nothing to do but unpack your bags & settle in. The main level offers a spacious entry area that functions well as a mudroom or sitting room, along with a sunny living room, dining room, & renovated kitchen featuring granite counters, center island, ss appliances, Sub-Zero fridge,

    Pirani & Wile Group Advisors Living - Winchester

    15 Governors Ave Unit 1, Winchester, MA 01890
  • 155 Highland Ave, Winchester, MA 01890
    155 Highland Ave, Winchester, MA 01890
    155 Highland Ave, Winchester, MA 01890
    /41

    $1,339,000 Open Sat 11AM - 12:30PM

    • 5 Beds
    • 2.5 Baths
    • 1,965 Sq Ft

    155 Highland Ave, Winchester, MA 01890

    Charming turn-of-the-century 5-bedroom Gambrel-style home in move-in condition, blending classic character with modern updates. This spacious residence features a beautifully updated interior with central air, a stunning primary suite with private bath, custom closet system, and generous living spaces throughout. The detached 2-car garage adds convenience, while the location offers unbeatable

    Pirani & Wile Group Advisors Living - Winchester

    155 Highland Ave, 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 Open Thu 4PM - 5PM

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

    $1,299,900 Open Sat 1PM - 3PM

    • 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
  • 7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    7 Sherman Place, Winchester, MA 01890
    /30

    $1,550,000 Open Thu 6PM - 7:30PM

    • 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
  • 5 Bacon St, Winchester, MA 01890
    5 Bacon St, Winchester, MA 01890
    5 Bacon St, Winchester, MA 01890
    /42

    $2,299,900

    • 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
  • 2 Lagrange St, Winchester, MA 01890
    2 Lagrange St, Winchester, MA 01890
    2 Lagrange St, Winchester, MA 01890
    /42

    $1,999,000

    • 7 Beds
    • 2.5 Baths
    • 3,413 Sq Ft

    2 Lagrange St, Winchester, MA 01890

    EXQUISITE 12 ROOM, 7 BEDROOMS, 2 STUNNING FIREPLACES, 2.5 BATH QUEEN ANNE VICTORIAN! Easy Stroll to Center of Town. Hear the Church Bells Strike the Hour. Delightfully Quiet Street with a Family Orientated Community. Beautiful Morning and Evening Sun. During the Day the Huge Sun Deck off the Kitchen with a SPACIOUS AWNING is both Shady and Warm. Multi Outdoor Opportunities for Living including a

    Alison Lules-Cuccio Don Baker Real Estate

    2 Lagrange St, Winchester, MA 01890
  • 17 Dennett Rd, Winchester, MA 01890
    17 Dennett Rd, Winchester, MA 01890
    17 Dennett Rd, Winchester, MA 01890
    /41

    $1,599,000

    • 3 Beds
    • 2.5 Baths
    • 2,283 Sq Ft

    17 Dennett Rd, Winchester, MA 01890

    Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized

    Kim Covino Compass

    17 Dennett Rd, Winchester, MA 01890
  • 166 Forest St, Winchester, MA 01890
    166 Forest St, Winchester, MA 01890
    166 Forest St, Winchester, MA 01890
    /4

    $1,890,000

    • 5 Beds
    • 5 Baths
    • 3,301 Sq Ft

    166 Forest St, Winchester, MA 01890

    Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A

    Ning Sun United Real Estate, LLC

    166 Forest St, Winchester, MA 01890
  • 200 Swanton St Unit 432, Winchester, MA 01890
    200 Swanton St Unit 432, Winchester, MA 01890
    200 Swanton St Unit 432, Winchester, MA 01890
    /21

    $419,900

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 432, Winchester, MA 01890

    This beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winchester—one of Massachusetts’ most desirable towns. Conveniently located within the building, this bright and inviting unit features a stylish kitchen with granite countertops and modern cabinetry, plus a renovated bathroom with contemporary finishes. Enjoy peaceful views from the private balcony. The

    Mark Gilson Keller Williams Realty

    200 Swanton St Unit 432, Winchester, MA 01890
  • 5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    /38

    $1,650,000

    • 4 Beds
    • 3.5 Baths
    • 2,755 Sq Ft

    5 Thornton Rd, Winchester, MA 01890

    This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

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

    5 Thornton Rd, Winchester, MA 01890
  • 60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    /16

    $1,150,000

    • 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

    $1,899,000 Open Sat 1:30PM - 2:30PM

    • 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
    /26

    $2,239,000

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

    61 Grove St, Winchester, MA 01890

    STUNNING CUSTOM-BUILT HOME, Welcome to this easy living, maintenance free sophisticated residence. Completely rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. 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 appliances,

    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
    /39

    $1,900,000

    • 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 Sat 11:30AM - 1PM

    • 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
  • 10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    /41

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

    • 7 Beds
    • 5.5 Baths
    • 5,864 Sq Ft

    10 Sheffield Rd, Winchester, MA 01890

    This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

    Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Sheffield Rd, 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 12PM - 1PM

    • 6 Beds
    • 6.5 Baths
    • 6,028 Sq Ft

    44 Cabot St, Winchester, MA 01890

    Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

    Andersen Group Realty Keller Williams Realty Boston Northwest

    44 Cabot St, Winchester, MA 01890
  • 80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    /33

    $3,475,000 Open Thu 5PM - 6PM

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

    80 Arlington St, Winchester, MA 01890

    With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement, and the chance to build instant equity through strategic upgrades. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved home offers 11 rooms, 5 bedrooms and 3.5 baths. Enjoy views from the sun-splashed eat-in

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

    80 Arlington 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 $1,388,630.
How many homes have sold over the last 12 months in Winchester, MA?
53 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, 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 West Side, North Main, The Flats, 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 $1,399,000. If you put a 20% down payment of $279,800 and had a 30-year fixed mortgage with an interest rate of 6.63%, your estimated principal and interest payment would be $7,170 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $307K 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 28 days on the market compared to the national average of 70 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,300,000, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,300,000
Median Single Family Sale Price
$2,750,000
Median Townhouse Sale Price
$1,635,000
Median 2 Bedroom Sale Price
$630,000
Median 1 Bedroom Sale Price
$995,000
Average Price Per Sq Ft
$558
Number of Homes for Sale
3
Last 12 months Home Sales
53
Months of Supply
0.70
Median List Price
$1,399,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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