Winchester, MA Homes for Sale

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  $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

  

  Tyson Lynch

  The Proper Nest Real Estate

  (781) 633-6582

  4 Chestnut St, Winchester, MA 01890
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  Explore Winchester

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  $4,200,000 Open Sun 12PM - 1:30PM

  • 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

  

  Kelty Agnew

  RE/MAX Innovative Properties

  (339) 333-7832

  18 Blueberry Ln, Lexington, MA 02420
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  $1,575,000 Open Sun 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

  

  Beverlee Vidoli

  RE/MAX Realty Experts

  (339) 217-7648

  9 Washington Ave, Woburn, MA 01801
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  $2,399,000 Open Sun 11AM - 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
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  $4,174,000

  • 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
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  $3,499,000

  • 5 Beds
  • 7 Baths
  • 7,101 Sq Ft

  257 High St, Winchester, MA 01890

  Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

  Kim Covino Compass

  257 High St, Winchester, MA 01890
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  $2,399,000 Open Sun 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
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  $2,999,999 Open Sun 12PM - 1:30PM

  • 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
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  $3,600,000 Open Sun 1PM - 3PM

  • 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

  Wei Wang WW Real Estate LLC

  20 Amberwood Dr, Winchester, MA 01890
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  $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
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  $2,689,000 Open Sun 11AM - 12:30PM

  • 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
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  $2,245,000

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

  5 Bacon St, Winchester, MA 01890

  This stunning Victorian home, in the style of Painted Ladies with soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & downtown Boston. The house lives as a harmonious single family with an inlaw apartment on the 1st floor. It has 6 beds & 4 baths, over 4,385 SF of living area on 3

  Anne Spry Barrett Sotheby's International Realty

  5 Bacon St, Winchester, MA 01890
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  $2,350,000 Open Sun 1PM - 2PM

  • 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
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  $2,239,000 Open Sun 1:30PM - 3PM

  • 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
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  $2,195,000 Open Sun 2PM - 3:30PM

  • 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
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  $2,399,000 Open Sun 12:30PM - 1:30PM

  • 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
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  $3,175,000

  • 5 Beds
  • 5.5 Baths
  • 5,737 Sq Ft

  22 Oldham Rd, Arlington, MA 02474

  Home for the holidays! Beautiful newer luxury custom home located in the sought-after Morningside area across from the Winchester Country Club. Showcasing 5 bedrooms 5.5 baths, custom millwork, substantial entry, 2 sets of stairs leading to 2nd floor. Feast your eyes on the dramatic two story sun drenched family room with windows galore and incredible ceiling detail. Start your day in the chef's

  Kathleen Lyons Century 21 North East

  22 Oldham Rd, Arlington, MA 02474
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  $1,049,995 New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 2,143 Sq Ft

  Jackson Plan at Highland at Vale - Northfield Collection, Woburn, MA 01801

  

  Pulte Homes

  Builder

  2 Stratton Drive St Unit 36461567, Woburn, MA 01801
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  $999,995 New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 1,921 Sq Ft

  Wheaton Plan at Highland at Vale - Northfield Collection, Woburn, MA 01801

  

  Pulte Homes

  Builder

  2 Stratton Drive St Unit 36491801, Woburn, MA 01801
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  $1,074,995 New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 2,300 Sq Ft

  Southbrook Plan at Highland at Vale - Northfield Collection, Woburn, MA 01801

  

  Pulte Homes

  Builder

  2 Stratton Drive St Unit 36496559, Woburn, MA 01801
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  $1,650,000 Open Sun 1:30PM - 3PM

  • 8 Beds
  • 2.5 Baths
  • 3,591 Sq Ft

  112 Church St, Winchester, MA 01890

  Rare Opportunity: Spacious Side-by-Side Two-Family Home Less Than 1 Mile from Town Center. This charming two-family home offers classic period details, including fireplaced living rooms, formal dining rooms with built-in china cabinets located directly off the kitchen. Each unit features two large bedrooms with hardwood floors and a full bath on the second floor, plus two additional bedrooms and

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

  112 Church St, Winchester, MA 01890
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  $875,000

  • 3 Beds
  • 2.5 Baths
  • 1,843 Sq Ft

  171 Swanton St Unit 5, Winchester, MA 01890

  Charming townhouse located at The Village, one of Winchester’s most sought-after and impeccably maintained communities, offers 1,843sf of living space. Featuring 3 generously sized bedrooms with full-height ceilings, and 2.5 updated bathrooms, it is one of the largest homes in the community. The home is flooded with natural light thanks to its end-unit position, windows on three sides, and a

  Jonathan Radford Coldwell Banker Realty - Boston

  171 Swanton St Unit 5, Winchester, MA 01890
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  $1,649,000

  • 5 Beds
  • 5 Baths
  • 3,508 Sq Ft

  166 Forest St, Winchester, MA 01890

  The buyer got cold feet. 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

  Ning Sun United Real Estate, LLC

  166 Forest St, Winchester, MA 01890
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  $1,050,000

  • 4 Beds
  • 2 Baths
  • 1,938 Sq Ft

  380 Cross St, Winchester, MA 01890

  This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a favorite place for family to congregate and get

  Pavan Patel Realty ONE Group Nest

  380 Cross St, Winchester, MA 01890
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  $999,999 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  16 Park Ave Unit 1, Winchester, MA 01890

  Breathtaking luxury condo just moments from Winchester Center and the commuter rail. This recently updated home offers bright, spacious, one-level living with hardwood floors and custom shutters throughout. The kitchen features quartz countertops, stainless steel appliances–including GE Cafe range and microwave, an oversized sink, and large peninsula with ample seating flows seamlessly to the

  Andrea Mackey Barrett Sotheby's International Realty

  16 Park Ave Unit 1, Winchester, MA 01890
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  $959,000 Open Sun 1:30PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,425 Sq Ft

  571 Washington St, Winchester, MA 01890

  Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for

  Ryan Wilson Keller Williams Realty

  571 Washington St, Winchester, MA 01890
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  $409,900

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  200 Swanton St Unit T11, Winchester, MA 01890

  Move right into this immaculate, renovated walk-in condo with an oversized layout and a highly sought-after private terrace patio. Terrace units rarely go on the market—don’t miss this opportunity to purchase a unit in the best location in the building. The sun-filled home offers an eat-in kitchen with granite counters, modern cabinets, newer stainless-steel appliances, and a dining area

  Shannon Jenkins RE/MAX Realty Experts

  200 Swanton St Unit T11, Winchester, MA 01890
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  $662,500 Open Sun 10:30AM - 12PM

  • 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
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  $2,695,000 Open Sun 1PM - 2PM

  • 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
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  $2,099,000 Open Sun 2PM - 3PM

  • 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
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  $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
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  $3,989,000 Open Sun 11AM - 12:30PM

  • 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
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  $1,249,000 Open Sun 11AM - 12:30PM

  • 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
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  $1,450,000 Open Sun 11AM - 12:30PM

  • 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
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  $3,199,000 Open Sun 12PM - 1PM

  • 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
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  $995,000

  • 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
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  $1,879,000 Open Sun 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
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  $1,729,000

  • 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
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  $2,799,000 Open Sun 1:30PM - 2:30PM

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

  10 Sheffield Rd, Winchester, MA 01890

  This stunning Colonial Revival home, 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 suite with walk-in closets and a Jacuzzi bath, along with

  Andersen Group Realty Keller Williams Realty Boston Northwest

  10 Sheffield Rd, Winchester, MA 01890
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  $3,099,000 Open Sun 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

Showing Results 1 - 40, Page 1 of 2

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 $1,943,961.

How many homes have sold over the last 12 months in Winchester, MA?

164 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 $1,725,000. If you put a 20% down payment of $345,000 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $8,510 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $365K 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, Arlington High School and Jonas Clarke Middle 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 21 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 $1,660,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,660,000

Median Single Family Sale Price

$1,900,000

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

$551

Number of Homes for Sale

29

Last 12 months Home Sales

164

Months of Supply

2.10

Median List Price

$1,725,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

13%