Winchester, MA Homes for Sale

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  /18

  $385,000

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  200 Swanton St Unit T28, Winchester, MA 01890

  Beautiful terrace-level 1-bedroom condo at Parkview Condos in Winchester! This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with

  

  Joan Powell

  RE/MAX Andrew Realty Services

  (781) 384-5553

  200 Swanton St Unit T28, Winchester, MA 01890
• Explore Winchester

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  /40

  $1,499,000

  • 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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  /42

  $2,075,000 Open Sat 1:30PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,658 Sq Ft

  8 Felsdale Close, Winchester, MA 01890

  Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells' scenic trails, the setting is both serene and convenient. Designed by renowned architect Harry M.

  Anne Spry Barrett Sotheby's International Realty

  8 Felsdale Close, Winchester, MA 01890
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  /39

  $2,695,000

  • 4 Beds
  • 4 Baths
  • 5,674 Sq Ft

  10 Viking Rd, Winchester, MA 01890

  Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

  Anne Spry Barrett Sotheby's International Realty

  10 Viking Rd, Winchester, MA 01890
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  /42

  $2,999,000 Open Thu 5PM - 6:30PM

  • 5 Beds
  • 5.5 Baths
  • 5,257 Sq Ft

  19 Town Way, Winchester, MA 01890

  Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive

  Philip Vita Compass

  19 Town Way, Winchester, MA 01890
• 

  

  /42

  $2,099,000

  • 4 Beds
  • 3 Baths
  • 2,519 Sq Ft

  30 Prospect St, Winchester, MA 01890

  One of Winchester’s most beloved neighborhoods sets the tone for 30 Prospect Street, a beautifully reimagined home transformed by an extensive remodel less than five years ago. A spectacular, fully renovated Chef's kitchen anchors the main level with high-end finishes and a seamless flow for living and entertaining. The living room is sunny and inviting, featuring an impressive fireplace,

  Karima Alami Compass

  30 Prospect St, Winchester, MA 01890
• 

  

  /37

  $2,299,000

  • 7 Beds
  • 5.5 Baths
  • 4,929 Sq Ft

  89 Wildwood St, Winchester, MA 01890

  Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  89 Wildwood St, Winchester, MA 01890
• 

  

  /42

  $2,299,000 Open Sun 11:30AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 3,953 Sq Ft

  19 Gershon Way, Winchester, MA 01890

  Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

  Philip Vita Compass

  19 Gershon Way, Winchester, MA 01890
• 

  

  /35

  $2,149,000

  • 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
• 

  

  /5

  $3,250,000

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  8 Priscilla Ln, Winchester, MA 01890

  Welcome to 8 Priscilla Ln, Winchester—a brand-new 5 bed, 5.5 bath luxury home designed by Salt & Stone Co where elevated craftsmanship meets everyday comfort. Spanning 6,500 ± sq ft, this home features a chef’s kitchen with custom cabinetry, premium appliances, and an oversized center island flowing into a dramatic two-story living room with fireplace and glass slider to the backyard. The

  The Pezzano Group Rise Signature Homes

  8 Priscilla Ln, Winchester, MA 01890
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  /37

  $2,799,000

  • 5 Beds
  • 4 Baths
  • 5,083 Sq Ft

  53 Winford Way, Winchester, MA 01890

  Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

  Andersen Group Realty Keller Williams Realty Boston Northwest

  53 Winford Way, Winchester, MA 01890
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  /42

  $2,275,000

  • 6 Beds
  • 2.5 Baths
  • 4,104 Sq Ft

  15 Wildwood St, Winchester, MA 01890

  Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized

  Kim Covino Compass

  15 Wildwood St, Winchester, MA 01890
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  /38

  $2,299,000

  • 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
• 

  

  /41

  $3,380,000

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

  22 Oldham Rd, Arlington, MA 02474

  Elegantly sited on Morningside Hill, this home is a luxury-built masterpiece. Thoughtfully designed & artfully crafted, it exudes opulence & cozy comfort. A gracious entry hall welcomes you into sophisticated living, highlighted by a breathtaking two-story living room adorned with countless windows. The chef's kitchen, a culinary haven, is equipped with state-of-the-art Thermador appliances,

  Suzanne Koller Compass

  22 Oldham Rd, Arlington, MA 02474
• 

  

  /17

  $269,000

  • 1 Bath
  • 388 Sq Ft

  200 Swanton St Unit 234, Winchester, MA 01890

  Sunny studio unit overlooking the pond and courtyard at Parkview Condos in Winchester. Unit features include large private balcony with large sliding door that lets in lots of natural sun light. New LVP flooring in the living room/bedroom area and hallway. Freshly painted all throughout. Kitchen has granite countertops and a new refrigerator and electric range. The condominium amenities include

  Devin Caglayan All County Select Property Management

  200 Swanton St Unit 234, Winchester, MA 01890
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  /40

  $1,869,000 Open Sat 1PM - 2PM

  • 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 Café 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
• 

  

  /25

  $989,000

  • 4 Beds
  • 1.5 Baths
  • 2,162 Sq Ft

  41 Squire Rd, Winchester, MA 01890

  Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest

  William Cordts Charlesgate Realty Group, llc

  41 Squire Rd, Winchester, MA 01890
• 

  

  /24

  $999,000

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  139 High St, Winchester, MA 01890

  This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

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

  139 High St, Winchester, MA 01890
• 

  

  /42

  $2,299,000 Open Sun 11:30AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 3,953 Sq Ft

  19 Gershon Way Unit 1, Winchester, MA 01890

  Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

  Philip Vita Compass

  19 Gershon Way Unit 1, Winchester, MA 01890
• 

  

  /16

  $799,999

  • 2 Beds
  • 2 Baths
  • 1,240 Sq Ft

  666 Main St Unit 312, Winchester, MA 01890

  Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry hook-ups, garage parking,

  Walace Nogueira

  666 Main St Unit 312, Winchester, MA 01890
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  /42

  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 2,153 Sq Ft

  6 Marchant Rd, Winchester, MA 01890

  Updated 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, the train, and route to Boston. The first floor offers an ideal layout with an updated kitchen, stainless steel appliances & island w seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc and dining room. A 3 season

  Kim Covino Compass

  6 Marchant Rd, Winchester, MA 01890
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  /41

  $1,475,000

  • 3 Beds
  • 2.5 Baths
  • 2,316 Sq Ft

  26 Berkshire Dr, Winchester, MA 01890

  Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

  DANIEL BEIRNE OpenDoor Brokerage LLC

  26 Berkshire Dr, Winchester, MA 01890
• 

  

  /16

  $899,900

  • Land
  • 0.23 Acre
  • $3,912,609 per Acre

  18 Raymond Place, Winchester, MA 01890

  An opportunity awaits at 18 Raymond Place! This property offers a nearly 10,000 sq/ft lot, ample parking, and a large structure in a quaint, idyllic neighborhood. This freestanding building offers over 2 levels of space with direct exterior lower access for separate quarters. High ceilings, and lots of natural sunlight, this property awaits your customization. Each floor has 2 bathrooms, and the

  Kim Covino Compass

  18 Raymond Place, Winchester, MA 01890
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  /34

  $1,499,000

  • 3 Beds
  • 2.5 Baths
  • 2,865 Sq Ft

  53 Bacon St, Winchester, MA 01890

  Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering

  Taleen Chiofaro Leading Edge Real Estate

  53 Bacon St, Winchester, MA 01890
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  /42

  $1,149,000

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  16 Ridge St, Winchester, MA 01890

  27,000 SF lot!!! Set far back from the street~ Don't miss this opportunity! Whether looking to lightly update/ expand or completely renovate; this well maintained 3 bedroom split entry home with a stunning oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning fireplace, a

  Kim Covino Compass

  16 Ridge St, Winchester, MA 01890
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  /42

  $1,999,000

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

  5 Azalea Rd, Winchester, MA 01890

  NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and

  Anthony Marino The Marino Group Collection

  5 Azalea Rd, Winchester, MA 01890
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  /37

  $3,099,000 Open Sat 12PM - 1:30PM

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

  80 Arlington St, Winchester, MA 01890

  New roof. New landscaping. New exterior paint. New price! With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement. 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 kitchen w/

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

  80 Arlington St, Winchester, MA 01890
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  /39

  $3,099,000 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
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  /30

  $2,850,000

  • 6 Beds
  • 7 Baths
  • 6,968 Sq Ft

  14 Nassau Dr, Winchester, MA 01890

  Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New

  Weidong Li WINN Real Estate & Consulting

  14 Nassau Dr, Winchester, MA 01890
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  /23

  $949,000

  • 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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  /35

  $898,000

  • 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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  /41

  $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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  /42

  $3,299,000

  • 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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  /36

  $3,600,000

  • 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
• 

  

  /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 steel

  Rajive Dogra Coldwell Banker Realty - Lexington

  2 George Rd Unit 2, Winchester, MA 01890
• 

  

  /40

  $2,000,000

  • 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
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  /42

  $3,499,000

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

  54 Johnson Rd, Winchester, MA 01890

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

  Kim Covino Compass

  54 Johnson Rd, Winchester, MA 01890
• 

  

  /27

  $1,399,000 Open Sat 11AM - 12PM

  • 4 Beds
  • 4.5 Baths
  • 2,500 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 2,500 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
• 

  

  /42

  $3,799,000 Open Sat 12:30PM - 1:30PM

  • 6 Beds
  • 4.5 Baths
  • 6,367 Sq Ft

  40 Foxcroft Rd, Winchester, MA 01890

  An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

  Monte Marrocco Coldwell Banker Realty - Lexington

  40 Foxcroft Rd, Winchester, MA 01890
• 

  /2

  $389,900

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  20 Arthur St, Winchester, MA 01890

  Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

  Dan O'Connell LAER Realty Partners

  20 Arthur 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 $1,947,405.

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

167 homes have sold in Winchester, MA over the last 12 months.

Is Winchester, MA a safe city?

In general, the safest neighborhoods in Winchester, MA with lower crime scores are West Side, The Flats, Grove Street, Winchester Highlands and Symmes Corner.

What are the most popular zip codes in Winchester, MA?

The most popular zip codes in Winchester, MA include 01890, 01801, 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 $1,762,450. If you put a 20% down payment of $352,500 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $8,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $372K 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 22 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,670,000, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,670,000

Median Single Family Sale Price

$1,877,000

Median Townhouse Sale Price

$1,475,000

Median 2 Bedroom Sale Price

$940,000

Median 1 Bedroom Sale Price

$710,000

Average Price Per Sq Ft

$560

Number of Homes for Sale

27

Last 12 months Home Sales

167

Months of Supply

1.90

Median List Price

$1,762,450

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

10%