9,245

Homes in ZIP Code 01890

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  • /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
  • /12

    $1,850 total monthly price

    • 1 Bed
    • 1 Bath
    • 394 Sq Ft
    • Condo for Rent

    200 Swanton St Unit 640, Winchester, MA 01890

    Bright and sunny 6th-floor studio available November 1 at desirable Parkview Condominiums in Winchester! This inviting top-floor unit offers an open layout with sliders to a private balcony overlooking the beautifully landscaped grounds and pond. Features include a well-kept kitchen and bath, ample closet space, and one assigned parking spot. Enjoy resort-style amenities such as a sparkling pool,

    Agent Photo

    Joan Powell

    Gibson Sotheby's International Realty

    (781) 785-9583

    200 Swanton St Unit 640, Winchester, MA 01890
  • /42

    $1,750,000 Sold Oct 31, 2025

    • 2,397 Sq Ft
    • $730/SF
    • 1 Day On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1937

    15 Westland Ave, Winchester, MA 01890

    OFFER ACCEPTED OH SUNDAY CANCELLED Taken down to the studs, this renovated and reimagined center entrance Colonial offers timeless elegance and modern comfort in one of Winchester’s most desirable neighborhoods. The gracious foyer gives way to a front-to-back living room anchored by a wood-burning fireplace with custom mantle. An adjacent sun-filled, south-facing room provides the perfect space

    Erica Carson Coldwell Banker Realty - Lexington

    15 Westland Ave, Winchester, MA 01890
    • /19

      Est $286,731 Not Listed For Sale

      • 1 Bed
      • 1 Bath
      • 450 Sq Ft

      200 Swanton St Unit T8, Winchester, MA 01890

      200 Swanton St Unit T8, Winchester, MA 01890
  • /40

    $1,650,000 Pending

    • 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

    Agent Photo

    Catherine Albiani

    Better Homes and Gardens Real Estate - The Shanahan Group

    (781) 332-5538

    112 Church St, Winchester, MA 01890
  • /10

    $2,200 total monthly price

    • 1 Bed
    • 1 Bath
    • 634 Sq Ft
    • Condo for Rent

    200 Swanton St Unit T28, Winchester, MA 01890

    Bright and sunny 1-bedroom condo in desirable Parkview Condominiums, Winchester! This charming unit features an open living and dining area with sliders to a patio overlooking the tranquil pond and landscaped grounds. Updated kitchen and bath, generous closet space, and one assigned parking spot. Enjoy amenities including a pool, picnic area, laundry facilities, and on-site management. Heat, hot

    Agent Photo

    Joan Powell

    Gibson Sotheby's International Realty

    (781) 746-6707

    200 Swanton St Unit T28, Winchester, MA 01890
  • /42

    $1,550,000 Sold Oct 31, 2025

    • 2,995 Sq Ft
    • $518/SF
    • 5 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1960

    205 Ridge St, Winchester, MA 01890

    Welcome to 205 Ridge Street, a stunning residence that blends timeless elegance with modern comfort, perfectly designed for today’s lifestyle. Nestled in one of Winchester’s most desirable neighborhoods, this five-bedroom, three-bath home offers the perfect balance of refined living and everyday convenience. From the moment you arrive, the property’s curb appeal and thoughtful details set the

    Debby Valdes eXp Realty

    205 Ridge St, Winchester, MA 01890
    • /39

      Est $2,335,271 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 4,539 Sq Ft

      38 Winthrop Street Extension, Winchester, MA 01890

      38 Winthrop Street Extension, Winchester, MA 01890
  • /42

    $2,599,000 Pending

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

    382 S Border Rd, Winchester, MA 01890

    NEW HIGH-END CONSTRUCTION - 13 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 Gibson Sotheby's International Realty

    382 S Border Rd, Winchester, MA 01890
  • /13

    $3,795 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Apartment for Rent

    7 Lewis Rd Unit 2, Winchester, MA 01890

    Wonderful opportunity to rent in Winchester, less than a half mile from the town common. Rarely available First floor unit with hardwood floors throughout, 2 bedrooms and one full tiled bath. Additional storage space in lower level that is wired to your specific unit...could be used for office space, home gym, craft room, etc. Carefree living with Heat, basic cable tv and all exterior maintenance

    Agent Photo

    Catherine Albiani

    Better Homes and Gardens Real Estate - The Shanahan Group

    (781) 404-8664

    7 Lewis Rd Unit 2, Winchester, MA 01890
  • /40

    $2,895,000 Sold Oct 30, 2025

    • 5,716 Sq Ft
    • $506/SF
    • 28 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2025

    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
    • /34

      Est $843,399 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,584 Sq Ft

      897 Main St Unit 1, Winchester, MA 01890

      897 Main St Unit 1, Winchester, MA 01890
  • /42

    $1,950,000

    • 3 Beds
    • 2.5 Baths
    • 2,443 Sq Ft

    5 Wood Ln, Winchester, MA 01890

    Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cypress shingle exterior, and classic New England design. Inside, three magnificent fireplaces, exquisite

    Kim Covino Compass

    5 Wood Ln, Winchester, MA 01890
  • /20

    $2,358 - $20,886 per month plus fees

    Sanctuary Winchester West

    Studio - 3 Beds

    416 Cambridge St, Winchester, MA 01890

    The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

    416 Cambridge St, Winchester, MA 01890
  • /38

    $2,000,000 Sold Oct 29, 2025

    • 5,000 Sq Ft
    • $400/SF
    • 3 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1968

    1 Fox Hunt Ln, Winchester, MA 01890

    Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office.

    Leigh Ventura Compass

    1 Fox Hunt Ln, Winchester, MA 01890
    • /33

      Est $1,704,114 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,254 Sq Ft

      20 Graystone Cir Unit 20, Winchester, MA 01890

      20 Graystone Cir Unit 20, Winchester, MA 01890
  • /40

    $2,785,000

    • 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
  • /34

    $4,700 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 1,482 Sq Ft
    • Condo for Rent

    7 Conant Rd Unit 16, Winchester, MA 01890

    Experience luxury living in this beautifully renovated 2-level townhome in the coveted Willows at Winchester community. This rare 3 bed, 2.5 bath residence offers an open layout with gleaming hardwood floors, a chef’s kitchen, dining area, and a spacious living room with gas fireplace and access to a private deck — perfect for entertaining. Upstairs features all bedrooms, including a luxurious

    William Natoli Compass

    7 Conant Rd Unit 16, Winchester, MA 01890
  • /41

    $3,900,000 Sold Oct 24, 2025

    • 5,069 Sq Ft
    • $769/SF
    • 2 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2016

    12 Ledgewood Rd, Winchester, MA 01890

    A rare Winchester offering set on an acre in a wooded enclave of luxury homes near town center. Custom-built, this 5-bedroom, 4.5-bath residence combines timeless design with balanced proportions across four levels. The primary suite includes a private deck, spa-like bath with soaking tub, and gas fireplace. The chef’s kitchen features quarter-sawn oak cabinetry, high-end appliances, large

    Leigh Ventura Compass

    12 Ledgewood Rd, Winchester, MA 01890
    • /42

      Est $2,869,935 Not Listed For Sale

      • 5 Beds
      • 5.5 Baths
      • 6,265 Sq Ft

      228 Ridge St, Winchester, MA 01890

      228 Ridge 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
  • /24

    $2,575 - $7,697 per month plus fees

    Sanctuary Winchester North

    1 - 3 Beds

    25-35 River St, Winchester, MA 01890

    The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and

    25-35 River St, Winchester, MA 01890
  • /42

    $4,450,000 Sold Oct 24, 2025

    • 7,679 Sq Ft
    • $580/SF
    • 1 Day On Market
    • 5 Beds
    • 7 Baths
    • Built 1937

    20 Foxcroft Rd, Winchester, MA 01890

    A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over 1⁄2 acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for

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

    20 Foxcroft Rd, Winchester, MA 01890
    • /40

      Est $1,375,352 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,529 Sq Ft

      15 Wincrest Dr, Winchester, MA 01890

      15 Wincrest Dr, Winchester, MA 01890
  • /30

    $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
  • /36

    $6,900 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 2,900 Sq Ft
    • Apartment for Rent

    846 Main St Unit 301, Winchester, MA 01890

    No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

    Anthony Marino The Marino Group Collection

    846 Main St Unit 301, Winchester, MA 01890
  • /31

    $1,050,000 Sold Oct 22, 2025

    • 1,296 Sq Ft
    • $810/SF
    • 9 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2021

    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
    • /33

      Est $1,525,632 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,034 Sq Ft

      10 Carriage Ln, Winchester, MA 01890

      10 Carriage Ln, Winchester, MA 01890
  • /42

    $1,425,000

    • 3 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    7 Wainwright Rd Unit 29, Winchester, MA 01890

    Welcome to The Ledges, Winchester’s premier hilltop community offering refined, resort-style living with modern convenience. This sun-filled, beautifully updated home features an open layout with cathedral ceilings, hardwood floors, and newly landscaped courtyard space by Mahoney’s. The gourmet kitchen with premium appliances. Living Room opens to a private wooded deck, ideal for entertaining or

    Joanne Sexeny Coldwell Banker Realty - Lexington

    7 Wainwright Rd Unit 29, Winchester, MA 01890
  • /7

    $2,100 per month plus fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 11, Winchester, MA 01890

    This nice 1 Bedroom 1 Bath place in the WINCHESTER area is available for Now.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was obtained.

    2 Elmwood Ave Unit 11, Winchester, MA 01890
  • /24

    $2,155,000 Sold Oct 21, 2025

    • 3,186 Sq Ft
    • $676/SF
    • 1 Day On Market
    • 3 Beds
    • 4.5 Baths
    • Built 1988

    7 Wainwright Rd Unit 13, Winchester, MA 01890

    Stunning townhouse with 3 bedrooms and 4.5 bathrooms, meticulously renovated with high-end, designer finishes. The sun-drenched living room features 13 ft. ceilings, 5-in. oak floors, custom built-in book shelves, and a double-sided marble-surround fireplace that flows seamlessly to the brand-new gourmet chef’s kitchen. The kitchen is a showpiece with a Sub-Zero fridge, Thermador range, Acadia

    Isabella Bruno William Raveis R.E. & Home Services

    7 Wainwright Rd Unit 13, Winchester, MA 01890
    • /35

      Est $1,710,477 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,926 Sq Ft

      16 Nassau Dr, Winchester, MA 01890

      16 Nassau Dr, Winchester, MA 01890
  • /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
  • /27

    $3,500 total monthly price

    • 2 Beds
    • 2 Baths
    • 1,338 Sq Ft
    • Condo for Rent

    7 Conant Rd Unit 21, Winchester, MA 01890

    Welcome to 7 Conant Road! This unit offers a spacious open floor plan with 1,338 square feet, featuring two bedrooms and two full bathrooms, including a roomy primary suite. Enjoy open concept living with nice flow from the kitchen to the living room & dining area. Updated & move-in ready, the bedrooms are large, complete with generous closet space. This rental showcases modern charm with an

    Kim Covino Compass

    7 Conant Rd Unit 21, Winchester, MA 01890
  • /30

    $900,000 Sold Oct 20, 2025

    • 1,843 Sq Ft
    • $488/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    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
    • /36

      Est $1,575,493 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,171 Sq Ft

      94 Johnson Rd, Winchester, MA 01890

      94 Johnson Rd, Winchester, MA 01890
  • /38

    $2,795,000

    • 4 Beds
    • 4.5 Baths
    • 5,233 Sq Ft

    18 Middlesex St, Winchester, MA 01890

    A masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of-the-art amenities.Step into a grand foyer, where a striking curved staircase sets the stage for the home’s sophisticated ambiance. Expansive living and entertaining spaces flow seamlessly, featuring soaring ceilings, custom millwork, and exquisite finishes. The Bespoke

    Candice Macoul Luxury Living Real Estate

    18 Middlesex St, Winchester, MA 01890
  • /16

    $2,000 per month plus fees

    • Studio
    • 1 Bath
    • Condo for Rent

    2 Elmwood Ave Unit 14, Winchester, MA 01890

    This nice Studio 1 Bath place in the WINCHESTER area is available for Now.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was obtained. We

    2 Elmwood Ave Unit 14, Winchester, MA 01890
  • /38

    $1,651,000 Sold Oct 17, 2025

    • 2,368 Sq Ft
    • $697/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1951

    4 Oakland Cir, Winchester, MA 01890

    Welcome to 4 Oakland Circle, a spacious home tucked away on a desirable cul-de-sac in Winchester. Thoughtfully designed with oversized rooms and a versatile layout, this residence provides comfort and flexibility for a variety of lifestyles. The main level features expansive living and dining areas along with a 1st floor primary bedroom option that opens onto a private deck, plus a dedicated home

    Surabhi Rathi Redfin Corp.

    4 Oakland Cir, Winchester, MA 01890
    • /32

      Est $1,635,093 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,622 Sq Ft

      104 Thornberry Rd, Winchester, MA 01890

      104 Thornberry Rd, Winchester, MA 01890

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