5,127

Medway, MA Homes

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  • /42

    $901,000 Sold Oct 09, 2025

    • 3,248 Sq Ft
    • $277/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1997

    16 Gray Squirrel Cir, Medway, MA 02053

    Welcome home to 16 Gray Squirrel Circle, a private summer retreat you’ll love year-round, set back on a 4-acre priv lot abutting woods! The Beautifully maintained 4BR, 2.5BA Colonial has an updated eat-in kitchen (2020) features quartz countertops w/tiled backsplash, a pantry, & opens to a vaulted great rm with views of the fenced backyard oasis-complete w/an inground pool, hot tub, patio, fire

    Linda Dumouchel Realty Executives Boston West

    16 Gray Squirrel Cir, Medway, MA 02053
    • /42

      Est $965,644 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,730 Sq Ft

      4 Stephanie Rd, Medway, MA 02053

      4 Stephanie Rd, Medway, MA 02053
  • /35

    $458,900

    • 2 Beds
    • 2.5 Baths
    • 1,488 Sq Ft

    14 Heritage Dr, Medway, MA 02053

    Welcome to Colonial Park Estates! This beautifully updated end-unit townhouse combines comfort, style, and convenience—all just minutes from downtown shops, restaurants, Choate Park, and walking trails. You’ll love the bright, open layout featuring a modern kitchen with stainless steel appliances, granite countertops, and Brazilian cherry hardwood floors that flow through the main level and up

    Team Rice RE/MAX Executive Realty

    14 Heritage Dr, Medway, MA 02053
  • /41

    $941,675 Sold Oct 09, 2025

    • 4,675 Sq Ft
    • $201/SF
    • 81 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1983

    5 Deerfield Rd, Medway, MA 02053

    MUST SEE! Nestled on a wooded lot in desirable neighborhood, this home offers: SOLAR, CENTRAL AIR, NEW SEPTIC, INDOOR HEATED POOL WITH SPA. Gourmet-sized kitchen w/ double ovens. Bright year-round solarium for entertaining off dining room. Four generous bedrooms – including primary w/ en suite full bath - and four additional bathrooms. First-floor office. Lower Level houses large family room with

    Deb Costa On the Move Real Estate

    5 Deerfield Rd, Medway, MA 02053
    • /42

      Est $862,114 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,282 Sq Ft

      4 Kimberly Dr, Medway, MA 02053

      4 Kimberly Dr, Medway, MA 02053
  • /42

    $1,250,000

    • 5 Beds
    • 4 Baths
    • 4,145 Sq Ft

    116 Winthrop St, Medway, MA 02053

    Are you tired of cookie-cutter new homes? It feels like every builder is churning out the same generic designs with no personality. At 116 Winthrop Street, a renowned local builder has masterfully blended historic charm with modern elegance, creating a home that stands out. From the exposed beams in the gourmet chef’s kitchen to the opulent marble finishes in all four full bathrooms, every detail

    Michael Gilbert Stuart St James, Inc.

    116 Winthrop St, Medway, MA 02053
  • /39

    $734,500 Sold Oct 07, 2025

    • 2,550 Sq Ft
    • $288/SF
    • 35 Days On Market
    • 6 Beds
    • 3 Baths
    • Built 1860

    18 Norfolk Ave, Medway, MA 02053

    Don't miss this opportunity to own this unique, beautiful property in Medway. Whether you are looking to move in and rent one unit, or are an investor planning on renting both units, this home is for you! Tucked on a beautiful side street yet close proximity to all the amenities you could ask for! Upon entering the front door, you will enter the hallway separating the two units. On the first

    The Allain Group Compass

    18 Norfolk Ave, Medway, MA 02053
    • /36

      Est $1,005,422 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,950 Sq Ft

      5 Alexsandria Dr, Medway, MA 02053

      5 Alexsandria Dr, Medway, MA 02053
  • /29

    $589,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,542 Sq Ft

    36 Lovering St, Medway, MA 02053

    Welcome to 36 Lovering Street, a beautifully maintained 4 bedroom, 2 bath Cape that blends timeless charm with today’s design trends. The inviting interior features warm hardwood floors, a cozy fireplace, and moody coastal vibes that make every space feel relaxed and stylish. The kitchen exudes timeless appeal with design choices that feel fresh and current, plus a delightful built-in that adds

    Shannon Hurley Century 21 Custom Home Realty

    36 Lovering St, Medway, MA 02053
  • /38

    $675,000 Sold Oct 03, 2025

    • 2,245 Sq Ft
    • $301/SF
    • 177 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2024

    29 Willow Pond Cir Unit 29, Medway, MA 02053

    Ready Now! Last 1 left at this amazing new price! Welcome home to the Bluebird Model at Willowside Medway - the town's most popular 55+ community featuring 54 townhomes located along the scenic Charles River! This free-standing Model home features luxury materials and 2,200+ square feet of amazing space easily adaptable to your own personal decor and lifestyle. From a welcoming front porch, enter

    Jeffrey Germagian ERA Key Realty Services-Bay State Group

    29 Willow Pond Cir Unit 29, Medway, MA 02053
    • /42

      Est $1,029,705 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,966 Sq Ft

      15 Alexsandria Dr, Medway, MA 02053

      15 Alexsandria Dr, Medway, MA 02053
  • /22

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 1,700 Sq Ft

    20 Broad St Unit A, Medway, MA 02053

    Brand New Townhome in the heart of Medway! In close proximity to many of the amenities and attractions of this quaint New England town, we are proud to present an elegant, charming and captivating 3 beds, 3 bathrooms home in a small 6-unit complex. These two newly constructed buildings were designed to replicate the timeless architecture of the imposing building that existed there before and,

    The Commonwealth Group Coldwell Banker Realty - Waltham

    20 Broad St Unit A, Medway, MA 02053
  • /40

    $649,000 Sold Oct 01, 2025

    • 2,674 Sq Ft
    • $243/SF
    • 26 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1966

    19 Village St, Medway, MA 02053

    Welcome Home! This well maintained & oversized raised ranch offers incredible space & versatility. The updated kitchen features quartz countertops, SS appliances & an eat-in dining that opens to an expansive addition w/ family/dining area & adjacent primary suite w/ a full bath offering flexibility to serve as an in-law suite. A 2nd living room w/ a working FP, 3 more bedrooms & another full bath

    Susan Marzo Equine Homes Real Estate, LLC

    19 Village St, Medway, MA 02053
    • /36

      Est $916,013 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,276 Sq Ft

      10 Alexsandria Dr, Medway, MA 02053

      10 Alexsandria Dr, Medway, MA 02053
  • /5

    $3,399,000

    • 12 Beds
    • 17 Baths
    • 8,800 Sq Ft

    20 Broad St, Medway, MA 02053

    Exceptional opportunity to own six newly built townhomes in the heart of Medway. Each unit offers approximately 1,400 sq ft of thoughtfully designed living space, featuring 3 bedrooms and 3 full baths. Bright open-concept layouts, quality finishes, and energy-efficient systems make this a solid investment for both owner-occupants and portfolio builders.The townhomes include modern kitchens,

    The Commonwealth Group Coldwell Banker Realty - Waltham

    20 Broad St, Medway, MA 02053
  • /40

    $677,453 Sold Sep 26, 2025

    • 2,245 Sq Ft
    • $302/SF
    • 94 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    27 Willow Pond Cir Unit 27, Medway, MA 02053

    AMAZING NEW PRICE! -- Hurry Just 2 left at this price! Welcome to the fabulous free-standing Blue Bird Model at Willowside Medway nearing completion & ready for occupancy soon! Enjoy a distinctive townhouse with 2,200+ square feet of great space easily adaptable to your decor & lifestyle. From a welcoming front porch, enter a foyer with custom moldings & closet open to a spacious open floor plan

    The Kattman Team ERA Key Realty Services-Bay State Group

    27 Willow Pond Cir Unit 27, Medway, MA 02053
    • /24

      Est $702,414 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,960 Sq Ft

      13 Hill St, Medway, MA 02053

      13 Hill St, Medway, MA 02053
  • /28

    $374,900

    • 2 Beds
    • 1.5 Baths
    • 830 Sq Ft

    14 Sanford St Unit 15, Medway, MA 02053

    Welcome to 14 Sanford Street, Unit 15 — a stunning corner unit in the historic Sanford Mill building, beautifully set along the Charles River. Originally built in 1890 and thoughtfully converted, this unique condo blends timeless character with modern comfort. This light-filled unit features an open-concept layout with soaring ceilings, exposed brick, and oversized windows that capture the home’s

    Kim Zogalis NorthStar Real Estate, LLC

    14 Sanford St Unit 15, Medway, MA 02053
  • /42

    $775,000 Sold Sep 25, 2025

    • 3,354 Sq Ft
    • $231/SF
    • 64 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1981

    10 Longmeadow Ln, Medway, MA 02053

    Experience your own private retreat. Set over 300 feet off the road, this stunning, fully updated home is nestled on 3.77 secluded acres, accessed by a winding, tree-lined drive. Inside, vaulted ceilings, exposed wood beams, and an open floor plan create a warm and inviting space filled with natural light. The updated kitchen is a showstopper, featuring gleaming quartz countertops, classic white

    Team Rice RE/MAX Executive Realty

    10 Longmeadow Ln, Medway, MA 02053
    • /42

      Est $702,414 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,320 Sq Ft

      15 Hill St, Medway, MA 02053

      15 Hill St, Medway, MA 02053
  • /38

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 2,418 Sq Ft

    106 Holliston St, Medway, MA 02053

    This beautiful antique home flawlessly combines modern conveniences with thoughtfully preserved historic charm. Spend evenings relaxing by the fireplace in your cozy family room with built in bookshelves. Enjoy entertaining? The eat-in kitchen with direct access to the outside allows for ideal indoor/outdoor entertaining and the large dining room is a perfect space for hosting the holidays. The

    Team Rice RE/MAX Executive Realty

    106 Holliston St, Medway, MA 02053
  • /6

    $681,716 Sold Sep 18, 2025

    • 2,245 Sq Ft
    • $304/SF
    • 1 Day On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    25 Willow Pond Cir Unit 25, Medway, MA 02053

    Welcome to the fabulous free-standing Blue Bird Model at Willowside Medway! Enjoy a distinctive townhouse with 2,200+ square feet of great space easily adaptable to your decor & lifestyle. From a welcoming front porch, enter a foyer with custom moldings & closet open to a spacious open floor plan including a living room with serene views & sliders to a private deck, dining area & stylish upgraded

    The Kattman Team ERA Key Realty Services-Bay State Group

    25 Willow Pond Cir Unit 25, Medway, MA 02053
    • /38

      Est $1,068,703 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,102 Sq Ft

      2 Homestead Dr, Medway, MA 02053

      2 Homestead Dr, Medway, MA 02053
  • /35

    $518,000

    • 3 Beds
    • 1.5 Baths
    • 1,119 Sq Ft

    224 Main St, Medway, MA 02053

    Discover this charming 3-bedroom colonial with an additional multi-purpose outbuilding on the property nestled in the wooded backyard. Whether you dream of an inspiring artist’s studio or productive home office, the possibilities are endless in the finished outbuilding. This home is filled with delightful updates that beautifully integrate rustic charm with modern comfort. Step into the main home

    Karen Watson Johnson Coldwell Banker Realty - Westwood

    224 Main St, Medway, MA 02053
  • /7

    $702,330 Sold Sep 11, 2025

    • 2,245 Sq Ft
    • $313/SF
    • 0 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    19 Willow Pond Cir Unit 19, Medway, MA 02053

    AMAZING NEW PRICE! -- Welcome to the fabulous free-standing Blue Bird Model at Willowside Medway nearing completion & ready for occupancy soon! Enjoy a distinctive townhouse with 2,200+ square feet of great space easily adaptable to your decor & lifestyle. From a welcoming front porch, enter a foyer with custom moldings & closet open to a spacious open floor plan including a living room with

    Jeffrey Germagian ERA Key Realty Services-Bay State Group

    19 Willow Pond Cir Unit 19, Medway, MA 02053
    • /36

      Est $1,271,223 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,500 Sq Ft

      27 Fairway Ln, Medway, MA 02053

      27 Fairway Ln, Medway, MA 02053
  • /24

    $699,900

    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft

    50 Main St, Medway, MA 02053

    Charming ranch-style home on a desirable corner lot with a fully fenced yard! Recent updates include newer central air, heating, windows, and a 2018 roof. Gorgeous new hardwood finishes and recessed lighting throughout create a warm, modern feel. The bright living and dining areas flow into an updated kitchen featuring stainless steel appliances and generous storage. With three bedrooms, two full

    Arleuza Maia Pablo Maia Realty

    50 Main St, Medway, MA 02053
  • /21

    $471,000 Sold Sep 10, 2025

    • 1,204 Sq Ft
    • $391/SF
    • 4 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1985

    17 Evergreen St Unit A, Medway, MA 02053

    ****Open Houses have been cancelled****This 3-bedroom, 1.5-bathroom townhouse style condominium offers a comfortable and practical layout for everyday living. The main level features a bright living room with a cozy fireplace, a spacious kitchen with eat-in area and a convenient half bath. Upstairs are the three well sized bedrooms and a full bathroom providing plenty of room for family, guests

    Mark LaLond Berkshire Hathaway HomeServices Page Realty

    17 Evergreen St Unit A, Medway, MA 02053
    • /42

      Est $1,173,356 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,316 Sq Ft

      25 Fairway Ln, Medway, MA 02053

      25 Fairway Ln, Medway, MA 02053
  • /34

    $555,000

    • 2 Beds
    • 2.5 Baths
    • 2,280 Sq Ft

    2 Kingson Ln Unit 2, Medway, MA 02053

    This meticulously maintained 2-bedroom, 2.5-bath townhouse style home offers 2280 sqft. of thoughtfully designed living space. A striking two-story foyer leads to the light-filled living room with hardwood floors, a gas fireplace framed in marble, and a slider to the private composite deck. The open floor plans combines both formal & Informal living spaces. The expansive primary suite features a

    Tammy Todaro RE/MAX Executive Realty

    2 Kingson Ln Unit 2, Medway, MA 02053
  • /38

    $1,050,000 Sold Sep 05, 2025

    • 4,232 Sq Ft
    • $248/SF
    • 27 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1999

    17 Stable Way, Medway, MA 02053

    Elegant 5-bedroom, 3.5-bathroom colonial situated on a landscaped, private lot with a gorgeous, salt-water in-ground pool and located near the interstate & area amenities. This luxury property boasts an expansive floor plan with 4 levels of finished space. The main level includes a spacious kitchen w/bump out eat-in area that opens to the cathedral ceiling family room. An oversized dining room &

    Lisa Paulette Coldwell Banker Realty - Framingham

    17 Stable Way, Medway, MA 02053
    • /36

      Est $952,376 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,825 Sq Ft

      4 Woodland Rd, Medway, MA 02053

      4 Woodland Rd, Medway, MA 02053
  • /23

    $569,000

    • 3 Beds
    • 1 Bath
    • 1,159 Sq Ft

    12 Lovering St, Medway, MA 02053

    Charming, move-in ready, 3 bedroom/1 bath ranch in lovely residential neighborhood close to elementary schools and walking trails, on a private .56 acre lot. Features long, turn-around driveway with convenient parking. Home has attached 1 1/2 car garage with storage closet. Home includes all major appliances, brick fireplace with stone mantle and hearth, soapstone wood stove, gas cooking and

    Kris Lippi Get Listed Realty, LLC

    12 Lovering St, Medway, MA 02053
  • /42

    $740,000 Sold Sep 02, 2025

    • 3,228 Sq Ft
    • $229/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    34 Maple St, Medway, MA 02053

    Welcome home to this spacious and sun-filled home set on a beautiful lot behind boasting a flexible floor plan. Relax in the over-sized fireplaced cathedral-ceilinged Great room with hickory hardwood flooring or spend time outdoors in the private wooded backyard.The main level is open and drenched in sunlight, opening to an updated eat-in kitchen w/sliders that lead to dual decks overlooking a

    Linda Dumouchel Realty Executives Boston West

    34 Maple St, Medway, MA 02053
    • /42

      Est $1,114,427 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,006 Sq Ft

      6 Walnut Ln, Medway, MA 02053

      6 Walnut Ln, Medway, MA 02053
  • /33

    $429,999

    • 3 Beds
    • 1 Bath
    • 1,232 Sq Ft

    9 Sanford St, Medway, MA 02053

    This isn't just a beautiful home—it's your next chapter! Refined Charm in the Heart of Medway Village, Discover timeless character and modern comfort in this updated 3-bedroom residence, ideally located near Medway’s top-rated schools, local shops, dining, and commuter access to Rte. 109, 495, and the rail. The home features a spacious, light-filled living room, updated kitchen, and beautifully

    Markese Daise Stony Brook & Lennox Realty Advisors

    9 Sanford St, Medway, MA 02053
  • /37

    $513,000 Sold Sep 02, 2025

    • 1,520 Sq Ft
    • $338/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1963

    32 Maple St, Medway, MA 02053

    Investor alert or perfect project for a hands-on buyer! This 3-bed, 1-bath Medway home offers 1,520 sqft of total living space, including a finished lower level ready for your vision. While it could benefit from cosmetic updates, many big-ticket improvements are already done: roof (~2017), oil tank (2022), boiler (2024), water heater (2013), wall oven (2024), and a brand-new 100-amp electric

    Team ROVI Real Broker MA, LLC

    32 Maple St, Medway, MA 02053
    • /40

      Est $1,233,456 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,446 Sq Ft

      17 Broken Tree Rd, Medway, MA 02053

      17 Broken Tree Rd, Medway, MA 02053
  • /2

    $1,400,000

    • Land
    • 1.47 Acres
    • $952,381 per Acre

    39 West St, Medway, MA 02053

    Bret O'Brien Greater Boston Commercial Properties, Inc.

    39 West St, Medway, MA 02053
  • /35

    $675,000 Sold Aug 29, 2025

    • 1,729 Sq Ft
    • $390/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1989

    15 Alder St, Medway, MA 02053

    Welcome home to this beautifully maintained 4-bed, 2-full bath Gambrel Cape on a peaceful country road. The renovated kitchen features modern finishes and opens to a back deck overlooking a wooded yard—perfect for relaxing. A dining room and living room offer great flow for daily living, while a cozy 4th bedroom serves as a home office. A full bath completes the main level. Upstairs, the spacious

    Laina Kaplan Realty Executives Boston West

    15 Alder St, Medway, MA 02053

Showing Results 41 - 80, Page 2 of 18

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