5,145

Medway, MA Homes

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  • 12 Alder St, Medway, MA 02053
    12 Alder St, Medway, MA 02053
    12 Alder St, Medway, MA 02053
    /41

    $989,900

    Open Sat 11AM - 1PM
    • 5 Beds
    • 2.5 Baths
    • 3,226 Sq Ft

    12 Alder St, Medway, MA 02053

    Welcome home to this beautifully remodeled Colonial offering 3,226 sq. ft. of thoughtfully updated living space. This move-in-ready home features 5 spacious bedrooms, 2.5 renovated bathrooms, and central A/C. The oversized kitchen with new appliances flows into the formal dining room, while the family room and separate living room with a fireplace create warm, inviting spaces for everyday living

    Kelly Vinha

    12 Alder St, Medway, MA 02053
  • 3 Meryl St, Medway, MA 02053
    3 Meryl St, Medway, MA 02053
    3 Meryl St, Medway, MA 02053
    /31

    $530,001

    Sold Dec 18, 2025

    3 Meryl St, Medway, MA 02053

    • 3 Beds
    • 1 Bath
    • 1,172 Sq Ft
    • Built 1961

    Last Sold Summary

    • $452/SF
    • 6 Days On Market

    Current Estimated Value $538,520

    Last Listing Agent Kathleen Craig ERA Key Realty Services

    3 Meryl St, Medway, MA 02053
    • 4 Woodland Rd, Medway, MA 02053
      4 Woodland Rd, Medway, MA 02053
      4 Woodland Rd, Medway, MA 02053
      /36

      Est $939,239

      Not Listed For Sale

      4 Woodland Rd, Medway, MA 02053

      • 4 Beds
      • 2.5 Baths
      • 2,825 Sq Ft
      • Built 1977
      4 Woodland Rd, Medway, MA 02053

      Last Sold Summary

      • 1 Day On Market

  • 5 Delmar Rd, Medway, MA 02053
    5 Delmar Rd, Medway, MA 02053
    5 Delmar Rd, Medway, MA 02053
    /15

    $425,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,512 Sq Ft

    5 Delmar Rd, Medway, MA 02053

    Welcome to all that the charming town of Medway has to offer! This affordable home presents a wonderful opportunity for buyers looking to build equity and bring their renovation ideas to life. Nestled in an established neighborhood overlooking Milk Pond, the property offers a picturesque setting without the requirement for flood insurance. Situated on a generous half-acre lot, there is plenty of

    Laina Kaplan Realty Executives Boston West

    5 Delmar Rd, Medway, MA 02053
  • 236 Village St, Medway, MA 02053
    236 Village St, Medway, MA 02053
    236 Village St, Medway, MA 02053
    /40

    $529,900

    Sold May 15, 2026

    236 Village St, Medway, MA 02053

    • 3 Beds
    • 1.5 Baths
    • 1,496 Sq Ft
    • Built 1956

    Last Sold Summary

    • $354/SF
    • 5 Days On Market

    Current Estimated Value $532,474

    Last Listing Agent Linda Dumouchel Realty Executives Boston West

    236 Village St, Medway, MA 02053
    • 6 Walnut Ln, Medway, MA 02053
      6 Walnut Ln, Medway, MA 02053
      6 Walnut Ln, Medway, MA 02053
      /42

      Est $1,048,971

      Not Listed For Sale

      6 Walnut Ln, Medway, MA 02053

      • 4 Beds
      • 2.5 Baths
      • 4,006 Sq Ft
      • Built 1999
      6 Walnut Ln, Medway, MA 02053

      Last Sold Summary

      • 2 Days On Market

  • 25 Milford St, Medway, MA 02053
    25 Milford St, Medway, MA 02053
    25 Milford St, Medway, MA 02053
    /28

    $599,900

    Pending
    • 4 Beds
    • 2 Baths
    • 1,977 Sq Ft

    25 Milford St, Medway, MA 02053

    OPEN HOUSE CANCELLED due to accepted offer. Charming 1920’s home set on a private lot surrounded by mature trees and acres of protected reserve land. Privacy while just minutes to I-495, shopping, dining & downtown Medway. Sun-filled interior with character and updates throughout, including custom hardwood floors, beautiful moldings, soaring ceilings, built-ins & abundant skylights. Updated

    Jeannine Coburn REMAX Executive Realty

    25 Milford St, Medway, MA 02053
  • 8 Winthrop St, Medway, MA 02053
    8 Winthrop St, Medway, MA 02053
    8 Winthrop St, Medway, MA 02053
    /40

    $559,000

    Sold Mar 23, 2026

    8 Winthrop St, Medway, MA 02053

    • 3 Beds
    • 2 Baths
    • 1,721 Sq Ft
    • Built 1847

    Last Sold Summary

    • 14% Above List Price
    • $325/SF
    • 5 Days On Market

    Current Estimated Value $547,733

    Last Listing Agent Tammy Todaro REMAX Executive Realty

    8 Winthrop St, Medway, MA 02053
    • 17 Broken Tree Rd, Medway, MA 02053
      17 Broken Tree Rd, Medway, MA 02053
      17 Broken Tree Rd, Medway, MA 02053
      /40

      Est $1,187,622

      Not Listed For Sale

      17 Broken Tree Rd, Medway, MA 02053

      • 4 Beds
      • 3.5 Baths
      • 4,446 Sq Ft
      • Built 2001
      17 Broken Tree Rd, Medway, MA 02053

      Last Sold Summary

      • 22 Days On Market

  • 64 Holliston St, Medway, MA 02053
    64 Holliston St, Medway, MA 02053
    64 Holliston St, Medway, MA 02053
    /16

    $489,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,299 Sq Ft

    64 Holliston St, Medway, MA 02053

    Welcome to this inviting multi-level home nestled on a spacious, level lot in sought-after Medway. Offering 3 bedrooms and 1.5 baths, this home combines comfort, functionality, and charm. The sun-filled living room with fireplace creates a cozy focal point for gathering, while the flexible lower level provides additional living space perfect for a family room, home office, gym, or playroom.

    George LeBlanc Cameron Real Estate Group

    64 Holliston St, Medway, MA 02053
  • 85 Fisher St, Medway, MA 02053
    85 Fisher St, Medway, MA 02053
    /2

    $660,000

    Sold Jan 23, 2026

    85 Fisher St, Medway, MA 02053

    • 3 Beds
    • 2 Baths
    • 2,728 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $242/SF
    • 11 Days On Market

    Current Estimated Value $683,350

    Last Listing Agent Beth Rossi Coldwell Banker Realty - Franklin

    85 Fisher St, Medway, MA 02053
    • 33 Broken Tree Rd, Medway, MA 02053
      33 Broken Tree Rd, Medway, MA 02053
      33 Broken Tree Rd, Medway, MA 02053
      /42

      Est $1,543,658

      Not Listed For Sale

      33 Broken Tree Rd, Medway, MA 02053

      • 6 Beds
      • 3.5 Baths
      • 4,949 Sq Ft
      • Built 2000
      33 Broken Tree Rd, Medway, MA 02053

      Last Sold Summary

      • 88 Days On Market

  • 5 Winchester Rd, Medway, MA 02053
    5 Winchester Rd, Medway, MA 02053
    5 Winchester Rd, Medway, MA 02053
    /42

    $874,900

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,640 Sq Ft

    5 Winchester Rd, Medway, MA 02053

    Tucked away at the end of a long private drive, 5 Winchester Road offers the rare combination of timeless Colonial living & a truly exceptional setting. Nestled on 1.7 acres of beautifully manicured grounds surrounded by mature trees, this property provides a sense of privacy and tranquility that is increasingly hard to find. Hardwood floors run throughout the entire home, complementing the

    Lisa Bailey Berkshire Hathaway HomeServices Evolution Properties

    5 Winchester Rd, Medway, MA 02053
  • 1 Walnut Ln, Medway, MA 02053
    1 Walnut Ln, Medway, MA 02053
    /2

    $990,000

    Sold Jan 29, 2026

    1 Walnut Ln, Medway, MA 02053

    • 3 Beds
    • 2.5 Baths
    • 3,585 Sq Ft
    • Built 1997

    Last Sold Summary

    • 1% Below List Price
    • $276/SF
    • 11 Days On Market

    Current Estimated Value $994,362

    Last Listing Agent Paul Rao Berkshire Hathaway HomeServices Page Realty

    1 Walnut Ln, Medway, MA 02053
    • 28 Broken Tree Rd, Medway, MA 02053
      28 Broken Tree Rd, Medway, MA 02053
      28 Broken Tree Rd, Medway, MA 02053
      /42

      Est $1,136,546

      Not Listed For Sale

      28 Broken Tree Rd, Medway, MA 02053

      • 4 Beds
      • 4 Baths
      • 4,335 Sq Ft
      • Built 1998
      28 Broken Tree Rd, Medway, MA 02053

      Last Sold Summary

      • 3 Days On Market

  • 16 Stable Way, Medway, MA 02053
    16 Stable Way, Medway, MA 02053
    16 Stable Way, Medway, MA 02053
    /41

    $1,075,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,361 Sq Ft

    16 Stable Way, Medway, MA 02053

    Move in ready Colonial w/flex space, dedicated office & a layout built for real life. This sun-drenched 4BR, 2.5BA home blends classic warmth with modern updates on a level 1-acre lot. A new brick walkway & professional landscaping introduce an effortless open-concept main level, centered around a spacious kitchen designed with entertaining in mind—a functional space that's perfectly ready for

    Andrea Feddersen RE/MAX Real Estate Center

    16 Stable Way, Medway, MA 02053
  • 3 Howe St, Medway, MA 02053
    3 Howe St, Medway, MA 02053
    3 Howe St, Medway, MA 02053
    /30

    $755,000

    Sold Jul 30, 2025

    3 Howe St, Medway, MA 02053

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • Built 1978

    Last Sold Summary

    • 1% Above List Price
    • $323/SF
    • 19 Days On Market

    Current Estimated Value $792,360

    Last Listing Agent Betsy Conlon Coldwell Banker Realty - Westwood

    3 Howe St, Medway, MA 02053
    • 3 Hickory Dr, Medway, MA 02053
      3 Hickory Dr, Medway, MA 02053
      3 Hickory Dr, Medway, MA 02053
      /42

      Est $1,206,950

      Not Listed For Sale

      3 Hickory Dr, Medway, MA 02053

      • 4 Beds
      • 3.5 Baths
      • 4,333 Sq Ft
      • Built 1998
      3 Hickory Dr, Medway, MA 02053

      Last Sold Summary

      • 4 Days On Market

  • 21 Stable Way, Medway, MA 02053
    21 Stable Way, Medway, MA 02053
    21 Stable Way, Medway, MA 02053
    /42

    $1,349,900

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,944 Sq Ft

    21 Stable Way, Medway, MA 02053

    Rare opportunity to own this beautifully maintained, one owner custom Colonial in sought after Broad Acres, set on a private, picturesque acre lot. This 12 room, sun-filled home features a welcoming open floor plan perfect for everyday living and entertaining. A stunning two-story foyer with palladium window greets you. The kitchen offers custom cabinetry, pantry, and a large center island,

    Laina Kaplan Realty Executives Boston West

    21 Stable Way, Medway, MA 02053
  • 19 Azalea Dr, Medway, MA 02053
    19 Azalea Dr, Medway, MA 02053
    19 Azalea Dr, Medway, MA 02053
    /42

    $958,000

    Sold Jul 29, 2025

    19 Azalea Dr, Medway, MA 02053

    • 4 Beds
    • 2.5 Baths
    • 2,560 Sq Ft
    • Built 1992

    Last Sold Summary

    • 8% Above List Price
    • $374/SF
    • 2 Days On Market

    Current Estimated Value $953,708

    Last Listing Agent Laina Kaplan Realty Executives Boston West

    19 Azalea Dr, Medway, MA 02053
    • 7 Birch Bark Rd, Medway, MA 02053
      7 Birch Bark Rd, Medway, MA 02053
      7 Birch Bark Rd, Medway, MA 02053
      /32

      Est $1,089,804

      Not Listed For Sale

      7 Birch Bark Rd, Medway, MA 02053

      • 4 Beds
      • 2.5 Baths
      • 3,817 Sq Ft
      • Built 1997
      7 Birch Bark Rd, Medway, MA 02053

      Last Sold Summary

      • 6 Days On Market

  • 14 Hemlock Dr, Medway, MA 02053
    14 Hemlock Dr, Medway, MA 02053
    14 Hemlock Dr, Medway, MA 02053
    /41

    $595,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,780 Sq Ft

    14 Hemlock Dr, Medway, MA 02053

    Move right into this bright and inviting ranch offering more space than meets the eye. The standout feature is the impressive family room with vaulted ceilings, exposed beams, and windows that fill the space with natural light and overlook the backyard. Hardwood floors extend through much of the main level, while the fireplaced living room creates a warm gathering space. The kitchen features

    Chris Dudzic Lamacchia Realty, Inc.

    14 Hemlock Dr, Medway, MA 02053
  • 14 Sanford St Unit 21, Medway, MA 02053
    14 Sanford St Unit 21, Medway, MA 02053
    14 Sanford St Unit 21, Medway, MA 02053
    /24

    $420,000

    Sold Jul 30, 2025

    14 Sanford St Unit 21, Medway, MA 02053

    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft
    • Built 1890

    Last Sold Summary

    • 7% Below List Price
    • $420/SF
    • 19 Days On Market

    Current Estimated Value $428,489

    Last Listing Agent Adam Sinewitz 29 Realty Group, Inc.

    14 Sanford St Unit 21, Medway, MA 02053
    • 4 Causeway St, Medway, MA 02053
      4 Causeway St, Medway, MA 02053
      4 Causeway St, Medway, MA 02053
      /35

      Est $677,741

      Not Listed For Sale

      4 Causeway St, Medway, MA 02053

      • 3 Beds
      • 1.5 Baths
      • 1,740 Sq Ft
      • Built 1977
      4 Causeway St, Medway, MA 02053

      Last Sold Summary

      • 68 Days On Market

  • 14 Sanford St Unit 66, Medway, MA 02053
    14 Sanford St Unit 66, Medway, MA 02053
    14 Sanford St Unit 66, Medway, MA 02053
    /16

    $399,900

    Pending
    • 2 Beds
    • 2 Baths
    • 939 Sq Ft

    14 Sanford St Unit 66, Medway, MA 02053

    Exposed brick, original wood beams, and an open layout give this condo in historic Sanford Mill plenty of charm and character. This move-in ready 2 bedroom, 2 full bath unit offers a warm urban loft feel along with thoughtful updates throughout, including renovated bathrooms, updated A/C, HVAC (2023), and hot water heater (2021).The open floor plan is ideal for entertaining and everyday living.

    Joshua Shalin ERA Key Realty Services-Bay State Group

    14 Sanford St Unit 66, Medway, MA 02053
  • 8 Sandstone Dr Unit 8, Medway, MA 02053
    8 Sandstone Dr Unit 8, Medway, MA 02053
    8 Sandstone Dr Unit 8, Medway, MA 02053
    /38

    $765,000

    Sold Aug 28, 2025

    8 Sandstone Dr Unit 8, Medway, MA 02053

    • 3 Beds
    • 2.5 Baths
    • 2,540 Sq Ft
    • Built 2015

    Last Sold Summary

    • 4% Below List Price
    • $301/SF
    • 8 Days On Market

    Current Estimated Value $826,200

    Last Listing Agent Rachel Stocker

    8 Sandstone Dr Unit 8, Medway, MA 02053
    • 174 Holliston St, Medway, MA 02053
      174 Holliston St, Medway, MA 02053
      174 Holliston St, Medway, MA 02053
      /25

      Est $559,875

      Not Listed For Sale

      174 Holliston St, Medway, MA 02053

      • 3 Beds
      • 2 Baths
      • 1,620 Sq Ft
      • Built 1948
      174 Holliston St, Medway, MA 02053

      Last Sold Summary

      • 41 Days On Market

  • 3 Stable Way, Medway, MA 02053
    3 Stable Way, Medway, MA 02053
    3 Stable Way, Medway, MA 02053
    /36

    $1,125,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    3 Stable Way, Medway, MA 02053

    Do not miss your opportunity to own this beautiful custom Colonial in one of Medway’s most sought-after neighborhoods! Greeted by a stunning two-story foyer, this effortlessly elegant home boasts a stunningly updated kitchen that flows seamlessly into a sun-drenched family room w/ soaring cathedral ceilings & a cozy gas fireplace. Functional mudroom w/ built-ins and first-floor laundry. A private

    Team Rice REMAX Executive Realty

    3 Stable Way, Medway, MA 02053
  • 36 Lovering St, Medway, MA 02053
    36 Lovering St, Medway, MA 02053
    36 Lovering St, Medway, MA 02053
    /29

    $585,000

    Sold Jan 07, 2026

    36 Lovering St, Medway, MA 02053

    • 4 Beds
    • 2 Baths
    • 1,542 Sq Ft
    • Built 1945

    Last Sold Summary

    • 1% Below List Price
    • $379/SF
    • 38 Days On Market

    Current Estimated Value $574,775

    Last Listing Agent Shannon Hurley Century 21 Custom Home Realty

    36 Lovering St, Medway, MA 02053
    • 11 Puddingstone Ln, Medway, MA 02053
      11 Puddingstone Ln, Medway, MA 02053
      11 Puddingstone Ln, Medway, MA 02053
      /40

      Est $755,327

      Not Listed For Sale

      11 Puddingstone Ln, Medway, MA 02053

      • 4 Beds
      • 1.5 Baths
      • 1,696 Sq Ft
      • Built 1978
      11 Puddingstone Ln, Medway, MA 02053

      Last Sold Summary

      • 3 Days On Market

  • 50 Milford St, Medway, MA 02053
    50 Milford St, Medway, MA 02053
    50 Milford St, Medway, MA 02053
    /15

    $525,000

    $25K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,632 Sq Ft

    50 Milford St, Medway, MA 02053

    Seller to provide Approved Septic Design Prior to Closing! BRAND NEW Roof, Windows, Garage Doors, and Hot Water Heater! This garrison colonial has had many of the big-ticket items addressed, it is ready for creative customization from the new buyer. Get into Medway for a low price and instantly build equity with this 4 Bedroom 1.5 Bathroom 2 Car Garage Home. The first floor features a convenient

    Molla Realty Team Costello Realty

    50 Milford St, Medway, MA 02053
  • 6 Freedom Trail, Medway, MA 02053
    6 Freedom Trail, Medway, MA 02053
    6 Freedom Trail, Medway, MA 02053
    /34

    $1,050,000

    Sold May 29, 2026

    6 Freedom Trail, Medway, MA 02053

    • 4 Beds
    • 4 Baths
    • 3,629 Sq Ft
    • Built 2006

    Last Sold Summary

    • 16% Below List Price
    • $289/SF
    • 259 Days On Market

    Current Estimated Value $1,065,485

    Last Listing Agent Paul Yorkis Patriot Real Estate, Inc.

    6 Freedom Trail, Medway, MA 02053
    • 22 Puddingstone Ln, Medway, MA 02053
      22 Puddingstone Ln, Medway, MA 02053
      22 Puddingstone Ln, Medway, MA 02053
      /32

      Est $714,661

      Not Listed For Sale

      22 Puddingstone Ln, Medway, MA 02053

      • 3 Beds
      • 2 Baths
      • 2,033 Sq Ft
      • Built 1979
      22 Puddingstone Ln, Medway, MA 02053

      Last Sold Summary

      • 10 Days On Market

  • 12 Kelley St, Medway, MA 02053
    12 Kelley St, Medway, MA 02053
    12 Kelley St, Medway, MA 02053
    /29

    $589,900

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,531 Sq Ft

    12 Kelley St, Medway, MA 02053

    Attractive Cape has been thoughtfully updated and improved and ready to move in! Freshly painted and with refinished hardwood flooring, this welcoming home has many special features including a sun streaked, fireplaced living room, new Kitchen appliances, a first floor laundry and mudroom. Both baths have been upgraded and accented. All three bedrooms are spacious and include ample closet space.

    The Rao Team

    12 Kelley St, Medway, MA 02053
  • 84 Winthrop St, Medway, MA 02053
    84 Winthrop St, Medway, MA 02053
    84 Winthrop St, Medway, MA 02053
    /42

    $608,000

    Sold Apr 24, 2026

    84 Winthrop St, Medway, MA 02053

    • 3 Beds
    • 1 Bath
    • 1,920 Sq Ft
    • Built 1959

    Last Sold Summary

    • 2% Above List Price
    • $317/SF
    • 6 Days On Market

    Current Estimated Value $600,440

    Last Listing Agent Modern Nest Group Modern Nest Group

    84 Winthrop St, Medway, MA 02053
    • 28 Causeway St, Medway, MA 02053
      28 Causeway St, Medway, MA 02053
      28 Causeway St, Medway, MA 02053
      /25

      Est $648,088

      Not Listed For Sale

      28 Causeway St, Medway, MA 02053

      • 3 Beds
      • 1.5 Baths
      • 1,512 Sq Ft
      • Built 1976
      28 Causeway St, Medway, MA 02053

      Last Sold Summary

      • 38 Days On Market

  • 204 Village St, Medway, MA 02053
    204 Village St, Medway, MA 02053
    204 Village St, Medway, MA 02053
    /42

    $1,299,000

    Open Sat 12PM - 2PM
    • 5 Beds
    • 4.5 Baths
    • 4,636 Sq Ft

    204 Village St, Medway, MA 02053

    Set gracefully back behind a sweeping U-shaped drive, the Julius C. Hurd House is a rare c.1845 antique Colonial and one of Medway’s most distinguished historic homes. Resting on 1.27 private acres, this 4,636 sq ft residence blends timeless craftsmanship with thoughtful modern comforts. Inside, 5 bedrooms, 4.5 baths, 9 fireplaces, wide-plank floors, a gracious double parlor and sun-filled

    Team ROVI Real Broker MA, LLC

    204 Village St, Medway, MA 02053
  • 6 Norfolk Ave, Medway, MA 02053
    6 Norfolk Ave, Medway, MA 02053
    6 Norfolk Ave, Medway, MA 02053
    /37

    $545,000

    Sold Oct 30, 2025

    6 Norfolk Ave, Medway, MA 02053

    • 3 Beds
    • 2 Baths
    • 1,622 Sq Ft
    • Built 1910

    Last Sold Summary

    • 5% Above List Price
    • $336/SF
    • 6 Days On Market

    Current Estimated Value $557,115

    Last Listing Agent Sherrilynn Lombard New Homes Marketing

    6 Norfolk Ave, Medway, MA 02053
    • 3 Causeway St, Medway, MA 02053
      3 Causeway St, Medway, MA 02053
      3 Causeway St, Medway, MA 02053
      /28

      Est $695,106

      Not Listed For Sale

      3 Causeway St, Medway, MA 02053

      • 3 Beds
      • 1.5 Baths
      • 1,642 Sq Ft
      • Built 1979
      3 Causeway St, Medway, MA 02053

      Last Sold Summary

      • 4 Days On Market

  • 118 Village St Unit A, Medway, MA 02053
    118 Village St Unit A, Medway, MA 02053
    118 Village St Unit A, Medway, MA 02053
    /25

    $365,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,263 Sq Ft

    118 Village St Unit A, Medway, MA 02053

    Wonderfully updated townhome offered at an absolutely exceptional value!! The main level features an open-concept layout with beautiful hardwood flooring throughout the kitchen, living room, and half bath. The kitchen is thoughtfully designed with custom cabinetry, granite countertops, stainless steel appliances, and a convenient breakfast bar. The 2nd floor offers a spacious primary bedroom and

    Patrick Murphy Coldwell Banker Realty - Belmont

    118 Village St Unit A, Medway, MA 02053

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