10,653

Brewster, MA Homes

Section Image
  • /33

    $1,675,001

    Sold Aug 19, 2025

    40 Linger Longer Cartway, Brewster, MA 02631

    • 3 Beds
    • 3 Baths
    • 2,312 Sq Ft
    • Built 2007

    Last Sold Summary

    • 8% Below List Price
    • $724/SF
    • 200 Days On Market

    Last Listing Agent John Cotton Sotheby's International Realty

    40 Linger Longer Cartway, Brewster, MA 02631
    • /40

      Est $1,013,342

      Not Listed For Sale

      34 Pleasant Ct, Brewster, MA 02631

      • 3 Beds
      • 2.5 Baths
      • 1,784 Sq Ft
      • Built 2004
      34 Pleasant Ct, Brewster, MA 02631

      Last Sold Summary

      • 1% Above List Price
      • $561/SF
      • 3 Days On Market
      • Last Sold Price $1,000,000
      • May 15, 2025

      Last Listing Agent Kayla Hilts Today Real Estate

  • /30

    $949,900

    • 5 Beds
    • 3 Baths
    • 2,295 Sq Ft

    38 Bittersweet Dr, Brewster, MA 02631

    Fantastic opportunity to own a home on a cul-de-sac north of Route 6A in Brewster.Large 5 bedroom, 3 full bath home with newer roof, low maintenance vinyl siding and wrapped trim. Layout is conducive to an in-law apartment of fabulous primary suite. Situated on just over 1/2 an acre. Convenient location. Needs updating.

    Michael Ulrich Cape Cod Associates R E

    38 Bittersweet Dr, Brewster, MA 02631
  • /34

    $444,000

    Sold Nov 25, 2025

    144 Eaton Ln, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 935 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $475/SF
    • 58 Days On Market

    Current Estimated Value $435,529

    Last Listing Agent A Cape Life Today Real Estate

    144 Eaton Ln, Brewster, MA 02631
    • /52

      Est $1,016,580

      Not Listed For Sale

      298 Cranview Rd, Brewster, MA 02631

      • 3 Beds
      • 2.5 Baths
      • 2,206 Sq Ft
      • Built 1998
      298 Cranview Rd, Brewster, MA 02631

      Last Sold Summary

      • $461/SF
      • 1 Day On Market
      • Last Sold Price $1,016,000
      • Apr 28, 2025

      Last Listing Agent Leighton Team Keller Williams Realty

  • /38

    $549,000

    Pending
    • 1 Bed
    • 1.5 Baths
    • 1,376 Sq Ft

    157 Jonathans Way, Brewster, MA 02631

    There are homes... and then there are homes you feel the moment you walk in. This is one of those.Tucked away in Brewster, this delightful retreat has been cherished by the same family for years--filled with warmth, laughter, and true Cape Cod memories. If you're searching for a typical Cape, this isn't it. This home offers something more.Soaring wood beam ceilings add character you simply can't

    Marirose Lynch RE/MAX Real Estate Center

    157 Jonathans Way, Brewster, MA 02631
  • /29

    $521,000

    Sold Apr 15, 2026

    103 Trevor Ln Unit 103, Brewster, MA 02631

    • 2 Beds
    • 1.5 Baths
    • 1,032 Sq Ft
    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • $505/SF
    • 26 Days On Market

    Current Estimated Value $539,976

    Last Listing Agent Susie Bent Greer Real Estate, LLC

    103 Trevor Ln Unit 103, Brewster, MA 02631
    • /36

      Est $870,139

      Not Listed For Sale

      228 Cranview Rd, Brewster, MA 02631

      • 3 Beds
      • 1.5 Baths
      • 1,162 Sq Ft
      • Built 1941
      228 Cranview Rd, Brewster, MA 02631

      Last Sold Summary

      • 9% Above List Price
      • $688/SF
      • 15 Days On Market
      • Last Sold Price $800,000
      • Jul 06, 2023

      Last Listing Agent Leighton Team Keller Williams Realty

  • /28

    $295,000

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    100 Fletcher Ln Unit G, Brewster, MA 02631

    Welcome to The Fletcher Condos within Ocean Edge Resort Community, one of Cape Cod's most desirable resort style living. This updated and fully renovated lower level condo with a bright, open-concept layout and with a private patio that opens up to a grassy area overlooking the Ocean Edge Golf Course. The renovated kitchen features quartz countertops, stainless steel appliances, and contemporary

    Leighton Team Keller Williams Realty

    100 Fletcher Ln Unit G, Brewster, MA 02631
  • /41

    $1,150,000

    Sold May 11, 2026

    13 Sand Dollar Ln, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 2,437 Sq Ft
    • Built 1985

    Last Sold Summary

    • 7% Above List Price
    • $472/SF
    • 5 Days On Market

    Current Estimated Value $1,044,469

    Last Listing Agent Amanda Govoni William Raveis Real Estate & Home Services

    13 Sand Dollar Ln, Brewster, MA 02631
    • /40

      Est $1,077,045

      Not Listed For Sale

      243 Greenland Pond Rd, Brewster, MA 02631

      • 4 Beds
      • 4 Baths
      • 2,782 Sq Ft
      • Built 1987
      243 Greenland Pond Rd, Brewster, MA 02631

      Last Sold Summary

      • 23% Above List Price
      • $315/SF
      • 24 Days On Market
      • Last Sold Price $875,000
      • Aug 03, 2023

      Last Listing Agent John Allen Gibson Sotheby's International Realty

  • /43

    $689,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    98 Sheep Pond Dr, Brewster, MA 02631

    Nestled in the sought-after Sheep Pond Beach Association neighborhood, this quintessential Cape home is brimming with charm and endless possibilities. Step inside to discover a warm and inviting first floor, featuring an eat-in kitchen, a cozy living room with a wood-burning stove, a separate dining room for gatherings, and the convenience of a first-floor bedroom and full bath.Upstairs, you'll

    Meghan Taylor Kinlin Grover Compass

    98 Sheep Pond Dr, Brewster, MA 02631
  • /14

    $817,000

    Sold Aug 06, 2025

    35 Pine Bay Ln, Brewster, MA 02631

    • 2 Beds
    • 1 Bath
    • 429 Sq Ft
    • Built 1964

    Last Sold Summary

    • 8% Above List Price
    • $1,904/SF
    • 339 Days On Market

    Current Estimated Value $864,332

    Last Listing Agent Eric Buliung LAER Realty Partners

    35 Pine Bay Ln, Brewster, MA 02631
    • /42

      Est $899,996

      Not Listed For Sale

      59 Valley Rd, Brewster, MA 02631

      • 3 Beds
      • 2 Baths
      • 2,108 Sq Ft
      • Built 1985
      59 Valley Rd, Brewster, MA 02631

      Last Sold Summary

      • 7% Above List Price
      • $398/SF
      • 96 Days On Market
      • Last Sold Price $840,000
      • Aug 02, 2024

      Last Listing Agent John Allen Gibson Sotheby's International Realty

  • /35

    $419,000

    • 2 Beds
    • 1.5 Baths
    • 1,296 Sq Ft

    81 Woodview Dr, Brewster, MA 02631

    Light filled and inviting, this 2 bedroom, 1.5 bath townhouse style condo in desirable Oakwood Village offers comfort, flexibility, and great potential. The open concept living and dining area is bright and welcoming, featuring a cozy fireplace and seamless flow into the kitchen, which includes first floor laundry, a half bath, and direct access to a spacious deck, perfect for relaxing or

    Carol Terrio Keller Williams Realty

    81 Woodview Dr, Brewster, MA 02631
  • /58

    $875,000

    Sold Aug 27, 2025

    19 Fishermans Landing Rd, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1993

    Last Sold Summary

    • 10% Above List Price
    • $558/SF
    • 2 Days On Market

    Current Estimated Value $883,901

    Last Listing Agent Amber Dauphinais Orleans Village Properties, LLC

    19 Fishermans Landing Rd, Brewster, MA 02631
    • /60

      Est $2,193,972

      Not Listed For Sale

      81 Whidah Way, Brewster, MA 02631

      • 5 Beds
      • 3.5 Baths
      • 4,714 Sq Ft
      • Built 2003
      81 Whidah Way, Brewster, MA 02631

      Last Sold Summary

      • 10% Above List Price
      • $423/SF
      • 7 Days On Market
      • Last Sold Price $1,995,000
      • May 09, 2025

      Last Listing Agent Dolores Alberti Gibson Sotheby's International Realty

  • /12

    $745,000

    • Land
    • 14,810 Sq Ft
    • $2,191,176 per Acre

    -0- Ambergris Cir, Brewster, MA 02631

    There are very few, if any, empty lots available in Salt Works, one of the most desirable North 6A Cape Cod Bay influenced locations in Brewster. A short stroll or a very quick drive of .1-.3 miles will bring you to both Mant's Landing and Saint's Landing to enjoy a bright & sunny day at the beach!Perc in 2017, this lot is pending final Board of Health approval once a construction location is

    Nina Tobin Gibson Sotheby's International Realty

    -0- Ambergris Cir, Brewster, MA 02631
  • /49

    $775,000

    Sold May 15, 2026

    142 Yankee Dr, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • Built 1994

    Last Sold Summary

    • 5% Above List Price
    • $473/SF
    • 7 Days On Market

    Current Estimated Value $788,926

    Last Listing Agent Kimberly Clark Bayside Realty Consultants

    142 Yankee Dr, Brewster, MA 02631
    • /83

      Est $2,023,912

      Not Listed For Sale

      14 Whidah Way, Brewster, MA 02631

      • 4 Beds
      • 3.5 Baths
      • 4,318 Sq Ft
      • Built 2005
      14 Whidah Way, Brewster, MA 02631

      Last Sold Summary

      • 1% Above List Price
      • $462/SF
      • 7 Days On Market
      • Last Sold Price $1,995,000
      • May 30, 2024

      Last Listing Agent Jeff Cusack Cove Road Real Estate

  • /24

    $315,000

    Open Thu 1:30PM - 3:30PM
    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    101 Fletcher Ln Unit L, Brewster, MA 02631

    Step into effortless one-level living in this beautifully renovated first-floor condo at sought-after Ocean Edge Resort. No stairs to navigate to get to this unit. This light-filled 1-bedroom, 1-bath home offers an open-concept design with a seamless, modern feel. The updated kitchen features quartz countertops, stainless steel appliances, stylish cabinetry, and contemporary lighting. A

    Leighton Team Keller Williams Realty

    101 Fletcher Ln Unit L, Brewster, MA 02631
  • /2

    $1,270,000

    Sold Dec 02, 2025

    70 Run Hill Rd, Brewster, MA 02631

    • 3 Beds
    • 3.5 Baths
    • 2,926 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Below List Price
    • $434/SF
    • 7 Days On Market

    Current Estimated Value $1,344,976

    Last Listing Agent Andrea Howell William Raveis Chatham

    70 Run Hill Rd, Brewster, MA 02631
    • /35

      Est $542,824

      Not Listed For Sale

      1619 Long Pond Rd, Brewster, MA 02631

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1973
      1619 Long Pond Rd, Brewster, MA 02631

      Last Sold Summary

      • 9% Above List Price
      • $473/SF
      • 7 Days On Market
      • Last Sold Price $499,900
      • Jan 15, 2025

      Last Listing Agent Natalia Weiner Gibson Sotheby's International Realty

  • /70

    $1,795,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,050 Sq Ft

    39 Spruce Run Dr, Brewster, MA 02631

    Nestled in the desirable Sheep's Landing neighborhood, with access to a private association beach on pristine Sheep Pond! The neighborhood boasts underground utilities and lovely homes on large lots. Inside this charming home, southern pine floors flow thru most of the 1st floor, including the living/dining room, kitchen, 2 bedrooms (BRs), and a year-round sun room that adds extra living space.

    Amy Harbeck Kinlin Grover Compass

    39 Spruce Run Dr, Brewster, MA 02631
  • /47

    $625,000

    Sold Dec 03, 2025

    105 Middlecott Ln Unit 105, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Below List Price
    • $525/SF
    • 10 Days On Market

    Current Estimated Value $647,691

    Last Listing Agent Nancy Whitehurst Realty Executives

    105 Middlecott Ln Unit 105, Brewster, MA 02631
    • /58

      Est $2,219,962

      Not Listed For Sale

      26 Oliver Dr, Brewster, MA 02631

      • 4 Beds
      • 3 Baths
      • 2,929 Sq Ft
      • Built 1996
      26 Oliver Dr, Brewster, MA 02631

      Last Sold Summary

      • 71% Above List Price
      • $444/SF
      • 134 Days On Market
      • Last Sold Price $1,300,000
      • Nov 01, 2024

      Last Listing Agent Laura Clements Cove Road Real Estate

  • /25

    $425,000

    • 2 Beds
    • 2 Baths
    • 935 Sq Ft

    11 Chilton Ln, Brewster, MA 02631

    Enjoy coastal living in this thoughtfully updated Ocean Edge condo, ready for summer enjoyment. Nestled in a quiet wooded setting just south of scenic 6A, this location offers easy access to the beautiful bayside beaches, the Cape Cod Rail Trail, local shopping, coffee shop and restaurants. Unpack and enjoy the already renovated space, which includes a brand new washer/dryer, wood floors

    Amanda Govoni William Raveis Real Estate & Homes Services

    11 Chilton Ln, Brewster, MA 02631
  • /54

    $806,000

    Sold Oct 07, 2025

    236 Yankee Dr, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft
    • Built 1995

    Last Sold Summary

    • 11% Above List Price
    • $471/SF
    • 7 Days On Market

    Current Estimated Value $835,466

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    236 Yankee Dr, Brewster, MA 02631
    • /73

      Est $1,591,984

      Not Listed For Sale

      61 Oliver Dr, Brewster, MA 02631

      • 4 Beds
      • 3.5 Baths
      • 4,102 Sq Ft
      • Built 1996
      61 Oliver Dr, Brewster, MA 02631

      Last Sold Summary

      • 8% Below List Price
      • $421/SF
      • 1 Day On Market
      • Last Sold Price $1,725,000
      • Jun 13, 2024

      Last Listing Agent Laura Clements Cove Road Real Estate

  • /13

    $375,000

    • Land
    • 16,117 Sq Ft
    • $1,013,514 per Acre

    0 Canoe Pond Dr, Brewster, MA 02631

    POND FRONT LOT in beautiful Brewster! This lot is on Canoe Pond where you can fish, boat & swim right from your own backyard. It also offers association access to Upper Mill Pond for sailing, kayaking, fishing & swimming for even more fresh water fun. Yes, two healthy ponds to enjoy & explore! This wooded lot is level near the street and closer to the back begins to slope towards the pond. The

    Karen Quinn William Raveis Real Estate & Home Services

    0 Canoe Pond Dr, Brewster, MA 02631
  • /40

    $800,000

    Sold Mar 05, 2026

    184 Barons Way, Brewster, MA 02631

    • 4 Beds
    • 2 Baths
    • 2,252 Sq Ft
    • Built 1973

    Last Sold Summary

    • 1% Above List Price
    • $355/SF
    • 17 Days On Market

    Current Estimated Value $813,963

    Last Listing Agent Susan Baker Gibson Sotheby's International Realty

    184 Barons Way, Brewster, MA 02631
    • /44

      Est $676,688

      Not Listed For Sale

      199 Timberlane Dr, Brewster, MA 02631

      • 4 Beds
      • 2.5 Baths
      • 1,612 Sq Ft
      • Built 1971
      199 Timberlane Dr, Brewster, MA 02631

      Last Sold Summary

      • 10% Below List Price
      • $466/SF
      • 3 Days On Market
      • Last Sold Price $751,000
      • Jul 23, 2024

      Last Listing Agent Karen Kennedy Kinlin Grover Compass

  • /27

    $699,900

    $30K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,872 Sq Ft

    1580 Main St, Brewster, MA 02631

    1580 Main Street A/K/A ''The Captain Freeman Bangs House''. Step back in time and be engaged in this eclectically charming home, mostly built in 1830 but some very charming newer spaces have been added. Currently a multi use property with a small lamp repair shop using the lower space..Beautiful appointments set on School House Pond, with views from several rooms. Nearly an acre of unspoiled

    Deborah McDevitt Hays McDevitt REALTORS

    1580 Main St, Brewster, MA 02631
  • /33

    $387,000

    Sold Sep 09, 2025

    40 Eaton Ln, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 935 Sq Ft
    • Built 1986

    Last Sold Summary

    • 9% Below List Price
    • $414/SF
    • 97 Days On Market

    Current Estimated Value $408,749

    Last Listing Agent Leighton Team Keller Williams Realty

    40 Eaton Ln, Brewster, MA 02631
    • /30

      Est $692,590

      Not Listed For Sale

      549 S Orleans Rd, Brewster, MA 02631

      • 3 Beds
      • 2.5 Baths
      • 1,783 Sq Ft
      • Built 1971
      549 S Orleans Rd, Brewster, MA 02631

      Last Sold Summary

      • 16% Below List Price
      • $460/SF
      • 46 Days On Market
      • Last Sold Price $820,000
      • May 22, 2024

      Last Listing Agent The Team of Cape Cod Seaport Village Realty

  • /6

    $309,000

    • Land
    • 35,719 Sq Ft
    • $376,829 per Acre

    0 Old Chatham Rd, Brewster, MA 02631

    Lot #33 cleared level lot at the end of a cul-de-sac abutting Ocean Edge golf course. Will support a 3 bedroom home. Buyer to verify information herein. Package deal if you buy lot and home at 235 Old Chatham rd. $725,000

    Isaac Sargent Christie's Int'l RE Atlantic Brokerage

    0 Old Chatham Rd, Brewster, MA 02631
  • /32

    $705,000

    Sold Jul 25, 2025

    89 Cliff Pond Rd, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • Built 1992

    Last Sold Summary

    • 6% Above List Price
    • $591/SF
    • 3 Days On Market

    Current Estimated Value $718,128

    Last Listing Agent Tracey Oringer Kinlin Grover Compass

    89 Cliff Pond Rd, Brewster, MA 02631
    • /32

      Est $1,055,410

      Not Listed For Sale

      45 John Myrick Cir, Brewster, MA 02631

      • 4 Beds
      • 3 Baths
      • 2,415 Sq Ft
      • Built 1998
      45 John Myrick Cir, Brewster, MA 02631

      Last Sold Summary

      • 10% Below List Price
      • $487/SF
      • 3 Days On Market
      • Last Sold Price $1,175,000
      • Jun 17, 2024

      Last Listing Agent nadine magazu Kinlin Grover Compass

  • /12

    $745,000

    • Land
    • 14,810 Sq Ft
    • $2,191,176 per Acre

    0 Ambergris Cir, Brewster, MA 02631

    There are very few, if any, empty lots available in Salt Works, one of the most desirable North 6A Cape Cod Bay influenced locations in Brewster. A short stroll or a very quick drive of .1-.3 miles will bring you to both Mant's Landing and Saint's Landing to enjoy a bright & sunny day at the beach! Owners of 182 Ambergris Circle, which is currently For Sale, also own this lot. They are are

    Nina Tobin Gibson Sotheby's International Realty

    0 Ambergris Cir, Brewster, MA 02631
  • /25

    $651,000

    Sold Sep 12, 2025

    55 Wayside Dr, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1984

    Last Sold Summary

    • 7% Below List Price
    • $511/SF
    • 117 Days On Market

    Last Listing Agent Sandra Tanco Kinlin Grover Compass

    55 Wayside Dr, Brewster, MA 02631

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