10,570

Brewster, MA Homes

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  • /69

    $2,400,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,212 Sq Ft

    47 Bay View Dr, Brewster, MA 02631

    This coastal contemporary cape style home by Eastward companies is one of a two lot Brewster subdivision close to beautiful Crosby Landing Beach, The Cape Cod Rail Trail and the Town of Orleans. Exceptional custom finish work enhances the superb floorplan and rich amenities. The cathedral great room incorporates the chef's kitchen with Thermador appliance package & 10' center island, fireplaced

    Jeff Cusack Cove Road Real Estate

    47 Bay View Dr, Brewster, MA 02631
  • /46

    $445,500

    Sold May 29, 2026

    104 Chilton Ln Unit 104, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 935 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Above List Price
    • $476/SF
    • 2 Days On Market

    Current Estimated Value $440,351

    Last Listing Agent Leighton Team Keller Williams Realty

    104 Chilton Ln Unit 104, Brewster, MA 02631
    • /24

      Est $854,124

      Not Listed For Sale

      83 Swamp Rd, Brewster, MA 02631

      • 3 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1980
      83 Swamp Rd, Brewster, MA 02631

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent LUXRECapeCod Gibson Sotheby's International Realty

  • /99

    $1,949,000

    $51K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,406 Sq Ft

    37 Autumn Ct, Brewster, MA 02631

    Where life slows to the rhythm of nature, over 800 acres of protected Punkhorn Conservation become a way of life. Hidden at the end of a quiet cul-de-sac in coveted Deerfield Estates, this nature's reserved area embraces Upper Mill & Seymour Ponds to create one of Brewster's most idyllic settings. There are places that invite you to visit & there are places that invite you to stay. This is one of

    Mariana Costa Dream Homes & Estates, Inc.

    37 Autumn Ct, Brewster, MA 02631
  • /60

    $1,015,000

    Sold May 19, 2026

    398 Lund Farm Way, Brewster, MA 02631

    • 4 Beds
    • 3 Baths
    • 2,448 Sq Ft
    • Built 1973

    Last Sold Summary

    • 22% Below List Price
    • $415/SF
    • 147 Days On Market

    Current Estimated Value $1,012,128

    Last Listing Agent Meghan Taylor Kinlin Grover Compass

    398 Lund Farm Way, Brewster, MA 02631
    • /38

      Est $1,220,539

      Not Listed For Sale

      112 Paines Creek Rd, Brewster, MA 02631

      • 4 Beds
      • 3 Baths
      • 2,423 Sq Ft
      • Built 2007
      112 Paines Creek Rd, Brewster, MA 02631

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Paula Casey Beach Realty

  • /38

    $1,399,000

    New Construction $100K PRICE DROP
    • 2 Beds
    • 4 Baths
    • 2,965 Sq Ft

    58 Old Chatham Rd, Brewster, MA 02631

    Price Reduced — Exceptional Value! This high end new custom-built smart home lives much larger than it appears, offering nearly 3,000 sq. ft. of flexible living space,featuring first floor office, second-floor study, and a finished lower level with a family area and workout/multipurpose room—all at an incredible value. Situated on a charming cul-de-sac with a local fruit farm across the street,

    Andrea Lousararian William Raveis Real Estate & Home Services

    58 Old Chatham Rd, Brewster, MA 02631
  • /36

    $645,000

    Sold Jan 05, 2026

    597 Great Fields Rd, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft
    • Built 1984

    Last Sold Summary

    • 5% Below List Price
    • $406/SF
    • 29 Days On Market

    Current Estimated Value $686,870

    Last Listing Agent Lisa Steele Steele Associates Real Estate

    597 Great Fields Rd, Brewster, MA 02631
    • /54

      Est $1,322,286

      Not Listed For Sale

      134 Main St, Brewster, MA 02631

      • 6 Beds
      • 4 Baths
      • 5,496 Sq Ft
      • Built 1989
      134 Main St, Brewster, MA 02631

      Last Sold Summary

      • 174 Days On Market

      Last Listing Agent Thom Schoepfer Keller Williams Realty

  • /35

    $595,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,070 Sq Ft

    937 Harwich Rd, Brewster, MA 02631

    Meticulously maintained and full of charm, this 3-bdrm home offers a cozy and inviting feel. Love biking and swimming? Enjoy easy access to Sheep Pond, about 1/4 mile away, via the bike path accessible through the back yard. The perfect spot for morning walks and simply enjoying the outdoors. This home has had many upgrades with beautiful retaining walls and circular drive added, gorgeous

    Tracey Oringer Kinlin Grover Compass

    937 Harwich Rd, Brewster, MA 02631
  • /51

    $862,500

    Sold Dec 22, 2025

    104 Sachemus Trail Unit 104, Brewster, MA 02631

    • 3 Beds
    • 2.5 Baths
    • 1,652 Sq Ft
    • Built 2016

    Last Sold Summary

    • 4% Below List Price
    • $522/SF
    • 21 Days On Market

    Current Estimated Value $1,005,808

    Last Listing Agent Nancy Whitehurst Christie's Int'l RE Atlantic Brokerage

    104 Sachemus Trail Unit 104, Brewster, MA 02631
    • /32

      Est $2,909,027

      Not Listed For Sale

      32 Oliver Dr, Brewster, MA 02631

      • 4 Beds
      • 2.5 Baths
      • 3,456 Sq Ft
      • Built 1994
      32 Oliver Dr, Brewster, MA 02631

      Last Sold Summary

      • 319 Days On Market

      Last Listing Agent Cindy Harrington Berkshire Hathaway HomeServices Robert Paul Properties

  • /35

    $975,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 3,086 Sq Ft

    215 Stony Brook Rd, Brewster, MA 02631

    SUNDAY SEPT. 20TH OPEN HOUSE CANCELLED. Privately set on 1.39 acres, this expanded Cape with over 3,000 sq ft of living space includes three bedrooms, two and a half baths and an office over the two car garage. On the first floor, the primary bedroom suite, with a jacuzzi tub and separate shower, opens to a secluded deck overlooking the woods. The kitchen, with granite countertops, a breakfast

    Matthew Burger Kinlin Grover Compass

    215 Stony Brook Rd, Brewster, MA 02631
  • /57

    $775,000

    Sold Jan 05, 2026

    3904 Main St, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft
    • Built 1950

    Last Sold Summary

    • $430/SF
    • 11 Days On Market

    Current Estimated Value $801,337

    Last Listing Agent Sandra Milano RE/MAX Executive Realty

    3904 Main St, Brewster, MA 02631
    • /26

      Est $702,665

      Not Listed For Sale

      9 Huckleberry Ln, Brewster, MA 02631

      • 3 Beds
      • 2 Baths
      • 1,555 Sq Ft
      • Built 1980
      9 Huckleberry Ln, Brewster, MA 02631

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent John Lynch Dwell360

  • /16

    $325,000

    Pending
    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    81 Fletcher Ln Unit I, Brewster, MA 02631

    Sought after Corner Unit with 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

    81 Fletcher Ln Unit I, Brewster, MA 02631
  • /41

    $424,000

    Sold Jul 13, 2026

    77 Chilton Ln Unit 77, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 935 Sq Ft
    • Built 1984

    Last Sold Summary

    • 6% Below List Price
    • $453/SF
    • 49 Days On Market

    Current Estimated Value $437,710

    Last Listing Agent Leighton Team Keller Williams Realty

    77 Chilton Ln Unit 77, Brewster, MA 02631
    • /24

      Est $720,602

      Not Listed For Sale

      30 Pleasant Ct, Brewster, MA 02631

      • 3 Beds
      • 1.5 Baths
      • 1,716 Sq Ft
      • Built 1985
      30 Pleasant Ct, Brewster, MA 02631

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Jennifer Lepard Beach Road Properties

  • /34

    $355,000

    Open Thu 3PM - 4PM
    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    102 Fletcher Ln Unit H, Brewster, MA 02631

    Beautifully updated and move-in ready, this top-floor 1-bed, 1-bath condo in the desirable Ocean Edge Resort community offers the perfect blend of style and comfort. Soaring cathedral ceilings and an open layout create a bright, airy atmosphere, while the private balcony provides sweeping views of the Nicklaus Design Golf Course. Recent renovations include a brand-new kitchen with modern

    Leighton Team Keller Williams Realty

    102 Fletcher Ln Unit H, Brewster, MA 02631
  • /23

    $445,000

    Sold Aug 17, 2026

    93 Chilton Ln Unit 93, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 935 Sq Ft
    • Built 1984

    Last Sold Summary

    • 1% Below List Price
    • $476/SF
    • 6 Days On Market

    Last Listing Agent Claire Cassidy RE/MAX Executive Realty

    93 Chilton Ln Unit 93, Brewster, MA 02631
    • /33

      Est $988,293

      Not Listed For Sale

      34 Pleasant Ct, Brewster, MA 02631

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

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Steven Titus Kinlin Grover Compass

  • /11

    $1,200,000

    • 5 Beds
    • 8 Baths
    • 3,233 Sq Ft

    2019 Main St, Brewster, MA 02631

    The property includes 5 bedrooms with en-suite bathrooms, a paver patio with hydrangeas and charm galore, and a large shell driveway.The property is within walkingdistance to the beach and can provide excellent work/life balance. Presently used as a restaurant

    Chuck Carey Carey Commerical, Inc.

    2019 Main St, Brewster, MA 02631
  • /42

    $1,600,000

    Sold May 21, 2026

    101 Evelyn's Dr, Brewster, MA 02631

    • 3 Beds
    • 3.5 Baths
    • 2,354 Sq Ft
    • Built 2026

    Last Sold Summary

    • $680/SF
    • 6 Days On Market

    Last Listing Agent Christine Lacava Jack Conway

    101 Evelyn's Dr, Brewster, MA 02631
    • /52

      Est $998,305

      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

      • 1 Day On Market

      Last Listing Agent Leighton Team Keller Williams Realty

  • /40

    $560,000

    Open Sat 10:30AM - 12PM $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,063 Sq Ft

    105 Trevor Ln, Brewster, MA 02631

    A pristine townhouse in one of Trevor Village's most desirable settings! Enjoy a peaceful view over a lush expanse of lawn from the slider and the private patio! Whether you're sipping a quiet morning coffee, enjoying your little family members/visitors as they scamper across the green grass, or unwinding during a colorful sunset over the horizon, the tranquil outdoor space will become your own

    Amy Harbeck Kinlin Grover Compass

    105 Trevor Ln, Brewster, MA 02631
  • /42

    $845,000

    Sold May 06, 2026

    102 Wildwood Rd, Brewster, MA 02631

    • 3 Beds
    • 2 Baths
    • 2,812 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $300/SF
    • 132 Days On Market

    Current Estimated Value $881,650

    Last Listing Agent Jan Pulit Kinlin Grover Compass

    102 Wildwood Rd, Brewster, MA 02631
    • /40

      Est $819,780

      Not Listed For Sale

      221 Greenland Pond Rd, Brewster, MA 02631

      • 3 Beds
      • 2 Baths
      • 1,471 Sq Ft
      • Built 1976
      221 Greenland Pond Rd, Brewster, MA 02631

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Sharon Mabile Berkshire Hathaway HomeServices Robert Paul Properties

  • /60

    $1,200,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,327 Sq Ft

    575 Harwich Rd, Brewster, MA 02631

    Perfectly positioned on nearly an acre, this beautiful custom-built home was thoughtfully designed for its current owners, who fell in love with Brewster's natural beauty, tidal flats, state park, and scenic bike trail. Twenty-three years later, their love for this special location has only grown—and now, their dream home can be yours. From the very beginning, the vision was clear: an

    Leighton Team Keller Williams Realty

    575 Harwich Rd, Brewster, MA 02631
  • /28

    $675,000

    Sold Oct 30, 2025

    153 Red Fawn Rd, Brewster, MA 02631

    • 4 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $427/SF
    • 22 Days On Market

    Current Estimated Value $714,983

    Last Listing Agent Tracey Oringer Kinlin Grover Compass

    153 Red Fawn Rd, Brewster, MA 02631
    • /74

      Est $936,430

      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

      • 74 Days On Market

      Last Listing Agent John Allen Gibson Sotheby's International Realty

  • /16

    $430,000

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft

    137 Eaton Ln, Brewster, MA 02631

    ESCAPE to the Cape at this 2 bedroom / 2 bath 2nd floor end unit at EATON VILLAGE at the OCEAN EDGE resort. End unit means extra WINDOWS! A/C recently upgraded to DUCTLESS Mitsubishi with units in both bedrooms and the living area. OPEN LAYOUT combines living / dining space and private deck with a nice view of the tee at the PGA-rated golf course. Sold fully FURNISHED (except for some personal

    Margaret Nilson Marietta Realty

    137 Eaton Ln, Brewster, MA 02631
  • /38

    $748,000

    Sold Aug 27, 2026

    83 Airline Rd, Dennis, MA 02641

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 2025

    Last Sold Summary

    • 10% Below List Price
    • $575/SF
    • 123 Days On Market

    Last Listing Agent Michelle Ryan Today Real Estate, Inc.

    83 Airline Rd, Dennis, MA 02641
    • /60

      Est $2,139,369

      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

      • 7 Days On Market

      Last Listing Agent Dolores Alberti Gibson Sotheby's International Realty

  • /27

    $335,000

    • 1 Bed
    • 1 Bath
    • 589 Sq Ft

    102 Fletcher Ln Unit A, 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 top floor condo with cathedral ceilings, sky light and a bright, open-concept layout and with a private deck. The renovated kitchen features quartz countertops, stainless steel appliances, and contemporary cabinetry, while the updated bathroom

    Leighton Team Keller Williams Realty

    102 Fletcher Ln Unit A, Brewster, MA 02631
  • /54

    $850,000

    Sold Oct 31, 2025

    19 Burning Bush Way, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 2,034 Sq Ft
    • Built 2002

    Last Sold Summary

    • 13% Above List Price
    • $418/SF
    • 19 Days On Market

    Current Estimated Value $888,091

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    19 Burning Bush Way, Brewster, MA 02631
    • /83

      Est $2,118,471

      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

      • 9 Days On Market

      Last Listing Agent Jeff Cusack Cove Road Real Estate

  • /40

    $1,844,000

    New Construction $586K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,337 Sq Ft

    0 Ridgewood Dr, Brewster, MA 02631

    On an exclusive cul de sac graced with executive homes, this new construction package is a rare opportunity to create your dream home in a picturesque setting! The lot (Lot 26-58) boasts privacy, natural beauty, and a view across Drummer Boy Park, Quivett Marsh, and Cape Cod Bay beyond! In collaboration with Millbrook Homes, the featured plan checks all the boxes--1st flr main bedroom suite, open

    Amy Harbeck Kinlin Grover Compass

    0 Ridgewood Dr, Brewster, MA 02631
  • /42

    $1,575,000

    Sold Nov 04, 2025

    663 Crowells Bog Rd, Brewster, MA 02631

    • 4 Beds
    • 3.5 Baths
    • 3,738 Sq Ft
    • Built 2001

    Last Sold Summary

    • 5% Below List Price
    • $421/SF
    • 47 Days On Market

    Current Estimated Value $1,616,796

    Last Listing Agent O'Neill Group Berkshire Hathaway HomeServices Robert Paul Properties

    663 Crowells Bog Rd, Brewster, MA 02631
    • /35

      Est $540,169

      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

      • 7 Days On Market

      Last Listing Agent Natalia Weiner Gibson Sotheby's International Realty

  • /52

    $925,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,323 Sq Ft

    52 Sachemus Trail Unit 52, Brewster, MA 02631

    This is the first 3-bedroom home with a finished walkout basement to come on the market in Brewster Landing! With 2,323 square feet of living space, this stand-alone condo offers plenty of room for entertaining. Built in 2017, this home checks all the boxes for today's buyer while offering easy access to everything that makes Brewster such a special place. The first floor features a spacious

    Leighton Team Keller Williams Realty

    52 Sachemus Trail Unit 52, Brewster, MA 02631

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