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Luxury Homes in Brewster, MA
28 listings

Luxury Homes in Brewster, MA

Luxury Homes in Brewster, MA

Show Map
17 of 28 Listings
Map

Luxury Homes in Brewster, MA

17 of 28 Listings

  1. Active

    $1,095,000

    3 bd · 4 ba · 2,889 sqft

    21 Cahoon Road, Brewster, MA

    Fran I Schofield · Berkshire Hathaway HomeServices Robert Paul Properties

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
  • 66 Roberts Rd — photoOpen house Sat, Oct 3 · 11:00 AM37Active

    $1,495,000

    4 bd · 2 ba · 1,344 sqft

    66 Roberts Rd, Brewster, MA

    Jill Cohen · Redfin Corp.

  • Active

    $1,849,000

    3 bd · 2 ba · 2,028 sqft

    33 Gilbert Road, Brewster, MA

    Peggy A Farber · Gibson Sotheby's International Realty

  • 9 Cockle Way Unit 9 — photo64Active

    $1,150,000

    2 bd · 2 ba · 1,650 sqft

    9 Cockle Way Unit 9, Brewster, MA

    Amy L Harbeck · Kinlin Grover Compass

  • 21 Lee Way — photoPrice Reduced30Active

    $1,095,000

    4 bd · 2 ba · 2,104 sqft

    21 Lee Way, Brewster, MA

    Kim L Terrio · William Raveis Real Estate & Home Services

  • 79 Old Freemans Way — photo41Active

    $1,100,000

    3 bd · 2 ba · 1,981 sqft

    79 Old Freemans Way, Brewster, MA

  • 674 Crowells Bog Rd — photo42Active

    $3,399,000

    6 bd · 5 ba · 5,430 sqft

    674 Crowells Bog Rd, Brewster, MA

    Natalia Weiner · Gibson Sotheby's International Realty

  • 80 Upland Circle — photoPrice ReducedOpen house Sat, Oct 3 · 12:00 PM51Active

    $1,495,000

    3 bd · 3 ba · 3,322 sqft

    80 Upland Circle, Brewster, MA

    Suzanne Newton · Kinlin Grover Compass

  • 155 Damon Rd — photoPrice Reduced42Active

    $1,249,999

    4 bd · 4 ba · 3,404 sqft

    155 Damon Rd, Brewster, MA

    Meghan Taylor · Kinlin Grover Compass

  • 69 Martingale Ln — photoPrice Reduced42Active

    $1,350,000

    3 bd · 4 ba · 2,545 sqft

    69 Martingale Ln, Brewster, MA

    Tracey Oringer · Kinlin Grover Compass

  • 37 Autumn Court — photoPrice ReducedOpen house Sat, Oct 3 · 11:00 AM99Active

    $1,949,000

    4 bd · 4 ba · 3,406 sqft

    37 Autumn Court, Brewster, MA

    DREAM International · Dream Homes & Estates, Inc.

  • 47 Bay View Drive — photo69Active

    $2,400,000

    4 bd · 5 ba · 4,212 sqft

    47 Bay View Drive, Brewster, MA

    Jeffrey E Cusack · Cove Road Real Estate

  • 206 Landing Drive — photoPrice Reduced90Active

    $1,375,000

    5 bd · 4 ba · 3,668 sqft

    206 Landing Drive, Brewster, MA

    Jeffrey E Cusack · Cove Road Real Estate

  • 2019 Main Street — photo11Active

    $1,200,000

    5 bd · 8 ba · 3,233 sqft

    2019 Main Street, Brewster, MA

  • 55 Bayview Drive — photo71Active

    $2,400,000

    4 bd · 6 ba · 4,250 sqft

    55 Bayview Drive, Brewster, MA

    Jeffrey E Cusack · Cove Road Real Estate

  • 232 Robbins Hill Road — photoPrice Reduced39Active

    $2,492,000

    3 bd · 2 ba · 1,502 sqft

    232 Robbins Hill Road, Brewster, MA

    Tracey E Oringer · Kinlin Grover Compass

  • 58 Old Chatham Rd — photoPrice ReducedOpen house Fri, Oct 2 · 4:00 PM39Active

    $1,399,000

    2 bd · 4 ba · 2,955 sqft

    58 Old Chatham Rd, Brewster, MA

    Andrea Lousararian · William Raveis R.E. & Home Services

  • 12
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    L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Listing data & MLS disclosures

    Cape Cod & Islands Association of REALTORS
    The data relating to real estate for sale on this site comes from the Broker Reciprocity of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than the brokerage firm owning this website are marked with the IDX Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor the brokerage firm owning this website shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright © 2026 Cape Cod & Islands Multiple Listing Service, Inc. All Rights Reserved.
    MLS Property Information Network (MLS PIN)
    The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
    Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-10-01 23:38:00 UTC

    Brewster housing market

    August 2026 · This period is still settling

    Selling at 99.1% of asking price

    Buyers here are paying below asking. MLS · 18 sales · as of Aug 31, 2026

    Homes on the market · MLS, as of Aug 31, 2026

    Median list price
    $975,000
    Homes for sale
    39
    Median days on market
    12 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    19.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 13, 2026

    Median home size
    1,631 sq. ft.

    Brewster, MA community profile

    Area
    25.5 sq. mi.

    Source: HJN community data