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Luxury Homes in Brewster, MA
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33 listings
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3 bedsNew constructionWith a pool

Luxury Homes in Brewster, MA

Luxury Homes in Brewster, MA

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16 of 33 Listings
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Luxury Homes in Brewster, MA

16 of 33 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
  1. 58 Fox Crossing Road — photoNew46Active

    $1,495,000

    4 bd · 5 ba · 3,506 sqft

    58 Fox Crossing Road, Brewster, MA

    Leighton Team · Keller Williams Realty

  2. 12 Pond Street — photo53Active

    $1,325,000

    3 bd · 3 ba · 2,384 sqft

    12 Pond Street, Brewster, MA

    Dee Higgins · Gibson Sotheby's International Realty

  3. 101 Spruce Run Drive — photo42Active

    $1,595,000

    4 bd · 3 ba · 2,912 sqft

    101 Spruce Run Drive, Brewster, MA

  4. 79 Old Freemans Way — photo41Active

    $1,100,000

    3 bd · 2 ba · 1,981 sqft

    79 Old Freemans Way, Brewster, MA

    David L White · OwnerEntry.com

  5. 575 Harwich Road — photo60Active

    $1,200,000

    4 bd · 3 ba · 2,327 sqft

    575 Harwich Road, Brewster, MA

    Leighton Team · Keller Williams Realty

  6. 674 Crowells Bog Road — photo52Active

    $3,399,000

    6 bd · 5 ba · 6,048 sqft

    674 Crowells Bog Road, Brewster, MA

    Natalia M Weiner · Gibson Sotheby's International Realty

  7. 80 Upland Circle — photoPrice Reduced39Active

    $1,550,000

    3 bd · 3 ba · 3,322 sqft

    80 Upland Circle, Brewster, MA

  8. 155 Damon Road — photoPrice Reduced76Active

    $1,249,999

    4 bd · 4 ba · 3,404 sqft

    155 Damon Road, Brewster, MA

    Jim & Regina Augat · Kinlin Grover Compass

  9. 69 Martingale Lane — photo47Active

    $1,450,000

    4 bd · 4 ba · 3,747 sqft

    69 Martingale Lane, Brewster, MA

    Tracey E Oringer · Kinlin Grover Compass

  10. 44 Brier Lane — photo33Active

    $1,479,000

    4 bd · 3 ba · 2,249 sqft

    44 Brier Lane, Brewster, MA

    Nadine L Magazu · Kinlin Grover Compass

  11. 37 Autumn Court — photo99Active

    $2,000,000

    4 bd · 4 ba · 3,406 sqft

    37 Autumn Court, Brewster, MA

    DREAM International · Dream Homes & Estates, Inc.

  12. 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

  13. 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

  14. 2019 Main Street — photo11Active

    $1,200,000

    5 bd · 8 ba · 3,233 sqft

    2019 Main Street, Brewster, MA

  15. 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

  16. 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

12

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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.
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Listing information ©2026 MLS Property Information Network, Inc®. All Rights Reserved. Last Updated: 2026-09-01 07:09:00 UTC
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Brewster, MA community profile

    Area
    25.5 sq. mi.

    Source: HJN community data

    Brewster housing market

    August 2026 · This period is still settling

    Selling at 99.3% of asking price

    Buyers here are paying below asking. MLS · 17 sales · as of Aug 28, 2026

    Homes on the market · MLS, as of Aug 28, 2026–Aug 31, 2026

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

    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.