10,645

Brewster, MA Homes

Section Image
  • 79 Chilton Ln, Brewster, MA 02631
    79 Chilton Ln, Brewster, MA 02631
    79 Chilton Ln, Brewster, MA 02631
    /27

    $409,000 Sold Aug 05, 2025

    79 Chilton Ln, Brewster, MA 02631

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

    Last Sold Summary

    • 2% Below List Price
    • $437/SF
    • 66 Days On Market

    Current Estimated Value $409,524

    Last Listing Agent Dawn Andalft-Newman Property Cape Cod

    79 Chilton Ln, Brewster, MA 02631
    • 59 Valley Rd, Brewster, MA 02631
      59 Valley Rd, Brewster, MA 02631
      59 Valley Rd, Brewster, MA 02631
      /42

      Est $877,488 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,108 Sq Ft

      59 Valley Rd, Brewster, MA 02631

      59 Valley Rd, Brewster, MA 02631
  • 0 Canoe Pond Dr, Brewster, MA 02631
    0 Canoe Pond Dr, Brewster, MA 02631
    0 Canoe Pond Dr, Brewster, MA 02631
    /13

    $375,000

    • Land
    • 0.37 Acre
    • $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 Linger Longer Cartway, Brewster, MA 02631
    40 Linger Longer Cartway, Brewster, MA 02631
    40 Linger Longer Cartway, Brewster, MA 02631
    /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
    • 14 Whidah Way, Brewster, MA 02631
      14 Whidah Way, Brewster, MA 02631
      14 Whidah Way, Brewster, MA 02631
      /83

      Est $2,083,113 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,318 Sq Ft

      14 Whidah Way, Brewster, MA 02631

      14 Whidah Way, Brewster, MA 02631
  • 1580 Main St, Brewster, MA 02631
    1580 Main St, Brewster, MA 02631
    1580 Main St, Brewster, MA 02631
    /20

    $729,900

    • 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
  • 144 Eaton Ln, Brewster, MA 02631
    144 Eaton Ln, Brewster, MA 02631
    144 Eaton Ln, 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

    Last Listing Agent A Cape Life Today Real Estate

    144 Eaton Ln, Brewster, MA 02631
    • 1619 Long Pond Rd, Brewster, MA 02631
      1619 Long Pond Rd, Brewster, MA 02631
      1619 Long Pond Rd, Brewster, MA 02631
      /35

      Est $534,712 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,056 Sq Ft

      1619 Long Pond Rd, Brewster, MA 02631

      1619 Long Pond Rd, Brewster, MA 02631
  • 1861 Main St, Brewster, MA 02631
    1861 Main St, Brewster, MA 02631
    1861 Main St, Brewster, MA 02631
    /42

    $2,995,000

    • 16 Beds
    • 15.5 Baths
    • 7,922 Sq Ft

    1861 Main St, Brewster, MA 02631

    Welcome to the distinguished Old Manse Inn, a romantic and historic Sea Captain's manor in the heart of Brewster, Cape Cod. A proud member of the Select Registry, this premier Bed and Breakfast blends timeless charm with modern comforts. The property offers 12 uniquely decorated guest rooms with en-suite baths, three elegant common areas, a dedicated dining room, and a fully equipped commercial

    Eva Scott Gibson Sotheby's International Realty

    1861 Main St, Brewster, MA 02631
  • 44 Trevor Ln Unit 44, Brewster, MA 02631
    44 Trevor Ln Unit 44, Brewster, MA 02631
    44 Trevor Ln Unit 44, Brewster, MA 02631
    /31

    $601,000 Sold May 09, 2025

    44 Trevor Ln Unit 44, Brewster, MA 02631

    • 2 Beds
    • 2 Baths
    • 1,157 Sq Ft
    • Built 1985

    Last Sold Summary

    • 10% Above List Price
    • $519/SF
    • 6 Days On Market

    Last Listing Agent William Raye Gibson Sotheby's International Realty

    44 Trevor Ln Unit 44, Brewster, MA 02631
    • 17 Hamilton Cartway, Brewster, MA 02631
      17 Hamilton Cartway, Brewster, MA 02631
      17 Hamilton Cartway, Brewster, MA 02631
      /42

      Est $1,587,530 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 3,218 Sq Ft

      17 Hamilton Cartway, Brewster, MA 02631

      17 Hamilton Cartway, Brewster, MA 02631
  • 184 Barons Way, Brewster, MA 02631
    184 Barons Way, Brewster, MA 02631
    184 Barons Way, Brewster, MA 02631
    /47

    $793,900 Pending

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

    184 Barons Way, Brewster, MA 02631

    This charming four-bedroom, two-bath home offers exceptional flexibility with two bedrooms on the first floor and two spacious bedrooms upstairs, plus abundant closet space throughout. The well-appointed kitchen features stainless steel appliances and flows seamlessly into a separate dining area, perfect for everyday living and entertaining. The inviting living room is highlighted by a

    Susan Baker Gibson Sotheby's International Realty

    184 Barons Way, Brewster, MA 02631
  • 35 Pine Bay Ln, Brewster, MA 02631
    35 Pine Bay Ln, Brewster, MA 02631
    35 Pine Bay Ln, 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 $837,035

    Last Listing Agent Eric Buliung LAER Realty Partners

    35 Pine Bay Ln, Brewster, MA 02631
    • 26 Oliver Dr, Brewster, MA 02631
      26 Oliver Dr, Brewster, MA 02631
      26 Oliver Dr, Brewster, MA 02631
      /58

      Est $2,088,720 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,929 Sq Ft

      26 Oliver Dr, Brewster, MA 02631

      26 Oliver Dr, Brewster, MA 02631
  • 737 Thousand Oaks Dr, Brewster, MA 02631
    737 Thousand Oaks Dr, Brewster, MA 02631
    737 Thousand Oaks Dr, Brewster, MA 02631
    /24

    $420,850 Pending

    • 2 Beds
    • 2 Baths
    • 1,302 Sq Ft

    737 Thousand Oaks Dr, Brewster, MA 02631

    3 bedroom ranch per field card with a 2 bedroom layout just waiting to be finished. Come and finish it the way that you want. Brewster Bay beaches, freshwater ponds, the bike path, mini golf, tennis courts, restaurants, Brewster General Store, Captain's Golf Course and Cape League Baseball is all near by..

    Team 300 Today Real Estate

    737 Thousand Oaks Dr, Brewster, MA 02631
  • 81 Whidah Way, Brewster, MA 02631
    81 Whidah Way, Brewster, MA 02631
    81 Whidah Way, Brewster, MA 02631
    /60

    $1,995,000 Sold May 09, 2025

    81 Whidah Way, Brewster, MA 02631

    • 5 Beds
    • 3.5 Baths
    • 4,714 Sq Ft
    • Built 2003

    Last Sold Summary

    • $423/SF
    • 7 Days On Market

    Current Estimated Value $2,079,493

    Last Listing Agent Dolores Alberti Gibson Sotheby's International Realty

    81 Whidah Way, Brewster, MA 02631
    • 61 Oliver Dr, Brewster, MA 02631
      61 Oliver Dr, Brewster, MA 02631
      61 Oliver Dr, Brewster, MA 02631
      /73

      Est $1,746,121 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 4,102 Sq Ft

      61 Oliver Dr, Brewster, MA 02631

      61 Oliver Dr, Brewster, MA 02631
  • 16 Commons Way, Brewster, MA 02631
    16 Commons Way, Brewster, MA 02631
    16 Commons Way, Brewster, MA 02631
    /36

    $719,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,838 Sq Ft

    16 Commons Way, Brewster, MA 02631

    Welcome to this ranch style home in the heart of Brewster. Just off Millstone Road, it offers 3 bedrooms and 2 full baths with hardwood floors in the living room and open formal dining room and wall to wall carpet in the bedrooms. A large eat-in kitchen showcases cathedral ceilings and a sunny bay window making it bright and inviting. Nice deck off of the formal dining room area is perfect for

    Richard Ormon McDevitt REALTORS

    16 Commons Way, Brewster, MA 02631
  • 19 Fishermans Landing Rd, Brewster, MA 02631
    19 Fishermans Landing Rd, Brewster, MA 02631
    19 Fishermans Landing Rd, 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 $858,733

    Last Listing Agent Amber Dauphinais Orleans Village Properties, LLC

    19 Fishermans Landing Rd, Brewster, MA 02631
    • 199 Timberlane Dr, Brewster, MA 02631
      199 Timberlane Dr, Brewster, MA 02631
      199 Timberlane Dr, Brewster, MA 02631
      /44

      Est $751,788 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,612 Sq Ft

      199 Timberlane Dr, Brewster, MA 02631

      199 Timberlane Dr, Brewster, MA 02631
  • 100 Fletcher Ln Unit E, Brewster, MA 02631
    100 Fletcher Ln Unit E, Brewster, MA 02631
    100 Fletcher Ln Unit E, Brewster, MA 02631
    /34

    $255,000 Pending

    • 1 Bed
    • 1 Bath
    • 579 Sq Ft

    100 Fletcher Ln Unit E, Brewster, MA 02631

    Welcome to your perfect escape in the highly sought-after Ocean Edge Resort community in Brewster. This beautifully updated one-bedroom, one-bathroom condo offers a flexible opportunity—as a summer retreat, investment property, or comfortable year-round home. Step inside to a refreshed interior featuring a modern kitchen with brand-new appliances and elegant quartz countertops. Enjoy tranquil

    Nicole Callahan Silverstone Capeside Realty Group

    100 Fletcher Ln Unit E, Brewster, MA 02631
  • 70 Run Hill Rd, Brewster, MA 02631
    70 Run Hill Rd, 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

    Last Listing Agent Andrea Howell William Raveis Harwich Port

    70 Run Hill Rd, Brewster, MA 02631
    • 549 S Orleans Rd, Brewster, MA 02631
      549 S Orleans Rd, Brewster, MA 02631
      549 S Orleans Rd, Brewster, MA 02631
      /30

      Est $782,687 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,783 Sq Ft

      549 S Orleans Rd, Brewster, MA 02631

      549 S Orleans Rd, Brewster, MA 02631
  • 102 Wildwood Rd, Brewster, MA 02631
    102 Wildwood Rd, Brewster, MA 02631
    102 Wildwood Rd, Brewster, MA 02631
    /42

    $889,000 Pending

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

    102 Wildwood Rd, Brewster, MA 02631

    This charming Cape-style home, set on a private .51 acre lot, offers a delightful blend of comfort and character. With 2,044 square feet of living space on the main floors, it features 8 rooms, 3 bedrooms and 2 full baths, plus a finished lower level.You will love the wide pine floors that flow through many rooms. A custom kitchen, with a window seat and an island breakfast bar, perfect for

    Jan Pulit Kinlin Grover Compass

    102 Wildwood Rd, Brewster, MA 02631
  • 105 Middlecott Ln Unit 105, Brewster, MA 02631
    105 Middlecott Ln Unit 105, Brewster, MA 02631
    105 Middlecott Ln Unit 105, 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

    Last Listing Agent Nancy Whitehurst Realty Executives

    105 Middlecott Ln Unit 105, Brewster, MA 02631
    • 45 John Myrick Cir, Brewster, MA 02631
      45 John Myrick Cir, Brewster, MA 02631
      45 John Myrick Cir, Brewster, MA 02631
      /32

      Est $1,125,036 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,415 Sq Ft

      45 John Myrick Cir, Brewster, MA 02631

      45 John Myrick Cir, Brewster, MA 02631
  • 0 Commons Way Unit 22504099, Brewster, MA 02631
    0 Commons Way Unit 22504099, Brewster, MA 02631
    0 Commons Way Unit 22504099, Brewster, MA 02631
    /12

    $319,999

    • Land
    • 0.58 Acre
    • $551,722 per Acre

    0 Commons Way Unit 22504099, Brewster, MA 02631

    Tucked near the end of the sought-after Commons Way neighborhood in Brewster, this spacious 0.58-acre (25,100 sq ft) lot offers the perfect setting for your Cape Cod dream home. Located in a quiet, established residential area, the property provides a balance of privacy and community charm.The lot has already passed a perc test and comes with approved septic plans for a 3-bedroom home with an

    Amber Dauphinais Orleans Village Properties, LLC

    0 Commons Way Unit 22504099, Brewster, MA 02631
  • 236 Yankee Dr, Brewster, MA 02631
    236 Yankee Dr, Brewster, MA 02631
    236 Yankee Dr, 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 $772,501

    Last Listing Agent Amy Harbeck Kinlin Grover Compass

    236 Yankee Dr, Brewster, MA 02631
    • 39 Moss Ln, Brewster, MA 02631
      39 Moss Ln, Brewster, MA 02631
      39 Moss Ln, Brewster, MA 02631
      /40

      Est $941,008 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,975 Sq Ft

      39 Moss Ln, Brewster, MA 02631

      39 Moss Ln, Brewster, MA 02631
  • 127 Eaton Ln Unit 127, Brewster, MA 02631
    127 Eaton Ln Unit 127, Brewster, MA 02631
    127 Eaton Ln Unit 127, Brewster, MA 02631
    /25

    $454,900 Pending

    • 2 Beds
    • 2 Baths
    • 935 Sq Ft

    127 Eaton Ln Unit 127, Brewster, MA 02631

    Beautifully updated 1st floor condo at Ocean Edge, being offered fully furnished and ready for immediate enjoyment. Overlooking the 5th hole of the Ocean Edge golf course, this inviting home perfectly blends comfort, convenience and coastal charm.Thoughtfully updated throughout, the condo features mini-split systems for efficient heating and air conditioning, new flooring, an additional kitchen

    Susie Bent Greer Real Estate, LLC

    127 Eaton Ln Unit 127, Brewster, MA 02631
  • 40 Eaton Ln, Brewster, MA 02631
    40 Eaton Ln, Brewster, MA 02631
    40 Eaton Ln, 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 $392,566

    Last Listing Agent Leighton Team Keller Williams Realty

    40 Eaton Ln, Brewster, MA 02631
    • 113 Greenland Pond Rd, Brewster, MA 02631
      113 Greenland Pond Rd, Brewster, MA 02631
      113 Greenland Pond Rd, Brewster, MA 02631
      /65

      Est $1,114,373 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,488 Sq Ft

      113 Greenland Pond Rd, Brewster, MA 02631

      113 Greenland Pond Rd, Brewster, MA 02631
  • 0 Pine Grove Rd Unit 73397945, Brewster, MA 02631
    0 Pine Grove Rd Unit 73397945, Brewster, MA 02631
    0 Pine Grove Rd Unit 73397945, Brewster, MA 02631
    /3

    $289,000

    • Land
    • 0.44 Acre
    • $656,818 per Acre

    0 Pine Grove Rd Unit 73397945, Brewster, MA 02631

    Financing Available For This Land!! This is a rare opportunity to own a fully approved, buildable lot on the border of Brewster & Orleans. This lot has had all engineering done to it, including approval for a 1560 sqft single family ranch style home—no delays, no hassles, just close and start building. Located in a peaceful, well-established neighborhood, this lot offers the perfect blend of

    Matthew Medeiros Millennium Realty Firm, LLC

    0 Pine Grove Rd Unit 73397945, Brewster, MA 02631
  • 89 Cliff Pond Rd, Brewster, MA 02631
    89 Cliff Pond Rd, Brewster, MA 02631
    89 Cliff Pond 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 $697,208

    Last Listing Agent Tracey Oringer Kinlin Grover Compass

    89 Cliff Pond Rd, Brewster, MA 02631
    • 237 Jonathans Way, Brewster, MA 02631
      237 Jonathans Way, Brewster, MA 02631
      237 Jonathans Way, Brewster, MA 02631
      /28

      Est $531,999 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft

      237 Jonathans Way, Brewster, MA 02631

      237 Jonathans Way, Brewster, MA 02631
  • 63 Trevor Ln Unit 63, Brewster, MA 02631
    63 Trevor Ln Unit 63, Brewster, MA 02631
    63 Trevor Ln Unit 63, Brewster, MA 02631
    /20

    $482,000 Pending

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

    63 Trevor Ln Unit 63, Brewster, MA 02631

    Welcome to 63 Trevor Lane, a ''C'' style townhome in Ocean Edge Resort. This property has enjoyed single ownership for 40 years. With plenty of natural light, this home has been thoughtfully updated over the years with a new storm door, newer wood laminate flooring, recessed lighting in the DR/LR and a dual inverter wall unit for heating and cooling. A newer Pella slider in the LR opens to a

    Deborah Collins Cutter Luxe Living

    63 Trevor Ln Unit 63, Brewster, MA 02631
  • 55 Wayside Dr, Brewster, MA 02631
    55 Wayside Dr, Brewster, MA 02631
    55 Wayside Dr, 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
    • 15 Oriole Cir, Brewster, MA 02631
      15 Oriole Cir, Brewster, MA 02631
      15 Oriole Cir, Brewster, MA 02631
      /37

      Est $652,998 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,376 Sq Ft

      15 Oriole Cir, Brewster, MA 02631

      15 Oriole Cir, Brewster, MA 02631
  • 14 Howland Cir Unit 14, Brewster, MA 02631
    14 Howland Cir Unit 14, Brewster, MA 02631
    14 Howland Cir Unit 14, Brewster, MA 02631
    /33

    $585,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    14 Howland Cir Unit 14, Brewster, MA 02631

    Welcome to this inviting A-style townhome at Ocean Edge offering two bedrooms, two baths, and a versatile loft ideal for extra living space or hosting guests. The home features three new mini-splits, stainless steel appliances, updated baths, a cozy fireplace, beautiful hardwood floors, new carpeting in the loft and bedrooms, and full size washer & dryer. Step outside to a private backyard,

    Suzanne Newton Kinlin Grover Compass

    14 Howland Cir Unit 14, Brewster, MA 02631
  • 180 W H Besse Cartway, Brewster, MA 02631
    180 W H Besse Cartway, Brewster, MA 02631
    180 W H Besse Cartway, Brewster, MA 02631
    /91

    $1,662,500 Sold Apr 14, 2025

    180 W H Besse Cartway, Brewster, MA 02631

    • 4 Beds
    • 3.5 Baths
    • 3,058 Sq Ft
    • Built 1965

    Last Sold Summary

    • 24% Below List Price
    • $544/SF
    • 203 Days On Market

    Last Listing Agent Jeff Cusack Cove Road Real Estate

    180 W H Besse Cartway, Brewster, MA 02631

Showing Results 41 - 80, Page 2 of 18

Massachusetts Barnstable County Brewster

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