24 Windswept Rd, Brewster, MA 02631
Property image
Property image
OFF MARKET

24 Windswept Rd
Brewster, MA 02631

  • 3 Beds
  • 3 Baths
  • 1,764 sqft (on 0.35 acres)

$875,300

Trulia Estimate
as of Jul 6, 2026

$875,300

Trulia Estimate
as of Jul 6, 2026
3 Beds
3 Baths
1,764 sqft
(on 0.35 acres)

Local Information

  • Map ViewExplore the area around 24 Windswept Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Fall in LOVE with this stunning property situated in the desirable neighborhood of Cliff Pond Estates. The perfect home for entertaining family and friends! Open-concept kitchen and living spaces feature a massive island, sun-drenched living room, and generously sized dining area. Vaulted ceilings and expansive windows in the family room invite breathtaking views of conservation land, with plenty of space for everyone to gather. Retreat to the serene master with full en-suite bath. Two additional bedrooms and a second full bathroom make up the remainder of the upper level. Located in the fully finished lower level is a fourth bedroom, third full bathroom, second living room, and bonus sunroom with views of the expansive backyard. Cool off in the outdoor shower. Enjoy grilling on the deck adjacent to the inviting fire pit and entertain guests on the spacious patio. Nickerson, Cliff Pond, and CCRT all just steps away from the front door. Come see for yourself! STRONG RENTAL HISTORY.
24 Windswept Rd, Brewster, MA 02631 is a 3 bedroom, 3 bathroom, 1,764 sqft single-family home built in 1995. It last sold for $541,900 on Oct 22, 2019. It is currently off market. The Trulia Estimate is $875,300, with a rent estimate of $4,116/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 24 Windswept Rd

Interior Features

Interior Details
BasementNumber of Rooms: 5Types of Rooms: Sun Room
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Linoleum Vinyl
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle Not Wood, VinylPatio
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1995Year Updated: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.35 acres

Price History for 24 Windswept Rd

DatePriceEventSource
10/22/2019$541,900Sold
N/A
09/10/2019$549,900PendingAgent Provided
09/05/2019$549,900Listed For SaleAgent Provided
11/21/2014$345,000Sold
CCIMLS #21408339
09/05/2014$363,500Listed For SaleAgent Provided
06/16/2014$389,900ListingRemovedAgent Provided
04/23/2014$389,900PriceChange
Agent Provided
12/11/2013$400,000Listed For SaleAgent Provided

Market trends in Brewster

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
51
5
MoM
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Property Tax and Assessment

Year2025
Tax$5,021
Assessment$729,800
Home facts updated by county records

Comparable Sales for 24 Windswept Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.06
Single-Family Home
$705,000
07/25/25
3
2
1,192
0.33
Single-Family Home
$700,000
04/30/26
3
2
1,838
0.28
Single-Family Home
$495,000
01/23/26
3
1
960
0.67
Single-Family Home
$505,000
01/21/26
3
2
1,278
0.59
Single-Family Home
$781,000
09/12/25
3
2
1,460
0.64
Single-Family Home
$699,000
09/26/25
3
2
1,672
0.78
Single-Family Home
$790,000
04/24/26
3
2.5
2,306
0.69
Single-Family Home
$800,000
09/19/25
3
2
1,764
0.64
Single-Family Home
$720,000
08/22/25
4
2
1,472
0.86
Single-Family Home
$725,000
11/21/25
3
2
1,680

Nearby homes

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Assigned Schools

These are the assigned schools for 24 Windswept Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Brewster

At least 52 Trulia users voted on each feature.
  • 93 % Say car is needed

  • 87 % Say parking is easy

  • 87 % Say it's quiet

  • 86 % Say it's dog friendly

  • 83 % Say yards are well-kept

  • 78 % Say people would walk alone at night

  • 76 % Say there's wildlife

  • 66 % Say there's holiday spirit

  • 63 % Say they plan to stay for at least 5 years

  • 57 % Say neighbors are friendly

  • 54 % Say kids play outside

  • 28 % Say there are community events

  • 27 % Say it's walkable to restaurants

  • 24 % Say there are sidewalks

  • 24 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Rheanna Hastings
    "Lots of families and a beautiful safe place to raise children with lots of outdoor space and things to do."
  • Skylar R.
    "Walking your dog and taking them down to the pond for a quick swim is very convenient located right on the bike path which is always a great spot to walk dogs."
  • Rheanna H.
    "The beach! Low tide, the stores, the restaurants and the farmers markets. Cape Cod is a one of a kind place. "
  • Deboravaughan
    "I really like it!! It is clean, friendly and close to the beach. Houses are well maintained and renters during the summer are great."
  • Peloquinbill
    "it is a small quaint neighborhood where everyone is friendly. Neighbors are always visiting and helping each other."
  • scarroll32
    "Ideal Cape Cod location For Golfing or swimming in salt water Cape Cod BAY or one of Brewster fresh water ponds Boating fishing "
  • Rick S.
    "This is a great town. Rural living, close to all the action of Dennis, Yarmouth and Hyannis. Easy access to the loweer Cape too!. "
  • Cathihill
    "Ocean Edge is a great resort community with obtainable membership fees. However, you do not have to be a member to live in a ocean edge. Billington II is the most quiet and least congested of the town home communities at Ocean Edge."
  • Teresa M.
    "Beautiful, quiet, peaceful place to live. The schools are excellent and the recreation areas amazing. The association beaches are beautiful and limited to only 11 families. The pool is a joy."
  • Nj3167
    "Quite, well manacured properties, very little traffic, quant, old historic Sea Captain's Homes restored into B&B's, Resturants,slower pace of life. Great for Retires."

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Apartments for Rent

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Homes for sale near 24 Windswept Rd

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Off Market Homes Near 24 Windswept Rd

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