24 Windswept Rd
Brewster, MA 02631
- 3 Beds
- 3 Baths
- 1,764 sqft (on 0.35 acres)
$875,300
as of Jul 6, 2026
$875,300
as of Jul 6, 2026
3 Beds
3 Baths
1,764 sqft
(on 0.35 acres)
Local Information
-- mins to
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
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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 |
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Exterior Home Features Roof: AsphaltDeckExterior: Shingle Not Wood, VinylPatio |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1995Year Updated: 2011 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
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Units in Building: 1 |
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Lot Area: 0.35 acres |
Price History for 24 Windswept Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 10/22/2019 | $541,900 | Sold | N/A |
| 09/10/2019 | $549,900 | Pending | Agent Provided |
| 09/05/2019 | $549,900 | Listed For Sale | Agent Provided |
| 11/21/2014 | $345,000 | Sold | CCIMLS #21408339 |
| 09/05/2014 | $363,500 | Listed For Sale | Agent Provided |
| 06/16/2014 | $389,900 | ListingRemoved | Agent Provided |
| 04/23/2014 | $389,900 | PriceChange | Agent Provided |
| 12/11/2013 | $400,000 | Listed For Sale | Agent Provided |
Market trends in Brewster
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
5MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 24 Windswept Rd.
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.
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