2 Windswept Cir, Brewster, NY 10509
OFF MARKET

2 Windswept Cir
Brewster, NY 10509

  • 4 Beds
  • 2.5 Baths
  • 2,550 sqft (on 1.46 acres)

$831,000

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $5,743/mo*
Refinance Your Home

$831,000

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $5,743/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,550 sqft
(on 1.46 acres)

Local Information

  • Map ViewExplore the area around 2 Windswept Cir.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
1.46 acres
Living Area
2,550 sqft
Price/Sqft
$326
Parking
Garage

About this House

This single-family home is located at 2 Windswept Cir, Brewster, NY. 2 Windswept Cir is in Brewster, NY and in ZIP code 10509. This property has 4 bedrooms, 3 bathrooms and approximately 2,550 sqft of floor space. This property has a lot size of 1.46 acres and was built in 1994.
2 Windswept Cir, Brewster, NY 10509 is a 4 bedroom, 3 bathroom, 2,550 sqft single-family home built in 1994. It last sold for $530,000 on Oct 31, 2016. It is currently off market. The Trulia Estimate is $831,000, with a rent estimate of $4,873/month.

Home Details for 2 Windswept Cir

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet
Heating & Cooling
Heating: Heat Pump, OilAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
DeckExterior: Vinyl
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.46 acres

Price History for 2 Windswept Cir

DatePriceEventSource
10/31/2016$530,000Sold
N/A
02/25/2016$529,999ListingRemovedAgent Provided
02/08/2016$529,999PriceChange
Agent Provided
01/04/2016$549,999Listed For SaleAgent Provided
11/27/2000$430,000Sold
N/A
08/14/1998$315,000Sold
N/A
04/03/1995$304,000Sold
N/A
03/29/1994$110,000Sold
N/A

Market trends in Brewster

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
67
7MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax
Assessment$759,500
Home facts updated by county records

Comparable Sales for 2 Windswept Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 Windswept Circle, Brewster, NY
0.10
Single-Family Home
$770,000
04/27/26
4
2.5
3,080
50 Maple Wood Drive, Brewster, NY
0.43
Single-Family Home
$635,000
11/25/25
3
3.5
2,542
81 Maple Wood Drive, Brewster, NY
0.56
Single-Family Home
$760,000
09/29/25
4
4
3,500
51 Sherwood Hill Road, Brewster, NY
0.71
Single-Family Home
$760,000
02/02/26
3
3.5
3,356
424 Gage Road, Brewster, NY
0.52
Single-Family Home
$854,000
01/23/26
4
2.5
3,406
2 Sherwood Hill Road, Brewster, NY
0.56
Single-Family Home
$1,112,500
09/15/25
4
3.5
3,800
747 Milltown Road, Brewster, NY
1.17
Single-Family Home
$575,000
02/04/26
3
3
2,613
1105 Farmdale Road, Brewster, NY
0.52
Single-Family Home
$455,000
10/14/25
2
2.5
2,632
667 Milltown Road, Brewster, NY
1.29
Single-Family Home
$675,000
05/06/26
3
3
2,695
1704 Windsor Lane, Brewster, NY
0.50
Single-Family Home
$415,000
12/03/25
2
1.5
1,654

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 2 Windswept Cir.
View nearby schools on GreatSchools
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 134 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 83 % Say parking is easy

  • 75 % Say there's holiday spirit

  • 75 % Say yards are well-kept

  • 74 % Say it's dog friendly

  • 72 % Say there's wildlife

  • 66 % Say it's quiet

  • 64 % Say people would walk alone at night

  • 62 % Say they plan to stay for at least 5 years

  • 61 % Say kids play outside

  • 54 % Say neighbors are friendly

  • 47 % Say there are community events

  • 39 % Say streets are well-lit

  • 37 % Say it's walkable to grocery stores

  • 35 % Say it's walkable to restaurants

  • 27 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Kate M
    "5 minutes to the train then hour and half. It’s challenging because there is no work-life balance. Find a job nearby "
    0
    Flag
  • Iracemaalmeida16
    "I live in this area for about 3 years, it’s safe and our neighbors are friendly. I have a few stores and eating places near by and I’ve been enjoying living here. "
    1
    Flag
  • Trulia User
    "Southeast/Brewster Hill is a very quiet, safe, neighborly place to live. Downtown Brewster leaves something to be desired which is a shame for the amount of taxes homeowners pay. "
    3
    Flag
  • Trulia User
    "There are a number of walking trails in the area but you need to be in a neighborhood for it to be safe to walk your dog. A lot of secondary roads with speeding drivers and no sidewalks."
    1
    Flag
  • Trulia User
    "I living in the neighborhood for 11 years we love it very good school restaurants and very close to anything like supermarket Hospitals "
    1
    Flag
  • Trulia User
    "Wide, quiet streets with low traffic lead to the Empire bike trail. People are out walking their dogs all day long."
    0
    Flag
  • Apryl.bedenbaugh
    "Neighbors really take the time to know who you are. Lake is at end of the street. Super quiet. Very private. "
    5
    Flag
  • Brian A.
    "I grew up here it’s a good town. People are very nice. Can still come to the city. Also very bucolic"
    1
    Flag
  • Cindy P.
    "Brewster is a beautifully blended Community and the schools are phenomenal. Hope to live here for a very long time. "
    2
    Flag
  • Maria S.
    "lots of space for dogs to run around in and distance between houses so barking is ok so its a great place for every pet "
    2
    Flag
  • MAS
    "farmers market, founders day, concerts including a music festival are just a few of the events that we have, plus firehouse events and baseball little league "
    6
    Flag
  • mas
    "lots of local events including music, art shows, events at public library, baseball leaugue, firehouse events, annual founders day, etc plus farmers market..."
    12
    Flag
  • Rebecca K.
    "There’s plenty of land or places to walk your dog, dog parks nearby are well kept and people are friendly "
    1
    Flag
  • Chiefking55
    "Very convenient and comfortable. It is also an express stop so your commute will be shorter than you anticipated. "
    1
    Flag
  • Trulia User
    "During the Summer grass cutting is not done ion a regular schedule and when it is done the outcome is very sloppy. My dog has limited spaces to safely walk."
    4
    Flag
  • Brendan C.
    "I like it a lot it is very short I only walk about 5 minutes lost people have to drive to work around here "
    0
    Flag
  • HomeOwner124
    "Have to get on the highway EXTREMELY early not to catch traffic, otherwise by 8am you’re toast. Might as well stay home..."
    4
    Flag
  • Erika L. T.
    "I mean we don’t have potlucks but we mind our business and still say hi from our driveways. It’s very laid back. "
    2
    Flag
  • Erika L. T.
    "There are lots of dogs and their owners walking around all the time. Great neighborhood for a good walk with your dogs and everyone is very friendly and welcoming. "
    1
    Flag
  • Rrockscouter
    "Tight community. Neighbors look out for each other. We don’t tolerate disruptive behaviors. Most are multigenerational homes. "
    0
    Flag
  • Frances B.
    "Nice, quiet neighborhood. Those you don't know mind their business but are friendly, those you know are super kind and take care of eachother. I've lived her for over 20 years."
    0
    Flag
  • Luci L.
    "I’ve lived here for three years and everyone is so friendly! It’s one of the few neighborhoods where the taxes are affordable, Putnam lake is great!"
    0
    Flag
  • Cynthia W.
    "Suburban neighborhood!Great location close to 684. Easy commute, "
    1
    Flag
  • Ssal
    "I have a friend that lives in Reed Farm and simply loves it. It is 3 minutes from the highway and the train. It is clean, friendly with lots of anemities. When I am ready to downsiize I will live there also."
    0
    Flag
  • pjgoor
    "I grew up here and the area is beautiful, friendly, commuter convenient to anywhere, has lake rights, golf course, community house with activities, great neighbors and a safe place to stroll, bike ride, swim, boating and lots more."
    1
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Air Conditioning

6 rentals with air conditioning in Brewster, NY

Homes for sale near 2 Windswept Cir

Skip to last item
Skip to first item

Off Market Homes Near 2 Windswept Cir

Skip to last item
Skip to first item