4 Windswept Cir, Brewster, NY 10509
OFF MARKET

$807,500

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,688 sqft (on 1.18 acres)

4 Windswept Cir, Brewster, NY 10509

Est. Refi. Payment $5,697/mo*
Refinance Your Home
Currently Off Market - Sold May 18, 1995 for $100,000

Home Value

Trulia Estimate
$808K
Since last month
Increased$3K (+0.4%)
Since last year
Increased$41K (+5.3%)
Since last sale
Increased$709K (+708.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +66% in the last 10 years
MonthEstimated value
2026
August 2026$809K
August 2026$808K
July 2026$806K
June 2026$804K
May 2026$799K
April 2026$781K
March 2026$782K
February 2026$752K
January 2026$761K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 Windswept Circle, Brewster, NY
0.05
Single-Family Home
$770,000
04/27/26
4
2.5
3,080
50 Maple Wood Drive, Brewster, NY
0.47
Single-Family Home
$635,000
11/25/25
3
3.5
2,542
282-284 Doansburg Road, Brewster, NY
0.25
Single-Family Home
$850,000
08/28/26
4
3
4,774
81 Maple Wood Drive, Brewster, NY
0.61
Single-Family Home
$760,000
09/29/25
4
4
3,500
51 Sherwood Hill Road, Brewster, NY
0.77
Single-Family Home
$760,000
02/02/26
3
3.5
3,356
40 Farrell Drive, Brewster, NY
0.75
Single-Family Home
$895,000
08/27/26
4
3.5
3,516
424 Gage Road, Brewster, NY
0.59
Single-Family Home
$854,000
01/23/26
4
2.5
3,406
1105 Farmdale Road, Brewster, NY
0.55
Single-Family Home
$455,000
10/14/25
2
2.5
2,632
2 Sherwood Hill Road, Brewster, NY
0.61
Single-Family Home
$1,112,500
09/15/25
4
3.5
3,800
747 Milltown Road, Brewster, NY
1.24
Single-Family Home
$575,000
02/04/26
3
3
2,613

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
9 Windswept Circle, Brewster, NY 10509
0.05
$770,000
4
2.5
3,080
Recently Sold
4 Townsend Ln, Brewster, NY 10509
0.18
$903,800
5
3.5
3,760
Off Market
1 Townsend Lane, Brewster, NY 10509
0.27
$969,300
4
2.5
4,000
Off Market
282-284 Doansburg Road, Brewster, NY 10509
0.25
$850,000
4
3
4,774
Recently Sold
181-183 Doansburg Road, Brewster, NY 10509
0.27
-
-
-
-
Off Market
20 Maple Wood Drive, Brewster, NY 10509
0.36
$792,300
4
2.5
2,776
Off Market
421 Gage Road, Brewster, NY 10509
0.46
$787,000
3
3
2,100
Off Market
50 Maple Wood Drive, Brewster, NY 10509
0.47
$635,000
3
3.5
2,542
Recently Sold
26 Mill Farm Lane, Brewster, NY 10509
0.51
$1,100,000
4
4.5
4,944
For Sale
66 Maple Wood Drive, Brewster, NY 10509
0.50
$725,000
3
2
2,968
For Sale
391 Gage Road, Brewster, NY 10509
0.50
$857,300
4
2.5
2,845
Off Market
381 Gage Road, Brewster, NY 10509
0.50
$831,900
4
3.5
3,072
Off Market

Local Information

  • Map ViewExplore the area around 4 Windswept Cir.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1996
1.18 acre lot
2,688 sqft
$300/sqft
Garage

About this House

This single-family home is located at 4 Windswept Cir, Brewster, NY. 4 Windswept Cir is in Brewster, NY and in ZIP code 10509. This property has 3 bedrooms, 3 bathrooms and approximately 2,688 sqft of floor space. This property has a lot size of 1.18 acres and was built in 1996.
4 Windswept Cir, Brewster, NY 10509 is a 3 bedroom, 3 bathroom, 2,688 sqft single-family home built in 1996. It last sold for $100,000 on May 18, 1995. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $807,500, with a rent estimate of $4,218/month.

Home Details for 4 Windswept Cir

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Other
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.18 acres

Price and Tax history

DateEventPrice
May 18, 1995
Source: N/A
Sold
$100,000

Market trends in Brewster

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
3MoM

Around this home

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

Frequently asked questions about 4 Windswept Cir

  • What is 4 Windswept Cir estimated to be worth?
    Trulia's estimated value for 4 Windswept Cir in Brewster, NY is $807,500.
  • What is the price history for 4 Windswept Cir?
    4 Windswept Cir in Brewster, NY last sold for $100,000 in May 1995.
  • Is Brewster a buyer's or seller's market?
    Brewster is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Brewster?
    Residents describe Brewster, NY as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Brewster, NY.
  • Does 4 Windswept Cir have air conditioning?
    Yes, 4 Windswept Cir in Brewster, NY has air conditioning.
  • Does 4 Windswept Cir have a pool?
    Yes, 4 Windswept Cir in Brewster, NY has a pool.

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