44 Cooledge Dr, Brewster, NY 10509
OFF MARKET

44 Cooledge Dr
Brewster, NY 10509

Brewster Hill
  • 5 Beds
  • 2 Baths
  • 1,701 sqft (on 0.26 acres)

$511,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,573/mo*
Refinance Your Home

$511,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,573/mo*
Refinance Your Home
5 Beds
2 Baths
1,701 sqft
(on 0.26 acres)

Local Information

  • Map ViewExplore the area around 44 Cooledge Dr.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1940
Lot Size
0.26 acres
Living Area
1,701 sqft
Price/Sqft
$301

About this House

This single-family home is located at 44 Cooledge Dr, Brewster, NY. 44 Cooledge Dr is in the Brewster Hill neighborhood in Brewster, NY and in ZIP code 10509. This property has 5 bedrooms, 2 bathrooms and approximately 1,701 sqft of floor space. This property has a lot size of 0.26 acres and was built in 1940.
44 Cooledge Dr, Brewster, NY 10509 is a 5 bedroom, 2 bathroom, 1,701 sqft single-family home in Brewster Hill, built in 1940. It last sold for $157,500 on May 1, 1988. It is currently off market. The Trulia Estimate is $511,600, with a rent estimate of $3,987/month.

Home Details for 44 Cooledge Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Other, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1.5
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Exterior Features

Exterior Home Features
Exterior: Other
Pool
Pool

Lot Information

Lot Area: 0.26 acres

Price History for 44 Cooledge Dr

DatePriceEventSource
05/01/1988$157,500Sold
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
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Property Tax and Assessment

Year2025
Tax
Assessment$383,900
Home facts updated by county records

Comparable Sales for 44 Cooledge Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
31 Shore Drive, Brewster, NY
0.20
Single-Family Home
$407,000
12/16/25
3
1.5
1,678
53 Crosby Avenue, Brewster, NY
0.55
Single-Family Home
$520,000
12/05/25
4
2
1,431
6 Meridian Drive, Brewster, NY
0.39
Single-Family Home
$487,500
09/18/25
3
2
1,829
31 Pumphouse Road, Brewster, NY
0.18
Single-Family Home
$725,000
10/07/25
3
3
1,956
74 Fairview Road, Brewster, NY
0.16
Single-Family Home
$220,000
06/22/26
2
1
560
14 Griffen Road, Brewster, NY
0.65
Single-Family Home
$450,000
02/19/26
3
1.5
1,516
7 Juniper Cir, Brewster, NY
0.39
Single-Family Home
$500,000
09/09/25
3
2
2,694
16 Crosby Avenue, Brewster, NY
0.63
Single-Family Home
$500,000
09/04/25
3
1.5
1,500
60 Pleasant Drive, Brewster, NY
0.59
Single-Family Home
$535,000
04/16/26
3
2
1,356
31 Larkspur Drive, Brewster, NY
0.60
Single-Family Home
$305,001
01/09/26
3
1
2,000

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Cooledge Dr.
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.

Neighborhood Overview

Brewster Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Brewster Hill

At least 13 Trulia users voted on each feature.

  • 100 % Say car is needed

  • 100 % Say parking is easy

  • 93 % Say it's dog friendly

  • 79 % Say there's wildlife

  • 77 % Say yards are well-kept

  • 73 % Say there's holiday spirit

  • 65 % Say people would walk alone at night

  • 61 % Say neighbors are friendly

  • 59 % Say kids play outside

  • 56 % Say they plan to stay for at least 5 years

  • 50 % Say there are community events

  • 41 % Say it's quiet

  • 27 % Say it's walkable to restaurants

  • 17 % Say it's walkable to grocery stores

  • 13 % 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
  • 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
    "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
  • 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
  • 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
  • Cynthia W.
    "Suburban neighborhood!Great location close to 684. Easy commute, "
    1
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Air Conditioning

7 rentals with air conditioning in Brewster, NY

Homes for sale near 44 Cooledge Dr

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Off Market Homes Near 44 Cooledge Dr

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Frequently asked questions about 44 Cooledge Dr

  • What is 44 Cooledge Dr estimated to be worth?
    Trulia's estimated value for 44 Cooledge Dr in Brewster, NY is $511,600.
  • What is the price history for 44 Cooledge Dr?
    44 Cooledge Dr in Brewster, NY last sold for $157,500 in May 1988.
  • 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 the Brewster Hill neighborhood?
    Residents describe the Brewster Hill neighborhood in Brewster, NY as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Brewster Hill, Brewster.
  • Does 44 Cooledge Dr have a pool?
    Yes, 44 Cooledge Dr in Brewster, NY has a pool.
  • How big is the lot at 44 Cooledge Dr?
    The lot at 44 Cooledge Dr in Brewster, NY is about 0.26 acres (11,200 sq ft).