44 Cooledge Dr, Brewster, NY 10509
OFF MARKET

$494,800

Trulia Estimate
  • 5 Beds
  • 2 Baths
  • 1,701 sqft (on 0.26 acres)

44 Cooledge Dr, Brewster, NY 10509

Brewster Hill
Est. Refi. Payment $3,687/mo*
Refinance Your Home
Currently Off Market - Sold May 1, 1988 for $157,500

Home Value

Trulia Estimate
$495K
Since last month
Decreased$8K (-1.5%)
Since last year
Increased$31K (+6.7%)
Since last sale
Increased$337K (+214.2%)
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 +92% in the last 10 years
MonthEstimated value
2026
October 2026$495K
September 2026$495K
August 2026$503K
July 2026$505K
June 2026$506K
May 2026$500K
April 2026$480K
March 2026$484K
February 2026$462K
January 2026$465K
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
8 Noel Court, Brewster, NY
0.38
Single-Family Home
$590,000
09/11/26
4
2
1,864
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
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
60 Pleasant Drive, Brewster, NY
0.59
Single-Family Home
$535,000
04/16/26
3
2
1,356
53 Hillcrest Avenue, Brewster, NY
0.81
Single-Family Home
$550,000
04/27/26
3
2
1,600
15 Sycamore Road, Brewster, NY
0.40
Single-Family Home
$677,000
07/29/26
3
3
2,146
10 Meridian Drive, Brewster, NY
0.39
Single-Family Home
$575,000
01/23/26
3
3
2,955

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
48 Cooledge Dr, Brewster, NY 10509
0.01
$415,600
3
1
1,248
Off Market
47 Tonetta Lake Way, Brewster, NY 10509
0.02
$450,000
2
1
1,162
For Sale
40 Cooledge Dr, Brewster, NY 10509
0.02
$632,300
5
3
2,136
Off Market
50 Cooledge Dr, Brewster, NY 10509
0.02
$408,700
3
1
1,248
Off Market
43 Tonetta Lake Way, Brewster, NY 10509
0.03
-
-
-
-
Off Market
51 Tonetta Lake Way, Brewster, NY 10509
0.03
$536,200
3
1
1,862
Off Market
38 Cooledge Dr, Brewster, NY 10509
0.03
-
Studio
-
-
Off Market
47 Cooledge Drive, Brewster, NY 10509
0.03
$428,800
2
1.5
1,596
Off Market
41 Cooledge Dr, Brewster, NY 10509
0.03
$343,200
2
1
840
Off Market
36 Cooledge Dr, Brewster, NY 10509
0.04
$347,200
3
1
1,032
Off Market
36 Cooledge Dr, Brewster, NY 10509
0.04
-
3
1
1,032
Off Market
36 Cooledge Dr, Brewster, NY 10509
0.04
-
3
1
1,032
Off Market
54 Cooledge Dr, Brewster, NY 10509
0.04
$631,400
6
3
2,618
Off Market
51 Cooledge Dr, Brewster, NY 10509
0.04
$447,100
3
2
1,280
Off Market
37 Cooledge Dr, Brewster, NY 10509
0.04
$418,000
2
2
1,244
Off Market
39 Tonetta Lake Way, Brewster, NY 10509
0.05
$404,400
3
2
1,296
Off Market
48 Tonetta Lake Way, Brewster, NY 10509
0.05
$339,900
2
1
756
Off Market
32 Fairview Rd, Brewster, NY 10509
0.05
$596,600
3
2
1,988
Off Market
44 Tonetta Lake Way, Brewster, NY 10509
0.05
$352,000
2
1
736
Off Market
57 Tonetta Lake Way, Brewster, NY 10509
0.05
$587,500
3
2.5
1,752
Off Market

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

Single-Family Home
Built in 1940
0.26 acre lot
1,701 sqft
$291/sqft

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $494,800, with a rent estimate of $4,134/month.

Home Details for 44 Cooledge Dr

Interior Features

Interior Details
Basement
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 and Tax history

DateEventPrice
May 1, 1988
Source: N/A
Sold
$157,500

Market trends in Brewster

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
6MoM

Around this home

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. "
    4
    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

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 $494,800.
  • 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).

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