27 Winding Brook Dr, Walden, NY 12586
Property image
Property image
OFF MARKET

$350,300

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,505 sqft

27 Winding Brook Dr, Walden, NY 12586

Est. Refi. Payment $2,490/mo*
Refinance Your Home
Currently Off Market - Sold May 18, 2023 for $296,000

Home Value

Trulia Estimate
$350K
Since last month
Decreased$3K (-0.8%)
Since last year
Increased$2K (+0.7%)
Since last sale
Increased$54K (+18.3%)
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 +165% in the last 10 years
MonthEstimated value
2026
September 2026$350K
August 2026$353K
July 2026$355K
June 2026$358K
May 2026$352K
April 2026$349K
March 2026$348K
February 2026$345K
January 2026$344K
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
13 Summer Set Drive, Montgomery, NY
3.63
Condo
$310,000
12/04/25
2
1.5
1,353
19 Brighton Drive #1703, Newburgh, NY
3.96
Condo
$469,000
10/02/25
3
2.5
1,748
804 Hawthorn Way, New Windsor, NY
7.10
Condo
$450,000
07/09/26
3
2.5
1,910
1004 Hawthorn Way, New Windsor, NY
7.13
Condo
$475,000
11/24/25
3
2.5
1,910
1404 Hawthorn Way, New Windsor, NY
7.20
Condo
$475,000
05/15/26
3
2.5
1,910
1210 Hawthorn Way, New Windsor, NY
7.18
Condo
$489,999
05/15/26
3
2.5
2,040
305 Balsam Drive, New windsor, NY
7.13
Condo
$485,000
01/29/26
3
3.5
2,890
917 Balsam Drive, New Windsor, NY
7.24
Condo
$464,900
04/03/26
2
3
1,990
1707 Hawthorn Way, New Windsor, NY
7.34
Condo
$450,000
07/17/26
2
2.5
1,758
1505 Balsam Drive, New Windsor, NY
7.33
Condo
$415,000
09/21/26
2
3
2,020

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
43 Winding Brook Drive #43, Walden, NY 12586
0.05
$371,300
2
2.5
1,505
Off Market
35 Winding Brook Drive, Walden, NY 12586
0.02
$340,000
2
2.5
1,515
Off Market
46 Winding Brook Drive, Walden, NY 12586
0.08
$365,000
3
2.5
1,505
Off Market
57 Winding Brook Drive, Walden, NY 12586
0.09
$340,000
2
2.5
1,535
Recently Sold
57 Winding Brook Drive, Walden, NY 12586
0.09
$340,000
2
2.5
1,535
Recently Sold
3 Pond Hill Lane, Walden, NY 12586
0.04
$353,100
3
2.5
1,576
Off Market
61 Winding Brook Drive, Walden, NY 12586
0.10
$347,400
3
2.5
1,535
Off Market
10 Pond Hill Lane, Walden, NY 12586
0.04
$362,300
3
2.5
1,576
Off Market
132 NORTH MONTGOMERY Street, Walden, NY 12586
0.10
-
2
1
840
Off Market
21 Pond Hill Lane, Walden, NY 12586
0.08
$352,700
3
2.5
1,576
Off Market
16 Pond Hill Lane, Walden, NY 12586
0.06
$365,600
3
2.5
1,576
Off Market
22 Pond Hill Lane, Walden, NY 12586
0.07
-
3
2.5
1,576
Off Market

Local Information

  • Map ViewExplore the area around 27 Winding Brook Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1993
1,505 sqft
$233/sqft
Garage

About this House

FOR SALE...WINDING BROOK COMPLEX...RARE FIND. Affordable 3 bed, 2.5 bath end unit 1,576' sq. townhouse/single family home in private community on cul-de-sac. Easy access to services, highways I-84 & I-87, Beacon Metro N train. Spacious & affordable with all amenities: c/air, private patio, master bedroom w/master bathroom & walk-in closet. Eat-in kitchen w/plenty of cabinets & tile flooring. Spacious open floor plan: dining & living room w/gas fireplace & glass slider to deck. Complex offers: beautiful grounds w/lush landscaping, inground swimming pool for hot days, playground & tennis court. Lawn maintenance and trash removal is part of HOA cost of $200/ month. Includes all kitchen appliances (refrigerator, oven/range, dishwasher & microwave) plus washer & dryer. One car garage, driveway & plenty of extra common parking area. Municipal water, sewer & natural gas. Just 20 min. to New Paltz, only 15 minutes to Newburgh. Pet friendly complex.
27 Winding Brook Dr, Walden, NY 12586 is a 3 bedroom, 3 bathroom, 1,505 sqft condo built in 1993. It last sold for $296,000 on May 18, 2023. More recently, it was listed as a rental in November 2019 with an asking price of $1,750 per month. That rental listing was removed on December 14, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $350,300, with a rent estimate of $2,550/month.

Home Details for 27 Winding Brook Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet
Interior Details
Number of Rooms: 5Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1993Year Updated: 1993
Property Type / Style
Property Type: CondoArchitecture: townhouse

Exterior Features

Exterior Home Features
Exterior: VinylFoundation Type: Piers
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 5486 sqft

Price and Tax history

DateEventPrice
May 18, 2023
Source: OneKey® MLS as distributed by MLS GRID #H6231158
Sold
$296,000
Mar 24, 2023
Source: OneKey® MLS as distributed by MLS GRID #H6231158
Pending
$296,000
Mar 20, 2023
Source: RE/MAX International
ListingRemoved
Feb 12, 2023
Source: OneKey® MLS as distributed by MLS GRID #H6231158
PriceChange
$296,000
Price increased by 2%
Feb 6, 2023
Source: OneKey® MLS as distributed by MLS GRID #H6231158
Listed For Sale
$289,000

Market trends in Walden

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
42
5MoM

Around this home

What Locals Say about Walden

At least 115 Trulia users voted on each feature.

  • 90 % Say yards are well-kept

  • 87 % Say it's dog friendly

  • 81 % Say car is needed

  • 76 % Say parking is easy

  • 75 % Say there's holiday spirit

  • 74 % Say it's walkable to grocery stores

  • 73 % Say there are sidewalks

  • 68 % Say kids play outside

  • 65 % Say it's walkable to restaurants

  • 63 % Say people would walk alone at night

  • 60 % Say there's wildlife

  • 59 % Say it's quiet

  • 54 % Say neighbors are friendly

  • 54 % Say streets are well-lit

  • 53 % Say they plan to stay for at least 5 years

  • 32 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Emily C Miller
    "We have sidewalks and parks around town, and it seems like there are more projects in the works to create more outdoor spaces in the area. "
    0
    Flag
  • Juan M.
    "This community is beautiful. A lovely area to raise a family. Most neighbors are quiet but very friendly. "
    0
    Flag
  • Ashley E.
    "the village of Walden is a true old-school village. there's a newsletter, a village center where all community services are in one spot, the kids all know each other, we even know the local police by name. Walden is frozen in time, in a good way. I enjoy living here. I'm originally from NYC so I also appreciate all the sidewalks and the rail trail so I can get around on foot instead of being chained to my car for everything. "
    7
    Flag
  • Tiffany V.
    "Great schools. All amenities are within a decent driving distance. Local produce and farms are great. Great walking community. Low driving speed in the village, safe for kids riding bikes and playing outside. "
    3
    Flag
  • Sarah B.
    "Montgomery has access to I-84 very easily, making commuting around Orange County very accessible. It is also a great mid point between Newburgh and Middletown which are our 2 big cities in the area. "
    1
    Flag
  • Brenda C. A.
    "Walden have activities fir the kids and trails it’s very quite. I love it. I would buy a house in this area"
    2
    Flag
  • Sarah B.
    "WALDEN does a lot of community events and involves the children a lot in festivals, trick or treating, tree lighting, summer camp, parks, etc. "
    1
    Flag
  • Brian M.
    "It’s very friendly. Not a lot of personal space, but there is a large area where dogs can be walked. Also there is a dog park 10 minutes away. "
    3
    Flag
  • Ciara M.
    "I like the back to school event they throw every year. It is a great turn out and really gets the community together."
    1
    Flag
  • Jcburst
    "There is easy access to all major highways in the area and very close to all the local amenities, such as grocery stores, restaurants, ice cream parlors, sporting goods stores and several beautiful parks!"
    4
    Flag
  • Riverscandymitch
    "I live in walden, but town of montgomery, i luked the neighborhood and at the same time the privacy. "
    1
    Flag
  • Guyaynesimmons
    "I commute about 24 min to work and it is pretty simple, not much traffic. Passing most frequently needed stores on the way ... groceries, drug store, gas, Dunkin’, dollar general for random things. "
    2
    Flag
  • Chilledseltzer
    "nosey neighbors no dog parks only sidewalks. other people don't watch their animals. alot of deer. to many that don't obey the leash laws"
    1
    Flag
  • Itsjohnayala
    "Very positive reviews overall. Montgomery is an overall safe area. A lot of nice, local shops/bars. Elementary, middle, and high Schools isn’t far from many that live in the area. Well organized and mostly friendly environment."
    2
    Flag
  • Isaiah S.
    "small town, necessary things nearby like grocery, gas. little to no crime. good location for commuter"
    2
    Flag
  • Ariel F.
    "Beautiful cul-de-sac. this is my residential residence."
    2
    Flag
  • jokoehn912
    "Walden is a small village, just 20 minutes away from the train to New York City. The community is very close knit and friendly, and offers a lot for families with kids. The library is a gem and many parks and playgrounds are in walking distance to the village square. There is a weekly farmers market and plenty of events hosted by library, village or the Hudson Conservatory (music and dance). The nature is beautiful and you are close to the Shawngunks (hiking, climbing, mountain biking, horseback riding). Lots of things to do outdoors, from horsebackriding to apple picking, snow tubing to ice skating. Surrounding villages offer antique stores, historic festivals. For Nightlife you have to drive to New Paltz, a college town, about 15 minutes away with the car."
    2
    Flag
  • Kajohn
    "Walden is a very pleasant place for families. The new bike path adds to the recreation potential."
    2
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Winding Brook Dr

  • What is 27 Winding Brook Dr estimated to be worth?
    Trulia's estimated value for 27 Winding Brook Dr in Walden, NY is $350,300.
  • What is the price history for 27 Winding Brook Dr?
    27 Winding Brook Dr in Walden, NY last sold for $296,000 in May 2023.
  • Is Walden a buyer's or seller's market?
    Walden is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Walden?
    Residents describe Walden, NY as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Walden, NY.
  • Does 27 Winding Brook Dr have air conditioning?
    Yes, 27 Winding Brook Dr in Walden, NY has air conditioning.
  • Does 27 Winding Brook Dr have laundry facilities?
    Yes, 27 Winding Brook Dr in Walden, NY has in-unit laundry.

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