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

53 Winding Brook Dr
Walden, NY 12586

  • 2 Beds
  • 2.5 Baths
  • 1,535 sqft

$345,500

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $2,359/mo*
Refinance Your Home

$345,500

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $2,359/mo*
Refinance Your Home
2 Beds
2.5 Baths
1,535 sqft

Local Information

  • Map ViewExplore the area around 53 Winding Brook Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

LOCATION ! LOCATION !!LOCATION !!! .... Don't Miss This Very Inviting 2 Bedroom / 2.5 Bath Unit in the Sought-After Development of Winding Brook. Freshly Painted in Neutral Colors, All laminate flooring, Large Open Kitchen with Stainless appliances and Dining Alcove. VERY LARGE BEDROOMS. The 2nd Bedroom was Originally Designed to be TWO Separate Bedrooms and can be split. Sliders off the Living room open onto a Concrete Patio and large flat lawn, front patio, Community Pool, tennis and Tot-Lot. HURRY !!!... UNIT WILL NOT LAST !!
53 Winding Brook Dr, Walden, NY 12586 is a 2 bedroom, 3 bathroom, 1,535 sqft single-family home built in 1992. It last sold for $165,500 on Aug 2, 2017. It is currently off market. The Trulia Estimate is $345,500, with a rent estimate of $2,647/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 53 Winding Brook Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 5
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Property Information

Year Built
Year Built: 1992Year Updated: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: townhouse

Exterior Features

Exterior Home Features
Exterior: OtherFoundation Type: PiersPatioPorch
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2792 sqft

Building

Fitness & Sports
Basketball CourtTennis Court

Price History for 53 Winding Brook Dr

DatePriceEventSource
08/02/2017$165,500Sold
OneKey® MLS as distributed by MLS GRID #H4722416
05/26/2017$163,000PriceChange
Agent Provided
05/22/2017$158,000Listed For SaleAgent Provided

Market trends in Walden

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
35
4MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$292,200
Home facts updated by county records

Comparable Sales for 53 Winding Brook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
57 Winding Brook Drive, Walden, NY
0.01
Single-Family Home
$340,000
04/17/26
2
2.5
1,535
5 Northgate Drive, Walden, NY
0.66
Single-Family Home
$213,500
05/01/26
3
1.5
1,360
64 Wait Street, Walden, NY
0.31
Single-Family Home
$405,000
06/24/26
3
1.5
1,248
1 Second Street, Walden, NY
0.36
Single-Family Home
$355,000
06/05/26
3
1.5
1,188
47 Capron Street, Walden, NY
0.64
Single-Family Home
$307,000
11/13/25
3
2
1,288
33 Bank Street, Walden, NY
0.60
Single-Family Home
$305,000
04/29/26
3
1.5
1,400
52 Valley Avenue, Walden, NY
0.70
Single-Family Home
$325,000
06/26/26
3
1.5
1,716
34 Houtman Drive, Walden, NY
0.18
Single-Family Home
$474,500
02/13/26
3
3
1,664
34 Alfred Place, Walden, NY
0.52
Single-Family Home
$260,000
11/25/25
3
1.5
1,544
66 Orchard Street, Walden, NY
0.71
Single-Family Home
$330,000
09/02/25
3
2
1,396

Nearby homes

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Assigned Schools

These are the assigned schools for 53 Winding Brook 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.

What Locals Say about Walden

At least 114 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

  • 75 % Say it's walkable to grocery stores

  • 74 % 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."
    1
    Flag
  • Kajohn
    "Walden is a very pleasant place for families. The new bike path adds to the recreation potential."
    2
    Flag

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Homes for sale near 53 Winding Brook Dr

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Off Market Homes Near 53 Winding Brook Dr

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