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$689,900 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2 Car Garage
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Welcome to 29 Deer Brook Drive, New Windsor - a well-maintained colonial set on 5.2 acres along a quiet road in a desirable location within the Washingtonville Central School District. Built in 1989, this spacious 3-bedroom, 2.5-bath home offers nearly 3,200 square feet of living space, which includes approximately 625ft in the finished basement, perfect for a recreation room, home office, or gym. The first floor offers a spacious eat-in kitchen, formal dining room, cozy sitting area which leads directly into the living room, laundry room and entrance to two car garage. Second floor with all new carpeting includes a generous sized primary bedroom with full bath and large walk-in closet, two additional bedrooms, loft area and full bath. Fully finished basement includes two large open spaces as well as a separate den/office area plus plenty of storage. This home features a classic colonial layout with generous sized rooms, central air, central vacuum, a cozy wood-burning stove in the family room, sliders from kitchen & family room to deck with retractable awning. Step outside to your own private retreat with a saltwater in-ground pool, surrounded by peaceful, wooded acreage-ideal for relaxing, entertaining, or enjoying nature year-round. Located on a private road, this property offers both privacy and convenience, making it a rare find in New Windsor. Despite the private location, this home is just minutes to shopping, dining, major roadways & transportation, offering easy access to everyday amenities while still feeling tucked away. Recent improvements during 2023 include new boiler with 3 separate heating zones and indirect water heater, well tank plus water softener and whole house filter. Pool liner also replaced in 2023. Central air replaced in 2024. A wonderful opportunity to enjoy space, privacy, and comfort - inside and out!!

Full Property Details for 29 Deer Brook Dr

General

  • Price: $689,900
  • Taxes: $13,793
  • Status: Pending
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 943411
  • Updated: 1/28/2026
  • Added to Site: 56 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), Central Vacuum, Eat-in Kitchen, Formal Dining, Open Floorplan, Primary Bathroom, Soaking Tub
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Wood Burning Stove
  • Appliances: Cooktop, Dishwasher, Dryer, Oven, Refrigerator, Washer
  • Flooring: Carpet, Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In-Ground

Exterior

  • Porch/Patio/Deck: Covered, Deck, Patio, Porch

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Driveway, Garage, Garage Door Opener

Location

  • County: Orange County
  • Cross Streets: Jackson Avenue
  • Driving Directions: Route 94 in New Windsor to Jackson Avenue to Deer Brook; or Route 207 in New Windsor to Jackson Avenue to Deer Brook

School Information

  • High School District: Washingtonville
  • Elementary School: Little Britain Elementary School
  • Middle School: Washingtonville Middle School
  • High School: Washingtonville Senior High School

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Baseboard, Oil
  • Heating Zones: 3

Utilities

  • Sewer: Septic Tank
  • Water: Well
  • Utility Description: Cable Connected, Electricity Connected

Structural Information

  • Architectural Style: Colonial
  • Detached/Attached: Detached
  • Construction: Frame, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Finished, Full Basement, Storage Space, Walk-Out Access
  • Sq. Ft. Source: Public Records
  • Year Built: 1989

Additional Structures

  • Other Structures: Shed(s)

Lot Features

  • Lot Size (Acres): 5.2
  • Lot Size (Sq. Ft.): 226,512
  • Road Maintenance: Private Maintained Road
  • Fence: Yes
  • Lot Features: Back Yard, Front Yard, Level
  • Fencing (Description): Partial

Financial Considerations

  • Tax Amount: $13,793

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 334800-054-000-0001-062.000-0000

Listed by RE/MAX Benchmark Realty Group

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Listing agent

— 29 Deer Brook Dr —

  • RE/MAX Benchmark Realty Group

845-565-0004

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 29 Deer Brook Dr

School District:Washingtonville Central School District
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 29 Deer Brook Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/27/2025
Listed
$689,900
57.87%
MLS
7/18/2005
Sold
$437,000
—
Public Record
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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 29 Deer Brook Dr

Year
Property Taxes
Change
Tax Assessment
Change
2021
-100%
$63,000
—
2021
$4,012
-68%
$63,000
—
2020
$12,623
2%
$63,000
—
2018
$12,412
4%
$63,000
—
2017
$11,932
4%
$63,000
—
2016
$11,498
-1%
$63,000
—
2015
$11,589
—
$63,000
—
2015
$11,597
3%
$63,000
—
2013
$11,227
—
$63,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by RE/MAX Benchmark Realty Group

29 Deer Brook Drive, New Windsor, NY 12553 (MLS# 943411) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 29 Deer Brook Drive is currently listed for $689,900 and was received on December 27, 2025. Want to learn more about 29 Deer Brook Drive? Do you have questions about finding other Single Family real estate for sale in New Windsor? You can browse all New Windsor real estate or contact a Coldwell Banker agent to request more information.

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