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$585,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2 Car Garage
  • Updated 4 days ago
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Welcome to this well-maintained 3-bedroom, 2.5-bath Colonial, beautifully situated on over 2 private acres near the Pawling border. Surrounded by mature trees, established gardens, and fruit trees, this property offers a peaceful and picturesque setting with plenty of room to relax, garden, and entertain. The main level features a spacious kitchen, attractive parquet wood flooring throughout much of the first floor, and a cozy wood-burning stove. A standout feature is the first-floor full bath with a Jacuzzi tub and separate shower, along with a convenient powder room for guests. Upstairs, you'll find three spacious bedrooms and an additional full bath, offering a comfortable and functional layout. The huge unfinished basement is filled with possibilities, featuring large windows and direct egress to the backyard, making it ideal for future recreational, fitness, office, or additional living space. Additional highlights include central air conditioning, a two-car garage, generator hookup, and a water catchment system. With its generous acreage, privacy, mature landscaping, fruit trees, and convenient location near the Pawling border, this inviting Colonial offers space, comfort, thoughtful features, and wonderful potential both inside and out.

Full Property Details for 36 Hillside Ave

General

  • Price: $585,000
  • Taxes: $8,098
  • Status: Active
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 1036661
  • Updated: 8/16/2026
  • Added to Site: 8 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Central Vacuum
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Wood Burning Stove
  • Appliances: Dishwasher, Dryer, Oven, Refrigerator, Washer
  • Laundry Facilities: Yes
  • Flooring: Ceramic Tile, Combination, Wood

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Hall

Exterior

  • Exterior Features: Balcony, Garden
  • Porch/Patio/Deck: Deck, Porch

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking Features: Attached

Location

  • County: Dutchess County
  • Driving Directions: From route 22 N from Pawling - Right on Rural Rd (.7 miles past 55/22 light) Right on Hillside Ave., house on left at top of the hill

School Information

  • High School District: Dover
  • Elementary School: Dover Elementary School
  • Middle School: Dover Middle School
  • High School: Dover High School

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Forced Air, Oil

Utilities

  • Sewer: Septic Tank
  • Water: Private
  • Utility Description: Cable Connected, Electricity Connected, Trash Collection Private, Water Connected

Structural Information

  • Architectural Style: Colonial
  • Detached/Attached: Detached
  • Construction: Frame, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Full Basement, Unfinished, Walk-Out Access
  • Sq. Ft. Source: Public Records
  • Year Built: 2003

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 2.03
  • Lot Size (Sq. Ft.): 88,427
  • Lot Features: Level, Part Wooded, Sloped, Views

Financial Considerations

  • Tax Amount: $8,098

Disclosures and Reports

  • Special Conditions: None
  • Exclusions: Chandelier in living room, fan with light in master bedroom
  • Inclusions: All Kitchen Appliances, Washer, Dryer, Light Fixtures
  • Property ID: 132600-7060-16-825443-0000
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 36 Hillside Ave —

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NMLS#: 1598647

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Schools serving 36 Hillside Ave

School District:Dover Union Free School District
NameGradesDistance
Wingdale Elementary School
6413 State Route 55, Wingdale, NY 12594
K-20.7 mi
Dover Elementary School
9 School Street, Dover Plains, NY 12522
3-55.8 mi
Dover Middle School, Dover Plains, NY
2368 New York 22, Dover Plains, NY 12522
6-82.1 mi
Dover High School, Dover Plains, NY
2368 New York 22, Dover Plains, NY 12522
9-122.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 36 Hillside Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/13/2026
Listed
$585,000
101.72%
MLS
11/03/2009
Sold
$290,000
—
Public Record
Get Price Alerts and Save Property
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 36 Hillside Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,557
-1%
$152,900
—
2024
$6,620
-12%
$152,900
—
2016
$7,499
-2%
$152,900
—
2020
$7,624
1%
$152,900
—
2018
$7,549
2%
$152,900
—
2017
$7,384
-1%
$152,900
—
2016
$7,478
—
$152,900
—
2015
$7,448
—
$152,900
—
2015
$7,446
1%
$152,900
—
2013
$7,348
—
$152,900
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 36 Hillside Ave

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

36 Hillside Avenue, Wingdale, NY 12594 (MLS# 1036661) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 36 Hillside Avenue is currently listed for $585,000 and was received on August 13, 2026. This property is listed by Jacqueline "Jackie" Calhoun from our Somers Office.Want to learn more about 36 Hillside Avenue? Do you have questions about finding other Single Family real estate for sale in Wingdale? You can browse all Wingdale real estate or contact a Coldwell Banker agent to request more information.

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