Your dream countryside retreat located in Orange County NY. This custom-built 4,000 sq. ft. Contemporary Ranch is situated on an expansive 61-acre property. (two separate parcels) It includes a two-story 35'x60' barn with 7 horse stalls, a lean-to, a silo, and a tack room. Above the barn, you'll find a 20'x64' loft area with a separate well and 100-amp electric service. The 25'x50' concrete garage is ideal for a workshop. Perfect for hunting ,fishing, ATV riding, and hiking along wooded trails that lead to the Shawangunk Kill, with 1,000 feet of frontage. The one-level living space features soaring cathedral ceilings, a huge family room, a Generac generator, central A/C (two 3-ton compressors), and Andersen windows throughout, including the 20'x25' sky-lit sunroom and heated garage. Is truly a rare find and is also possible subdividable for future development. Located just 75 miles from Manhattan, it offers both convenience and serenity. (2 parcels being sold together )
For sale
$1,600,000
565 Prosperous Valley Road, Middletown, NY 10940
4beds
4,000sqft
Single Family Residence, Residential
Built in 1986
22.7 Acres Lot
$-- Zestimate®
$400/sqft
$-- HOA
What's special
Heated garageHuge family roomGenerac generatorAndersen windows throughoutSoaring cathedral ceilings
- 319 days |
- 536 |
- 9 |
Zillow last checked: 7 hours ago
Listing updated: March 11, 2026 at 12:01am
Listing by:
Real Estate Circuit Inc 845-344-1480,
Michelle P Gruberger 845-800-3905
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 858885
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Heating
- See Remarks
Cooling
- Zoned
Appliances
- Included: Other
- Laundry: Washer/Dryer Hookup, Laundry Room
Features
- First Floor Bedroom, First Floor Full Bath, Cathedral Ceiling(s), Eat-in Kitchen, Formal Dining, High Speed Internet, Storage
- Flooring: Combination
- Has basement: No
- Attic: Dormer,See Remarks
Interior area
- Total structure area: 4,000
- Total interior livable area: 4,000 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage
- Garage spaces: 2
Lot
- Size: 22.7 Acres
Details
- Parcel number: 3352000060000001048.0000000
- Special conditions: None
- Horses can be raised: Yes
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary
- Property subtype: Single Family Residence, Residential
Materials
- Other
- Foundation: Other
Condition
- Estimated
- Year built: 1986
Utilities & green energy
- Sewer: Septic Tank
- Utilities for property: Cable Available
Community & HOA
HOA
- Has HOA: No
Location
- Region: Middletown
Financial & listing details
- Price per square foot: $400/sqft
- Tax assessed value: $97,100
- Annual tax amount: $14,255
- Date on market: 5/7/2025
- Cumulative days on market: 358 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 2/27/2026 | Listed for rent | $4,500$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 2/27/2026 | Listing removed | $4,500$1/sqft |
Source: OneKey® MLS as distributed by MLS GRID #935022 Report a problem | ||
| 1/26/2026 | Listed for rent | $4,500$1/sqft |
Source: OneKey® MLS as distributed by MLS GRID #935022 Report a problem | ||
| 1/24/2026 | Listing removed | $4,500$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 1/16/2026 | Listed for rent | $4,500$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/7/2025 | Listed for sale | $1,600,000-15.8%$400/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #858885 Report a problem | ||
| 4/21/2025 | Listing removed | $1,900,000$475/sqft |
Source: NY State MLS #11457412 Report a problem | ||
| 3/10/2025 | Listed for sale | $1,900,000+162.1%$475/sqft |
Source: OneKey® MLS as distributed by MLS GRID #826205 Report a problem | ||
| 2/24/2021 | Sold | $725,000-9.4%$181/sqft |
Source: OneKey® MLS as distributed by MLS GRID #H6068329 Report a problem | ||
| 11/24/2020 | Pending sale | $800,000$200/sqft |
Source: OneKey® MLS as distributed by MLS GRID #H6068329 Report a problem | ||
| 9/9/2020 | Listed for sale | $800,000+16.8%$200/sqft |
Source: BHG Rand Realty #H6068329 Report a problem | ||
| 4/1/2020 | Listing removed | $684,900$171/sqft |
Source: Keller Williams Realty - Valley Realty #5009386 Report a problem | ||
| 9/4/2019 | Listed for sale | $684,900-2%$171/sqft |
Source: Keller Williams Valley Realty #5009386 Report a problem | ||
| 7/6/2018 | Listing removed | $699,000$175/sqft |
Source: CENTURY 21 Ed & Margaret Williams Realty #4746216 Report a problem | ||
| 4/27/2018 | Price change | $699,000-12.5%$175/sqft |
Source: CENTURY 21 Ed & Margaret Williams Realty #4746216 Report a problem | ||
| 10/18/2017 | Listed for sale | $799,000$200/sqft |
Source: CENTURY 21 Ed & Margaret Williams Realty #4746216 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $97,100 |
| 2023 | -- | $97,100 |
| 2022 | -- | $97,100 |
| 2021 | -- | $97,100 +3.6% |
| 2020 | -- | $93,700 |
| 2019 | -- | $93,700 |
| 2018 | -- | $93,700 |
| 2017 | $11,064 | $93,700 |
| 2016 | -- | $93,700 |
| 2015 | -- | $93,700 |
| 2014 | -- | $93,700 |
| 2013 | -- | $93,700 |
| 2012 | -- | $93,700 |
| 2011 | -- | $93,700 |
| 2010 | -- | $93,700 |
| 2009 | -- | $93,700 |
| 2007 | -- | $93,700 |
| 2006 | -- | $93,700 |
| 2005 | -- | $93,700 |
| 2004 | -- | $93,700 |
| 2002 | -- | $93,700 |
| 2001 | -- | $93,700 |
| 2000 | -- | $93,700 |
Find assessor info on the county website
BuyAbility℠ payment
Estimated monthly payment
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Neighborhood: 10940
Nearby schools
GreatSchools rating
- 4/10Circleville Elementary SchoolGrades: PK-5Distance: 3.1 mi
- 6/10Circleville Middle SchoolGrades: 6-8Distance: 3.4 mi
- 6/10Pine Bush Senior High SchoolGrades: 9-12Distance: 8.6 mi
Schools provided by the listing agent
- Elementary: Circleville Elementary School
- Middle: Circleville Middle School
- High: Pine Bush Senior High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 10940
- New York
- Orange County
- Middletown
- 10940
- 565 Prosperous Valley Road
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