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MLS ID KEY1046894Last updated Oct 27, 2026

Single Family

289 Pine Grove Road

Active · Middletown · Orange County, NY 10940

Bedrooms
4 Beds
Bathrooms
4 Baths
Year built
1989
Est. monthly taxes
$1,070.43

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About this home

Tucked away on 4 sprawling, private acres, this 5,360-square-foot contemporary estate delivers the rare combination of country seclusion, equestrian-ready grounds, and true move-in luxury. Whether you're searching for a peaceful retreat, room to bring your horses, or a multigenerational layout with built-in flexibility, 289 Pine Grove Road checks every box. Step through the soaring foyer into a light-filled main level anchored by cathedral ceilings, skylights, and rich hardwood floors throughout. The gourmet eat-in kitchen, with granite countertops and a generous pantry flows into a formal dining room built for hosting, while the sunken living room and enclosed sunroom with its own wet bar create effortless indoor entertaining space. Upstairs, the primary suite is a true retreat: vaulted ceilings, a cozy fireplace, a dedicated sitting area, and a private balcony overlooking sweeping water and countryside views. The spa-inspired primary bath features custom stone finishes, and two additional spacious bedrooms plus a second full bath complete the upper level. The fully finished, walk-out lower level adds exceptional flexibility, with its own kitchen, full bath, bedroom and additional office/den makes it the perfect accessory apartment, guest suite, or home office setup. Outside, the property truly sets itself apart: mature barn structures and stables ready for horses, a peaceful stream winding through the land, a custom Koi pond, and a charming gazebo overlooking the fenced yard. Multiple deck, patio, and balcony areas make it easy to take in the Hudson Valley sunsets from every angle. Rounding out the offering is a 2-car attached garage all set within the highly regarded Minisink Valley Central School District. Properties combining this much land, living space, and equestrian infrastructure rarely come to market. Schedule your private tour today before it's gone.

Listing snapshot

Days on site
49 days
Listed on MLS
Sep 8, 2026
Full baths
3
Half baths
1
Annual property tax (MLS)
$12,845.21
Tax year
2025
Area source (MLS)
Public Records
Listing brokerage
Curasi Realty, Inc.
MLS ID
KEY1046894
Last updated
Oct 27, 2026

General features

Property type
Single Family
Property subtype
Single Family Residence
Year built
1989
Garage
Yes
Garage spaces
2
Total parking
4
Parking
Driveway, Garage
Water source
Well
Sewer
Septic Tank
Utilities
Cable Connected, Electricity Connected, Phone Connected, Trash Collection Private, Water Connected

Interior features

Basement
Partially Finished, Walk-Out Access
Heating
Forced Air, Oil
Cooling
Central Air, Electric, Multi Units
Interior
Beamed Ceilings, Breakfast Bar, Cathedral Ceiling(s), Ceiling Fan(s), Chandelier, Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, In-Law Floorplan, Natural Woodwork, Open Kitchen, Primary Bathroom, Soaking Tub, Storage, Walk-In Closet(s), Wet Bar
Appliances
Dishwasher, Disposal, Dryer, Electric Oven, Electric Range, Microwave, Refrigerator, Washer, Oil Water Heater, Water Softener Owned
Flooring
Ceramic Tile, Combination, Hardwood
Fireplace
Yes
Fireplaces
3

Exterior features

Architectural style
Contemporary, Includes Legal Accessory Apartment
Construction materials
Stone, Wood Siding
Exterior
Balcony, Mailbox
Private pool
No

Schools (MLS)

Elementary school
Otisville Elementary School
Elementary school district
Minisink Valley
Middle school
Minisink Valley Middle School
Middle school district
Minisink Valley
High school
Minisink Valley High School
High school district
Minisink Valley

School information is provided by the MLS. Confirm attendance eligibility with the school district.

Recent activity

  1. Listing updated from MLS
  2. First seen on this site
  3. MLS status changed

Location

Middletown · Orange County, NY 10940Show interactive map
289 Pine Grove Road

Middletown · Orange County, NY 10940

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Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
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Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.