Skip to content
122 Castle High Road, Middletown, photo 1
View all 44 photos
122 Castle High Road, photo 2
122 Castle High Road, photo 3
122 Castle High Road, photo 4
122 Castle High Road, photo 5
122 Castle High Road, photo 6
122 Castle High Road, photo 7
122 Castle High Road, photo 8
122 Castle High Road, photo 9
122 Castle High Road, photo 10
122 Castle High Road, photo 11
122 Castle High Road, photo 12
122 Castle High Road, photo 13
122 Castle High Road, photo 14
122 Castle High Road, photo 15
122 Castle High Road, photo 16
122 Castle High Road, photo 17
122 Castle High Road, photo 18
122 Castle High Road, photo 19
122 Castle High Road, photo 20
122 Castle High Road, photo 21
122 Castle High Road, photo 22
122 Castle High Road, photo 23
122 Castle High Road, photo 24
122 Castle High Road, photo 25
122 Castle High Road, photo 26
122 Castle High Road, photo 27
122 Castle High Road, photo 28
122 Castle High Road, photo 29
122 Castle High Road, photo 30
122 Castle High Road, photo 31
122 Castle High Road, photo 32
122 Castle High Road, photo 33
122 Castle High Road, photo 34
122 Castle High Road, photo 35
122 Castle High Road, photo 36
122 Castle High Road, photo 37
122 Castle High Road, photo 38
122 Castle High Road, photo 39
122 Castle High Road, photo 40
122 Castle High Road, photo 41
122 Castle High Road, photo 42
122 Castle High Road, photo 43
122 Castle High Road, photo 44

122 Castle High Road

Middletown, NY 10940 · Orange County

Beds
3
Baths
1
Sqft
1,830
Status
Active
On site
68 days

Know your budget before you tour. Get pre-qualified

About this home

Set on approximately 2 acres, this 1920’s unique multi-level home provides plenty of room to enjoy the outdoors. A standout feature is the property's unique location, offering road frontage on two separate roads, Castle High Road and Eatontown Road and both Agricultural and Residential zoning. Whether you've dreamed of creating your own homestead, raising chickens or other livestock, planting extensive gardens, or simply enjoying the flexibility that comes with agricultural zoning, this property offers endless possibilities while still being convenient to local amenities. The house has benefited from some renovations, but there is still scope for further updates to restore it to its full potential. As you enter, you'll find the kitchen on the lower level featuring a new butcher block countertop and newer appliances. Just beyond is a versatile finished bonus room that can easily serve as a dining room, home office or sitting area with French doors leading to the patio and outdoor space. The main level features a spacious living room along with the primary bedroom. The updated full bathroom showcases shiplap accents and vinyl flooring, while the upper level offers two additional bedrooms, providing separation and privacy. With fresh paint and updated flooring, these rooms can easily be transformed into comfortable, move-in-ready living spaces. Within the last five years the following updates were completed: the roof, siding, windows, boiler, and hot water heater, giving buyers added peace of mind. With these major investments already in place, the home offers a great opportunity for its next owner to update and customize the interior to suit their personal style. Conveniently located just minutes from shopping, restaurants, schools, and major commuter routes, you'll enjoy easy access to Middletown, Goshen, Warwick, and the surrounding Hudson Valley. Outdoor enthusiasts will appreciate nearby Highland Lakes State Park, the Heritage Trail, local wineries, breweries, golf courses, and farmers' markets. Popular destinations such as LEGOLAND New York Resort, Resorts World Catskills, and The Kartrite Resort & Indoor Waterpark are all within easy driving distance, making this location ideal for both everyday living and weekend adventures. If you've been searching for a property with acreage, and the opportunity to add value through cosmetic improvements, 122 Castle High Road is a great opportunity to create a space that reflects your own style while enjoying everything Orange County has to offer. Minisink School District

Listed with Curasi Realty, Inc. · Denise S Clancy · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 6:08 PM ET. ©2026 One Key MLS.

Estimate Your Monthly Payment

Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and Private Mortgage Insurance.

$2,283.44Total / mo

Estimated Monthly Payment

Principal & interest
$1,595.94 (69.9%)
Taxes
$487.50 (21.3%)
Insurance
$200.00 (8.8%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

Never miss a property

Be the first to know when a Orange County home hits the market.

Save this search

Market Insights

The market around Middletown, NY

Current Listings

New in the last 30 days

77

Sep 2026

Average Price

Active listings

$559,183

Sep 2026

Average Days on Market

Active listings

153 days

Sep 2026

Computed from 325 active OneKey MLS listings in Middletown, NY.

Similar homes in Orange County

See all 612
291 1st Street, Newburgh, NY
Photo 1 of 2
Coming SoonNew

$279,999

3 Bed • 2 Bath • 1,248 Sq. Ft.

291 1st Street

Newburgh, NY 12550

Listed with Howard Hanna Rand Realty

10 Woodycrest Trail, Monroe, NY
Photo 1 of 20
Coming SoonNew

$349,900

3 Bed • 2 Bath • 1,928 Sq. Ft.

10 Woodycrest Trail

Monroe, NY 10950

Listed with LPT Realty Tri-State, LLC

143 Deer Court Drive, Middletown, NY
Photo 1 of 26
Coming SoonNew

$299,000

2 Bed • 2 Bath • 1,291 Sq. Ft.

143 Deer Court Drive

Middletown, NY 10940

Listed with Howard Hanna Rand Realty