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

255 Howells Road

Middletown, NY 10940 · Orange County

Beds
5
Baths
4.5
Sqft
4,200
Status
Active
On site
18 days

Know your budget before you tour. Get pre-qualified

About this home

Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas complete the setting. The original 1821 Colonial estate serves as the main house, blending historic character with thoughtfully updated features throughout. The expansive grounds provide abundant opportunities for recreation, including horseback riding, farming, snowmobiling, four-wheeling, fishing, and more. With numerous updates and an array of versatile structures, this exceptional property offers a rare combination of privacy, history, and functionality. The land is also subdivisible, providing potential for future development. Amenities: Storage, multiple barns, natural pond, extensive acreage.

Listed with KW Hudson Valley United · Jonathon Z. Lee · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 2, 2026, 1:08 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.

$5,272.78Total / mo

Estimated monthly payment

Principal & interest
$4,181.95(79.3%)
Taxes
$890.83(16.9%)
Insurance
$200.00(3.8%)

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 an Orange County home hits the market.

Save this search

Market insights

The market around Middletown, NY

Current listings

New in the last 30 days

80

Nov 2026

Average price

Active listings

$538,776

Nov 2026

Average days on market

Active listings

154 days

Nov 2026

Computed from 334 active OneKey MLS listings in Middletown, NY.

Similar homes in Orange County

See all 732
38 Chapel Court, Pine Bush, $650,000
38 Chapel Court, Pine Bush, NY
Photo 1 of 41
Coming SoonNew

$650,000

3 Bed • 3 Bath • 2,603 Sq. Ft.

38 Chapel Court

Pine Bush, NY 12566

Listed with eXp Realty

459 Ridge Road, Campbell Hall, $625,000
459 Ridge Road, Campbell Hall, NY
Photo 1 of 38
Coming SoonNew

$625,000

3 Bed • 2.5 Bath • 2,400 Sq. Ft.

459 Ridge Road

Campbell Hall, NY 10916

Listed with Weichert Realtors