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

165 Benedict Road

Montgomery, NY 12549 · Orange County

Beds
3
Baths
2.5
Sqft
2,030
Status
Active
On site
119 days

Know your budget before you tour. Get pre-qualified

About this home

VALLEY CENTRAL SCHOOLS | 3 BEDS + DEDICATED HOME OFFICE | 3 PRIVATE WOODED ACRES! Tucked away on three secluded acres, this turnkey Colonial Farmhouse pairs quintessential Hudson Valley charm with MAJOR UPGRADES UNDER 5 YEARS OLD: NEW CENTRAL A/C, NEW HIGH-EFFICIENCY BOILER, NEW EXPANSIVE ENTERTAINER’S DECK, OUTDOOR JACUZZI, AND INDOOR INFRARED SAUNA. Inside, warm wide-plank wood floors and a classic brick fireplace anchor the main living space, flowing into a formal dining room and a custom country kitchen with exposed timber beams, stainless gas appliances, built-in wine cooler, and breakfast bar. Work remotely without sacrificing sleeping space in the DEDICATED MAIN-FLOOR HOME OFFICE, complemented by a first-floor laundry room and powder room. Upstairs features three generous bedrooms with solid knotty pine doors, including a primary suite with crown molding, separate walk-in shower, and a deep whirlpool soaking tub framing peaceful tree views. Step out to a resort-style backyard complete with an IN-GROUND SWIMMING POOL, stamped concrete patio, new dining deck, hot tub, attached 2-car garage, and a full basement with sauna. While designed as an idyllic primary sanctuary, the property offers proven carrying-cost relief, generating OVER $50,000/YEAR IN AIRBNB INCOME ON UNDER 75 BOOKED NIGHTS. Minutes to Winding Hills Park, historic Montgomery Village dining, and major commuter routes.

Listed with Keller Williams Realty · Richard Baxter · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 14, 2026, 8:07 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.

$4,432.37Total / mo

Estimated monthly payment

Principal & interest
$3,324.87(75.0%)
Taxes
$907.50(20.5%)
Insurance
$200.00(4.5%)

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 Montgomery, NY

Current listings

New in the last 30 days

7

Nov 2026

Average price

Active listings

$927,420

Nov 2026

Average days on market

Active listings

238 days

Nov 2026

Computed from 63 active OneKey MLS listings in Montgomery, NY.

Similar homes in Orange County

See all 940