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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.
Your happily ever after starts here. A 1776 inspired shaker design, complimented with modern farmhouse finishes, is so impressive inside and out. Set back off a quiet country road, on 3 picturesque acres, offers privacy yet conveniently located only 3 miles outside the historic Village of Montgomery, renowned for it variety of eateries and quaint shops. The attention to detail is impeccable in each and every room with wide plank pine flooring throughout, solid wood custom-made reproduction interior doors & cabinetry, crown molding, handcrafted copper outdoor lights, lamppost lantern,and brass chandelier and wall sconces, brick fireplace w/gas insert, private laundry/mudroom, master bedroom en suite w/large walk-in closet. The backyard is your own private retreat with a glorious in-ground pool, beautifully landscaped with stamped concrete patio, Black Jerith aluminum fencing, a 24' deck with retractable awning and an outdoor shower. Plenty of storage. A must see!! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,
Public Records
May 30, 1991
Sold
$40,000
$20/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$10,818
$49,000 + $148,700
$197,700
2025
$10,818 (+4.1%)
$49,000 + $148,700
$197,700
2024
$10,395 (+5.9%)
$49,000 + $148,700
$197,700
2023
$9,812 (−2.6%)
$49,000 + $148,700
$197,700
2022
$10,072 (+0.8%)
$49,000 + $148,700
$197,700
2021
$9,997 (−1.5%)
$49,000 + $148,700
$197,700
2020
$10,145 (+8.9%)
$49,000 + $148,700
$197,700
2019
$9,319 (+2.7%)
$49,000 + $148,700
$197,700
2018
$9,077 (+3.5%)
$49,000 + $148,700
$197,700
2017
$8,770 (−8.7%)
$49,000 + $148,700
$197,700
2016
$9,605 (+10.0%)
$49,000 + $148,700
$197,700
2015
$8,729 (+1.4%)
$49,000 + $148,700
$197,700
2014
$8,609
$49,000 + $148,700
$197,700
Public record
Beds
3
Baths
2.5
Stories
2
Lot width
—
Lot depth
—
Lot size
3 Acres
Year renovated
1992
Finished Sq. Ft.
2,030
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,030
Year built
1992
Style
Single Family Residential
County
Orange County
APN
334289A02800000010510000000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 8, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
3/10 Fire Factor
0.62% chance of being in a wildfire in next 30 years
4/10 Heat Factor
7 days above 100° expected this year, 14 days in 30 years
4/10 Wind Factor
9% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 2 days in 30 years
Provided by First Street
Historical weather
Montgomery, NY • 12549
Average low and high temperatures (°F)
32
16
36
19
54
31
63
40
70
49
80
58
84
64
80
56
75
52
63
42
52
33
37
22
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
48/ 100
Low sunlight
Sunscore
There appears to be significant shading by surrounding buildings, terrain, and vegetation.
7.8 hrs
0.4 hr
JuneDecember
Provided by Shadowmap
Redfin Estimate for 165 Benedict Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $520,000 and $899,900.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $520K to $900K.