Off Market Sep 2019 for $725K

$1,194,420

Est. refi paymentEst. refi $4,687/mo

•

3,800

sq ft

166 Benedict Rd, Montgomery, NY 12549

About this home

MAGNIFICIENT private estate nestled within the highly desired Winding Hills Park. Dramatic custom Post-and-Beam Contemporary design with no expenses spared. Elegant formal dining and living room with soaring ceilings, showcased with cove lighting, and wide plank maple floors. A chef’s dream kitchen with fireplace that flows into a sun lit covered porch, mahogany flooring, and wood-burning stove for year-round relaxation. 1st floor master bedroom with private en-suite and enclosed porch where you will hear the sounds of the babbling brook and overlook the serene landscaped grounds. Guest quarters for extended family and friends, ideal for possible B&B. Home features all high-end finishes, radiant heat, heated 3+1 car garage, generator and so much more. Your own private retreat, yet only a few miles drive from the quaint village of Montgomery where you'll enjoy the finest restaurants and shopping. Conveniently located near NY Stewart International airport and NJ Transit/Metro North Additional Information: Amenities:Guest Quarters,ParkingFeatures:3 Car Attached,

Single-familyProperty Type

2003Year Built

2.3 acresLot Size

$314Est. Price/Sq.Ft.

3 car garageParking

Listing by JoAnn Maxwell • Howard Hanna Rand Realty

Bought with Jonathon Lee • KW Hudson Valley United

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #H4923708

Redfin Estimate

$1,194,420

$469K since sold in September 2019$24K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 70.6% higher than the average sale price ($700K) of 6 comparable homes.

SOLD FEB 19, 2026
$625,000
A
4 beds3.5 baths2,912 sq ft
135 Benedict Rd, Montgomery, NY 12549
Listing by Keller Williams Realty
SOLD AUG 14, 2026
$599,000
B
3 beds2.5 baths2,236 sq ft
18 Locust Dr, Montgomery, NY 12549
Listing by Keller Williams Realty
SOLD AUG 13, 2026
$899,900
C
3 beds3.5 baths3,668 sq ft
41 Fern Wood Way, Montgomery, NY 12549
Listing by Realty Promotions Inc
SOLD AUG 17, 2026
$647,500
D
4 beds2.5 baths2,956 sq ft
1 Boxwood Ln, Montgomery, NY 12549
Listing by Howard Hanna Rand Realty
SOLD JUL 8, 2026
$719,000
E
4 beds2.5 baths2,984 sq ft
15 Ferrante Dr, Montgomery, NY 12549
Listing by RE/MAX Benchmark Realty Group
SOLD SEP 7, 2026
$710,000
F
4 beds3.5 baths2,982 sq ft
55 Noelle Dr, Walden, NY 12586
Listing by Flag Realty Group

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Sell

$625,776

Est. take-home

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Refinance

Est. cash available

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Rent

$3,409/mo

Redfin rental estimate

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Market trends in 12549, NY

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.4%

0.8% MoM

Median sale price

$510K

$62K MoM

Avg. days on market

39d

2 days MoM

Recently sold homes

6 MoM

New listings for sale

OPEN SAT, 11AM TO 1PM
$769,000
4 beds2.5 baths3,078 sq ft
28 Enright Ln, Montgomery, NY 12549
Listing by Serhant LLC
$729,999
4 beds2.5 baths2,454 sq ft
392 Bailey Rd, Montgomery, NY 12549
Listing by Curasi Realty, Inc.
See all

Provided by Redfin

Sale history for 166 Benedict Rd

Year

Property tax

Land + Additions

Assessment*

2025

$24,077 (+4.1%)

$80,000 + $360,000

$440,000

2024

$23,134 (+5.9%)

$80,000 + $360,000

$440,000

2023

$21,838 (−2.6%)

$80,000 + $360,000

$440,000

2022

$22,416 (+0.8%)

$80,000 + $360,000

$440,000

2021

$22,249 (−1.5%)

$80,000 + $360,000

$440,000

2020

$22,579 (+3.9%)

$80,000 + $360,000

$440,000

2019

$21,728 (+2.1%)

$80,000 + $360,000

$440,000

2018

$21,279 (+3.2%)

$80,000 + $360,000

$440,000

2017

$20,621 (−3.5%)

$80,000 + $360,000

$440,000

2016

$21,377 (+4.3%)

$80,000 + $360,000

$440,000

2015

$20,487 (+1.4%)

$80,000 + $360,000

$440,000

2014

$20,199

$80,000 + $360,000

$440,000

Tax history for 166 Benedict Rd

Year

Property tax

Land + Additions

Assessment*

2025

$24,077 (+4.1%)

$80,000 + $360,000

$440,000

2024

$23,134 (+5.9%)

$80,000 + $360,000

$440,000

2023

$21,838 (−2.6%)

$80,000 + $360,000

$440,000

2022

$22,416 (+0.8%)

$80,000 + $360,000

$440,000

2021

$22,249 (−1.5%)

$80,000 + $360,000

$440,000

2020

$22,579 (+3.9%)

$80,000 + $360,000

$440,000

2019

$21,728 (+2.1%)

$80,000 + $360,000

$440,000

2018

$21,279 (+3.2%)

$80,000 + $360,000

$440,000

2017

$20,621 (−3.5%)

$80,000 + $360,000

$440,000

2016

$21,377 (+4.3%)

$80,000 + $360,000

$440,000

2015

$20,487 (+1.4%)

$80,000 + $360,000

$440,000

2014

$20,199

$80,000 + $360,000

$440,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

2.5

Stories

1.7

Lot width

—

Lot depth

—

Lot size

2.3 Acres

Year renovated

—

Sq. Ft.

3,800

Year built

2003

Style

Single Family Residential

County

Orange County

APN

334289A02800000020130000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 13, 2026.

Property details

Parking

Parking Information
Parking Total: 3
Parking Features: Attached, Driveway, Garage Door Opener, Garage, Heated Garage

Garage Information
Garage Spaces: 3
Has Garage

Interior

Virtual Tour Information

Fireplace Information
Has Fireplace
Fireplaces Total: 2
Fireplace Features: Wood Burning Stove

Heating & Cooling
Cooling: Central Air
Heating: Forced Air, Propane, Radiant

Interior Features
Interior Features: Cathedral Ceiling(s),Chandelier,Eat-in Kitchen,Entertainment Cabinets,Entrance Foyer,ENERGY STAR Qualified Door(s),Formal Dining,Granite Counters,Master Downstairs,Primary Bathroom
Window Features: ENERGY STAR Qualified Windows, Screens, Skylight(s)
Laundry Features: Inside
Appliances: Dishwasher, Dryer, ENERGY STAR Qualified Appliances, Microwave, Refrigerator, Washer, Gas Water Heater
Flooring: Hardwood
Levels: Two
Patio And Porch Features: Deck, Porch

Room Information
Basement YN: Yes
Attic: Dormer,Finished
Rooms Total: 10
Basement: Full, Unfinished, Walk-Out Access

Bathroom Information
Bathrooms Full: 3
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Cedar, Shake Siding, Structurally Insulated Panels
Security Features: Security System
Waterfront YN: Yes

Pool Information
Has Spa

Lot Information
Additional Parcels YN: No
Lot Features: Near Public Transit, Near School, Near Shops, Part Wooded, Views

Property Information
Stories: 2
Other Equipment: Generator, Intercom
Living Area Source: Public Records
Property Sub Type: Single Family Residence
Property Condition: Actual

Financial

Tax Information
Tax Year: 2018
Tax Source: Municipality
Tax Annual Amount: $22,000

Financial Information
Buyer Financing: Cash

Utilities

Utility Information
Electric Company: NYSEG
Sewer: Septic Tank
Utilities: Trash Collection Private

Location

HOA Information
Association Amenities: Park, Sauna

School Information
Elementary School: Montgomery Elementary School
Middle Or Junior School: Valley Central Middle School
High School: Valley Central High School
High School District: Valley Central (Montgomery)

Location Information
Directions: Interestate Route 84 to Exit 6/NY 17-k, Left on N Kaisertown Rd and Right onto Benedict Rd, property on Right #166
County Or Parish: Orange County

Community Information
Community Features: Park

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 3,800
Stories: 1.7
Lot Size: 2.3 acres
Style: Single Family Residential
Year Built: 2003
Year Renovated: —
County: Orange County
APN: 334289A02800000020130000000

Home facts updated by county records on Aug 13, 2026

Around this home

Schools

Some nearby schools may not be within this home's attendance zone. Please check the Valley Central School District (Montgomery) website to verify.

Montgomery Elementary School

Public K-5 • 1.8mi

5/10

Valley Central Middle School

Public 6-8 • 3.0mi

6/10

Valley Central High School

Public 9-12 • 3.1mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

4/10 Fire Factor

0.93% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 100° expected this year, 15 days in 30 years

4/10 Wind Factor

10% 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)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 3.8 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

3.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.14M – $1.37M

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New listings for sale in 12549

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28 Enright Ln, Montgomery, NY 12549

Listing by Serhant LLC

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4 beds2.5 baths2,454 sq ft

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Listing by Curasi Realty, Inc.

Home values near 166 Benedict Rd

Data from public records.

Address	Redfin Estimate
177 Benedict Road, Montgomery, NY 4 Beds \| 3 Baths \| 2040 Sq. Ft.	$604,676
193 Benedict Road, Montgomery, NY 4 Beds \| 2.5 Baths \| 2100 Sq. Ft.	$638,201

Address	Redfin Estimate
185 Benedict Road, Montgomery, NY 2 Beds \| 2.5 Baths \| 1813 Sq. Ft.	$573,042
143 Benedict Road, Montgomery, NY 4 Beds \| 3.5 Baths \| 3264 Sq. Ft.	$599,099

Address	Redfin Estimate
135 Benedict Road, Montgomery, NY 4 Beds \| 3.5 Baths \| 2912 Sq. Ft.	$694,986
159 Benedict Road, Montgomery, NY 3 Beds \| 2.5 Baths \| 2265 Sq. Ft.	$603,726

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2019. This data may not match . Learn more.

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