Hudson Valley Estate on 2.8 Private Acres | 4,839 SqFt Colonial | 45 Min to NYC: Experience a rare Hudson Valley estate where privacy, scale, and timeless craftsmanship meet 2.80 acres / 121,968 sqft of park-like grounds. 141 Old Tuxedo Road in Monroe, Orange County is a custom-built 1999 Colonial offering 4,839 square feet of finished living space across three levels. This is not just a "mountain house" it’s a true estate designed for elegant entertaining, multi-generational living, and everyday Hudson Valley luxury. Arrive via a winding private drive where mature woodlands frame open lawns and stone walkways lead to the home. The property sits elevated on nearly 3 acres, providing total privacy, serenity, and room to grow while remaining minutes from village amenities. Main Level: A dramatic two-story foyer with soaring ceilings sets the tone. Hardwood floors flow throughout, with oversized windows and French doors bringing in abundant natural light. The heart of the home is an expansive chef's kitchen with custom cabinetry and ample workspace, opening to formal living and dining rooms perfect for holidays and gatherings. A cozy family room with fireplace offers casual living. A first-floor laundry/mudroom and powder room add convenience. Multiple exits lead directly to a 1,000+ sqft deck overlooking the tranquil grounds - ideal for summer entertaining and morning coffee with views. Second Level: The primary suite is a private sanctuary featuring scenic views, a spa-inspired bath with jacuzzi tub and oversized shower, and dual walk-in closets. Three additional bedrooms and two full baths provide comfort for family and guests. Finished Lower Level: Nearly 2,400 additional square feet expand the home’s versatility. Use it for a media room, home gym, office, guest suite, or recreation space. With this level, the home offers almost 4,900 sqft of usable living space for work, play, and hosting. The Grounds: This is estate living. 2.80 acres of curated landscape with mature specimen trees, stone paths, open lawns, and intimate garden areas. There’s space for recreation, gardening, and outdoor gatherings, all while enjoying complete privacy and peace. The grounds blend natural beauty with thoughtful design, creating a true retreat feel. Location: Minutes from the historic villages of Tuxedo and Warwick with boutique shopping, top restaurants, wineries, and farmers markets. Outdoor recreation at Harriman State Park and Sterling Forest is just minutes away for hiking, biking, and lakes. For commuters, NYC is 45 minutes by car with nearby rail access from Tuxedo - perfect for weekend escapes or full-time country living. Additional Features: 4BD, 4BA, 3-car garage, 2 fireplaces, central air, baseboard heat, drilled well, septic, and extensive storage. Built in 1999 with quality construction throughout. 141 Old Tuxedo Road delivers the luxury of tranquility, the space of an estate, and a lifestyle removed from the ordinary - without ever being far from everything you need. Experience the difference nearly 3 acres makes.
Single-familyProperty Type
1999Year Built
2.8 acresLot Size
$227Price/Sq.Ft.
3 garage spacesParking
Listing by Adam Blankfort• Corcoran Baer & McIntosh
Bank Owned. Sold "AS IS". Limited Service Listing. No additional information available. See attachment for details and fees to buyer.
OneKey® MLS as Distributed by MLS Grid #H4420813
Oct 30, 2014
Sold
$378,589
$78/sq ft
Jun 18, 2014
Listed
$375,000
$77/sq ft
Bank Owned. Sold "AS IS". Limited Service Listing. No additional information available. See attachment for details and fees to buyer. Additional Information: ParkingFeatures:3 Car Attached,
Public Records
Apr 7, 2004
Sold
$520,000
$107/sq ft
Public Records
Nov 28, 2001
Sold
$390,000
$81/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$15,112
$14,200 + $48,000
$62,200
2025
$15,112 (+2.1%)
$14,200 + $48,000
$62,200
2024
$14,805 (+1.2%)
$14,200 + $48,000
$62,200
2023
$14,628 (+1.4%)
$14,200 + $48,000
$62,200
2022
$14,431 (+0.6%)
$14,200 + $48,000
$62,200
2021
$14,347
$14,200 + $48,000
$62,200
2020
$14,348 (+0.7%)
$14,200 + $48,000
$62,200
2019
$14,247 (+1.3%)
$14,200 + $48,000
$62,200
2018
$14,059 (+1.8%)
$14,200 + $48,000
$62,200
2017
$13,817 (−14.5%)
$14,200 + $48,000
$62,200
2016
$16,166 (−4.4%)
$14,200 + $48,000
$62,200
2015
$16,903 (+1.4%)
$14,200 + $63,000
$77,200
2014
$16,669
$14,200 + $63,000
$77,200
Public record
Beds
4
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
2.8 Acres
Year renovated
—
Finished Sq. Ft.
3,606
Unfinished Sq. Ft.
—
Total Sq. Ft.
3,606
Year built
1999
Style
Single Family Residential
County
Orange County
APN
335489A06100000010402200000
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
0.46% chance of being in a wildfire in next 30 years
4/10 Heat Factor
7 days above 95° expected this year, 16 days in 30 years
4/10 Wind Factor
14% 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
Greenwood Lake, NY • 10950
Average low and high temperatures (°F)
32
17
36
19
53
32
62
41
69
50
79
59
83
65
78
57
75
53
64
42
51
34
36
22
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
87/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Greenwood Lake. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.7 hrs
5.5 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 141 Old Tuxedo Rd
There isn’t enough information to generate an accurate estimate at this time. Learn More