Set in a delightful neighborhood where homes are thoughtfully spaced for privacy, this postmodern home was designed with a sense of ease and flow, where spaces open naturally to one another while still maintaining definition and purpose. From the moment you enter, a double-height foyer introduces the home with light, anchored by a graceful staircase and framed views into the rooms beyond. The living room expands outward, grounded by oak flooring and a striking stone fireplace that serves as a natural focal point. Columns and subtle shifts in ceiling height define space without interrupting the open flow, while large windows and glass doors continue the connection to the outdoors. A more formal dining room sits just off the foyer beneath a soft archway, offering a slightly more intimate setting while remaining visually tied to the rest of the home. Also, off the foyer, a separate room, enclosed by French doors provides flexibility, well-suited as a home office, library or quiet sitting room. At its center, the kitchen is both functional and inviting, with generous counter space and quality appliances, and easy access to the butler's pantry and mudroom. The dine-in area has French doors that open to a spacious deck and outdoor entertainment space, all viewing the fabulous pool and waterfall. An outdoor kitchen connects the covered porch with views of the Gunite, salt water pool and private backyard. Upstairs, the primary suite has a spacious bath with large soaking tub beneath an expansive window, double vanity and glass enclosed walk-in shower. The three additional bedrooms, all with wood floors, are spacious with ample closets. Rounding out the second floor is a large media or game room, offering a flexible space for entertainment and gathering. Set near the heart of Red Hook, a village rooted in Hudson Valley history and known today for its vibrant Main Street, local shops, restaurants, and welcoming small-town atmosphere. Nearby parks, including Tivoli Bays and Poet's Walk, along with golf, trails, and river access, offer a range of outdoor pursuits.
Single-familyProperty Type
2000Year Built
3.48 acresLot Size
$329Price/Sq.Ft.
3 car garageParking
Listing by Jill Rose• Houlihan Lawrence Inc.
Contact: 845-876-4443
Bought with Tracy Dober• Rouse + Co Real Estate LLC
Est. $3,409 per month, based on comparable rentals
Sale and tax history for 58 Deer Run Rd
Sale History
Tax History
Date
Event
Price
HVCRMLS #20261436
Jun 18, 2026
Sold
$1,200,000
$329/sq ft
May 29, 2026
Pending
—
Apr 23, 2026
Contingent
—
Apr 7, 2026
Price Changed
$1,200,000
$329/sq ft
Apr 7, 2026
Listed
$120,000
$33/sq ft
+23
Set in a delightful neighborhood where homes are thoughtfully spaced for privacy, this postmodern home was designed with a sense of ease and flow, where spaces open naturally to one another while still maintaining definition and purpose. From the moment you enter, a double-height foyer introduces the home with light, anchored by a graceful staircase and framed views into the rooms beyond. The living room expands outward, grounded by oak flooring and a striking stone fireplace that serves as a natural focal point. Columns and subtle shifts in ceiling height define space without interrupting the open flow, while large windows and glass doors continue the connection to the outdoors. A more formal dining room sits just off the foyer beneath a soft archway, offering a slightly more intimate setting while remaining visually tied to the rest of the home. Also, off the foyer, a separate room, enclosed by French doors provides flexibility, well-suited as a home office, library or quiet sitting room. At its center, the kitchen is both functional and inviting, with generous counter space and quality appliances, and easy access to the butler's pantry and mudroom. The dine-in area has French doors that open to a spacious deck and outdoor entertainment space, all viewing the fabulous pool and waterfall. Upstairs, the primary suite has a spacious bath with large soaking tub beneath an expansive window, double vanity and glass enclosed walk-in shower. The three additional bedrooms, all with wood floors, are spacious with ample closets. Rounding out the second floor is a large media or game room, offering a flexible space for entertainment and gathering. Set near the heart of Red Hook, a village rooted in Hudson Valley history and known today for its vibrant Main Street, local shops, restaurants, and welcoming small-town atmosphere. Nearby parks, including Tivoli Bays and Poet's Walk, along with golf, trails, and river access, offer a range of outdoor pursuits.
OneKey® MLS as Distributed by MLS Grid #979982
Jun 18, 2026
Sold
$1,200,000
$329/sq ft
May 10, 2026
Pending
—
Apr 7, 2026
Listed
$1,200,000
$329/sq ft
HVCRMLS #132156
Aug 26, 2020
Sold
$785,000
$215/sq ft
Jun 10, 2020
Listed
$785,000
$215/sq ft
+20
A truly private retreat in peaceful Upper Red Hook, this generously-sized home sits at the end of a handsome approach. Enjoy over 3600 sf of open & airy living space with many upgrades like a new modern kitchen and master suite. There are two open sitting areas on the main floor as well as a formal dining room, office, butler's pantry & half bath. Upstairs you'll find the large master suite, a gorgeous full bathroom with glass-walled shower and soaking tub, three additional bedrooms, plus an oversized game/media room. The 9′ dug-out poured concrete basement has plenty of room for storage, a large gym area & up-to-date mechanicals. The covered porch and deck lead to the stone patio where you'll find the glorious waterfall pool, as well as a built-in stone fire pit area for outdoor enjoyment. The property is fully fenced and surrounded by perennial gardens and mature landscaping with a separate fenced vegetable garden. So much to enjoy! Nearly 3.5 acres, AC and security system in place.
Public Records
Jun 26, 2007
Sold
$730,000
$200/sq ft
HGMLS #2613323
Aug 8, 2006
Delisted
—
May 9, 2006
Listed
*
Public Records
Apr 21, 1998
Sold
$48,500
$13/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$21,996 (+3.2%)
$186,100 + $949,000
$1,135,100
2024
$21,320 (+1.0%)
$170,700 + $870,644
$1,041,344
2023
$21,109 (+2.1%)
$161,000 + $821,400
$982,400
2022
$20,677 (+1.8%)
$145,000 + $724,400
$869,400
2021
$20,318 (−0.5%)
$145,000 + $598,100
$743,100
2020
$20,419 (+0.7%)
$145,000 + $569,500
$714,500
2019
$20,270 (+0.3%)
$145,000 + $569,500
$714,500
2018
$20,203 (+0.9%)
$145,000 + $569,500
$714,500
2017
$20,025 (+0.9%)
$145,000 + $569,500
$714,500
2016
$19,847 (+3.9%)
$145,000 + $569,500
$714,500
2015
$19,107 (+1.5%)
$145,000 + $569,500
$714,500
2014
$18,820
$145,000 + $569,500
$714,500
Public record
Public record
Zoning
Beds
4
Baths
2.5
Stories
2
Lot width
—
Lot depth
—
Lot size
3.48 Acres
Year renovated
—
Sq. Ft.
5,400
Year built
2000
Style
Single Family Residential
County
Dutchess County
APN
134889A00637300005399670000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 3, 2026.
RD3
Rural Development 3
The Rural Development 3 (RD3) District is intended to allow a mix of agricultural use and compatible moderate-density rural residential development and other conservation, recreation and open space uses consistent with established land use patterns. In order to conserve prime agricultural and other environmentally sensitive lands throughout the RD3 District, as well to maintain the overall rural and scenic character of the district, use of the residential cluster subdivision technique, encouragement of conservation density subdivisions and limitations on the scale of development that may be authorized are provided.