Nestled among mature trees on beautifully landscaped grounds, this extraordinary four-bedroom, three full-bath residence offers timeless architecture, luxurious updates, and an exceptional indoor-outdoor lifestyle. Every room has been thoughtfully designed to maximize comfort, elegance, and an abundance of natural light. A gracious circular driveway welcomes you home, where classic curb appeal and lush landscaping create an unforgettable first impression. Inside, stunning white oak flooring flows throughout the living and dining rooms. The inviting living room is anchored by a charming wood-burning fireplace and oversized windows that fill the space with warm, natural light. One of the true centerpieces of the home is the spectacular conservatory-style dining room. Surrounded by graceful arched walls of windows, this breathtaking space feels as though you’re dining in the garden, offering panoramic views of the surrounding landscape and an atmosphere unlike anything else. Just beyond, a separate greenhouse provides the perfect retreat for year-round gardening, cultivating orchids, herbs, or simply enjoying a quiet morning coffee. Designed for both everyday living and effortless entertaining, the beautifully renovated eat-in kitchen boasts expansive countertops, abundant custom cabinetry, stainless steel appliances, a double oven, gas cooktop, prep sink, under-cabinet lighting, and soft-close drawers. Newer washer and dryer complete the convenient first-floor laundry area. The warm and inviting family room showcases exposed beam ceilings, a new gas fireplace insert, and direct access to the brand-new deck overlooking the property’s private backyard oasis. Privately situated on the main level, the spacious primary suite offers a soaring vaulted ceiling, a stunning Palladian window with a motorized shade, two custom-designed walk-in closets, and a beautiful en-suite bath featuring a new sink, toilet, and vent fan. A beautifully appointed guest bath offers custom cabinetry, a bay window, a relaxing jetted soaking tub, a glass-enclosed walk-in shower, and abundant storage. Upstairs, natural light continues to fill two generously sized bedrooms (one having access to an oversized cedar closet), accompanied by a beautifully designed full bath with a linen closet. The full unfinished basement offers incredible potential to create additional living space, a fitness studio, media room, or workshop. Step outside and discover your own private resort. The expansive brand-new deck overlooks meticulously landscaped grounds and a smart-controlled heated saltwater pool surrounded by new fencing. Significant recent improvements include a brand-new septic tank, a new heat pump system serving both the first and second floors, upgraded insulation throughout, recessed lighting, a smart irrigation system, refreshed landscaping, and countless thoughtful enhancements. A two-car garage completes this remarkable offering. Rarely does a home combine timeless craftsmanship, modern conveniences, exceptional natural light, and resort-style outdoor living so seamlessly. Just minutes to the Arlington Town Center, Vassar Hospital, Mid-Hudson Regional Hospital, Vassar College, Marist College, The Culinary Institute of America, Poughkeepsie Train Station (Metro North), the Bardavon Performing Arts Center and Poughkeepsie's thriving culinary and arts scene. This is more than a home - it’s a destination where every season can be enjoyed in comfort, beauty, and style.
Single-familyProperty Type
1966Year Built
0.45 acresLot Size
$233Price/Sq.Ft.
2 car garageParking
Listing by Jennifer Stapleton• Houlihan Lawrence Inc.
A spacious and well-kept four bed, three bath home with something for everyone in the Town of Poughkeepsie. Perfect for a growing family or weekender with the private tree-lined backyard with beautiful landscaping and heated pool. Many upgrades, customizations and endless storage opportunities, this home features beautiful new hardwood floors throughout first floor, remodeled bathroom, interior greenhouse, fireplace, back deck, and large patio. Massive first floor master en suite with two large walk-in closets and full bath. Great neighborhood close to parks, walking trails, restaurants, bars, golf and more. Less than 5 miles from stunning Vassar College campus. Start enjoying your new picturesque upstate lifestyle! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached,
Year
Property tax
Land + Additions
Assessment*
2025
$20,264 (+16.8%)
$82,800 + $428,700
$511,500
2024
$17,343 (−13.7%)
$82,800 + $428,700
$511,500
2023
$20,098 (−3.5%)
$82,800 + $428,700
$511,500
2022
$20,831 (+11.8%)
$75,200 + $416,300
$491,500
2021
$18,635 (+55.9%)
$75,200 + $351,800
$427,000
2020
$11,953 (+2.7%)
$75,200 + $289,800
$365,000
2019
$11,638 (+10.7%)
$75,200 + $289,800
$365,000
2018
$10,511 (+2.2%)
$75,200 + $289,800
$365,000
2017
$10,288 (+5.9%)
$75,200 + $245,300
$320,500
2016
$9,710 (−1.4%)
$75,200 + $240,800
$316,000
2015
$9,850 (+1.3%)
$75,200 + $240,800
$316,000
2014
$9,727
$79,500 + $244,500
$324,000
Public record
Public record
Zoning
Beds
4
Baths
3
Stories
1.7
Lot width
—
Lot depth
—
Lot size
0.45 Acres
Year renovated
1986
Finished Sq. Ft.
2,790
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,790
Year built
1966
Style
Single Family Residential
County
Dutchess County
APN
134689A00626000031222140000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 31, 2026.
R-20
Residence, Single-family 20,000 Square Foot District
This district recognizes and is intended to preserve the principally single-family residential development pattern within the Town's established neighborhoods by promoting continuing opportunity for single-family residential and smaller-scale community facility uses within these neighborhoods consistent with their established character. To the extent undeveloped land within this district is available for major subdivision, the use of open space preservation techniques such as clustering of homes is encouraged in order to establish links to existing open space areas.
Permitted uses
Include but are not limited to:
Housing-Group
Housing-Single unit
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
4/10 Heat Factor
7 days above 98° expected this year, 14 days in 30 years
4/10 Wind Factor
13% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Historical weather
Poughkeepsie, NY • 12603
Average low and high temperatures (°F)
33
18
37
18
54
31
64
41
71
51
82
60
87
67
82
58
77
54
67
43
53
33
38
22
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
93/ 100
Exceptional sunlight
Sunscore
This home receives average direct sun exposure in Poughkeepsie. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.1 hrs
5.5 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 44 Pleasant Ridge Dr
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $500,000 and $610,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $500K to $610K.