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Land with Home for Sale in Pleasant Valley, New York

101 Drake Rd, Pleasant Valley, NY 12569

$1,195,000
3 acres
Active sale
$80k drop
Est $8,003/mo

Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind residence and companion pool house, creating a private retreat unlike anything else available in the Hudson Valley. From the moment you arrive, the home's timeless architecture tells a story. Inside, soaring vaulted ceilings, original hand-hewn beams, wide-plank floors, and authentic post-and-beam construction showcase the craftsmanship of a bygone era while providing the comfort and functionality today's buyers expect. Expansive walls of glass flood the interior with natural light and frame views of the surrounding countryside, creating a seamless connection between indoor and outdoor living. The main residence offers warm, inviting living spaces designed for both everyday living and entertaining. Rich architectural details, exposed timber framing, and carefully preserved historic elements create a sense of authenticity rarely found in modern construction. Every room balances rustic elegance with refined finishes, resulting in a home that feels both sophisticated and welcoming. Complementing the main residence is a beautifully converted barn pool house, providing exceptional flexibility for guests, entertaining, creative pursuits, or a private wellness retreat. The outdoor spaces are equally impressive, offering a peaceful setting to relax, gather, and enjoy the natural beauty of Dutchess County. Located just minutes from Millbrook, Rhinebeck, Poughkeepsie, and the region's renowned farms, wineries, restaurants, and outdoor recreation, this property delivers the best of Hudson Valley living while remaining easily accessible to New York City. Whether you're searching for a luxury barn conversion, a post-and-beam home, a historic country estate, or a weekend retreat in the Hudson Valley, 101 Drake Road represents a truly rare offering where history, architecture, and modern comfort come together in perfect balance.

2,820
Sq feet
3
Beds
2
Full baths
1
1/2 bath
1900
Built

Location

Street address
101 Drake Rd
Zip code
12569
School district
Arlington
Elevation
378 feet
Coordinates
41.7464, -73.7912

Property details

Acreage
2.94 acres
MLS #
MLSLI 951502
Posted

Property taxes

2025
$22,775

Parcels

  • 134400-6463-02-782662-0000

Details and features

Listing

Type
Residential
Subtype
Single Family Residence

Exterior

Parking Spaces
10
Parking
Garage
Pool
Private
Structures
Storage

Structure

Water
Well
Sewer
Septic Tank
Heating
Baseboard
Materials
Frame

Interior

Room Count
9
Rooms
Bathroom x 3, Bedroom x 3
Fireplaces
Yes
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Features
Beamed Ceilings, Built-In Features, Eat-In Kitchen, High Ceilings, High Speed Internet, Open Floorplan, Open Kitchen, Original Details, Primary Bathroom, Recessed Lighting, Smart Thermostat, Walk-In Closet(s), Washer/Dryer Hookup

Nearby schools

NameTypeDistrict
Traver Road Primary SchoolElementaryArlington
Titusville IntermediateMiddleArlington
Arlington High SchoolHighArlington

Listing history

DateEventPriceChangeSource
May 15, 2026Price drop$1,195,000$80,000 -6.3%MLSLI
Apr 22, 2026Price drop$1,275,000$100,000 -7.3%MLSLI
Feb 10, 2026New listing$1,375,000MLSLI
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This 2.94-acre property is located at 101 Drake Rd in Pleasant Valley, NY 12569. The property is available for sale, priced at $1,195,000. It has a 2,820 square foot 3-bedroom, 2.5-bath house built in 1900.

Listed by Serhant, (646) 480-7665

Checked 2 hours agoUpdated Source

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