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For sale
$1,195,000
3beds
2,820sqft

101 Drake Road, Pleasant Valley, NY 12569

3beds
2,820sqft
Single family residence, residential
Built in 1900
2.94 Acres
1 Garage space
$424 price/sqft

What's special

Expansive walls of glassNatural lightAuthentic post-and-beam constructionWarm inviting living spacesExposed timber framingRich architectural detailsCarefully preserved historic elements

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.

209 days
|
600
|
40
|
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 951502MLS Logo
Travel times

Family Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Serhant LLC 646-480-7665,

Jake Garay 914-772-2603

Source: OneKey® MLS as distributed by MLS GRID,MLS#: 951502MLS Logo

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 3
  • Bathrooms: 3
  • Full bathrooms: 2
  • 1/2 bathrooms: 1
Heating
  • Baseboard
Cooling
  • None
Appliances
  • Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Laundry: Washer/Dryer Hookup, Inside
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, Storage, Walk-In Closet(s)
  • Basement: None
  • Attic: Dormer
  • Number of fireplaces: 1
Interior area
  • Total structure area: 2,820
  • Total interior livable area: 2,820 sqft

Property

Parking
  • Total spaces: 10
  • Parking features: Attached, Garage
  • Garage spaces: 1
Features
  • Has private pool: Yes
Lot
  • Size: 2.94 Acres
Details
  • Parcel number: 1344006463027826620000
  • Special conditions: None

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: A-Frame,Barndominium,Cabin,Carriage House,Farmhouse,Mini Estate
  • Property subtype: Single Family Residence, Residential
Materials
  • Frame
  • Foundation: Pillar/Post/Pier
Condition
  • Year built: 1900

Utilities & green energy

  • Sewer: Septic Tank
  • Water: Well
  • Utilities for property: Electricity Connected, Trash Collection Private

Community & HOA

HOA
  • Has HOA: No
Location
  • Region: Pleasant Valley

Financial & listing details

  • Price per square foot: $424/sqft
  • Tax assessed value: $540,800
  • Annual tax amount: $22,775
  • Date on market: 2/10/2026
  • Cumulative days on market: 208 days
  • Listing agreement: Exclusive Right To Sell
  • Electric utility on property: Yes

Price history

DateEventPrice
5/14/2026Price change$1,195,000-6.3%$424/sqft
Source: OneKey® MLS as distributed by MLS GRID #951502 Report a problem
4/22/2026Price change$1,275,000-7.3%$452/sqft
Source: OneKey® MLS as distributed by MLS GRID #951502 Report a problem
2/10/2026Listed for sale$1,375,000-1.4%$488/sqft
Source: OneKey® MLS as distributed by MLS GRID #951502 Report a problem
12/11/2025Listing removed$1,395,000$495/sqft
Source: OneKey® MLS as distributed by MLS GRID #868763 Report a problem
10/21/2025Price change$1,395,000-8.5%$495/sqft
Source: OneKey® MLS as distributed by MLS GRID #868763 Report a problem
6/6/2025Listed for sale$1,525,000-10%$541/sqft
Source: OneKey® MLS as distributed by MLS GRID #868763 Report a problem
11/16/2024Listing removed$1,695,000$601/sqft
Source: OneKey® MLS as distributed by MLS GRID #H6303156 Report a problem
4/26/2024Listed for sale$1,695,000-2.9%$601/sqft
Source: OneKey® MLS as distributed by MLS GRID #H6303156 Report a problem
4/14/2024Listing removed--
Source: HVCRMLS #20233030 Report a problem
2/28/2024Price change$1,745,000-2.8%$619/sqft
Source: HVCRMLS #20233030 Report a problem
10/13/2023Listed for sale$1,795,000+176.2%$637/sqft
Source: HVCRMLS #20233030 Report a problem
10/23/2013Sold$650,000+11.1%$230/sqft
Source: Public Record Report a problem
2/24/2011Sold$585,000-9.6%$207/sqft
Source: Public Record Report a problem
10/9/2010Price change$647,000-13.4%$229/sqft
Source: Houlihan Lawrence #3025241 Report a problem
10/2/2010Price change$747,000-6.3%$265/sqft
Source: Houlihan Lawrence #3025241 Report a problem
7/30/2010Listed for sale$797,000+111.4%$283/sqft
Source: HOULIHAN LAWRENCE INC #290109 Report a problem
2/28/2001Sold$377,000$134/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025-- $540,800
2024-- $540,800
2023-- $540,800
2022-- $540,800
2021-- $540,800
2020-- $540,800
2019-- $540,800 +5.4%
2018-- $513,200 +5.7%
2017$16,388 $485,700
2016-- $485,700
2015-- $485,700
2014-- $485,700 -3.5%
2012-- $503,300 -8.5%
2011-- $550,000 +158.2%
2010-- $213,000
2009-- $213,000
2008-- $213,000
2007-- $213,000
2006-- $213,000
2005-- $213,000
2004-- $213,000
2003-- $213,000 +4.7%
2002-- $203,400
2001-- $203,400
2000-- $203,400

Find assessor info on the county website

Monthly payment

Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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Estimated market value

Not available

Estimated sales range

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Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 12569

Nearby schools

Traver Road Primary School
Grades K-2 • 1.3 miles
N/A
GreatSchools® Rating
Lagrange Middle School
Grades 6-8 • 5.9 miles
3/10
GreatSchools® Rating
Test Score Rating
3/10
Student Progress Rating
2/10
Arlington High School
Grades 9-12 • 5 miles
6/10
GreatSchools® Rating
Test Score Rating
7/10
College Readiness Rating
4/10

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