101 Drake Rd
Description
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...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.
- Listed by Jake Garay • Serhant LLCP: (646)-480-7665 C: (914)-772-2603 jakegaray@serhant.com
Property Details for 101 Drake Road
Property Details for 101 Drake Road
| Status | Active |
|---|---|
| MLS # | 951502 |
| Days on Market | 147 |
| Taxes | $22,775 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Single Family |
| MLS Type | Single Family |
| Year Built | 1900 |
| Lot Size | 2.94 AC / 128,066 SF |
| County | Dutchess County |
Location
Building Information for 101 Drake Road
Payment Calculator
$7,853 per month
30 year fixed, 6.36% Interest
$5,955
$1,898
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1Property Information for 101 Drake Road
- Senior Community YN: No
- Property Attached: No
- Structure Type: Detached
- State Or Province: NY
- School District: Arlington
- Elementary School District: Arlington
- Elementary School: Traver Road Primary School
- Middle Or Junior School District: Arlington
- Middle Or Junior School: TITUSVILLE INTERMEDIATE
- High School District: Arlington
- High School: Arlington High School
- Lease Considered: No
- Building Units Total: 1
- Parcel Number: 134400-6463-02-782662-0000
- Tax Assessed Value: $540,800.00
- Tax Source: Municipality
- Tax Year: 2025.0
- Association: No
- Amenities: A-Frame, Barndominium, Beamed Ceilings, Built-in Features, Cabin, Carriage House, Eat in Kitchen, Farmhouse, High Ceilings, High Speed Internet, Inside, Mini Estate, Open Floorplan, Open Kitchen, Original Details, Primary Bathroom, Recessed Lighting, Smart Thermostat, Storage, Walk In Closet, Washer/Dryer Hookup, Well
- Interior 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), Washer/Dryer Hookup
- Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Number Of Kitchens: 1.0
- Total Rooms: 9
- Basement: None
- Attic Description: Dormer
- Fireplace: Yes
- Fireplaces Total: 1
- Location Amenities: Eat in Kitchen, High Ceilings, High Speed Internet, Open Kitchen, Original Details, Storage, Walk In Closet, WD Hookup
- Laundry Features: Inside
- Living Area: 2,820.00
- Foundation Details: Pillar/Post/Pier
- Basement: No
- Exterior Property Features: Attached, Garage
- Elevation Certificate: No
- Construction Materials: Frame
- Pool Private: Yes
- Building Area Units: Square Feet
- Parking Features: Attached, Garage
- Parking Total: 10.00
- Garage: Yes
- Carport: No
- Cooling: None
- Heating: Baseboard
- Heat Fuel Type: Baseboard
- Sewer: Septic Tank
- Water Source: Well
- Utilities: Electricity Connected, Trash Collection Private
- Green Features: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Baseboard
- Down Payment Resource: No
Property History for 101 Drake Road
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 14, 2026 | Price Change ONEKEY #951502 | $1,195,000 | — |
| May 14, 2026 | Price Change ONEKEY #951502 | $1,950,000 | — |
| Apr 22, 2026 | Price Change ONEKEY #951502 | $1,275,000 | — |
| Mar 1, 2026 | Expired ONEKEY #868763 | $1,395,000 | — |
| Feb 10, 2026 | Listed (Active) ONEKEY #951502 | $1,375,000 | — |
| Dec 11, 2025 | Withdrawn ONEKEY #868763 | $1,395,000 | — |
| Dec 11, 2025 | Temporarily Off Market ONEKEY #868763 | $1,395,000 | — |
| Jun 6, 2025 | Listed (Active) ONEKEY #868763 | $1,525,000 | — |
| Feb 1, 2025 | Expired ONEKEY #H6303156 | $1,695,000 | — |
| Jan 10, 2025 | Withdrawn ONEKEY #H6303156 | $1,695,000 | — |
| Apr 26, 2024 | Listed (Active) ONEKEY #H6303156 | $1,695,000 | — |
| Apr 14, 2024 | Expired HVCR MLS #20233030 | $1,745,000 | — |
| Apr 13, 2024 | Expired ONEKEY #M417633 | $1,745,000 | — |
| Apr 13, 2024 | Expired ONEKEY #H6273886 | $1,745,000 | — |
| Apr 13, 2024 | Expired ONEKEY #HM417633 | $1,745,000 | — |
| Nov 26, 2023 | Listed (Active) ONEKEY #H6273886 | $1,795,000 | — |
| Oct 13, 2023 | Listed (Active) MHMLS #417633 | $1,795,000 | — |
| Oct 13, 2023 | Listed (Active) ONEKEY #HM417633 | $1,795,000 | — |
| Oct 13, 2023 | Listed (Active) HVCR MLS #20233030 | $1,795,000 | — |
| Oct 13, 2023 | Listed (Active) ONEKEY #M417633 | $1,795,000 | — |
| Sep 27, 2013 | Sold (Public Record) Public Record #390142629 | $650,000 | +4.1% / yr |
| Feb 18, 2011 | Sold (Public Record) Public Record #306580763 | $585,000 | — |
| Feb 18, 2011 | Sold MHMLS #290109 | $585,000 | — |
| Dec 16, 2010 | Pending MHMLS #290109 | — | |
| Nov 22, 2010 | Contract HGMLS #3025241 | — | |
| Jul 28, 2010 | Listed (Active) MHMLS #290109 | $647,000 | — |
| Jul 28, 2010 | Listed (Active) HGMLS #3025241 | $797,000 | — |
| Feb 16, 2001 | Sold MHMLS #110395 | $377,000 | — |
| Dec 1, 2000 | Pending MHMLS #110395 | — | |
| Jun 27, 2000 | Listed (Active) MHMLS #110395 | $395,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/14/2026 | Price Change ONEKEY #951502 | $1,195,000 |
| 05/14/2026 | Price Change ONEKEY #951502 | $1,950,000 |
| 04/22/2026 | Price Change ONEKEY #951502 | $1,275,000 |
| 03/01/2026 | Expired ONEKEY #868763 | $1,395,000 |
| 02/10/2026 | Listed (Active) ONEKEY #951502 | $1,375,000 |
| 12/11/2025 | Withdrawn ONEKEY #868763 | $1,395,000 |
| 12/11/2025 | Temporarily Off Market ONEKEY #868763 | $1,395,000 |
| 06/06/2025 | Listed (Active) ONEKEY #868763 | $1,525,000 |
| 02/01/2025 | Expired ONEKEY #H6303156 | $1,695,000 |
| 01/10/2025 | Withdrawn ONEKEY #H6303156 | $1,695,000 |
| 04/26/2024 | Listed (Active) ONEKEY #H6303156 | $1,695,000 |
| 04/14/2024 | Expired HVCR MLS #20233030 | $1,745,000 |
| 04/13/2024 | Expired ONEKEY #M417633 | $1,745,000 |
| 04/13/2024 | Expired ONEKEY #H6273886 | $1,745,000 |
| 04/13/2024 | Expired ONEKEY #HM417633 | $1,745,000 |
| 11/26/2023 | Listed (Active) ONEKEY #H6273886 | $1,795,000 |
| 10/13/2023 | Listed (Active) MHMLS #417633 | $1,795,000 |
| 10/13/2023 | Listed (Active) ONEKEY #HM417633 | $1,795,000 |
| 10/13/2023 | Listed (Active) HVCR MLS #20233030 | $1,795,000 |
| 10/13/2023 | Listed (Active) ONEKEY #M417633 | $1,795,000 |
| 09/27/2013 | Sold (Public Record) Public Record #390142629 | $650,000 +4.1% / yr |
| 02/18/2011 | Sold (Public Record) Public Record #306580763 | $585,000 |
| 02/18/2011 | Sold MHMLS #290109 | $585,000 |
| 12/16/2010 | Pending MHMLS #290109 | — |
| 11/22/2010 | Contract HGMLS #3025241 | — |
| 07/28/2010 | Listed (Active) MHMLS #290109 | $647,000 |
| 07/28/2010 | Listed (Active) HGMLS #3025241 | $797,000 |
| 02/16/2001 | Sold MHMLS #110395 | $377,000 |
| 12/01/2000 | Pending MHMLS #110395 | — |
| 06/27/2000 | Listed (Active) MHMLS #110395 | $395,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 101 Drake Road
Schools near 101 Drake Road
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | K to 2 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | 3 to 5 |
Rating | School | Distance |
|---|---|---|
Traver Road Primary School PublicK to 2 | ||
Lagrange Middle School Public6 to 8 | ||
Arlington High School Public9 to 12 | ||
West Road/d'Aquannis Intermediate School Public3 to 5 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.
Listing Courtesy of Serhant LLC
Based on information submitted to the MLS GRID as of 06/16/2026 10:16 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.
