2,820 Sq. Ft.
$488 / Sq. Ft.
2,820
Sq. Ft.
$488
per Sq. Ft.

Description

Tucked behind a quiet country approach, two meticulously restored 19th-century barns have been reimagined into a refined luxury residence and companion pool house that feel timeless in character and elevated in execution. Inside the main residence, soaring vaulted ceilings, original hand-hewn beams, and wide-plank floors establish a sense of warmth and permanence, while expansive walls of glass invite natural light and create a seamless connection to the surrounding landscape. At the heart of the...Tucked behind a quiet country approach, two meticulously restored 19th-century barns have been reimagined into a refined luxury residence and companion pool house that feel timeless in character and elevated in execution. Inside the main residence, soaring vaulted ceilings, original hand-hewn beams, and wide-plank floors establish a sense of warmth and permanence, while expansive walls of glass invite natural light and create a seamless connection to the surrounding landscape. At the heart of the home, a beautifully appointed country kitchen anchored by a wood-burning fireplace is designed for both slow mornings and elegant entertaining. A dramatic great room and adjoining music room provide generous gathering spaces, while three bedrooms offer private, hotel-level comfort for guests. Outdoors, a heated in-ground pool is set among stone terraces and anchored by a fully outfitted luxury pool house with kitchen, bedroom, and bath, ideal for hosting, unwinding, or extended stays. The setting offers exceptional privacy while remaining effortlessly connected. Located less than 75 miles from New York City and just 10 minutes from the center of Millbrook, the property delivers the best of Hudson Valley living. World-class wineries, scenic hiking trails, equestrian estates, and farm-to-table dining are moments away, creating a lifestyle defined by balance, where weekend escape meets full-time retreat. This is not a conversion. It is a destination. A rare offering where historic architecture, modern luxury, and the rhythms of country life converge, all within easy reach of the city.
  1. Listed by Jake Garay • Serhant LLC
    P: (646)-480-7665 C: (914)-772-2603 jakegaray@serhant.com

Property Details for 101 Drake Road

City/Township
Pleasant Valley
Architectural Style
Cabin, Farmhouse, Mini Estate
Garage Spaces
1.00
Waterfront
No
LISTING UPDATED: 02/11/2026 05:03 AM

Property Details for 101 Drake Road

StatusActive
MLS #951502
Days on Market1
Taxes$22,775 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1900
Lot Size2.94 AC / 128,066 SF
CountyDutchess County

Location

Listing Courtesy of Serhant LLC
Add your commute

Building Information for 101 Drake Road

Stories-Year Built1900Building Size-Lot Size2.94 AC / 128,066 SF

Payment Calculator

$8,599 per month

30 year fixed, 6.15% Interest

Principal and Interest

$6,702

Property Taxes

$1,898

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 101 Drake Road

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: false
  • State Or Province: NY
School Information
  • 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
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 134400-6463-02-782662-0000
  • Tax Assessed Value: $540,800.00
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: Beamed Ceilings, Built-in Features, Cabin, 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
  • Basement: No
Exterior Features
  • Exterior Property Features: Attached, Garage
  • Elevation Certificate: No
  • Construction Materials: Frame
  • Pool Private: Yes
Lot Information
  • Building Area Units: Square Feet
Parking
  • Parking Features: Attached, Garage
  • Parking Total: 10.00
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: None
  • Heating: Baseboard
  • Heat Fuel Type: Baseboard
  • Sewer: Septic Tank
  • Water Source: Well
  • Utilities: Electricity Connected, Trash Collection Private
Green Features
  • Green Features: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Baseboard
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 101 Drake Road

DateEvent & SourcePriceAppreciation
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 #HM417633

$1,745,000—
Apr 13, 2024

Expired

ONEKEY #H6273886

$1,745,000—
Apr 13, 2024

Expired

ONEKEY #M417633

$1,745,000—
Nov 26, 2023

Listed (Active)

ONEKEY #H6273886

$1,795,000—
Oct 13, 2023

Listed (Active)

ONEKEY #HM417633

$1,795,000—
Oct 13, 2023

Listed (Active)

MHMLS #417633

$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—
DateEvent & SourcePrice
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 #HM417633

$1,745,000
04/13/2024

Expired

ONEKEY #H6273886

$1,745,000
04/13/2024

Expired

ONEKEY #M417633

$1,745,000
11/26/2023

Listed (Active)

ONEKEY #H6273886

$1,795,000
10/13/2023

Listed (Active)

ONEKEY #HM417633

$1,795,000
10/13/2023

Listed (Active)

MHMLS #417633

$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, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 101 Drake Road

Taxable ValueLand$124,700Additions$416,100Total$540,800
Tax Record2024$17,390 ($1,449 / month)
Home Facts
Beds3Baths2.5Total Finished SqFt2,820 SqFtAbove Grade Finished SqFt2,820 SqFtStories2Lot Size128,066 SqFtStyleSingle Family ResidenceYear Built1900ZoningRRCountyDUTCHESSAPN134400 6463-02-782662-0000Fireplace TypeHas Fireplace

Schools near 101 Drake Road

This home is within Arlington Central School District.
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

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.

Similar Homes

Similar Sold Homes

101 Drake Road is a single family home for sale in Pleasant Valley, NY 12569. This property was listed for sale on February 10, 2026 by Serhant LLC, it's currently listed at $1,375,000. It has been on the market for a total of 1 days and was last sold on September 27, 2013. This listing's school district is Arlington Central School District. Nearby schools include Traver Road Primary School, Lagrange Middle School and Arlington High School. 101 Drake Road is a 3-bed, 3-bath, 2,820 sqft single family home built in 1900.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims 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 discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Serhant LLC

Based on information submitted to the MLS GRID as of 02/11/2026 05:03 AM. 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.