40 Windy Hill Rd. Priv, Millbrook, NY 12545

Off Market Oct 2014 for $5M

$10,793,137

Est. refi paymentEst. refi $32,579/mo

•

8,659

sq ft

40 Windy Hill Rd. Priv, Millbrook, NY 12545

About this home

Enveloped in rural splendor and set amid the region's premier equestrian farms, this distinguished Hunt Country Estate features a character-rich Colonial which shares the memorable landscape with extensive outbuildings and fine equestrian amenities. Lovely gardens, a large lake, pool,carriage barn with 3-bedroom guest house, 8-stall barn,two cottages,a large barn/office and indoor tennis court are other highlights of this breathtaking setting, one of Millbrook's most illustrious offerings.,AMENITIES:Medical Facility,Basement:Interior Access,FLOORING:Wood,Ceramic Tile,Level 1 Desc:EF,FDR,FLR,DEN,LIB,SCR.PRCH.,EIK,FR,LDRY.,MUD RM.,OFF.,FBTH,,Below Grnd Sq Feet:1200,Level 3 Desc:ATTIC STORAGE,AboveGrade:7459,OTHERROOMS:Laundry/Util. Room,Professional Suite,Other School:SEVERAL PRIVATE,InteriorFeatures:Electric Dryer Connection,French Doors,Walk-In Closets,Washer Connection,Level 2 Desc:MSTR BD, 2 MSTR BTH,5 ADD BD,5BTH,GYM,SITTING RM,ExteriorFeatures:Landscaped,Outside Lighting,Unfinished Square Feet:1200,ROOF:Asphalt Shingles,FOUNDATION:Stone,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors Additional Information: Amenities:Guest Quarters,

Single-familyProperty Type

1820Year Built

157.18 acresLot Size

$1,246Est. Price/Sq.Ft.

Listing by John Friend • Houlihan Lawrence Inc.

Bought with John Friend • Houlihan Lawrence Inc.

Redfin checked: 2 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #M310286

Redfin Estimate

$10,793,137

$5.8M since sold in October 2014$1.7M since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 238.9% higher than the average sale price ($3.18M) of 6 comparable homes.

SOLD MAR 11, 2026
$5,775,000
A
6 beds8 baths8,117 sq ft
465 Shunpike, Millbrook, NY 12545
Listing by Corcoran Country Living
SOLD DEC 22, 2025
$6,250,000
B
5 beds5.5 baths5,162 sq ft
47-49 Crescent Rd, Millbrook, NY 12545
Listing by Elyse Harney Real Estate
SOLD AUG 11, 2026
$2,725,000
C
3 beds5 baths4,134 sq ft
97 Valley Farm Rd, Millbrook, NY 12545
Listing by George T Whalen Real Estate
SOLD NOV 14, 2025
$980,000
D
5 beds3.5 baths3,664 sq ft
3715 Route 44, Millbrook, NY 12545
Listing by Compass Greater NY, LLC
SOLD JUN 5, 2026
$2,400,000
E
8 beds4.5 baths3,010 sq ft
2039 Salt Point Tpke, Salt Point, NY 12578
Listing by Compass Greater NY LLC
SOLD AUG 24, 2026
$979,000
F
4 beds3 baths2,606 sq ft
2498 Salt Point Tpke, Clinton Corners, NY 12514
Listing by Corcoran Country Living

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$7,240,526

Est. take-home

List your home with Redfin and save $107,931

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,716/mo

Redfin rental estimate

List your home for rent

Market trends in 12545, NY

Last updated August 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

100.0%

3.9% MoM

Median sale price

$882K

$25K MoM

Avg. days on market

57d

24 days MoM

Recently sold homes

2 MoM

New listings for sale

NEW 6 HRS AGO
$799,000
2 beds1.5 baths1,056 sq ft
672 Tower Hill Rd, Millbrook, NY 12545
Listing by Houlihan Lawrence Inc.
$1,500,000
4 beds3.5 baths3,034 sq ft
3244 Sharon Tpke, Millbrook, NY 12545
Listing by Houlihan Lawrence Inc.
$5,750,000
4 beds3 baths3,810 sq ft
81-85 Fraleigh Hill Rd, Millbrook, NY 12545
Listing by Compass Greater NY, LLC
$635,000
3 beds2 baths2,234 sq ft
163 Horseshoe Rd, Millbrook, NY 12545
Listing by Compass Greater NY, LLC
$16,750,000
5 beds5.5 baths7,108 sq ft
482 Overlook Rd, Millbrook, NY 12545
Listing by Compass Greater NY, LLC
OPEN SUN, 1PM TO 3PM
$895,000
3 beds2 baths1,868 sq ft
3315 Franklin Ave, Millbrook, NY 12545
Listing by George T Whalen Real Estate
See all

Provided by Redfin

Sale history for 40 Windy Hill Rd. Priv

Date

Event

Price

HGMLS #3226768

Oct 1, 2014

Sold

$5,000,000

$577/sq ft

Oct 1, 2014

Price Changed

$5,000,000

$577/sq ft

Jul 28, 2014

Contingent

—

Jul 28, 2014

Price Changed

$9,500,000

$1,097/sq ft

Apr 4, 2014

Listed

$9,500,000

$1,097/sq ft

Enveloped in rural splendor and set amid the region's premier equestrian farms, this distinguished Hunt Country Estate features a character-rich Colonial, which shares the memorable landscape with extensive outbuildings and fine equestrian amenities. Lovely gardens, a large lake, pool, carriage barn with 3-bedroom guest house, 8-stall barn, two cottages, a large barn/office and indoor tennis court are other highlights of this breathtaking setting, one of Millbrook's most illustrious offerings.

OneKey® MLS as Distributed by MLS Grid #H3226768

Oct 1, 2014

Sold

$5,000,000

$577/sq ft

Sep 4, 2012

Listed

$9,500,000

$1,097/sq ft

OneKey® MLS as Distributed by MLS Grid #M310286

Oct 1, 2014

Sold

$5,000,000

$577/sq ft

Sep 4, 2012

Listed

$9,500,000

$1,097/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$99,019 (+1.8%)

$2,640,600 + $2,359,400

$5,000,000

2024

$97,277 (+3.9%)

$2,640,600 + $2,359,400

$5,000,000

2023

$93,628 (+0.3%)

$2,640,600 + $2,359,400

$5,000,000

2022

$93,366 (−10.4%)

$2,640,600 + $2,359,400

$5,000,000

2021

$104,157 (+65.7%)

$2,640,600 + $2,359,400

$5,000,000

2020

$62,861 (+0.2%)

$2,640,600 + $2,359,400

$5,000,000

2019

$62,733 (+3.5%)

$2,640,600 + $2,359,400

$5,000,000

2018

$60,597 (−10.0%)

$2,640,600 + $2,359,400

$5,000,000

2017

$67,316 (+3.3%)

$2,640,600 + $2,359,400

$5,000,000

2016

$65,184 (−1.9%)

$2,640,600 + $2,484,700

$5,125,300

2015

$66,437 (−0.8%)

$2,640,600 + $2,423,100

$5,063,700

2014

$66,987

$2,640,600 + $2,423,100

$5,063,700

Tax history for 40 Windy Hill Rd. Priv

Year

Property tax

Land + Additions

Assessment*

2025

$99,019 (+1.8%)

$2,640,600 + $2,359,400

$5,000,000

2024

$97,277 (+3.9%)

$2,640,600 + $2,359,400

$5,000,000

2023

$93,628 (+0.3%)

$2,640,600 + $2,359,400

$5,000,000

2022

$93,366 (−10.4%)

$2,640,600 + $2,359,400

$5,000,000

2021

$104,157 (+65.7%)

$2,640,600 + $2,359,400

$5,000,000

2020

$62,861 (+0.2%)

$2,640,600 + $2,359,400

$5,000,000

2019

$62,733 (+3.5%)

$2,640,600 + $2,359,400

$5,000,000

2018

$60,597 (−10.0%)

$2,640,600 + $2,359,400

$5,000,000

2017

$67,316 (+3.3%)

$2,640,600 + $2,359,400

$5,000,000

2016

$65,184 (−1.9%)

$2,640,600 + $2,484,700

$5,125,300

2015

$66,437 (−0.8%)

$2,640,600 + $2,423,100

$5,063,700

2014

$66,987

$2,640,600 + $2,423,100

$5,063,700

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

8.5

Stories

Lot width

—

Lot depth

—

Lot size

157.27 Acres

Year renovated

1987

Sq. Ft.

7,459

Year built

1900

Style

Single Family Residential

County

Dutchess County

APN

135889A00686600009707350000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 31, 2026.

Property details

Parking

Parking Information
Parking Features: Garage Door Opener, Garage

Interior

Fireplace Information
Has Fireplace
Fireplaces Total: 8

Heating & Cooling
Cooling: Wall/Window Unit(s)
Heating: Baseboard, Hot Water

Interior Features
Interior Features: High Ceilings,Primary Bathroom,Wet Bar
Window Features: Triple Pane Windows
Appliances: Dishwasher, Refrigerator, Washer
Patio And Porch Features: Patio, Porch

Room Information
Basement YN: Yes
Basement: Full, Unfinished

Bathroom Information
Bathrooms Full: 8
Bathrooms Half: 1

Exterior

Exterior Features
Construction Materials: Cedar, Frame
Fencing: Fenced
Other Structures: Barn(s), Shed(s), Stable(s)
Waterfront YN: Yes

Pool Information
Pool Features: In Ground

Lot Information
Additional Parcels YN: No
Lot Features: Level, Views
Zoning: R10

Property Information
Living Area Source: Public Records
Property Sub Type: Single Family Residence

Financial

Tax Information
Tax Year: 2013
Tax Annual Amount: $67,160

Financial Information
Buyer Financing: Cash, Conventional

Location

HOA Information
Association Amenities: Park

School Information
Elementary School: Elm Drive Elementary School
Middle Or Junior School: Millbrook Middle School
High School: Millbrook High School
High School District: Millbrook

Location Information
Directions: Rte. 44 East to left on Kennels Rd. to right on Windy Hill Rd. (Private)
County Or Parish: Dutchess County

Community Information
Community Features: Fitness Center, Golf, Park

Public facts

Beds: 6
Baths: 8.5
Sq. Ft.: 7,459
Stories: 2.0
Lot Size: 157.27 acres
Style: Single Family Residential
Year Built: 1900
Year Renovated: 1987
County: Dutchess County
APN: 135889A00686600009707350000

Home facts updated by county records on Jul 31, 2026

Around this home

Schools

Elm Drive Elementary School

Public PreK-2 • Assigned • 3.9mi

Millbrook Middle School

Public 6-8 • Assigned • 4.0mi

5/10

Millbrook High School

Public 9-12 • Assigned • 4.1mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

3/10 Heat Factor

7 days above 95° expected this year, 16 days in 30 years

4/10 Wind Factor

15% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Millbrook, NY • 12545

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 4 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$10.25M – $12.41M

Reach more buyers when you sell with Redfin. Save up to $107,931 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

$2,700,000

4 beds4 baths4,032 sq ft

1197 Bulls Head Rd, Clinton Corners, NY 12514

Listing by Compass Greater NY, LLC

NEW 6 HRS AGO

$799,000

2 beds1.5 baths1,056 sq ft

672 Tower Hill Rd, Millbrook, NY 12545

Listing by Houlihan Lawrence Inc.

$339,000

2 beds1 bath1,316 sq ft

85 Bella Vista Rd, Amenia, NY 12501

Listing by Havens Real Estate

$3,750,000

7 beds6 baths6,138 sq ft

151 Benson Hill Rd, Dover Plains, NY 12522

Listing by Houlihan Lawrence Inc.

$895,000

2 beds1 bath1,126 sq ft

8 Old North Anson Way, Stanfordville, NY 12581

Listing by Corcoran Country Living

3D WALKTHROUGH

$649,000

5 beds3 baths4,000 sq ft

226 Charwill Dr, Clinton Corners, NY 12514

Listing by Mondello Upstate Properties

New listings for sale in 12545

NEW 6 HRS AGO

$799,000

2 beds1.5 baths1,056 sq ft

672 Tower Hill Rd, Millbrook, NY 12545

Listing by Houlihan Lawrence Inc.

$1,500,000

4 beds3.5 baths3,034 sq ft

3244 Sharon Tpke, Millbrook, NY 12545

Listing by Houlihan Lawrence Inc.

$5,750,000

4 beds3 baths3,810 sq ft

81-85 Fraleigh Hill Rd, Millbrook, NY 12545

Listing by Compass Greater NY, LLC

$635,000

3 beds2 baths2,234 sq ft

163 Horseshoe Rd, Millbrook, NY 12545

Listing by Compass Greater NY, LLC

$16,750,000

5 beds5.5 baths7,108 sq ft

482 Overlook Rd, Millbrook, NY 12545

Listing by Compass Greater NY, LLC

OPEN SUN, 1PM TO 3PM

$895,000

3 beds2 baths1,868 sq ft

3315 Franklin Ave, Millbrook, NY 12545

Listing by George T Whalen Real Estate

Home values near 40 Windy Hill Rd. Priv

Data from public records.

Address	Redfin Estimate
295 Kennels Road, Millbrook, NY 6 Beds \| 3 Baths \| 3000 Sq. Ft.	$1,572,669
461 N Mabbettsville Road, Millbrook, NY 3 Beds \| 1.5 Baths \| 1904 Sq. Ft.	$3,916,864

Address	Redfin Estimate
289 Kennels Road, Millbrook, NY 2 Beds \| 1 Baths \| 2025 Sq. Ft.	$825,713
141 Kennels Road, Millbrook, NY 5 Beds \| 4 Baths \| 4280 Sq. Ft.	$2,009,905

Address	Redfin Estimate
81-85 Fraleigh Hill Road, Millbrook, NY 4 Beds \| 3 Baths \| 3810 Sq. Ft.	$5,550,396
1215 Shunpike, Millbrook, NY 4 Beds \| 4 Baths \| 3516 Sq. Ft.	$1,470,753

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2012. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

New Fairfield homes for sale
Brookfield homes for sale
Woodbury homes for sale
Monroe homes for sale
Southbury homes for sale

12501 homes for sale
12522 homes for sale
12585 homes for sale
12569 homes for sale
12581 homes for sale

Houses for sale near me	New York, NY homes for sale	Yonkers, NY homes for sale
Land for sale near me	Manhattan, NY homes for sale	Scarsdale, NY homes for sale
Open Houses near me	Rochester, NY homes for sale	Washington Property Records
Condos for sale near me	Buffalo, NY homes for sale	NY New Listings
Agents near me	White Plains, NY homes for sale	Washington Housing Market

Rhinebeck homes for sale
Kingston homes for sale
Poughkeepsie homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 12545, NY

Sale history for 40 Windy Hill Rd. Priv

Tax history for 40 Windy Hill Rd. Priv

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 12545

Home values near 40 Windy Hill Rd. Priv

More real estate resources