40 Windy Hill Rd. Priv, Millbrook, NY 12545

Off market oct 2014 for $5M

$16,931,383

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

$1,955Est. 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

$16,931,383

$11.9M since sold in October 2014$10.3M since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 187.7% higher than the average sale price ($5.88M) of 5 comparable homes.

SOLD OCT 21, 2026
$1,175,000
A
4 beds4.5 baths3,090 sq ft
36 Market Ln, Clinton Corners, NY 12514
Listing by Patricia A. Hinkein Realty
SOLD MAR 11, 2026
$5,775,000
B
6 beds8 baths8,117 sq ft
465 Shunpike, Millbrook, NY 12545
Listing by Corcoran Country Living
SOLD DEC 22, 2025
$6,250,000
C
5 beds5.5 baths5,162 sq ft
47-49 Crescent Rd, Millbrook, NY 12545
Listing by Elyse Harney Real Estate
SOLD NOV 2, 2026
$13,500,000
D
4 beds6.5 baths7,500 sq ft
365 Tower Hill Rd, Wassaic, NY 12592
Listing by Compass Greater NY, LLC
SOLD AUG 11, 2026
$2,725,000
E
3 beds5 baths4,134 sq ft
97 Valley Farm Rd, Millbrook, NY 12545
Listing by George T Whalen Real Estate

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Earn from this home

Sell

$13,045,437

Est. take-home

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Refinance

Est. cash available

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Rent

$4,552/mo

Redfin rental estimate

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Market trends in 12545, NY

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

97.9%

+1.9% MoM

Median sale price

$725K

$81K MoM

Avg. days on market

84d

0 days MoM

Recently sold homes

3 MoM

New listings for sale

$1,700,000
7 beds6 baths10,887 sq ft
3893 Route 82, Millbrook, NY 12545
Listing by Tactical Realty LLC
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*

2026

$99,019

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

$5,000,000

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*

2026

$99,019

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

$5,000,000

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 Oct 16, 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 Oct 16, 2026

Around this home

Schools

K - 12
Preschool & daycare

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)

32°

16°

36°

18°

53°

31°

62°

41°

69°

50°

80°

59°

83°

65°

78°

57°

75°

53°

62°

42°

51°

33°

37°

21°

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

$16.09M – $19.47M

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Nearby similar homes

$799,000

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Listing by Corcoran Country Living

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Listing by Coldwell Banker Realty

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NEW CONSTRUCTION

$1,895,000

3 beds4 baths2,470 sq ft

53 Cedar Berry Ln, Dover Plains, NY 12522

Double height loft • Airtight envelope • 3.48 acre lot

New listings for sale in 12545

$1,700,000

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Secluded acres • Sweeping staircase • Statement chandelier

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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.	$1,584,744
81 Fraleigh Hill Road, Millbrook, NY 4 Beds \| 3 Baths \| 3810 Sq. Ft.	—
3947 Northome Drive, Millbrook, NY 3 Beds \| 5.5 Baths \| 5281 Sq. Ft.	$6,609,233
4249 Route 44, Millbrook, NY 4 Beds \| 4 Baths \| 4220 Sq. Ft.	$1,261,281
235 Kennels Road, Millbrook, NY 4 Beds \| 3 Baths \| 3300 Sq. Ft.	$1,599,279
1033 Shunpike, Millbrook, NY 5 Beds \| 3 Baths \| 2583 Sq. Ft.	$1,077,388

Address	Redfin Estimate
289 Kennels Road, Millbrook, NY 2 Beds \| 1 Baths \| 2025 Sq. Ft.	$968,073
141 Kennels Road, Millbrook, NY 5 Beds \| 4 Baths \| 4280 Sq. Ft.	$2,296,517
52 Fraleigh Hill Road, Millbrook, NY 3 Beds \| 1 Baths \| 1450 Sq. Ft.	$665,533
88 Fraleigh Hill Road, Millbrook, NY 4 Beds \| 5 Baths \| 4976 Sq. Ft.	$4,174,366
39 Pig Lane, Millbrook, NY 3 Beds \| 3.5 Baths \| 3848 Sq. Ft.	$2,965,302
85 Fraleigh Hill Road, Millbrook, NY 4 Beds \| 3 Baths \| 3810 Sq. Ft.	$4,748,566

Address	Redfin Estimate
461 N Mabbettsville Road, Millbrook, NY 3 Beds \| 1.5 Baths \| 1904 Sq. Ft.	$3,427,302
1215 Shunpike, Millbrook, NY 4 Beds \| 4 Baths \| 3516 Sq. Ft.	$1,424,932
4255 Route 44, Millbrook, NY 5 Beds \| 2.5 Baths \| 2128 Sq. Ft.	$711,581
4281 Route 44, Millbrook, NY 2 Beds \| 2 Baths \| 2147 Sq. Ft.	$711,146
979-981 Shunpike, Millbrook, NY 4 Beds \| 2 Baths \| 2600 Sq. Ft.	$1,231,184

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

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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