Most expensive homes for sale in Woodbury, NY

$16,000,000

14 beds • 6.5 baths • 10,041 sqft

Address Not Disclosed, Highland Mills, NY 10930

#H6303268, Listing office: Keller Williams Hudson Valley

$4,250,000

6 beds • 4.5 baths • 8,000 sqft

84 S Woods Rd, Woodbury, NY 11797

#855607, Listing office: Douglas Elliman Real Estate

Save big

You could save thousands when you partner with Rocket Homes℠ and Rocket Mortgage®

$3,999,000

5 beds • 6 baths • 6,300 sqft

31 Fairbanks Blvd, Woodbury, NY 11797

#856249, Listing office: Signature Premier Properties

$3,950,000

6 beds • 7 baths • 6,000 sqft

3 The Brae, Woodbury, NY 11797

#872528, Listing office: Douglas Elliman Real Estate

$3,000,000

6 beds • 5 baths • 3,400 sqft

6 Whitney Ln, Woodbury, NY 11797

#841487, Listing office: Signature Premier Properties

$2,850,000

6 beds • 5.5 baths • 4,300 sqft

17 The Drawbridge, Woodbury, NY 11797

#855902, Listing office: Signature Premier Properties

$2,799,000

4 beds • 3 baths • 4,050 sqft

15 Wagamon Dr, Woodbury, NY 11797

#860167, Listing office: Compass Greater NY LLC

Room to negotiate?

Median Sold Price

$650K

Avg. Sale Time

37 Days

Based on our May 2025 Market Report.

$10,000 Closing Credit¹

$2,495,000

4 beds • 3.5 baths • 4,000 sqft

2 Arthur Pl, Woodbury, NY 11797

#811132, Listing office: The Agency Northshore NY

$10,000 Closing Credit¹

$1,959,000

5 beds • 4 baths • 3,401 sqft

21 Kodiak Dr, Woodbury, NY 11797

#L3554948, Listing office: Daniel Gale Sothebys Intl Rlty

$10,000 Closing Credit¹

$1,650,000

5 beds • 4.5 baths • 2,706 sqft

17 Juneau Blvd, Woodbury, NY 11797

#865813, Listing office: Real Broker NY LLC

$10,000 Closing Credit¹

$1,599,999

5 beds • 3 baths

208 Woodbury Rd, Woodbury, NY 11797

#L3579325, Listing office: Douglas Elliman Real Estate

$10,000 Closing Credit¹

$1,599,900

4 beds • 4.5 baths • 5,142 sqft

221 Smith Clove Rd, Highland Mills, NY 10930

#859312, Listing office: Weichert Realtors

419 Woodbury Rd, Woodbury, NY 11797 - view of front of house featuring an outdoor structure and driveway

Coming soon

$10,000 Closing Credit¹

$1,599,000

4 beds • 3.5 baths

419 Woodbury Rd, Woodbury, NY 11797

#872208, Listing office: BERKSHIRE HATHAWAY

$10,000 Closing Credit¹

$1,560,000

3 beds • 2.5 baths • 1,716 sqft

17 Irving Dr, Woodbury, NY 11797

#865933, Listing office: EXP Realty

$10,000 Closing Credit¹

$1,500,000

9 beds • 4.5 baths • 5,478 sqft

111 Summit Ave, Central Valley, NY 10917

#811250, Listing office: eRealty Advisors, Inc

$10,000 Closing Credit¹

$1,498,000

4 beds • 2.5 baths • 2,762 sqft

36 Roseanne Dr, Woodbury, NY 11797

#867296, Listing office: Daniel Gale Sothebys Intl Rlty

$10,000 Closing Credit¹

$1,400,000

6 beds • 5.5 baths • 4,171 sqft

26 Pullman Rte, Monroe, NY 10950

#816374, Listing office: eRealty Advisors, Inc

$10,000 Closing Credit¹

$1,350,000

6 beds • 5.5 baths • 4,171 sqft

18 Pullman Rte, Monroe, NY 10950

#862666, Listing office: eRealty Advisors, Inc

$10,000 Closing Credit¹

$1,279,999

4 beds • 3 baths • 3,855 sqft

21 Castleton Dr, Highland Mills, NY 10930

#815438, Listing office: Keller Williams Realty

6 days on Rocket

$10,000 Closing Credit¹

$1,200,000

3 beds • 2.5 baths • 3,100 sqft

51 Eagle Chase, Woodbury, NY 11797

#872200, Listing office: Compass Greater NY LLC

$10,000 Closing Credit¹

$1,199,000

4 beds • 2.5 baths • 1,998 sqft

40 Winthrop Dr, Woodbury, NY 11797

#854390, Listing office: BERKSHIRE HATHAWAY

$10,000 Closing Credit¹

$1,050,000

4 beds • 3.5 baths • 3,575 sqft

27 Catskill High Rail, Monroe, NY 10950

#859224, Listing office: eRealty Advisors, Inc

5 days on Rocket

$10,000 Closing Credit¹

$1,049,900

5 beds • 2 baths • 2,032 sqft

9 Hillside Ave, Woodbury, NY 11797

#874367, Listing office: Compass Greater NY LLC

$10,000 Closing Credit¹

$1,000,000

4 beds • 4 baths • 4,400 sqft

13 Montesi Dr, Highland Mills, NY 10930

#848623, Listing office: Howard Hanna Rand Realty

$10,000 Closing Credit¹

$999,000

3 beds • 2 baths • 1,798 sqft

17 Woodbury Rd, Woodbury, NY 11797

#864288, Listing office: Compass Greater NY LLC

$10,000 Closing Credit¹

$975,000

3 beds • 2 baths • 1,344 sqft

297 Estrada Rd, Central Valley, NY 10917

#810522, Listing office: eXp Realty

$10,000 Closing Credit¹

$974,000

5 beds • 2 baths • 1,923 sqft

25A Winthrop Dr, Woodbury, NY 11797

#833397, Listing office: Signature Premier Properties

$10,000 Closing Credit¹

$950,000

6 beds • 3.5 baths • 4,517 sqft

3 Caledonia Cir, Highland Mills, NY 10930

#866929, Listing office: Preferred Properties Real Esta

$10,000 Closing Credit¹

$899,000

3 beds • 2.5 baths • 2,355 sqft

121 Terrace Ct Unit 121, Woodbury, NY 11797

#859612, Listing office: Renaissance Realty Cons Group

7 days on Rocket

$9,488 Closing Credit¹

$799,000

3 beds • 2.5 baths • 1,838 sqft

24 Hampton Ct, Woodbury, NY 11797

#872892, Listing office: Century 21 Excelsior Realty

$9,263 Closing Credit¹

$780,000

4 beds • 2.5 baths • 2,434 sqft

33 Sutherland Dr, Highland Mills, NY 10930

#836206, Listing office: RE/MAX Benchmark Realty Group

Coming soon

$8,894 Closing Credit¹

$749,000

3 beds • 2.5 baths • 1,480 sqft

17 Sheffield Hl Unit 105, Woodbury, NY 11797

#875168, Listing office: Daniel Gale Sothebys Intl Rlty

$8,728 Closing Credit¹

$735,000

4 beds • 2.5 baths • 2,004 sqft

4 Sequoia Trl, Highland Mills, NY 10930

#856755, Listing office: MK Realty Inc

$8,549 Closing Credit¹

$719,900

5 beds • 3.5 baths • 2,876 sqft

10 Leone Ct, Woodbury, NY 10930

#831553, Listing office: Keller Williams Valley Realty

$8,313 Closing Credit¹

$700,000

7 beds • 3 baths • 2,504 sqft

117 Woodland Rd, Highland Mills, NY 10930

#853711, Listing office: HomeSmart Homes & Estates

$8,301 Closing Credit¹

$699,000

4 beds • 2.5 baths • 2,994 sqft

14 Smith Clove Rd, Central Valley, NY 10917

#864508, Listing office: Century 21 Realty Center

11 hours on Rocket

$8,253 Closing Credit¹

$695,000

4 beds • 2.5 baths • 2,960 sqft

38 Buena Vista Ter, Central Valley, NY 10917

#876648, Listing office: Exit Realty Group

$8,063 Closing Credit¹

$679,000

3 beds • 2.5 baths • 2,386 sqft

35 Depalma Dr, Highland Mills, NY 10930

#H6336334, Listing office: MK Realty Inc

$8,016 Closing Credit¹

$675,000

4 beds • 3 baths • 2,959 sqft

55 Midland Ave, Central Valley, NY 10917

#858916, Listing office: Howard Hanna Rand Realty

5 days on Rocket

$7,707 Closing Credit¹

$649,000

4 beds • 2.5 baths • 2,314 sqft

8 Adrianne Dr, Highland Mills, NY 10930

#874275, Listing office: Century 21 Realty Center

Woodbury, NY Real Estate Market Overview

There are 54 most expensive homes for sale in Woodbury, NY. The following market insights reflect all property types in the Woodbury, NY real estate market. The number of homes in Woodbury, NY increased by 11.1% between April 2025 and May 2025. In May 2025, listings were on the market for 37 days. During the same period, the median list price in this real estate market was $650,000. Woodbury, NY housing market in May 2025 saw over 4 listings sold above listed price, more than 2 sold at listed price and over 4 sold below.

From Rocket Homes Real Estate and based on county public records data

Most expensive homes for sale in Woodbury, NY

Woodbury, NY Real Estate Market Overview

Schools near Woodbury, NY

Housing market reports in Orange County

Homes for sale near Woodbury, NY

Top real estate cities in New York