Call us at (516) 871-3423 to learn more about active adult communities in Woodbury
Woodbury, NY 55+ active adult communities & homes for sale - Page 21
Living in Woodbury
Woodbury is a town located in Upstate New York's Orange County, and is part of the Poughkeepsie metropolitan area. Its comfortable lifestyle have made it an ideal retirement…
Woodbury is a town located in Upstate New York's Orange County, and is part of the Poughkeepsie metropolitan area. Its comfortable lifestyle have made it an ideal retirement destination for active adults who enjoy the relaxed environment of a small town while still having easy access to New York City and all the world-class experiences available there.
Climate & Geography
Woodbury experiences four distinct seasons with warm and wet summers, freezing winters, and partly cloudy skies year round.
Recreation, Culture & Entertainment
Woodbury is a small town with a neighborly feel; its downtown consists mainly of local businesses and restaurants and there are regular community events, holiday parades, and more. It's surrounded by plenty of nature areas such as Lake Tiorati, Trail View State Park, and Tamarack Nature Preserve which residents can visit for hiking, biking, camping, canoeing, and other outdoor recreation. Golfers can also tee off at the Falkirk Golf & Country Club.
Residents benefit from the town's close proximity to New York City, with only an hour trip via car or rail to get to Manhattan. For longer trips the New York Stewart International Airport is just 20 minutes away.
Cost of Living & Taxes
The overall cost of living in Woodbury is significantly higher than the national average, mainly due to its expensive housing costs. The cost of transportation and utilities are also much much higher.
New York does not tax Social Security benefits, and in-state and federal public pension plans are also exempt. Retirement savings accounts and all other pensions are taxable, but with a $20,000 deduction. Residents 65 and older qualify to have their property taxes reduced by 50 percent based on income requirements, and they may also be eligible for the Enhanced STAR Program which allows additional exemptions. The combined sales tax rate in Woodbury is 8.63 percent.
Health Care
There are three highly rated hospitals and medical centers within Woodbury. They are Plainview Hospital, St. Joseph Hospital-Bethpage and Glen Cove Hospital. Within a 12 mile radius, residents can also find three hospitals which are nationally ranked by U.S News: Huntington Hospital, NYU Winthrop Hospital and St. Francis Hospital-Roslyn.
Frequently Asked Questions
In Woodbury, there is 1 small community with less than 500 homes.
The smallest 55+ community in Woodbury has 80 homes, the largest has 80 homes, and the average community consists of 80 homes.
Yes, there is new 55+ home available in Woodbury. The most recent community started in Woodbury include Kensington Estates. There is also 1 community in Woodbury that offers new construction homes, including Kensington Estates.
Yes, there is gated 55+ community in Woodbury. The only 55+ community in Woodbury is gated. For instance, Kensington Estates is a gated community with 80 homes.
On average, listings in 55+ community in Woodbury stay on the market for around 542 days. The average price of homes for sale in this community is approximately $1,824,435, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Kensington Estates average around $1,824,435.
233 communities near Woodbury
1,321 homes near Woodbury
Relevance
2 beds
|2 baths
|1,288 sq ft
3 beds
|3 baths
|3,005 sq ft
2 beds
|1 baths
|1,144 sq ft
|Condo
2 beds
|2 baths
|1,398 sq ft
|Condo
1 beds
|1 baths
|800 sq ft
|Condo
2 beds
|2 baths
|1,356 sq ft
|Ranch
3 beds
|3 baths
|House
3 beds
|2 baths
|1,903 sq ft
|Ranch
2 beds
|2 baths
|1,262 sq ft
|Ranch
2 beds
|2 baths
|938 sq ft
|Condo
2 beds
|2 baths
|1,602 sq ft
|Ranch
2 beds
|2 baths
|1,258 sq ft
|Condo
2 beds
|2 baths
|1,440 sq ft
|Condo
2 beds
|2 baths
|1,100 sq ft
|Ranch
2 beds
|2 baths
|1,314 sq ft
|House
3 beds
|2 baths
|2,042 sq ft
|House
2 beds
|2 baths
|1,356 sq ft
|Ranch
3 beds
|2 baths
|Condo
2 beds
|2 baths
|1,599 sq ft
|Condo
3 beds
|2 baths
|1,588 sq ft
|Adult Community
3 beds
|3 baths
|2,006 sq ft
|Condo
2 beds
|2 baths
|1,092 sq ft
|Ranch
1 beds
|1 baths
|886 sq ft
|Condo
3 beds
|2 baths
|1,381 sq ft
|Adult Community
2 beds
|2 baths
|1,663 sq ft
|Condo
1 beds
|1 baths
|1,072 sq ft
|Ranch
2 beds
|2 baths
|1,036 sq ft
2 beds
|1 baths
|1,124 sq ft
|Ranch
1 beds
|2 baths
|1,499 sq ft
|Condo
2 beds
|3 baths
|1,771 sq ft
|House
3 beds
|2 baths
|1,317 sq ft
|Manufactured Home
2 beds
|1 baths
|1,100 sq ft
|Ranch
2 beds
|2 baths
|1,544 sq ft
|Ranch
1 beds
|1 baths
|700 sq ft
|Condo
3 beds
|2 baths
|2,472 sq ft
|Ranch
Frequently Asked Questions
In Woodbury, there is 1 small community with less than 500 homes.
The smallest 55+ community in Woodbury has 80 homes, the largest has 80 homes, and the average community consists of 80 homes.
Yes, there is new 55+ home available in Woodbury. The most recent community started in Woodbury include Kensington Estates. There is also 1 community in Woodbury that offers new construction homes, including Kensington Estates.
Yes, there is gated 55+ community in Woodbury. The only 55+ community in Woodbury is gated. For instance, Kensington Estates is a gated community with 80 homes.
On average, listings in 55+ community in Woodbury stay on the market for around 542 days. The average price of homes for sale in this community is approximately $1,824,435, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Kensington Estates average around $1,824,435.
Want more information about active adult communities around Woodbury?
Want to learn more about 55+ communities in Woodbury?
The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Oct 08, 2026.
This application does not include information on all of the properties available for sale at this time.
