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Woodbury, NY 55+ active adult communities & homes for sale
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.
232 communities near Woodbury
1,276 homes near Woodbury
Relevance
2 beds
|2 baths
|1,555 sq ft
|Ranch
2 beds
|2 baths
|1,078 sq ft
|Condo
3 beds
|3 baths
|2,294 sq ft
|House
2 beds
|2 baths
|1,092 sq ft
|Ranch
2 beds
|2 baths
|1,130 sq ft
|Condo
2 beds
|2 baths
|1,008 sq ft
|Ranch
2 beds
|2 baths
|2,129 sq ft
|Ranch
2 beds
|1 baths
|1,124 sq ft
|Ranch
2 beds
|2 baths
|1,210 sq ft
|House
2 beds
|2 baths
|1,615 sq ft
|Ranch
2 beds
|2 baths
|1,624 sq ft
|Manufactured Home
2 beds
|2 baths
|1,436 sq ft
|House
1 beds
|1 baths
|928 sq ft
|Mobile Home
1 beds
|1 baths
|920 sq ft
|Condo
2 beds
|1 baths
|982 sq ft
|Duplex
2 beds
|2 baths
|1,391 sq ft
|Duplex
2 beds
|2 baths
|Condo
2 beds
|2 baths
|1,564 sq ft
|Ranch
2 beds
|2 baths
|1,105 sq ft
|Condo
2 beds
|2 baths
|1,417 sq ft
|House
2 beds
|2 baths
|1,667 sq ft
|Ranch
3 beds
|3 baths
|3,256 sq ft
|House
3 beds
|3 baths
|3,042 sq ft
|House
2 beds
|2 baths
|1,398 sq ft
|Condo
2 beds
|2 baths
|1,132 sq ft
|House
2 beds
|2 baths
|1,404 sq ft
|Ranch
2 beds
|2 baths
|1,404 sq ft
|Ranch
2 beds
|1 baths
|1,130 sq ft
|Adult Community
2 beds
|2 baths
|1,484 sq ft
|Condo
2 beds
|3 baths
|1,868 sq ft
|Condo
2 beds
|2 baths
|2,130 sq ft
|Ranch
2 beds
|2 baths
|1,092 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.
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REIN updates its listings on a daily basis. Data last updated: Sep 21, 2026.
This application does not include information on all of the properties available for sale at this time.
