Middletown, NY 55+ active adult communities & homes for sale

96 communities near Middletown

Sort by:

Relevance

Bald Eagle Commons

$100ks - $300ks

Bald Eagle Commons, West Milford, NJ

Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

3 rating (2 reviews)

Heritage Hills

$400ks - $800ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

Traditions of America at ...

$500ks - $600ks

Traditions of America at ..., Bethlehem, PA

Resale Only | 55+ age-restricted | Built 2019 - present | 229 homes

Apple Ridge

$500ks - $1Ms

Apple Ridge, Mahwah, NJ

Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes

5 rating (1 reviews)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Fox Hills

$300ks - $600ks

Fox Hills, Rockaway, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2003 | 672 homes

Clove Hill Manor

$200ks - $300ks

Clove Hill Manor, Wantage, NJ

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 117 homes

Fox Crest

$300ks - $600ks

Fox Crest, Rockaway, NJ

New Construction | 55+ age-restricted | Built 2020 - present | 41 homes

Greenbriar at Fox Ridge

$300ks - $500ks

Greenbriar at Fox Ridge, Rockaway, NJ

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 336 homes

Horizons at Mount Arlingt...

$400ks

Horizons at Mount Arlingt..., Mount Arlington, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 144 homes

1 rating (1 reviews)

Brookfield Estates

$300ks

Brookfield Estates, Belvidere, NJ

Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

Hawk Pointe

$300ks - $500ks

Hawk Pointe, Washington, NJ

New and Resale | 55+ age-restricted | Built 2019 - present | 85 homes

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes

Reserve at Hawk Pointe

$400ks - $500ks

Reserve at Hawk Pointe, Washington, NJ

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 120 homes

5 rating (1 reviews)

Delaware Crossing

$200ks - $300ks

Delaware Crossing, Lopatcong, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 158 homes

The Pointe

$300ks - $600ks

The Pointe, Livingston, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

5 rating (1 reviews)

Four Seasons at Great Not...

$400ks - $700ks

Four Seasons at Great Not..., Woodland Park, NJ

Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes

The Hollows at Blue Hill

$500ks - $700ks

The Hollows at Blue Hill, Pearl River, NY

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes

Lakeside Villas

$400ks - $500ks

Lakeside Villas, Watchung, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 42 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

Four Seasons at Chester

$600ks - $700ks

Four Seasons at Chester, Chester, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2002 | 120 homes

Riverview Estates Active ...

$500ks - $600ks

Riverview Estates Active ..., Easton, PA

Resale Only | 55+ age-restricted | Built 2005 - present | 92 homes

Nolan's Ridge

$400ks - $700ks

Nolan's Ridge, Mount Arlington, NJ

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 156 homes

The Village at Fox Crossi...

$200ks - $300ks

The Village at Fox Crossi..., Easton, PA

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 135 homes

Four Seasons at Readingto...

$400ks - $500ks

Four Seasons at Readingto..., Readington Township, NJ

Resale Only | 55+ age-restricted | Built 2001 - 2002 | 98 homes

Glenmoor

$300ks - $400ks

Glenmoor, Easton, PA

Resale Only | 55+ age-restricted | Built 2004 - 2008 | 182 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes

Regency at Readington

$600ks - $700ks

Regency at Readington, Readington Township, NJ

Resale Only | 55+ age-restricted | Built 2014 - 2019 | 209 homes

Four Seasons at Bridgewat...

$300ks - $400ks

Four Seasons at Bridgewat..., Bridgewater, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 homes

The Highlands at Glenmoor

$300ks - $400ks

The Highlands at Glenmoor, Easton, PA

Resale Only | 55+ age-restricted | Built 2004 - 2007 | 251 homes

The Hamlet at Town Center

$200ks - $400ks

The Hamlet at Town Center, Sparta, NJ

Resale Only | 55+ age-restricted | Built 2008 - 2008 | 44 homes

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

Legacy at Morgan Hill

$400ks - $500ks

Legacy at Morgan Hill, Easton, PA

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 127 homes

The Meadows at Panther Va...

$300ks - $400ks

The Meadows at Panther Va..., Hackettstown, NJ

Resale Only | Age-targeted | Built 2010 - 2021 | 312 homes

1 2...3

Heritage Hills

567 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$469,900

1 beds

2 baths

967 sq ft

Condo

567 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Brookfield Estates

11 STAFFORD LN, WHITE TWP., NJ, 07823, White Twp., NJ 07823

2 beds

3 baths

1,568 sq ft

7113 POLK DR, ROCKAWAY TWP., NJ, 07885

Community: Greenbriar at Fox Ridge

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

New The Seasons at East Meadow

115 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$615,000

2 beds

2 baths

1,367 sq ft

Condo

115 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

New Bald Eagle Commons

1101 RICHMOND RD 101, WEST MILFORD, NJ, ..., West Milford, NJ 07480

$320,000

2 beds

2 baths

Condo

1101 RICHMOND RD 101, WEST MILFORD, NJ, ...

Community: Bald Eagle Commons

New Bald Eagle Commons

1101 RICHMOND RD 101, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480

$320,000

2 beds

2 baths

1101 RICHMOND RD 101, WEST MILFORD TWP.,...

Community: Bald Eagle Commons

New Meadowbrook Pointe Athletic Club & Spa

236 ROOSEVELT WAY 3306, HEMPSTEAD, NY, 1..., Hempstead, NY 11590

$910,000

2 beds

2 baths

1,349 sq ft

Condo

236 ROOSEVELT WAY 3306, HEMPSTEAD, NY, 1...

Community: Meadowbrook Pointe Athletic Club & Spa

New The Pointe

5211 POINTE GATE DR, LIVINGSTON, NJ, 070..., Livingston, NJ 07039

$599,000

6 beds

3 baths

Condo

5211 POINTE GATE DR, LIVINGSTON, NJ, 070...

Community: The Pointe

New Brookfield Estates

30 VICTORIA DR, WHITE TWP., NJ, 07823, White Twp., NJ 07823

$399,000

2 beds

2 baths

30 VICTORIA DR, WHITE TWP., NJ, 07823

Community: Brookfield Estates

New Reserve at Hawk Pointe

124 CLUB HOUSE DR, WASHINGTON TWP., NJ, ..., Washington Twp., NJ 07882

$749,000

3 beds

3 baths

3,054 sq ft

124 CLUB HOUSE DR, WASHINGTON TWP., NJ, ...

Community: Reserve at Hawk Pointe

New Clove Hill Manor

13 FAIRCHILD LN, WANTAGE TWP., NJ, 07461, Wantage Twp., NJ 07461

$469,000

2 beds

4 baths

13 FAIRCHILD LN, WANTAGE TWP., NJ, 07461

Community: Clove Hill Manor

New Winthrop Court

9104 RAVENSCROFT RD, CLIFTON CITY, NJ, 0..., Clifton City, NJ 07013

$525,000

2 beds

2 baths

9104 RAVENSCROFT RD, CLIFTON CITY, NJ, 0...

Community: Winthrop Court

New Jefferson Village

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598, Yorktown, NY 10598

$455,000

2 beds

2 baths

1,100 sq ft

Condo

51 JEFFERSON OVAL E, YORKTOWN, NY, 10598

Community: Jefferson Village

New The Pointe

5211 POINTE GATE DR, LIVINGSTON TWP., NJ..., Livingston Twp., NJ 07039

$599,000

2 beds

3 baths

5211 POINTE GATE DR, LIVINGSTON TWP., NJ...

Community: The Pointe

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

New The Highlands at Glenmoor

45 MOOR DR, PALMER TWP, PA, 18045, Palmer Twp, PA 18045

$374,900

2 beds

2 baths

1,535 sq ft

Townhouse

45 MOOR DR, PALMER TWP, PA, 18045

Community: The Highlands at Glenmoor

New The Meadows at Panther Valley

14 LUPINE LN, ALLAMUCHY, NJ, 07840, Allamuchy, NJ 07840

$649,900

3 beds

3 baths

Townhouse

14 LUPINE LN, ALLAMUCHY, NJ, 07840

Community: The Meadows at Panther Valley

New The Meadows at Panther Valley

14 LUPINE LN, ALLAMUCHY TWP., NJ, 07840, Allamuchy Twp., NJ 07840

$649,900

3 beds

3 baths

2,800 sq ft

14 LUPINE LN, ALLAMUCHY TWP., NJ, 07840

Community: The Meadows at Panther Valley

New Four Seasons at Troy Hills

11 HOPKINS CT, PARSIPPANY-TROY HILLS TWP..., Parsippany-troy Hills Twp., NJ 07054

$699,000

4 beds

3 baths

11 HOPKINS CT, PARSIPPANY-TROY HILLS TWP...

Community: Four Seasons at Troy Hills

New Heritage Hills

900 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$742,000

2 beds

3 baths

1,552 sq ft

Condo

900 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

New Meadowbrook Pointe Athletic Club & Spa

318 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ..., North Hempstead, NY 11590

$989,000

2 beds

2 baths

1,438 sq ft

Condo

318 ROOSEVELT WAY, NORTH HEMPSTEAD, NY, ...

Community: Meadowbrook Pointe Athletic Club & Spa

New Apple Ridge

143 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$975,000

3 beds

4 baths

Townhouse

143 FISHER RD, MAHWAH, NJ, 07430

Community: Apple Ridge

New Apple Ridge

143 FISHER RD, MAHWAH TWP., NJ, 07430, Mahwah Twp., NJ 07430

$975,000

3 beds

4 baths

2,446 sq ft

143 FISHER RD, MAHWAH TWP., NJ, 07430

Community: Apple Ridge

New Wanaque Reserve

3118 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$599,900

2 beds

2 baths

2,119 sq ft

3118 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

New Bald Eagle Commons

1208 RICHMOND 208, WEST MILFORD, NJ, 074..., West Milford, NJ 07480

$249,900

1 beds

1 baths

Condo

1208 RICHMOND 208, WEST MILFORD, NJ, 074...

Community: Bald Eagle Commons

New Bald Eagle Commons

1208 RICHMOND RD 208, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480

$249,900

1 beds

1 baths

1208 RICHMOND RD 208, WEST MILFORD TWP.,...

21 SYLVIA ST, LOPATCONG TWP., NJ, 08865

Community: Delaware Crossing

New Heritage Hills

33 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$599,000

2 beds

2 baths

1,320 sq ft

Condo

33 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Four Seasons at Great Notch Spa and Club

5 GRANITE RD A2, WOODLAND PARK, NJ, 0742..., Woodland Park, NJ 07424

2 beds

2 baths

1,840 sq ft

16 MAIN ST U1, SPARTA TWP., NJ, 07871

Community: The Hamlet at Town Center

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

Apple Ridge

227 WESTERVELT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$865,000

3 beds

3 baths

Townhouse

227 WESTERVELT LN, MAHWAH, NJ, 07430

Community: Apple Ridge

Apple Ridge

227 WESTERVELT LN, MAHWAH TWP., NJ, 0743..., Mahwah Twp., NJ 07430

$865,000

3 beds

3 baths

227 WESTERVELT LN, MAHWAH TWP., NJ, 0743...

Community: Apple Ridge

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middletown?

The smallest 55+ community in Middletown has 283 homes, the largest has 283 homes, and the average community consists of 283 homes.

Are there gated 55+ communities in Middletown?

Yes, there is gated 55+ community in Middletown. The only 55+ community in Middletown is gated. For instance, Wildflowers at Wallkill is a gated community with 283 homes.

How long do listings in 55+ communities in Middletown typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in Middletown stay on the market for around 411 days. The average price of homes for sale in this community is approximately $520,887, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Wildflowers at Wallkill average around $520,887.

Want more information about active adult communities around Middletown?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Middletown?

Call us: (845) 479-5674

96 communities

Remove Boundaries ×

Map Satellite

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: Jun 05, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Middletown, NY 55+ active adult communities & homes for sale

96 communities near Middletown

192 homes near Middletown

1 beds

2 baths

967 sq ft

Condo

2 beds

2 baths

2 beds

2 baths

1,562 sq ft

2 beds

2 baths

1,408 sq ft

2 beds

3 baths

1,568 sq ft

2 beds

2 baths

1,367 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

2 beds

2 baths

1,349 sq ft

Condo

6 beds

3 baths

Condo

2 beds

2 baths

3 beds

3 baths

3,054 sq ft

2 beds

4 baths

2 beds

2 baths

2 beds

2 baths

1,100 sq ft

Condo

2 beds

3 baths

2 beds

2 baths

1,535 sq ft

Townhouse

3 beds

3 baths

Townhouse

3 beds

3 baths

2,800 sq ft

4 beds

3 baths

2 beds

3 baths

1,552 sq ft

Condo

2 beds

2 baths

1,438 sq ft

Condo

3 beds

4 baths

Townhouse

3 beds

4 baths

2,446 sq ft

2 beds

2 baths

2,119 sq ft

1 beds

1 baths