Call us at (845) 479-5674 to learn more about active adult communities near Middletown

Middletown, NY 55+ active adult communities & homes for sale - Page 3

92 communities near Middletown

Sort by:

Relevance

Relevance

Eden Park
$500Ks - $600Ks
Eden Park, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes
The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
Knickerbocker Bay Club
$700Ks - $3Ms
Knickerbocker Bay Club, Port Washington, NY
New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes
The Coach Homes at Ridgef...
$200Ks - $500Ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Dawson Brook
$600Ks - $700Ks
Dawson Brook, Randolph, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 30 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
5 rating (2 reviews) Blackburne Farm Townhomes
$500Ks - $500Ks
Blackburne Farm Townhomes, Campbell Hall, NY
New Construction | 55+ age-restricted | Built 2019 - present | 29 homes
Briar Hill
$600Ks - $700Ks
Briar Hill, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 2012 - 2015 | 28 homes
Sterling Mist
$600Ks - $700Ks
Sterling Mist, Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2002 - 2006 | 28 homes
Brooklake Park
$400Ks - $400Ks
Brooklake Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2008 | 25 homes
Melrose at Chatham
$1Ms - $1Ms
Melrose at Chatham, Chatham, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 19 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.
Whitfield
$600Ks - $700Ks
Whitfield, Metuchen, NJ
Resale Only | 55+ age-restricted | 17 homes
1 rating (2 reviews) Knoll Edge
$600Ks - $700Ks
Knoll Edge, Boonton, NJ
New Construction | 55+ age-restricted | Built 2024 - present | 16 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
New Heritage Hills 593 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$619,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

593 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Bald Eagle Commons 5318 RICHMOND RD # 318, WEST MILFORD, NJ..., West Milford, NJ 07480
$239,000

2 beds

|

1 baths

5318 RICHMOND RD # 318, WEST MILFORD, NJ...
Community: Bald Eagle Commons
Apple Ridge 39 LITCHULT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$750,000

2 beds

|

4 baths

|

Condo

39 LITCHULT LN, MAHWAH, NJ, 07430
Community: Apple Ridge
Heritage Hills 370 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$899,000

3 beds

|

2 baths

|

1,793 sq ft

|

Condo

370 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Glassbury Court at Cold Spring 11 REVOLUTION RD, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$515,000

2 beds

|

3 baths

|

1,806 sq ft

|

Condo

11 REVOLUTION RD, COLD SPRING, NY, 10516
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Regency at Fishkill 423 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,000

1 beds

|

2 baths

|

1,450 sq ft

|

Condo

423 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Heritage Hills 150 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$550,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

150 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New Heritage Hills 262 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$550,000

2 beds

|

2 baths

|

1,427 sq ft

|

Condo

262 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New The Hollows at Blue Hill 41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ..., Pearl River, NY 10965
$999,000

2 beds

|

3 baths

|

2,210 sq ft

|

Condo

41 MICHAEL ROBERTS CT, PEARL RIVER, NY, ...
New Heritage Hills 418 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$999,000

2 beds

|

2 baths

|

1,764 sq ft

|

Condo

418 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
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.
New Jefferson Village 34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1..., Yorktown Heights, NY 10598
$379,900

2 beds

|

2 baths

|

970 sq ft

|

Condo

34 WARWICK PL D, YORKTOWN HEIGHTS, NY, 1...
Community: Jefferson Village
New Jefferson Village 170 LONG HILL DR A, YORKTOWN HEIGHTS, NY..., Yorktown Heights, NY 10598
$675,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

170 LONG HILL DR A, YORKTOWN HEIGHTS, NY...
Community: Jefferson Village
New Heritage Hills 882 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$825,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

882 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
The Seasons at East Meadow 383 SUMMER CT, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$640,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

383 SUMMER CT, EAST MEADOW, NY, 11554
Heritage Hills 438 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$569,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

438 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Jefferson Village 117 VILLAGE RD D, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598
$389,000

2 beds

|

2 baths

|

1,159 sq ft

|

Condo

117 VILLAGE RD D, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
New Jefferson Village 99 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598
$499,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

99 MOLLY PITCHER LN B, YORKTOWN HEIGHTS,...
Community: Jefferson Village
New Jefferson Village 98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598
$559,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,...
Community: Jefferson Village
New The Seasons at East Meadow 419 AUTUMN DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$628,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

419 AUTUMN DR, EAST MEADOW, NY, 11554
New Regency at Fishkill 736 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,000

1 beds

|

2 baths

|

1,543 sq ft

|

House

736 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
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.
Heritage Hills 972 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$575,000

2 beds

|

2 baths

|

1,468 sq ft

|

Condo

972 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Meadowbrooke Pointe East Meadow 305 EMANUEL WAY, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$855,000

1 beds

|

3 baths

|

961 sq ft

|

Condo

305 EMANUEL WAY, EAST MEADOW, NY, 11554
Heritage Hills 489 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$665,000

2 beds

|

2 baths

|

1,483 sq ft

|

Condo

489 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New Meadowbrook Pointe Athletic Club & Spa 471 PACING WAY, WESTBURY, NY, 11590, Westbury, NY 11590
$1,150,000

2 beds

|

3 baths

|

1,630 sq ft

|

Condo

471 PACING WAY, WESTBURY, NY, 11590
Jefferson Village 141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$675,000

2 beds

|

2 baths

|

1,555 sq ft

|

Condo

141 FLINTLOCK WAY B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Meadowbrooke Pointe East Meadow 123 EMANUEL WAY, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$729,000

2 beds

|

2 baths

|

1,390 sq ft

|

Condo

123 EMANUEL WAY, EAST MEADOW, NY, 11554
Jefferson Village 159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$569,999

2 beds

|

2 baths

|

1,300 sq ft

|

House

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Heritage Hills 348 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,428 sq ft

|

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Overlook 1037 COTTAGE DR 18, CARMEL, NY, 10512, Carmel, NY 10512
$959,000

2 beds

|

3 baths

|

2,496 sq ft

|

Condo

1037 COTTAGE DR 18, CARMEL, NY, 10512
Community: Overlook
Overlook 4057 FAIRWAYS DR # 129, CARMEL, NY, 1051..., Carmel, NY 10512
$699,000

3 beds

|

4 baths

|

2,131 sq ft

|

Condo

4057 FAIRWAYS DR # 129, CARMEL, NY, 1051...
Community: Overlook
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.
Overlook 4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512
$668,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512
Community: Overlook
Overlook 4073 FAIRWAYS DR # 137, CARMEL, NY, 1051..., Carmel, NY 10512
$665,000

3 beds

|

3 baths

|

1,914 sq ft

|

Condo

4073 FAIRWAYS DR # 137, CARMEL, NY, 1051...
Community: Overlook
Meadowbrook Pointe Athletic Club & Spa 323 ROOSEVELT WAY, WESTBURY, NY, 11590, Westbury, NY 11590
$875,000

2 beds

|

2 baths

|

1,328 sq ft

|

Condo

323 ROOSEVELT WAY, WESTBURY, NY, 11590
Jefferson Village 148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$499,000

2 beds

|

2 baths

|

1,159 sq ft

|

Condo

148 FLINTLOCK WAY D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Heritage Hills 688 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$725,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

688 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Heritage Hills 627 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$525,000

1 beds

|

2 baths

|

1,098 sq ft

|

Condo

627 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 593 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$1,100,000

3 beds

|

2 baths

|

1,905 sq ft

|

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Glassbury Court at Cold Spring 43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$729,000

2 beds

|

3 baths

|

2,620 sq ft

|

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516
Glassbury Court at Cold Spring 5 NORWEGIAN WOOD, COLD SPRING, NY, 10516, Cold Spring, NY 10516
$695,000

2 beds

|

2 baths

|

1,974 sq ft

|

Condo

5 NORWEGIAN WOOD, COLD SPRING, NY, 10516
Heritage Hills 356 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$750,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

356 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
1234…5

Frequently Asked Questions


Want more information about active adult communities around Middletown?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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
92 communities near Middletown
Remove Boundaries ×
Map Satellite

Reinmlsx

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.
© 2025 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: Nov 08, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top