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

Middletown, NY 55+ active adult communities & homes for sale - Page 2

118 homes near Middletown

Sort by:

Relevance

Relevance

Wildflowers at Wallkill
$500Ks - $600Ks
Wildflowers at Wallkill, Middletown, NY
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 homes
3 rating (2 reviews) Heritage Hills
$300Ks - $900Ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Rivington
$400Ks - $600Ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
4 rating (1 reviews) Jefferson Village
$200Ks - $600Ks
Jefferson Village, Yorktown Heights, NY
Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes
5 rating (1 reviews) Four Seasons at Great Not...
$600Ks - $800Ks
Four Seasons at Great Not..., Woodland Park, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2018 | 814 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
4.8 rating (4 reviews) Wanaque Reserve
$400Ks
Wanaque Reserve, Wanaque, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes
Meadowbrook Pointe Athlet...
$800Ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Fox Hills
$300Ks - $500Ks
Fox Hills, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2003 | 672 homes
Bald Eagle Commons
$100Ks - $200Ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 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.
The Seasons at East Meado...
$500Ks - $600Ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 homes
Dutchgate
$400Ks - $500Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Greenbriar at Fox Ridge
$300Ks - $500Ks
Greenbriar at Fox Ridge, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 336 homes
The Commons at Mendham
$400Ks - $700Ks
The Commons at Mendham, Mendham, NJ
Resale Only | Age-targeted | Built 1978 - 1985 | 330 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
The Meadows at Panther Va...
$500Ks
The Meadows at Panther Va..., Hackettstown, NJ
Resale Only | Age-targeted | Built 2010 - 2021 | 312 homes
The Retreat at Carmel
$400Ks - $600Ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Overlook
$600Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Apple Ridge
$700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 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.
Regency at Flanders
$800Ks - $1Ms
Regency at Flanders, Flanders, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 275 homes
1 rating (1 reviews) Brookfield Estates
$500Ks
Brookfield Estates, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 homes
Winthrop Court
$400Ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
HarborView
$900Ks - $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
The Highlands at Glenmoor
$400Ks - $500Ks
The Highlands at Glenmoor, Easton, PA
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 251 homes
Del Webb Florham Park
$700Ks - $1Ms
Del Webb Florham Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2018 - 2022 | 242 homes
Four Seasons at Wayne
$500Ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
Traditions of America at ...
$600Ks - $700Ks
Traditions of America at ..., Bethlehem, PA
Resale Only | 55+ age-restricted | Built 2019 - present | 229 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.
5 rating (1 reviews) Legacy at Mansfield Meado...
$500Ks
Legacy at Mansfield Meado..., Port Murray, NJ
New Construction | 55+ age-restricted | Built 2017 - present | 226 homes
Regency at Wappinger
$600Ks - $700Ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
5 rating (1 reviews) Warwick Grove
$600Ks - $800Ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes
Regency at Readington
$700Ks - $800Ks
Regency at Readington, Readington Township, NJ
Resale Only | 55+ age-restricted | Built 2014 - 2019 | 209 homes
Four Seasons at The Prome...
$1Ms
Four Seasons at The Prome..., Warren, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 208 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Glenmoor
$300Ks - $500Ks
Glenmoor, Easton, PA
Resale Only | 55+ age-restricted | Built 2004 - 2008 | 182 homes
The Pointe
$500Ks
The Pointe, Livingston, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes
Regency at Fishkill
$400Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
5 rating (1 reviews) Delaware Crossing
$300Ks
Delaware Crossing, Lopatcong, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 158 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.
Four Seasons at Cedar Gro...
$700Ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
Nolan's Ridge
$400Ks - $700Ks
Nolan's Ridge, Mount Arlington, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 156 homes
Venue at The American
$800Ks - $1Ms
Venue at The American, Morris Plains, NJ
New and Resale | 55+ age-restricted | Built 2021 - present | 156 homes
Four Seasons at Bridgewat...
$300Ks - $400Ks
Four Seasons at Bridgewat..., Bridgewater, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Horizons at Mount Arlingt...
$400Ks
Horizons at Mount Arlingt..., Mount Arlington, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 144 homes
Regency at Denville
$700Ks - $800Ks
Regency at Denville, Denville, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 140 homes
Fox Hills 4300 CLEVELAND LN, ROCKAWAY BORO, NJ, 07..., Rockaway Boro, NJ 07866
$449,999

2 beds

|

2 baths

|

1,369 sq ft

4300 CLEVELAND LN, ROCKAWAY BORO, NJ, 07...
Community: Fox Hills
Kimbolton 20 WHITAKER LN, FAR HILLS, NJ, 07931, Far Hills, NJ 07931
$1,199,990

3 beds

|

3 baths

|

2,775 sq ft

20 WHITAKER LN, FAR HILLS, NJ, 07931
Community: Kimbolton
Bald Eagle Commons 5318 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$239,000

2 beds

|

1 baths

|

Condo

5318 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Bald Eagle Commons 7308 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$279,000

2 beds

|

2 baths

|

Condo

7308 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Bald Eagle Commons 2 RICHMOND RD 210, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$264,900

2 beds

|

2 baths

|

Condo

2 RICHMOND RD 210, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Bald Eagle Commons 2 RICHMOND RD APT 210 210, WEST MILFORD,..., West Milford, NJ 07480
$264,900

2 beds

|

2 baths

|

985 sq ft

2 RICHMOND RD APT 210 210, WEST MILFORD,...
Community: Bald Eagle Commons
Bald Eagle Commons 7417 RICHMOND RD # 417, WEST MILFORD, NJ..., West Milford, NJ 07480
$319,000

2 beds

|

2 baths

7417 RICHMOND RD # 417, WEST MILFORD, NJ...
Community: Bald Eagle Commons
Brookfield Glen 6015 BROOKFIELD GLEN DR # 15, BELVIDERE,..., Belvidere, NJ 07823
$264,900

2 beds

|

2 baths

|

1,179 sq ft

6015 BROOKFIELD GLEN DR # 15, BELVIDERE,...
Community: Brookfield Glen
Wanaque Reserve 9116 WARRENS WAY # 116, WANAQUE, NJ, 074..., Wanaque, NJ 07465
$449,000

2 beds

|

2 baths

9116 WARRENS WAY # 116, WANAQUE, NJ, 074...
Community: Wanaque Reserve
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.
Bald Eagle Commons 7308 RICHMOND RD # 308, WEST MILFORD, NJ..., West Milford, NJ 07480
$279,000

2 beds

|

2 baths

7308 RICHMOND RD # 308, WEST MILFORD, NJ...
Community: Bald Eagle Commons
Greenbriar at Fox Ridge 5307 VETERANS DR, WHARTON, NJ, 07885, Wharton, NJ 07885
$469,000

2 beds

|

3 baths

5307 VETERANS DR, WHARTON, NJ, 07885
Fox Hills 2210 JOHNSON DR, ROCKAWAY BORO, NJ, 0786..., Rockaway Boro, NJ 07866
$500,000

2 beds

|

2 baths

|

1,837 sq ft

2210 JOHNSON DR, ROCKAWAY BORO, NJ, 0786...
Community: Fox Hills
Brookfield Estates 2 STAFFORD LN, BELVIDERE, NJ, 07823, Belvidere, NJ 07823
$510,000

2 beds

|

2 baths

|

1,662 sq ft

|

Ranch

2 STAFFORD LN, BELVIDERE, NJ, 07823
Community: Brookfield Estates
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Winthrop Court 8205 HARCOURT RD # 8205, CLIFTON, NJ, 07..., Clifton, NJ 07013
$499,000

2 beds

|

2 baths

|

Condo

8205 HARCOURT RD # 8205, CLIFTON, NJ, 07...
Community: Winthrop Court
Wanaque Reserve 7414 WARRENS WAY # 414, WANAQUE, NJ, 074..., Wanaque, NJ 07465
$442,000

2 beds

|

2 baths

|

1,768 sq ft

7414 WARRENS WAY # 414, WANAQUE, NJ, 074...
Community: Wanaque Reserve
The Meadows at Panther Valley 17 ALEXANDERS RD, HACKETTSTOWN, NJ, 0784..., Hackettstown, NJ 07840
$550,000

3 beds

|

3 baths

17 ALEXANDERS RD, HACKETTSTOWN, NJ, 0784...
Four Seasons at Bridgewater 353 VICTORIA DR, BRIDGEWATER, NJ, 08807, Bridgewater, NJ 08807
$425,000

2 beds

|

2 baths

|

1,130 sq ft

353 VICTORIA DR, BRIDGEWATER, NJ, 08807
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.
Four Seasons at Cedar Grove 911 HOLLY LN, CEDAR GROVE, NJ, 07009, Cedar Grove, NJ 07009
$775,000

2 beds

|

2 baths

|

Condo

911 HOLLY LN, CEDAR GROVE, NJ, 07009
Greenbriar at Fox Ridge 1213 HALE DR, ROCKAWAY TWP., NJ, 07866, Rockaway Twp., NJ 07866
$495,000

2 beds

|

3 baths

1213 HALE DR, ROCKAWAY TWP., NJ, 07866
Brookfield Estates 29 STAFFORD LN, BELVIDERE, NJ, 07823, Belvidere, NJ 07823
$549,000

2 beds

|

2 baths

|

1,837 sq ft

29 STAFFORD LN, BELVIDERE, NJ, 07823
Community: Brookfield Estates
Brookfield Estates 107 KENSINGTON CIR, BELVIDERE, NJ, 07823, Belvidere, NJ 07823
$510,000

2 beds

|

2 baths

107 KENSINGTON CIR, BELVIDERE, NJ, 07823
Community: Brookfield Estates
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Four Seasons at Bridgewater 259 VICTORIA DR, BRIDGEWATER, NJ, 08807, Bridgewater, NJ 08807
$399,500

2 beds

|

2 baths

259 VICTORIA DR, BRIDGEWATER, NJ, 08807
Horizons at Mount Arlington 29 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07..., Mount Arlington, NJ 07856
$478,888

2 beds

|

2 baths

|

1,840 sq ft

29 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07...
The Commons at Mendham 16 GALWAY DR, MENDHAM, NJ, 07945, Mendham, NJ 07945
$749,999

3 beds

|

3 baths

|

2,292 sq ft

16 GALWAY DR, MENDHAM, NJ, 07945
Hawk Pointe 10 SPARROWHAWK ST, WASHINGTON, NJ, 07882, Washington, NJ 07882
$519,500

2 beds

|

3 baths

|

1,910 sq ft

10 SPARROWHAWK ST, WASHINGTON, NJ, 07882
Community: Hawk Pointe
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.
Bald Eagle Commons 7417 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$319,000

2 beds

|

2 baths

|

Condo

7417 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Sterling Mist 72 SCHINDLER CT, PARSIPPANY, NJ, 07054, Parsippany, NJ 07054
$779,000

7 beds

|

6 baths

|

Townhouse

72 SCHINDLER CT, PARSIPPANY, NJ, 07054
Community: Sterling Mist
New The Seasons at East Meadow 294 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$639,999

2 beds

|

2 baths

|

1,050 sq ft

|

Condo

294 SPRING DR, EAST MEADOW, NY, 11554
Jefferson Village 96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598
$479,000

2 beds

|

2 baths

|

1,050 sq ft

|

Condo

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...
Community: Jefferson Village
New Blackburne Farm Townhomes 4 STRASSER PL, CAMPBELL HALL, NY, 10916, Campbell Hall, NY 10916
$559,000

2 beds

|

3 baths

|

1,791 sq ft

|

House

4 STRASSER PL, CAMPBELL HALL, NY, 10916
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Jefferson Village 15 ESSEX PL 15K, YORKTOWN, NY, 10598, Yorktown, NY 10598
$375,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

15 ESSEX PL 15K, YORKTOWN, NY, 10598
Community: Jefferson Village
New Meadowbrook Pointe Athletic Club & Spa 365 TROTTING LN, WESTBURY, NY, 11590, Westbury, NY 11590
$799,999

1 beds

|

2 baths

|

1,128 sq ft

|

Condo

365 TROTTING LN, WESTBURY, NY, 11590
New Heritage Hills 537 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Overlook 4071 FAIRWAYS DR 136, CARMEL, NY, 10512, Carmel, NY 10512
$649,000

2 beds

|

3 baths

|

1,914 sq ft

|

Condo

4071 FAIRWAYS DR 136, CARMEL, NY, 10512
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.
Heritage Hills 390 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$699,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

390 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New Wildflowers at Wallkill 24 JUNIPER CIR, MIDDLETOWN, NY, 10940, Middletown, NY 10940
$625,000

2 beds

|

3 baths

|

2,975 sq ft

|

House

24 JUNIPER CIR, MIDDLETOWN, NY, 10940
Jefferson Village 159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$560,000

2 beds

|

2 baths

|

1,300 sq ft

|

Condo

159 CARRIAGE CT C, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Jefferson Village 98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598
$525,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

98 MOLLY PITCHER LN A, YORKTOWN HEIGHTS,...
Community: Jefferson Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Heritage Hills 749 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$779,000

2 beds

|

2 baths

|

1,526 sq ft

|

Condo

749 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 443 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

443 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
12…3

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
118 homes
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.
© 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: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top