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Middletown, NY 55+ active adult communities & homes for sale - Page 4

181 homes near Middletown

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4.8 rating (4 reviews) Wanaque Reserve
$300ks - $500ks
Wanaque Reserve, Wanaque, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes
3 rating (2 reviews) Heritage Hills
$400ks - $900ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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
Bald Eagle Commons
$100ks - $300ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
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Questions? Call us: (845) 479-5674
Greenbriar at Fox Ridge
$300ks - $500ks
Greenbriar at Fox Ridge, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 336 homes
Fox Hills
$300ks - $600ks
Fox Hills, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2003 | 672 homes
Traditions of America at ...
$500ks - $600ks
Traditions of America at ..., Bethlehem, PA
Resale Only | 55+ age-restricted | Built 2019 - present | 229 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
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.
1 rating (1 reviews) Brookfield Estates
$300ks
Brookfield Estates, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 homes
5 rating (1 reviews) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
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Questions? Call us: (845) 479-5674
Fox Crest
$300ks - $600ks
Fox Crest, Rockaway, NJ
New Construction | 55+ age-restricted | Built 2020 - present | 41 homes
Four Seasons at Bridgewat...
$300ks - $400ks
Four Seasons at Bridgewat..., Bridgewater, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 homes
The Pointe
$300ks - $600ks
The Pointe, Livingston, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 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.
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Horizons at Mount Arlingt...
$400ks
Horizons at Mount Arlingt..., Mount Arlington, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 144 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
Four Seasons at Wayne
$300ks - $400ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
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Questions? Call us: (845) 479-5674
5 rating (2 reviews) Blackburne Farm Townhomes
$400ks
Blackburne Farm Townhomes, Campbell Hall, NY
New Construction | 55+ age-restricted | Built 2019 - present | 29 homes
Wildflowers at Wallkill
$400ks - $500ks
Wildflowers at Wallkill, Middletown, NY
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 homes
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Winthrop Court
$400ks - $600ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 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 Seaford
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
Four Seasons at Cedar Gro...
$400ks - $600ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
Clove Hill Manor
$200ks - $300ks
Clove Hill Manor, Wantage, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 117 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Hawk Pointe
$300ks - $500ks
Hawk Pointe, Washington, NJ
New and Resale | 55+ age-restricted | Built 2019 - present | 85 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Glassbury Court at Cold S...
$500ks - $700ks
Glassbury Court at Cold S..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2009 - 2014 | 90 homes
Lakeside Villas
$400ks - $500ks
Lakeside Villas, Watchung, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 42 homes
Four Seasons at Troy Hill...
$500ks
Four Seasons at Troy Hill..., Parsippany, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2007 | 46 homes
Riverview Estates Active ...
$500ks - $600ks
Riverview Estates Active ..., Easton, PA
Resale Only | 55+ age-restricted | Built 2005 - present | 92 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) Delaware Crossing
$200ks - $300ks
Delaware Crossing, Lopatcong, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 158 homes
Regency at Flanders
$400ks - $900ks
Regency at Flanders, Flanders, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 275 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
Nolan's Ridge
$400ks - $700ks
Nolan's Ridge, Mount Arlington, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 156 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Meadowbrooke Pointe East ...
$500ks - $600ks
Meadowbrooke Pointe East ..., East Meadow, NY
New Construction | 62+ age-restricted | Built 2019 - present | 104 homes
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
12...3
Wanaque Reserve 10323 WARRENS WAY, WANAQUE BORO, NJ, 074..., Wanaque Boro, NJ 07465
$419,888

2 beds

|

2 baths

10323 WARRENS WAY, WANAQUE BORO, NJ, 074...
Community: Wanaque Reserve
Jefferson Village 113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$469,999

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

113 VILLAGE RD B, YORKTOWN, NY, 10598
Community: Jefferson Village
Greenbriar at Fox Ridge 5301 VETERANS DR, ROCKAWAY TWP., NJ, 078..., Rockaway Twp., NJ 07866
$460,775

2 beds

|

3 baths

|

1,568 sq ft

5301 VETERANS DR, ROCKAWAY TWP., NJ, 078...
Glassbury Court at Cold Spring 15 REVOLUTION RD, PHILIPSTOWN, NY, 10516, Philipstown, NY 10516
$556,904

2 beds

|

3 baths

|

1,785 sq ft

|

Condo

15 REVOLUTION RD, PHILIPSTOWN, NY, 10516
Wanaque Reserve 6406 WARRENS WAY TOP  & DEE, WANAQUE, NJ..., Wanaque, NJ 07465
$424,000

2 beds

|

2 baths

|

Condo

6406 WARRENS WAY TOP & DEE, WANAQUE, NJ...
Community: Wanaque Reserve
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Bald Eagle Commons 1202 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$179,000

1 beds

|

1 baths

|

Condo

1202 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Regency at Fishkill 734 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$569,900

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

734 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Heritage Hills 40 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$615,000

2 beds

|

2 baths

|

1,139 sq ft

|

Condo

40 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Breton Hills 709 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$675,000

2 beds

|

2 baths

|

1,362 sq ft

|

Condo

709 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton 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.
Brookfield Estates 6 WEYBOURNE LN, WHITE TWP., NJ, 07823, White Twp., NJ 07823
$449,000

3 beds

|

2 baths

|

1,837 sq ft

6 WEYBOURNE LN, WHITE TWP., NJ, 07823
Community: Brookfield Estates
Heritage Hills 680 HERITAGE HILLS DR C, SOMERS, NY, 105..., Somers, NY 10589
$589,000

1 beds

|

2 baths

|

1,296 sq ft

|

Condo

680 HERITAGE HILLS DR C, SOMERS, NY, 105...
Community: Heritage Hills
Villas at Seminary Hill 7102 PANKIN DR, CARMEL, NY, 10512, Carmel, NY 10512
$439,999

2 beds

|

2 baths

|

1,144 sq ft

|

Condo

7102 PANKIN DR, CARMEL, NY, 10512
Heritage Hills 243 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589
$739,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

243 HERITAGE HILLS DR B, SOMERS, NY, 105...
Community: Heritage Hills
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Warwick Grove 15 COWDREY ST, WARWICK, NY, 10990, Warwick, NY 10990
$799,000

3 beds

|

3 baths

|

2,482 sq ft

|

House

15 COWDREY ST, WARWICK, NY, 10990
Community: Warwick Grove
Wanaque Reserve 5408 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$449,000

2 beds

|

2 baths

|

Condo

5408 WARRENS WAY, WANAQUE, NJ, 07465
Community: Wanaque Reserve
Overlook 3014 EASTVIEW LN 110, CARMEL, NY, 10512, Carmel, NY 10512
$749,000

2 beds

|

3 baths

|

2,466 sq ft

|

Condo

3014 EASTVIEW LN 110, CARMEL, NY, 10512
Community: Overlook
Four Seasons at Wayne 109 FOUR SEASONS DR 109, WAYNE, NJ, 0747..., Wayne, NJ 07470
$525,000

2 beds

|

2 baths

|

Condo

109 FOUR SEASONS DR 109, WAYNE, NJ, 0747...
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 Crest 301 FISCHER CT, ROCKAWAY TWP., NJ, 07866, Rockaway Twp., NJ 07866
$559,900

2 beds

|

2 baths

|

1,408 sq ft

301 FISCHER CT, ROCKAWAY TWP., NJ, 07866
Community: Fox Crest
Fox Hills 3302 CLEVELAND LN 302, ROCKAWAY TWP., NJ..., Rockaway Twp., NJ 07866
$269,000

1 beds

|

1 baths

3302 CLEVELAND LN 302, ROCKAWAY TWP., NJ...
Community: Fox Hills
Jefferson Village 50 JEFFERSON OVAL A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$449,000

2 beds

|

2 baths

|

910 sq ft

|

Condo

50 JEFFERSON OVAL A, YORKTOWN, NY, 10598
Community: Jefferson Village
Jefferson Village 53 JEFFERSON OVAL B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$439,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

53 JEFFERSON OVAL B, YORKTOWN, NY, 10598
Community: Jefferson Village
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
The Retreat at Carmel 18 WHEELER CT, CARMEL, NY, 10512, Carmel, NY 10512
$725,000

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

18 WHEELER CT, CARMEL, NY, 10512
Meadowbrook Pointe Athletic Club & Spa 568 PACING WAY 568, HEMPSTEAD, NY, 11590, Hempstead, NY 11590
$875,000

2 beds

|

2 baths

|

1,328 sq ft

|

Condo

568 PACING WAY 568, HEMPSTEAD, NY, 11590
Traditions of America at Green Pond 3855 VICTORS WAY, EASTON, PA, 18045, Easton, PA 18045
$769,900

3 beds

|

4 baths

|

3,387 sq ft

3855 VICTORS WAY, EASTON, PA, 18045
Traditions of America at Green Pond 3855 VICTORS WAY, BETHLEHEM TWP, PA, 180..., Bethlehem Twp, PA 18045
$769,900

3 beds

|

4 baths

|

3,387 sq ft

|

Detached

3855 VICTORS WAY, BETHLEHEM TWP, PA, 180...
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.
Blackburne Farm Townhomes 45 OTTAWAY LN, HAMPTONBURGH, NY, 10916, Hamptonburgh, NY 10916
$555,000

2 beds

|

3 baths

|

1,746 sq ft

|

House

45 OTTAWAY LN, HAMPTONBURGH, NY, 10916
Rivington 85 WINDING RIDGE WAY 85, DANBURY, CT, 06..., Danbury, CT 06810
$825,000

3 beds

|

4 baths

|

1,794 sq ft

|

Condo

85 WINDING RIDGE WAY 85, DANBURY, CT, 06...
Community: Rivington
The Retreat at Carmel 2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512, Carmel, NY 10512
$449,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

2 BLAIR HEIGHTS 3317, CARMEL, NY, 10512
Blackburne Farm Townhomes 4 STRASSER PL, HAMPTONBURGH, NY, 10916, Hamptonburgh, NY 10916
$549,000

2 beds

|

3 baths

|

1,862 sq ft

|

House

4 STRASSER PL, HAMPTONBURGH, NY, 10916
Wanaque Reserve 3214 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$449,900

2 beds

|

2 baths

|

1,768 sq ft

3214 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Clove Hill Manor 11 FAIRCHILD LN 11, WANTAGE, NJ, 07461, Wantage, NJ 07461
$450,000

2 beds

|

4 baths

|

Townhouse

11 FAIRCHILD LN 11, WANTAGE, NJ, 07461
Community: Clove Hill Manor
Wanaque Reserve 1116 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$399,000

2 beds

|

2 baths

|

Condo

1116 WARRENS WAY, WANAQUE, NJ, 07465
Community: Wanaque Reserve
Wanaque Reserve 1116 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$399,000

2 beds

|

2 baths

|

1,768 sq ft

1116 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
Fox Hills 3209 CLEVELAND LN, ROCKAWAY TWP., NJ, 07..., Rockaway Twp., NJ 07866
$325,000

1 beds

|

1 baths

3209 CLEVELAND LN, ROCKAWAY TWP., NJ, 07...
Community: Fox 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.
Greenbriar at Fox Ridge 7113 POLK DR, ROCKAWAY TWP., NJ, 07885, Rockaway Twp., NJ 07885
$468,000

2 beds

|

3 baths

|

1,568 sq ft

7113 POLK DR, ROCKAWAY TWP., NJ, 07885
Heritage Hills 59 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$675,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

59 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Wanaque Reserve 4203 WARRENS WAY 203, WANAQUE BORO, NJ, ..., Wanaque Boro, NJ 07465
$414,900

2 beds

|

2 baths

|

1,768 sq ft

4203 WARRENS WAY 203, WANAQUE BORO, NJ, ...
Community: Wanaque Reserve
Wanaque Reserve 3121 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$449,000

2 beds

|

2 baths

3121 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Overlook 2042 SUMMIT LOOP 58, CARMEL, NY, 10512, Carmel, NY 10512
$849,000

2 beds

|

4 baths

|

1,957 sq ft

|

Condo

2042 SUMMIT LOOP 58, CARMEL, NY, 10512
Community: Overlook
Overlook 2080 SUMMIT LOOP 75, CARMEL, NY, 10512, Carmel, NY 10512
$915,000

2 beds

|

3 baths

|

2,496 sq ft

|

Condo

2080 SUMMIT LOOP 75, CARMEL, NY, 10512
Community: Overlook
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