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

189 homes near Middletown

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Wildflowers at Wallkill
$400Ks - $500Ks
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
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4.8 rating (4 reviews) Wanaque Reserve
$400Ks - $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
$200Ks - $600Ks
Fox Hills, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2003 | 672 homes
Bald Eagle Commons
$100Ks - $300Ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes
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
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
$400Ks - $400Ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Greenbriar at Fox Ridge
$400Ks - $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
The Meadows at Panther Va...
$500Ks - $600Ks
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
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
Apple Ridge
$700Ks - $700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
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 - $500Ks
Brookfield Estates, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 homes
Winthrop Court
$400Ks - $400Ks
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.
HarborView
$900Ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
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 - $500Ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
Traditions of America at ...
$500Ks - $800Ks
Traditions of America at ..., Bethlehem, PA
Resale Only | 55+ age-restricted | Built 2019 - present | 229 homes
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5 rating (1 reviews) Legacy at Mansfield Meado...
$500Ks - $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 - $900Ks
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 - $1Ms
Four Seasons at The Prome..., Warren, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 208 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.
Glenmoor
$400Ks - $400Ks
Glenmoor, Easton, PA
Resale Only | 55+ age-restricted | Built 2004 - 2008 | 182 homes
The Pointe
$500Ks - $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 - $300Ks
Delaware Crossing, Lopatcong, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 158 homes
Four Seasons at Cedar Gro...
$600Ks - $600Ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
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
Horizons at Mount Arlingt...
$400Ks - $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
Regency at Fishkill 326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$527,000

1 beds

|

2 baths

|

1,543 sq ft

|

Condo

326 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Jefferson Village 108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ..., Yorktown Heights, NY 10598
$464,900

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

108 VILLAGE RD B, YORKTOWN HEIGHTS, NY, ...
Community: Jefferson Village
Breton Hills 512 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542
$639,000

2 beds

|

2 baths

|

1,430 sq ft

|

Condo

512 BRETON WAY, GLEN COVE, NY, 11542
Community: Breton Hills
The Seasons at East Meadow 331 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$575,000

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

331 SPRING DR, EAST MEADOW, NY, 11554
Warwick Grove 15 CROPSEY ST # 15-3A, WARWICK, NY, 1099..., Warwick, NY 10990
$625,000

2 beds

|

2 baths

|

1,823 sq ft

|

House

15 CROPSEY ST # 15-3A, WARWICK, NY, 1099...
Community: Warwick Grove
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Dutchgate 1120 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$480,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1120 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
Heritage Hills 523 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$669,000

2 beds

|

2 baths

|

1,468 sq ft

|

Condo

523 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$375,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Dutchgate 1228 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$498,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1228 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
Heritage Hills 247 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$389,900

1 beds

|

1 baths

|

955 sq ft

|

Condo

247 HERITAGE HLS A, 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.
Jefferson Village 2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10..., Yorktown Heights, NY 10598
$299,999

1 beds

|

1 baths

|

800 sq ft

|

Condo

2 HAMPTON CT A, YORKTOWN HEIGHTS, NY, 10...
Community: Jefferson Village
Heritage Hills 798 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$619,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

798 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Jefferson Village 41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598
$399,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

41 JEFFERSON OVAL B, YORKTOWN HEIGHTS, N...
Community: Jefferson Village
Breton Hills 704 BRETON WAY # 704, GLEN COVE, NY, 115..., Glen Cove, NY 11542
$629,000

2 beds

|

2 baths

|

1,440 sq ft

|

Condo

704 BRETON WAY # 704, GLEN COVE, NY, 115...
Community: Breton Hills
The Seasons at East Meadow 272 SPRING DR, EAST MEADOW, NY, 11554, East Meadow, NY 11554
$639,000

2 beds

|

3 baths

|

1,030 sq ft

|

Condo

272 SPRING DR, EAST MEADOW, NY, 11554
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Dutchgate 1002 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$485,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1002 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
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
Regency at Fishkill 334 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$539,900

2 beds

|

2 baths

|

1,499 sq ft

|

Condo

334 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Dutchgate 802 WILLOW LN UPPR LEVEL, VALLEY STREAM,..., Valley Stream, NY 11580
$480,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

802 WILLOW LN UPPR LEVEL, VALLEY STREAM,...
Community: Dutchgate
Warwick Grove 11 ASKE ST, WARWICK, NY, 10990, Warwick, NY 10990
$985,000

4 beds

|

3 baths

|

2,752 sq ft

|

House

11 ASKE ST, WARWICK, NY, 10990
Community: Warwick Grove
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 Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$569,800

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Jefferson Village 156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,..., Yorktown Heights, NY 10598
$339,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

156 CARRIAGE CT G, YORKTOWN HEIGHTS, NY,...
Community: Jefferson Village
Warwick Grove 2 SLY ST, WARWICK, NY, 10990, Warwick, NY 10990
$849,000

2 beds

|

3 baths

|

2,256 sq ft

|

House

2 SLY ST, WARWICK, NY, 10990
Community: Warwick Grove
The Seasons at East Meadow 133 SPRING DR # 133, EAST MEADOW, NY, 11..., East Meadow, NY 11554
$599,999

2 beds

|

2 baths

|

1,272 sq ft

|

Condo

133 SPRING DR # 133, EAST MEADOW, NY, 11...
HarborView 100 HARBOR VIEW DR 423, PORT WASHINGTON,..., Port Washington, NY 11050
$658,000

1 beds

|

2 baths

|

1,161 sq ft

|

Condo

100 HARBOR VIEW DR 423, PORT WASHINGTON,...
Community: HarborView
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
HarborView 100 HARBOR VIEW DR 439, PORT WASHINGTON,..., Port Washington, NY 11050
$875,000

2 beds

|

3 baths

|

1,420 sq ft

|

Condo

100 HARBOR VIEW DR 439, PORT WASHINGTON,...
Community: HarborView
Meadowbrook Pointe Athletic Club & Spa 481 PACING WAY, WESTBURY, NY, 11590, Westbury, NY 11590
$1,100,000

2 beds

|

3 baths

|

2,800 sq ft

|

Condo

481 PACING WAY, WESTBURY, NY, 11590
The Village at Upstream Farm 1572 UPSTREAM FARM RD, EASTON, PA, 18040, Easton, PA 18040
$300,000

2 beds

|

2 baths

|

1,180 sq ft

1572 UPSTREAM FARM RD, EASTON, PA, 18040
New Traditions of America at Green Pond 3871 VICTORS WAY, EASTON, PA, 18045, Easton, PA 18045
$599,900

2 beds

|

2 baths

|

1,671 sq ft

|

Detached

3871 VICTORS WAY, EASTON, PA, 18045
New Fox Hills 2210 JOHNSON DR, ROCKAWAY BORO, NJ, 0786..., Rockaway Boro, NJ 07866
$520,000

2 beds

|

2 baths

|

1,837 sq ft

2210 JOHNSON DR, ROCKAWAY BORO, NJ, 0786...
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.
Legacy at Morgan Hill 610 QUAKER RIDGE TER, EASTON, PA, 18042, Easton, PA 18042
$634,900

3 beds

|

3 baths

|

3,217 sq ft

610 QUAKER RIDGE TER, EASTON, PA, 18042
Traditions of America at Green Pond 3732 LOYAL LN, EASTON, PA, 18045, Easton, PA 18045
$650,000

2 beds

|

2 baths

|

2,244 sq ft

3732 LOYAL LN, EASTON, PA, 18045
Traditions of America at Green Pond 3767 FOUNDERS XING, EASTON, PA, 18045, Easton, PA 18045
$549,900

3 beds

|

3 baths

|

2,080 sq ft

|

Townhouse

3767 FOUNDERS XING, EASTON, PA, 18045
Traditions of America at Green Pond 3858 VICTORS WAY, EASTON, PA, 18045, Easton, PA 18045
$744,900

3 beds

|

3 baths

|

2,622 sq ft

|

Detached

3858 VICTORS WAY, EASTON, PA, 18045
The Village at Fox Crossing 3813 BELCOURT DR, FORKS TWP, PA, 18040, Forks Twp, PA 18040
$275,000

2 beds

|

2 baths

|

1,302 sq ft

|

Manufactured Home

3813 BELCOURT DR, FORKS TWP, PA, 18040
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Traditions of America at Green Pond 3868 VICTORS WAY, EASTON, PA, 18045, Easton, PA 18045
$610,000

2 beds

|

2 baths

|

2,477 sq ft

|

Detached

3868 VICTORS WAY, EASTON, PA, 18045
Traditions of America at Green Pond 3803 LOYAL LN, EASTON, PA, 18045, Easton, PA 18045
$624,000

3 beds

|

2 baths

|

2,174 sq ft

|

Detached

3803 LOYAL LN, EASTON, PA, 18045
Winthrop Court 6102 HARCOURT RD # 519, CLIFTON, NJ, 070..., Clifton, NJ 07013
$515,000

2 beds

|

2 baths

|

Condo

6102 HARCOURT RD # 519, CLIFTON, NJ, 070...
Community: Winthrop Court
Traditions of America at Green Pond 3801 LOYAL LN, EASTON, PA, 18045, Easton, PA 18045
$854,900

3 beds

|

3 baths

|

3,021 sq ft

3801 LOYAL LN, EASTON, PA, 18045
Wanaque Reserve 1319 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$499,000

2 beds

|

2 baths

|

Condo

1319 WARRENS WAY, WANAQUE, NJ, 07465
Community: Wanaque Reserve
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189 homes near Middletown
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