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

207 homes near Middletown

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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
3 rating (2 reviews) Heritage Hills
$400ks - $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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
Want to learn more about 55+ communities in Middletown? 55places can help!
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
5 rating (1 reviews) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 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) Delaware Crossing
$200ks - $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.
Lakeside Villas
$400ks - $500ks
Lakeside Villas, Watchung, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 42 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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 Meadows at Panther Va...
$300ks - $400ks
The Meadows at Panther Va..., Hackettstown, NJ
Resale Only | Age-targeted | Built 2010 - 2021 | 312 homes
Reserve at Hawk Pointe
$400ks - $500ks
Reserve at Hawk Pointe, Washington, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 120 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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
Clove Hill Manor
$200ks - $300ks
Clove Hill Manor, Wantage, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 117 homes
1 rating (1 reviews) Brookfield Estates
$300ks
Brookfield Estates, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 homes
HarborView
$800ks - $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.
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Campagna
$300ks - $400ks
Campagna, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 1980 - 1986 | 136 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Four Seasons at Bridgewat...
$300ks - $400ks
Four Seasons at Bridgewat..., Bridgewater, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 homes
Fox Crest
$300ks - $600ks
Fox Crest, Rockaway, NJ
New Construction | 55+ age-restricted | Built 2020 - present | 41 homes
Riverview Estates Active ...
$500ks - $600ks
Riverview Estates Active ..., Easton, PA
Resale Only | 55+ age-restricted | Built 2005 - present | 92 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
The Bel Aire at East Mead...
$300ks - $400ks
The Bel Aire at East Mead..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 95 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 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 Hollows at Blue Hill
$500ks - $700ks
The Hollows at Blue Hill, Pearl River, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Bear's Cove
$800ks - $900ks
Bear's Cove, Ramsey, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 104 homes
Brookfield Glen
$100ks - $200ks
Brookfield Glen, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 124 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
Woodcrest at Jacobs Hill
$200ks - $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
Regency at Denville
$700ks - $800ks
Regency at Denville, Denville, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 140 homes
Kimbolton
$900ks - $1Ms
Kimbolton, Far Hills, NJ
New Construction | 55+ age-restricted | Built 2024 - present | 105 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
Four Seasons at The Prome...
$700ks - $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.
12...3
Four Seasons at Bridgewater 379 VICTORIA DR, BRIDGEWATER TWP., NJ, 0..., Bridgewater Twp., NJ 08807
$595,000

3 beds

|

3 baths

|

2,294 sq ft

379 VICTORIA DR, BRIDGEWATER TWP., NJ, 0...
Brookfield Estates 11 STAFFORD LN, WHITE TWP., NJ, 07823, White Twp., NJ 07823
$429,900

2 beds

|

2 baths

11 STAFFORD LN, WHITE TWP., NJ, 07823
Community: Brookfield Estates
Fox Crest 301 FISCHER CT, ROCKAWAY TWP., NJ, 07866, Rockaway Twp., NJ 07866
$555,000

2 beds

|

2 baths

|

1,408 sq ft

301 FISCHER CT, ROCKAWAY TWP., NJ, 07866
Community: Fox Crest
Greenbriar at Fox Ridge 7113 POLK DR, ROCKAWAY TWP., NJ, 07885, Rockaway Twp., NJ 07885
$449,900

2 beds

|

3 baths

|

1,568 sq ft

7113 POLK DR, ROCKAWAY TWP., NJ, 07885
New HarborView 100 HARBORVIEW DR 301, NORTH HEMPSTEAD, ..., North Hempstead, NY 11050
$1,200,000

3 beds

|

3 baths

|

Condo

100 HARBORVIEW DR 301, NORTH HEMPSTEAD, ...
Community: HarborView
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
New Wanaque Reserve 8421 WARRENS WAY 421, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$369,000

2 beds

|

2 baths

|

Condo

8421 WARRENS WAY 421, WANAQUE, NJ, 07465
Community: Wanaque Reserve
New Greenbriar at Fox Ridge 1305 HALE DR 305, ROCKAWAY TWP., NJ, 078..., Rockaway Twp., NJ 07885
$455,000

2 beds

|

3 baths

1305 HALE DR 305, ROCKAWAY TWP., NJ, 078...
New Bald Eagle Commons 135 RICHMOND RD, WEST MILFORD TWP., NJ, ..., West Milford Twp., NJ 07480
$505,000

3 beds

|

3 baths

|

2,300 sq ft

135 RICHMOND RD, WEST MILFORD TWP., NJ, ...
Community: Bald Eagle Commons
New Wanaque Reserve 8421 WARRENS WAY 421, WANAQUE BORO, NJ, ..., Wanaque Boro, NJ 07465
$369,000

2 beds

|

2 baths

|

1,768 sq ft

8421 WARRENS WAY 421, WANAQUE BORO, NJ, ...
Community: Wanaque Reserve
New Meadowbrook Pointe Athletic Club & Spa 34 SHADY LN, HEMPSTEAD, NY, 11590, Hempstead, NY 11590
$877,000

2 beds

|

2 baths

|

1,319 sq ft

|

Condo

34 SHADY LN, HEMPSTEAD, NY, 11590
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 Wanaque Reserve 7118 WARRENS WAY 118, WANAQUE BORO, NJ, ..., Wanaque Boro, NJ 07465
$580,000

2 beds

|

2 baths

|

2,119 sq ft

7118 WARRENS WAY 118, WANAQUE BORO, NJ, ...
Community: Wanaque Reserve
New Fox Hills 202 CLEVELAND LN, ROCKAWAY TWP., NJ, 078..., Rockaway Twp., NJ 07866
$300,000

1 beds

|

1 baths

|

791 sq ft

202 CLEVELAND LN, ROCKAWAY TWP., NJ, 078...
Community: Fox Hills
New Regency at Readington 105 VAN CLEEF DR, READINGTON TWP., NJ, 0..., Readington Twp., NJ 08889
$950,000

2 beds

|

3 baths

105 VAN CLEEF DR, READINGTON TWP., NJ, 0...
New Wanaque Reserve 1113 WARREN 113, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$399,900

2 beds

|

2 baths

|

Condo

1113 WARREN 113, WANAQUE, NJ, 07465
Community: Wanaque Reserve
New Wanaque Reserve 1113 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$399,900

2 beds

|

2 baths

1113 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
New Heritage Hills 34 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

3 baths

|

1,545 sq ft

|

Condo

34 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
New The Village at Fox Crossing 870 BILTMORE AVE, FORKS TWP, PA, 18040, Forks Twp, PA 18040
$279,900

2 beds

|

2 baths

|

1,232 sq ft

|

Detached

870 BILTMORE AVE, FORKS TWP, PA, 18040
New Regency at Denville 79 MACKENZIE LN, DENVILLE TWP., NJ, 0783..., Denville Twp., NJ 07834
$945,000

3 beds

|

3 baths

|

3,100 sq ft

79 MACKENZIE LN, DENVILLE TWP., NJ, 0783...
Community: Regency at Denville
New The Retreat at Carmel 4 REESE CT, CARMEL, NY, 10512, Carmel, NY 10512
$699,000

2 beds

|

2 baths

|

1,979 sq ft

|

House

4 REESE CT, CARMEL, NY, 10512
New Heritage Hills 128 HERITAGE HILLS DR B, SOMERS, NY, 105..., Somers, NY 10589
$450,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

128 HERITAGE HILLS DR B, SOMERS, NY, 105...
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 Heritage Hills 156 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$649,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

156 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Bald Eagle Commons 1311 RICHMOND RD 311, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$159,000

1 beds

|

1 baths

|

655 sq ft

1311 RICHMOND RD 311, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
Bald Eagle Commons 1311 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$159,000

1 beds

|

1 baths

|

Condo

1311 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$630,000

2 beds

|

4 baths

|

1,572 sq ft

11 MERCY ST 11, DANBURY, CT, 06810
Community: Rivington
Four Seasons at Chester 7 DICKERSON CT, CHESTER TWP., NJ, 07930, Chester Twp., NJ 07930
$745,000

2 beds

|

3 baths

|

2,248 sq ft

7 DICKERSON CT, CHESTER TWP., NJ, 07930
Bald Eagle Commons 2 RICHMOND RD 302, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$349,000

2 beds

|

2 baths

|

Condo

2 RICHMOND RD 302, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
Bald Eagle Commons 7215 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$289,000

2 beds

|

2 baths

|

Condo

7215 RICHMOND RD, WEST MILFORD, NJ, 0748...
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 302, WEST MILFORD TWP., NJ..., West Milford Twp., NJ 07480
$349,000

2 beds

|

2 baths

|

1,581 sq ft

2 RICHMOND RD 302, WEST MILFORD TWP., NJ...
Community: Bald Eagle Commons
Bald Eagle Commons 7215 RICHMOND RD, WEST MILFORD TWP., NJ,..., West Milford Twp., NJ 07480
$289,000

2 beds

|

2 baths

|

1,220 sq ft

7215 RICHMOND RD, WEST MILFORD TWP., NJ,...
Community: Bald Eagle Commons
Greenbriar at Fox Ridge 4215 HOOVER LN, ROCKAWAY TWP., NJ, 07885, Rockaway Twp., NJ 07885
$465,000

2 beds

|

3 baths

4215 HOOVER LN, ROCKAWAY TWP., NJ, 07885
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 1120 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580
$510,000

2 beds

|

2 baths

|

941 sq ft

|

Condo

1120 WILLOW LN, HEMPSTEAD, NY, 11580
Community: Dutchgate
Overlook 2059 SUMMIT LOOP 97, CARMEL, NY, 10512, Carmel, NY 10512
$920,000

2 beds

|

3 baths

|

2,873 sq ft

|

Condo

2059 SUMMIT LOOP 97, CARMEL, NY, 10512
Community: Overlook
Overlook 2057 SUMMIT LOOP 96, CARMEL, NY, 10512, Carmel, NY 10512
$885,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2057 SUMMIT LOOP 96, CARMEL, NY, 10512
Community: Overlook
Overlook 4091 FAIRWAYS DR 146, CARMEL, NY, 10512, Carmel, NY 10512
$772,000

3 beds

|

4 baths

|

2,131 sq ft

|

Condo

4091 FAIRWAYS DR 146, CARMEL, NY, 10512
Community: Overlook
Overlook 2003 SUMMIT LOOP 82, CARMEL, NY, 10512, Carmel, NY 10512
$799,000

2 beds

|

2 baths

|

1,948 sq ft

|

Condo

2003 SUMMIT LOOP 82, CARMEL, NY, 10512
Community: Overlook
Overlook 4085 FAIRWAYS DR 143, CARMEL, NY, 10512, Carmel, NY 10512
$727,000

3 beds

|

3 baths

|

1,931 sq ft

|

Condo

4085 FAIRWAYS DR 143, CARMEL, NY, 10512
Community: Overlook
Regency at Readington 96 VAN CLEEF DR, READINGTON TWP., NJ, 08..., Readington Twp., NJ 08889
$974,900

2 beds

|

4 baths

96 VAN CLEEF DR, READINGTON TWP., NJ, 08...
Overlook 4087 FAIRWAYS DR 144, CARMEL, NY, 10512, Carmel, NY 10512
$669,000

3 beds

|

4 baths

|

2,141 sq ft

|

Condo

4087 FAIRWAYS DR 144, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
The Village at Upstream Farm 2740 UPSTREAM FARM RD, FORKS TWP, PA, 18..., Forks Twp, PA 18040
$289,000

2 beds

|

2 baths

|

1,123 sq ft

|

Townhouse

2740 UPSTREAM FARM RD, FORKS TWP, PA, 18...
Stoneleigh Woods at Carmel 205 EGRETS LNDG 205, CARMEL, NY, 10512, Carmel, NY 10512
$475,000

2 beds

|

2 baths

|

1,344 sq ft

|

Condo

205 EGRETS LNDG 205, CARMEL, NY, 10512
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.
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