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

192 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
Bald Eagle Commons
$100ks - $300ks
Bald Eagle Commons, West Milford, NJ
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 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
3 rating (2 reviews) Heritage Hills
- $800ks
Heritage Hills, Somers, NY
Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 homes
Fox Hills
$300ks - $600ks
Fox Hills, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2003 | 672 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
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) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes
Regency at Fishkill
$300ks - $400ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes
The Highlands at Glenmoor
$300ks - $400ks
The Highlands at Glenmoor, Easton, PA
Resale Only | 55+ age-restricted | Built 2004 - 2007 | 251 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.
Greenbriar at Fox Ridge
$300ks - $500ks
Greenbriar at Fox Ridge, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 336 homes
Reserve at Hawk Pointe
$400ks - $500ks
Reserve at Hawk Pointe, Washington, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 120 homes
Lakeside Villas
$400ks - $500ks
Lakeside Villas, Watchung, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2020 | 42 homes
Fox Crest
$300ks - $600ks
Fox Crest, Rockaway, NJ
New Construction | 55+ age-restricted | Built 2020 - present | 41 homes
Nolan's Ridge
$400ks - $700ks
Nolan's Ridge, Mount Arlington, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 156 homes
Apple Ridge
$500ks - $1Ms
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Breton Hills
$500ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Horizons at Mount Arlingt...
$400ks
Horizons at Mount Arlingt..., Mount Arlington, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2004 | 144 homes
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
Clove Hill Manor
$200ks - $300ks
Clove Hill Manor, Wantage, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 117 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
The Seasons at Seaford
$600ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
The Retreat at Carmel
$300ks - $800ks
The Retreat at Carmel, Carmel, NY
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes
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
1 rating (1 reviews) Brookfield Estates
$300ks
Brookfield Estates, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 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
Enclave at Shackamaxon
$1Ms
Enclave at Shackamaxon, Scotch Plains, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 56 homes
Brookfield Glen
$100ks - $200ks
Brookfield Glen, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 124 homes
5 rating (1 reviews) Legacy at Mansfield Meado...
$300ks - $500ks
Legacy at Mansfield Meado..., Port Murray, NJ
New Construction | 55+ age-restricted | Built 2017 - present | 226 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
Regency at Flanders, Flanders, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2022 | 275 homes
Knickerbocker Bay Club
$700ks - $3Ms
Knickerbocker Bay Club, Port Washington, NY
New and Resale | 55+ age-restricted | Built 2014 - present | 32 homes
5 rating (1 reviews) Paris Square
$500ks - $700ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
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
Four Seasons at The Prome...
$700ks - $1Ms
Four Seasons at The Prome..., Warren, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 208 homes
Four Seasons at Bridgewat...
$300ks - $400ks
Four Seasons at Bridgewat..., Bridgewater, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 homes
Riverview Estates Active ...
$500ks - $600ks
Riverview Estates Active ..., Easton, PA
Resale Only | 55+ age-restricted | Built 2005 - present | 92 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Wildflowers at Wallkill
$400ks - $500ks
Wildflowers at Wallkill, Middletown, NY
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 homes
Regency at Denville
$700ks - $800ks
Regency at Denville, Denville, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 140 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
Meadowbrook Pointe Athletic Club & Spa 401 PACING WAY 4101, HEMPSTEAD, NY, 1159..., Hempstead, NY 11590
$875,000

2 beds

|

2 baths

|

1,353 sq ft

|

Condo

401 PACING WAY 4101, HEMPSTEAD, NY, 1159...
Nolan's Ridge 15 ZACHARY WAY 9615, MOUNT ARLINGTON BOR..., Mount Arlington Boro, NJ 07856
$499,999

2 beds

|

2 baths

15 ZACHARY WAY 9615, MOUNT ARLINGTON BOR...
Community: Nolan's Ridge
Overlook 2084 SUMMIT LOOP 77, CARMEL, NY, 10512, Carmel, NY 10512
$779,000

2 beds

|

3 baths

|

2,214 sq ft

|

Condo

2084 SUMMIT LOOP 77, CARMEL, NY, 10512
Community: Overlook
The Highlands at Glenmoor 81 MOOR DR, PALMER TWP, PA, 18045, Palmer Twp, PA 18045
$519,000

3 beds

|

3 baths

|

2,300 sq ft

|

Semi Detached

81 MOOR DR, PALMER TWP, PA, 18045
Traditions of America at Green Pond 3717 LOYAL LN, EASTON, PA, 18045, Easton, PA 18045
$724,900

2 beds

|

3 baths

|

2,284 sq ft

|

Detached

3717 LOYAL LN, EASTON, PA, 18045
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Bear's Cove 33 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446
$1,250,000

3 beds

|

4 baths

|

Townhouse

33 WINDSOR LN, RAMSEY, NJ, 07446
Community: Bear's Cove
Bald Eagle Commons 1302 RICHMOND RD 302, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$179,900

1 beds

|

1 baths

|

655 sq ft

1302 RICHMOND RD 302, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
Greenbriar at Fox Ridge 6102 VETERANS DR 102, ROCKAWAY TWP., NJ,..., Rockaway Twp., NJ 07885
$468,000

2 beds

|

3 baths

6102 VETERANS DR 102, ROCKAWAY TWP., NJ,...
Nolan's Ridge 2 HARRISON WAY, MOUNT ARLINGTON BORO, NJ..., Mount Arlington Boro, NJ 07856
$725,000

3 beds

|

3 baths

2 HARRISON WAY, MOUNT ARLINGTON BORO, NJ...
Community: Nolan's Ridge
Wanaque Reserve 10402 WARRENS WAY 4TH  NEW, WANAQUE, NJ,..., Wanaque, NJ 07465
$409,988

2 beds

|

2 baths

|

Condo

10402 WARRENS WAY 4TH NEW, WANAQUE, NJ,...
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.
Wanaque Reserve 10402 WARRENS WAY 402, WANAQUE BORO, NJ,..., Wanaque Boro, NJ 07465
$409,988

2 beds

|

2 baths

10402 WARRENS WAY 402, WANAQUE BORO, NJ,...
Community: Wanaque Reserve
The Seasons at Seaford 107 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783
$799,000

2 beds

|

2 baths

|

1,408 sq ft

|

Condo

107 SPRING DR, HEMPSTEAD, NY, 11783
The Seasons at Seaford 13 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783
$799,000

2 beds

|

2 baths

|

1,408 sq ft

|

Condo

13 SPRING DR, HEMPSTEAD, NY, 11783
Reserve at Hawk Pointe 6 OSPREY CT, WASHINGTON TWP., NJ, 07882, Washington Twp., NJ 07882
$699,900

3 beds

|

4 baths

|

2,337 sq ft

6 OSPREY CT, WASHINGTON TWP., NJ, 07882
Apple Ridge 134 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$950,000

4 beds

|

4 baths

|

Townhouse

134 FISHER RD, MAHWAH, NJ, 07430
Community: Apple Ridge
The Hollows at Blue Hill 4201 FRED ILL JR CT, ORANGETOWN, NY, 109..., Orangetown, NY 10965
$699,000

2 beds

|

2 baths

|

1,245 sq ft

|

Condo

4201 FRED ILL JR CT, ORANGETOWN, NY, 109...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Legacy at Morgan Hill 560 QUAKER RIDGE TER, WILLIAMS TWP, PA, ..., Williams Twp, PA 18042
$535,000

3 beds

|

3 baths

|

3,038 sq ft

|

Townhouse

560 QUAKER RIDGE TER, WILLIAMS TWP, PA, ...
Traditions of America at Green Pond 3912 INDEPENDENCE DR, EASTON, PA, 18045, Easton, PA 18045
$825,000

3 beds

|

4 baths

|

3,270 sq ft

3912 INDEPENDENCE DR, EASTON, PA, 18045
Traditions of America at Green Pond 3912 INDEPENDENCE DR, BETHLEHEM TWP, PA,..., Bethlehem Twp, PA 18045
$825,000

3 beds

|

4 baths

|

3,270 sq ft

|

Detached

3912 INDEPENDENCE DR, BETHLEHEM TWP, PA,...
Heritage Hills 798 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$875,000

2 beds

|

2 baths

|

1,663 sq ft

|

Condo

798 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.
Bald Eagle Commons 2 RICHMOND RD 306, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$359,000

2 beds

|

2 baths

|

Condo

2 RICHMOND RD 306, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
Bald Eagle Commons 2 RICHMOND RD 306, WEST MILFORD TWP., NJ..., West Milford Twp., NJ 07480
$359,000

2 beds

|

2 baths

2 RICHMOND RD 306, WEST MILFORD TWP., NJ...
Community: Bald Eagle Commons
Apple Ridge 41 LITCHULT LN, MAHWAH TWP., NJ, 07430, Mahwah Twp., NJ 07430
$810,000

3 beds

|

3 baths

|

2,385 sq ft

41 LITCHULT LN, MAHWAH TWP., NJ, 07430
Community: Apple Ridge
Jefferson Village 142 FLINTLOCK WAY F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$629,000

2 beds

|

2 baths

|

1,302 sq ft

|

Condo

142 FLINTLOCK WAY F, YORKTOWN, NY, 10598
Community: Jefferson Village
Apple Ridge 41 LITCHULT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$810,000

3 beds

|

3 baths

|

Townhouse

41 LITCHULT LN, MAHWAH, NJ, 07430
Community: Apple Ridge
Heritage Hills 220 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$575,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

220 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Four Seasons at Great Notch Spa and Club 3 SLATE CT D-1, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$599,999

2 beds

|

2 baths

|

Condo

3 SLATE CT D-1, WOODLAND PARK, NJ, 07424
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Jefferson Village 15F ESSEX PL F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$439,000

2 beds

|

1 baths

|

925 sq ft

|

Condo

15F ESSEX PL F, YORKTOWN, NY, 10598
Community: Jefferson Village
Lakeside Villas 29 SCHMIDT CIR, WATCHUNG BORO, NJ, 07069, Watchung Boro, NJ 07069
$620,000

2 beds

|

2 baths

29 SCHMIDT CIR, WATCHUNG BORO, NJ, 07069
Community: Lakeside Villas
Jefferson Village 37 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$359,000

2 beds

|

1 baths

|

935 sq ft

|

Condo

37 SUSSEX DR B, YORKTOWN, NY, 10598
Community: Jefferson Village
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.
Wanaque Reserve 3213 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$435,000

2 beds

|

2 baths

|

Condo

3213 WARRENS WAY, WANAQUE, NJ, 07465
Community: Wanaque Reserve
Wanaque Reserve 3213 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$435,000

2 beds

|

2 baths

3213 WARRENS WAY, WANAQUE BORO, NJ, 0746...
Community: Wanaque Reserve
Fox Hills 1303 JOHNSON DR, ROCKAWAY TWP., NJ, 0786..., Rockaway Twp., NJ 07866
$550,000

2 beds

|

2 baths

1303 JOHNSON DR, ROCKAWAY TWP., NJ, 0786...
Community: Fox Hills
Four Seasons at The Promenade 19 BETSY ROSS DR, WARREN TWP., NJ, 07059, Warren Twp., NJ 07059
$1,399,000

3 beds

|

4 baths

|

3,326 sq ft

19 BETSY ROSS DR, WARREN TWP., NJ, 07059
Four Seasons at Bridgewater 467 VICTORIA DR, BRIDGEWATER TWP., NJ, 0..., Bridgewater Twp., NJ 08807
$434,999

2 beds

|

2 baths

467 VICTORIA DR, BRIDGEWATER TWP., NJ, 0...
Bald Eagle Commons 9224 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$315,000

2 beds

|

2 baths

|

Condo

9224 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Bald Eagle Commons 9224 RICHMOND RD 224, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$315,000

2 beds

|

2 baths

9224 RICHMOND RD 224, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
The Hollows at Blue Hill 4105 FRED ILL JR CT, ORANGETOWN, NY, 109..., Orangetown, NY 10965
$769,900

2 beds

|

2 baths

|

1,420 sq ft

|

Condo

4105 FRED ILL JR CT, ORANGETOWN, NY, 109...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Legacy at Mansfield Meadows 74 MOUNTAIN VIEW LN, PORT MURRAY, NJ, 07..., Port Murray, NJ 07865
$515,000

2 beds

|

2 baths

|

1,370 sq ft

74 MOUNTAIN VIEW LN, PORT MURRAY, NJ, 07...
Bald Eagle Commons 6412 RICHMOND RD 412, WEST MILFORD, NJ, ..., West Milford, NJ 07480
$240,000

2 beds

|

2 baths

|

Condo

6412 RICHMOND RD 412, WEST MILFORD, NJ, ...
Community: Bald Eagle Commons
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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