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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
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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
New Bald Eagle Commons 4 RICHMOND RD 216, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$209,900

1 beds

|

2 baths

4 RICHMOND RD 216, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
Winthrop Court 1110 WICKHAM TER # 1110, CLIFTON, NJ, 07..., Clifton, NJ 07013
$599,500

2 beds

|

2 baths

|

Condo

1110 WICKHAM TER # 1110, CLIFTON, NJ, 07...
Community: Winthrop Court
Bald Eagle Commons 2 RICHMOND RD 315, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$259,900

2 beds

|

2 baths

2 RICHMOND RD 315, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
The Pointe 1202 POINTE GATE DR, LIVINGSTON, NJ, 070..., Livingston, NJ 07039
$569,900

2 beds

|

3 baths

|

Condo

1202 POINTE GATE DR, LIVINGSTON, NJ, 070...
Community: The Pointe
Four Seasons at Great Notch Spa and Club 23 COPPA RD, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$849,000

2 beds

|

3 baths

|

Townhouse

23 COPPA RD, WOODLAND PARK, NJ, 07424
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Four Seasons at Bridgewater 252 VICTORIA DR, BRIDGEWATER, NJ, 08807, Bridgewater, NJ 08807
$440,000

2 beds

|

2 baths

|

1,031 sq ft

252 VICTORIA DR, BRIDGEWATER, NJ, 08807
Fox Hills 204 CLEVELAND LN, ROCKAWAY BORO, NJ, 078..., Rockaway Boro, NJ 07866
$489,000

2 beds

|

2 baths

204 CLEVELAND LN, ROCKAWAY BORO, NJ, 078...
Community: Fox Hills
Four Seasons at Bridgewater 354 VICTORIA DR, BRIDGEWATER, NJ, 08807, Bridgewater, NJ 08807
$465,000

2 beds

|

2 baths

354 VICTORIA DR, BRIDGEWATER, NJ, 08807
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
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
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 Pointe at Garwood 613 MAPLE CT, GARWOOD, NJ, 07027, Garwood, NJ 07027
$795,000

2 beds

|

4 baths

|

2,300 sq ft

613 MAPLE CT, GARWOOD, NJ, 07027
Clove Hill Manor 21 PROSPECT CI CI, WANTAGE TWP., NJ, 074..., Wantage Twp., NJ 07461
$467,000

3 beds

|

3 baths

21 PROSPECT CI CI, WANTAGE TWP., NJ, 074...
Community: Clove Hill Manor
Hawk Pointe 7 HARRIER LN, WASHINGTON, NJ, 07882, Washington, NJ 07882
$549,000

3 beds

|

3 baths

7 HARRIER LN, WASHINGTON, NJ, 07882
Community: Hawk Pointe
The Pointe 5101 POINTE GATE DR # 101, LIVINGSTON, N..., Livingston, NJ 07039
$435,000

2 beds

|

2 baths

|

1,342 sq ft

5101 POINTE GATE DR # 101, LIVINGSTON, N...
Community: The Pointe
Four Seasons at Great Notch Spa and Club 6 PEBBLE RD UNIT D1, WOODLAND PARK, NJ, ..., Woodland Park, NJ 07424
$629,000

2 beds

|

2 baths

|

Townhouse

6 PEBBLE RD UNIT D1, WOODLAND PARK, NJ, ...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Horizons at Mount Arlington 89 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07..., Mount Arlington, NJ 07856
$485,000

2 beds

|

2 baths

|

1,840 sq ft

89 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07...
Regency at Flanders 31 DRAKE WAY, ROXBURY TWP, NJ, 07836, Roxbury Twp, NJ 07836
$399,900

2 beds

|

2 baths

31 DRAKE WAY, ROXBURY TWP, NJ, 07836
Community: Regency at Flanders
Regency at Readington 9 VAN CLEEF DR, WHITEHOUSE STATION, NJ, ..., Whitehouse Station, NJ 08889
$765,000

2 beds

|

3 baths

9 VAN CLEEF DR, WHITEHOUSE STATION, NJ, ...
The Meadows at Panther Valley 21 JUNEGRASS WAY, HACKETTSTOWN, NJ, 0784..., Hackettstown, NJ 07840
$549,000

3 beds

|

3 baths

21 JUNEGRASS WAY, HACKETTSTOWN, NJ, 0784...
Horizons at Mount Arlington 38 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07..., Mount Arlington, NJ 07856
$487,000

2 beds

|

2 baths

|

1,840 sq ft

38 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07...
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.
Horizons at Mount Arlington 104 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 0..., Mount Arlington, NJ 07856
$465,000

2 beds

|

2 baths

104 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 0...
Bald Eagle Commons 1311 RICHMOND RD # 311, WEST MILFORD, NJ..., West Milford, NJ 07480
$170,000

1 beds

|

1 baths

1311 RICHMOND RD # 311, WEST MILFORD, NJ...
Community: Bald Eagle Commons
Brookfield Glen 4002 BROOKFIELD GLEN DR, BELVIDERE, NJ, ..., Belvidere, NJ 07823
$302,500

2 beds

|

2 baths

|

1,365 sq ft

4002 BROOKFIELD GLEN DR, BELVIDERE, NJ, ...
Community: Brookfield Glen
Greenbriar at Fox Ridge 5307 VETERANS DR, WHARTON, NJ, 07885, Wharton, NJ 07885
$479,000

2 beds

|

3 baths

5307 VETERANS DR, WHARTON, NJ, 07885
Fox Hills 2100 JOHNSON DR # 1, ROCKAWAY BORO, NJ, ..., Rockaway Boro, NJ 07866
$339,900

1 beds

|

2 baths

2100 JOHNSON DR # 1, ROCKAWAY BORO, NJ, ...
Community: Fox Hills
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Wanaque Reserve 9116 WARRENS WAY # 116, WANAQUE, NJ, 074..., Wanaque, NJ 07465
$469,000

2 beds

|

2 baths

9116 WARRENS WAY # 116, WANAQUE, NJ, 074...
Community: Wanaque Reserve
The Commons at Mendham 54 PEMBROKE DR, MENDHAM, NJ, 07945, Mendham, NJ 07945
$490,000

2 beds

|

2 baths

|

1,440 sq ft

54 PEMBROKE 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
Four Seasons at Ridgemont 301 FOUR SEASONS LN, MONTVALE, NJ, 07645, Montvale, NJ 07645
$879,000

2 beds

|

2 baths

|

Condo

301 FOUR SEASONS LN, MONTVALE, NJ, 07645
Bear's Cove 45 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446
$1,275,000

3 beds

|

3 baths

|

Condo

45 WINDSOR LN, RAMSEY, NJ, 07446
Community: Bear's Cove
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
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 Estates 4 ASCOT DR, BELVIDERE, NJ, 07823, Belvidere, NJ 07823
$524,900

2 beds

|

2 baths

|

1,648 sq ft

4 ASCOT DR, BELVIDERE, NJ, 07823
Community: Brookfield Estates
Wanaque Reserve 4319 WARRENS WAY DEEDED GARAGE, WANAQUE,..., Wanaque, NJ 07465
$459,900

2 beds

|

2 baths

|

Condo

4319 WARRENS WAY DEEDED GARAGE, WANAQUE,...
Community: Wanaque Reserve
Bald Eagle Commons 1311 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$170,000

1 beds

|

1 baths

|

Condo

1311 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
Kimbolton 20 WHITAKER LN, FAR HILLS, NJ, 07931, Far Hills, NJ 07931
$1,157,039

3 beds

|

3 baths

|

2,775 sq ft

20 WHITAKER LN, FAR HILLS, NJ, 07931
Community: Kimbolton
Four Seasons at Wayne 1302 FOUR SEASONS DR, WAYNE, NJ, 07470, Wayne, NJ 07470
$510,000

2 beds

|

2 baths

|

Condo

1302 FOUR SEASONS DR, WAYNE, NJ, 07470
Fox Hills 1111 CLINTON LN # 111, ROCKAWAY BORO, NJ..., Rockaway Boro, NJ 07866
$499,000

2 beds

|

2 baths

|

1,782 sq ft

1111 CLINTON LN # 111, ROCKAWAY BORO, NJ...
Community: Fox Hills
Bald Eagle Commons 4 RICHMOND RD APT 112 112, WEST MILFORD,..., West Milford, NJ 07480
$180,000

1 beds

|

1 baths

4 RICHMOND RD APT 112 112, WEST MILFORD,...
Community: Bald Eagle Commons
Fox Hills 1211 CLINTON LN, ROCKAWAY BORO, NJ, 0786..., Rockaway Boro, NJ 07866
$514,000

2 beds

|

2 baths

1211 CLINTON LN, ROCKAWAY BORO, NJ, 0786...
Community: Fox Hills
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189 homes near Middletown
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