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

95 communities near Middletown

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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 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
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Regency at Denville
$700ks - $800ks
Regency at Denville, Denville, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 140 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Four Seasons at Ridgemont
$800ks - $1Ms
Four Seasons at Ridgemont, Montvale, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes
5 rating (1 reviews) Paris Square
$500ks - $700ks
Paris Square, Northvale, NJ
New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes
The Commons at Mendham
$300ks - $600ks
The Commons at Mendham, Mendham, NJ
Resale Only | Age-targeted | Built 1978 - 1985 | 330 homes
Four Seasons at Chester
$600ks - $700ks
Four Seasons at Chester, Chester, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 120 homes
Eagle Ridge at East Hanov...
$200ks - $300ks
Eagle Ridge at East Hanov..., East Hanover, NJ
Resale Only | 55+ age-restricted | Built 1992 - 1993 | 50 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) The Village at Upstream F...
$100ks - $200ks
The Village at Upstream F..., Easton, PA
Resale Only | 55+ age-restricted | Built 2002 - 2009 | 124 homes
Melrose at Chatham
$1Ms
Melrose at Chatham, Chatham, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 19 homes
1 rating (2 reviews) Knoll Edge
$600ks - $700ks
Knoll Edge, Boonton, NJ
New Construction | 55+ age-restricted | Built 2024 - present | 16 homes
Stoneleigh Woods at Carme...
$400ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
The Seasons at East Meado...
$400ks - $600ks
The Seasons at East Meado..., East Meadow, NY
Resale Only | 55+ age-restricted | Built 2009 - 2012 | 404 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
The Coach Homes at Ridgef...
$300ks - $400ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
Regency at Wappinger
$500ks
Regency at Wappinger, Wappingers Falls, NY
Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes
Woodcrest at Jacobs Hill
$200ks - $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
The Woods at Dunham Pond
$200ks - $400ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 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.
77 Sunset Lane
$400ks - $700ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
Glassbury Court at Hunter...
$500ks - $700ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
Wolfe Landing
$500ks - $600ks
Wolfe Landing, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 43 homes
Eden Park
$500ks - $600ks
Eden Park, Clarkstown, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 34 homes
The Views at Pomona
$200ks - $400ks
The Views at Pomona, Pomona, NY
Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 homes
The Residences at Butterf...
$500ks - $600ks
The Residences at Butterf..., Cold Spring, NY
Resale Only | 55+ age-restricted | Built 2018 - 2023 | 49 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
Villas at Seminary Hill
$200ks - $300ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 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
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.
Regency at Readington
$600ks - $700ks
Regency at Readington, Readington Township, NJ
Resale Only | 55+ age-restricted | Built 2014 - 2019 | 209 homes
5 rating (1 reviews) Four Seasons at North Cal...
$700ks - $800ks
Four Seasons at North Cal..., North Caldwell, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2015 | 108 homes
Meadowbrooke Pointe East ...
$500ks - $600ks
Meadowbrooke Pointe East ..., East Meadow, NY
New Construction | 62+ age-restricted | Built 2019 - present | 104 homes
Four Seasons at Wayne
$300ks - $400ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes
Four Seasons at Readingto...
$400ks - $500ks
Four Seasons at Readingto..., Readington Township, NJ
Resale Only | 55+ age-restricted | Built 2001 - 2002 | 98 homes
Legacy at Readington
$300ks
Legacy at Readington, Readington Township, NJ
Resale Only | 55+ age-restricted | Built 2010 - 2014 | 51 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
Enclave at Long Valley
$600ks - $700ks
Enclave at Long Valley, Washington Township, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2017 | 45 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Dawson Brook
$600ks - $700ks
Dawson Brook, Randolph, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 30 homes
The Meadows at Panther Va...
$300ks - $400ks
The Meadows at Panther Va..., Hackettstown, NJ
Resale Only | Age-targeted | Built 2010 - 2021 | 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.
New Jefferson Village 23 DORSET CT C, YORKTOWN, NY, 10598, Yorktown, NY 10598
$339,000

1 beds

|

1 baths

|

700 sq ft

|

Condo

23 DORSET CT C, YORKTOWN, NY, 10598
Community: Jefferson Village
New Regency at Readington 8 VAN CLEEF DR, READINGTON TWP., NJ, 088..., Readington Twp., NJ 08889
$950,000

2 beds

|

4 baths

8 VAN CLEEF DR, READINGTON TWP., NJ, 088...
New Fox Hills 4209 CLEVELAND LN, ROCKAWAY TWP., NJ, 07..., Rockaway Twp., NJ 07866
$315,000

1 beds

|

1 baths

4209 CLEVELAND LN, ROCKAWAY TWP., NJ, 07...
Community: Fox Hills
New Enclave at Shackamaxon 504 TILLINGHAST TURN, SCOTCH PLAINS TWP...., Scotch Plains Twp., NJ 07076
$1,360,000

3 beds

|

4 baths

504 TILLINGHAST TURN, SCOTCH PLAINS TWP....
New Four Seasons at Chester 18 WYCKOFF WAY, CHESTER TWP., NJ, 07930, Chester Twp., NJ 07930
$830,000

3 beds

|

3 baths

18 WYCKOFF WAY, CHESTER TWP., NJ, 07930
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
New Brookfield Glen 4020 BROOKFIELD GLEN DR, WHITE TWP., NJ,..., White Twp., NJ 07823
$279,900

2 beds

|

2 baths

4020 BROOKFIELD GLEN DR, WHITE TWP., NJ,...
Community: Brookfield Glen
New Regency at Fishkill 145 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$539,999

2 beds

|

2 baths

|

1,803 sq ft

|

Condo

145 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
New Jefferson Village 113 VILLAGE RD B, YORKTOWN, NY, 10598, Yorktown, NY 10598
$449,999

2 beds

|

2 baths

|

1,200 sq ft

|

Condo

113 VILLAGE RD B, YORKTOWN, NY, 10598
Community: Jefferson Village
New The Woods at Dunham Pond 29 HERON VIEW RD 29, NEW FAIRFIELD, CT, ..., New Fairfield, CT 06812
$334,000

1 beds

|

2 baths

|

1,590 sq ft

|

Condo

29 HERON VIEW RD 29, NEW FAIRFIELD, CT, ...
New Heritage Hills 37 HERITAGE HILLS DR A, SOMERS, NY, 1058..., Somers, NY 10589
$500,000

1 beds

|

1 baths

|

955 sq ft

|

Condo

37 HERITAGE HILLS DR A, SOMERS, NY, 1058...
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 Fox Hills 3227 FRANKLIN LN, ROCKAWAY TWP., NJ, 078..., Rockaway Twp., NJ 07866
$485,000

2 beds

|

2 baths

|

1,620 sq ft

3227 FRANKLIN LN, ROCKAWAY TWP., NJ, 078...
Community: Fox Hills
New Horizons at Mount Arlington 29 RIDGEVIEW LN, MOUNT ARLINGTON BORO, N..., Mount Arlington Boro, NJ 07856
$448,000

2 beds

|

2 baths

29 RIDGEVIEW LN, MOUNT ARLINGTON BORO, N...
New Heritage Hills 757 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$569,000

2 beds

|

2 baths

|

1,296 sq ft

|

Condo

757 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
New Four Seasons at Ridgemont 602 FOUR SEASONS LN, MONTVALE, NJ, 07645, Montvale, NJ 07645
$915,000

2 beds

|

2 baths

|

Condo

602 FOUR SEASONS LN, MONTVALE, NJ, 07645
New Regency at Fishkill 246 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$499,999

1 beds

|

2 baths

|

1,543 sq ft

|

Condo

246 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Wanaque Reserve 5206 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$389,000

2 beds

|

2 baths

5206 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
Hawk Pointe 21 HARRIS HAWK RD, WASHINGTON TWP., NJ, ..., Washington Twp., NJ 07882
$669,500

3 beds

|

3 baths

|

2,626 sq ft

21 HARRIS HAWK RD, WASHINGTON TWP., NJ, ...
Community: Hawk Pointe
The Highlands at Glenmoor 45 INVERNESS LN, PALMER TWP, PA, 18045, Palmer Twp, PA 18045
$589,900

3 beds

|

5 baths

|

3,972 sq ft

|

Detached

45 INVERNESS LN, PALMER TWP, PA, 18045
Bald Eagle Commons 5319 RICHMOND RD 319, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$269,500

2 beds

|

1 baths

|

957 sq ft

5319 RICHMOND RD 319, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
Apple Ridge 224 WESTERVELT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$825,000

2 beds

|

3 baths

|

Townhouse

224 WESTERVELT LN, MAHWAH, NJ, 07430
Community: Apple Ridge
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 23 DORSET CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$315,000

2 beds

|

1 baths

|

925 sq ft

|

Condo

23 DORSET CT F, YORKTOWN, NY, 10598
Community: Jefferson Village
Wildflowers at Wallkill 28 CYPRUS DR, WALLKILL, NY, 10940, Wallkill, NY 10940
$499,900

2 beds

|

2 baths

|

1,473 sq ft

|

House

28 CYPRUS DR, WALLKILL, NY, 10940
The Highlands at Glenmoor 45 INVERNESS LN, EASTON, PA, 18045, Easton, PA 18045
$589,900

3 beds

|

5 baths

|

3,972 sq ft

|

Condo

45 INVERNESS LN, EASTON, PA, 18045
Regency at Fishkill 326 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524
$519,000

1 beds

|

2 baths

|

1,543 sq ft

|

Condo

326 REGENCY DR, FISHKILL, NY, 12524
Community: Regency at Fishkill
Jefferson Village 80 C INDEPENDENCE CT, YORKTOWN, NY, 1059..., Yorktown, NY 10598
$359,000

1 beds

|

1 baths

|

850 sq ft

|

Condo

80 C INDEPENDENCE CT, YORKTOWN, NY, 1059...
Community: Jefferson Village
Heritage Hills 567 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$469,900

1 beds

|

2 baths

|

967 sq ft

|

Condo

567 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Heritage Hills 586 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

586 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Traditions of America at Green Pond 3991 VICTORS WAY, EASTON, PA, 18045, Easton, PA 18045
$779,900

3 beds

|

2 baths

|

2,568 sq ft

|

Detached

3991 VICTORS WAY, EASTON, PA, 18045
Four Seasons at Great Notch Spa and Club 3 PEBBLE RD D1, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424
$649,000

2 beds

|

2 baths

|

Condo

3 PEBBLE RD D1, WOODLAND PARK, NJ, 07424
The Commons at Mendham 8 PEMBROKE DR, MENDHAM BORO, NJ, 07945, Mendham Boro, NJ 07945
$599,000

2 beds

|

4 baths

8 PEMBROKE DR, MENDHAM BORO, 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.
Del Webb Florham Park 2 VANDERBILT BLVD 106, FLORHAM PARK BORO..., Florham Park Boro, NJ 07932
$999,000

2 beds

|

2 baths

|

1,700 sq ft

2 VANDERBILT BLVD 106, FLORHAM PARK BORO...
Regency at Denville 4 JADE CIR, DENVILLE TWP., NJ, 07834, Denville Twp., NJ 07834
$799,000

3 beds

|

3 baths

4 JADE CIR, DENVILLE TWP., NJ, 07834
Community: Regency at Denville
Heritage Hills 415 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589
$875,000

3 beds

|

2 baths

|

1,909 sq ft

|

Condo

415 HERITAGE HLS C, SOMERS, NY, 10589
Community: Heritage Hills
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
Fox Hills 4202 CLEVELAND LN 202, ROCKAWAY TWP., NJ..., Rockaway Twp., NJ 07866
$269,000

1 beds

|

1 baths

4202 CLEVELAND LN 202, ROCKAWAY TWP., NJ...
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.

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