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

95 communities near Middletown

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Apple Ridge
$700Ks
Apple Ridge, Mahwah, NJ
Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes
Fox Crest
$500Ks
Fox Crest, Rockaway, NJ
New Construction | 55+ age-restricted | Built 2020 - present | 41 homes
The Pointe at Garwood
$600Ks - $700Ks
The Pointe at Garwood, Garwood, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2007 | 44 homes
Glassbury Court at Hunter...
$500Ks - $700Ks
Glassbury Court at Hunter..., Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 64 homes
Four Seasons at Bridgewat...
$300Ks - $400Ks
Four Seasons at Bridgewat..., Bridgewater, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 homes
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Eagle Ridge at East Hanov...
$300Ks
Eagle Ridge at East Hanov..., East Hanover, NJ
Resale Only | 55+ age-restricted | Built 1992 - 1993 | 50 homes
1 rating (2 reviews) Knoll Edge
$600Ks - $700Ks
Knoll Edge, Boonton, NJ
New Construction | 55+ age-restricted | Built 2024 - present | 16 homes
Melrose at Chatham
$1Ms
Melrose at Chatham, Chatham, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 19 homes
Overlook
$600Ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 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.
Northgate at Florham Park
$900Ks - $1Ms
Northgate at Florham Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2009 | 33 homes
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Fields at Lafayette W...
$400Ks - $600Ks
The Fields at Lafayette W..., Easton, PA
New Construction | 55+ age-restricted | Built 2026 - present | 200 homes
Glenmoor
$300Ks - $500Ks
Glenmoor, Easton, PA
Resale Only | 55+ age-restricted | Built 2004 - 2008 | 182 homes
77 Sunset Lane
$400Ks - $700Ks
77 Sunset Lane, Ridgefield, CT
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 54 homes
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The Woods at Dunham Pond
$400Ks - $500Ks
The Woods at Dunham Pond, New Fairfield, CT
Resale Only | 55+ age-restricted | Built 2004 - 2015 | 33 homes
The Coach Homes at Ridgef...
$200Ks - $500Ks
The Coach Homes at Ridgef..., Ridgefield, CT
New Construction | 55+ age-restricted | Built 2019 - present | 30 homes
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Stoneleigh Woods at Carme...
$400Ks
Stoneleigh Woods at Carme..., Carmel, NY
Resale Only | 55+ age-restricted | Built 2012 - 2017 | 68 homes
Woodcrest at Jacobs Hill
$300Ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 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.
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
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Hollows at Blue Hill
$1Ms
The Hollows at Blue Hill, Pearl River, NY
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 126 homes
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The Seasons at Seaford
$700Ks
The Seasons at Seaford, Seaford, NY
Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 homes
Villas at Seminary Hill
$400Ks
Villas at Seminary Hill, Carmel, NY
New Construction | 55+ age-restricted | Built 2018 - present | 50 homes
Meadowbrooke Pointe East ...
$700Ks - $800Ks
Meadowbrooke Pointe East ..., East Meadow, NY
New Construction | 62+ age-restricted | Built 2019 - present | 104 homes
Breton Hills
$600Ks
Breton Hills, Glen Cove, NY
New Construction | 55+ age-restricted | Built 2019 - present | 72 homes
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
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
$400Ks - $500Ks
Regency at Fishkill, Fishkill, NY
Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 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
Four Seasons at Ridgemont
$800Ks - $1Ms
Four Seasons at Ridgemont, Montvale, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes
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...
$1Ms
Four Seasons at The Prome..., Warren, NJ
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 208 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Winthrop Court
$400Ks
Winthrop Court, Clifton, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes
Regency at Denville
$700Ks - $800Ks
Regency at Denville, Denville, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2009 | 140 homes
Regency at Readington
$700Ks - $800Ks
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
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.
Four Seasons at Chester
$600Ks - $700Ks
Four Seasons at Chester, Chester, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2002 | 120 homes
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Questions? Call us: (845) 479-5674
Four Seasons at Cedar Gro...
$700Ks
Four Seasons at Cedar Gro..., Cedar Grove, NJ
Resale Only | 55+ age-restricted | Built 2000 - 2005 | 156 homes
Bear's Cove
$1Ms
Bear's Cove, Ramsey, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 104 homes
Legacy at Readington
$400Ks
Legacy at Readington, Readington Township, NJ
Resale Only | 55+ age-restricted | Built 2010 - 2014 | 51 homes
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Questions? Call us: (845) 479-5674
5 rating (1 reviews) Delaware Crossing
$300Ks
Delaware Crossing, Lopatcong, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 158 homes
Enclave at Shackamaxon
$1Ms
Enclave at Shackamaxon, Scotch Plains, NJ
Resale Only | 55+ age-restricted | Built 2016 - 2018 | 56 homes
Heritage Hills 182 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$475,000

2 beds

|

2 baths

|

1,205 sq ft

|

Condo

182 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Blackburne Farm Townhomes 45 OTTAWAY LN, CAMPBELL HALL, NY, 10916, Campbell Hall, NY 10916
$569,000

2 beds

|

3 baths

|

1,746 sq ft

|

House

45 OTTAWAY LN, CAMPBELL HALL, NY, 10916
The Retreat at Carmel 4 FROST CT, CARMEL, NY, 10512, Carmel, NY 10512
$759,900

2 beds

|

3 baths

|

2,035 sq ft

|

Condo

4 FROST CT, CARMEL, NY, 10512
Regency at Flanders 7 DRAKE WAY, ROXBURY TWP, NJ, 07836, Roxbury Twp, NJ 07836
$325,000

1 beds

|

2 baths

7 DRAKE WAY, ROXBURY TWP, NJ, 07836
Community: Regency at Flanders
Regency at Flanders 7 DRAKE WAY, ROXBURY TOWNSHIP, NJ, 07836, Roxbury Township, NJ 07836
$325,000

1 beds

|

2 baths

|

Condo

7 DRAKE WAY, ROXBURY TOWNSHIP, NJ, 07836
Community: Regency at Flanders
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Rivington 184 WARRINGTON ROUND # 184, DANBURY, CT,..., Danbury, CT 06810
$599,000

3 beds

|

3 baths

|

1,600 sq ft

|

Condo

184 WARRINGTON ROUND # 184, DANBURY, CT,...
Community: Rivington
Bald Eagle Commons 1310 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$250,000

2 beds

|

2 baths

|

Condo

1310 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Apple Ridge 272 BELMONT PL # 272, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$869,000

3 beds

|

3 baths

|

Townhouse

272 BELMONT PL # 272, MAHWAH, NJ, 07430
Community: Apple Ridge
Rivington 85 WINDING RIDGE WAY # 85, DANBURY, CT, ..., Danbury, CT 06810
$825,000

3 beds

|

4 baths

|

1,794 sq ft

|

Condo

85 WINDING RIDGE WAY # 85, DANBURY, CT, ...
Community: Rivington
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.
Clove Hill Manor 19 PROSPECT CI CI, WANTAGE TWP., NJ, 074..., Wantage Twp., NJ 07461
$455,000

3 beds

|

3 baths

|

2,077 sq ft

19 PROSPECT CI CI, WANTAGE TWP., NJ, 074...
Community: Clove Hill Manor
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Blackburne Farm Townhomes 27 OTTAWAY LN, CAMPBELL HALL, NY, 10916, Campbell Hall, NY 10916
$579,900

3 beds

|

3 baths

|

2,290 sq ft

|

House

27 OTTAWAY LN, CAMPBELL HALL, NY, 10916
Brookfield Estates 14 STAFFORD LN, BELVIDERE, NJ, 07823, Belvidere, NJ 07823
$489,000

3 beds

|

2 baths

14 STAFFORD LN, BELVIDERE, NJ, 07823
Community: Brookfield Estates
The Retreat at Carmel 2 BLAIR HTS UNIT 3317, CARMEL, NY, 10512, Carmel, NY 10512
$459,900

2 beds

|

2 baths

|

1,323 sq ft

|

Condo

2 BLAIR HTS UNIT 3317, CARMEL, NY, 10512
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Dutchgate 817 WILLOW LN, VALLEY STREAM, NY, 11580, Valley Stream, NY 11580
$519,990

2 beds

|

2 baths

|

941 sq ft

|

Condo

817 WILLOW LN, VALLEY STREAM, NY, 11580
Community: Dutchgate
Meadowbrook Pointe Athletic Club & Spa 365 TROTTING LN, WESTBURY, NY, 11590, Westbury, NY 11590
$799,999

1 beds

|

2 baths

|

1,128 sq ft

|

Condo

365 TROTTING LN, WESTBURY, NY, 11590
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Heritage Hills 537 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$600,000

2 beds

|

2 baths

|

1,470 sq ft

|

Condo

537 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
Blackburne Farm Townhomes 4 STRASSER PL, CAMPBELL HALL, NY, 10916, Campbell Hall, NY 10916
$559,000

2 beds

|

3 baths

|

1,862 sq ft

|

House

4 STRASSER PL, CAMPBELL HALL, NY, 10916
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.
Wildflowers at Wallkill 24 JUNIPER CIR, MIDDLETOWN, NY, 10940, Middletown, NY 10940
$625,000

2 beds

|

3 baths

|

2,975 sq ft

|

House

24 JUNIPER CIR, MIDDLETOWN, NY, 10940
Apple Ridge 183 VAN WINKLE LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430
$849,000

3 beds

|

3 baths

|

Townhouse

183 VAN WINKLE LN, MAHWAH, NJ, 07430
Community: Apple Ridge
Four Seasons at Wayne 511 FOUR SEASONS DR 511, WAYNE, NJ, 0747..., Wayne, NJ 07470
$545,000

2 beds

|

2 baths

|

Condo

511 FOUR SEASONS DR 511, WAYNE, NJ, 0747...
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Legacy at Morgan Hill 400 INVERNESS CIR, EASTON, PA, 18042, Easton, PA 18042
$549,999

3 beds

|

3 baths

|

2,929 sq ft

|

Townhouse

400 INVERNESS CIR, EASTON, PA, 18042
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Bald Eagle Commons 9212 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480
$199,900

1 beds

|

1 baths

|

Condo

9212 RICHMOND RD, WEST MILFORD, NJ, 0748...
Community: Bald Eagle Commons
Four Seasons at Readington 17 EBERSOHL CIR, WHITEHOUSE STATION, NJ,..., Whitehouse Station, NJ 08889
$550,000

3 beds

|

3 baths

17 EBERSOHL CIR, WHITEHOUSE STATION, NJ,...
Clove Hill Manor 11 FAIRCHILD LN # 11, WANTAGE, NJ, 07461, Wantage, NJ 07461
$476,200

2 beds

|

4 baths

|

Townhouse

11 FAIRCHILD LN # 11, WANTAGE, NJ, 07461
Community: Clove Hill Manor
Wanaque Reserve 1116 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465
$429,000

2 beds

|

2 baths

|

Condo

1116 WARRENS WAY, WANAQUE, NJ, 07465
Community: Wanaque Reserve
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
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.
Fox Hills 3209 CLEVELAND LN, ROCKAWAY BORO, NJ, 07..., Rockaway Boro, NJ 07866
$325,000

1 beds

|

1 baths

3209 CLEVELAND LN, ROCKAWAY BORO, NJ, 07...
Community: Fox Hills
Greenbriar at Fox Ridge 8214 POLK DR, WHARTON, NJ, 07885, Wharton, NJ 07885
$464,700

2 beds

|

3 baths

|

Condo

8214 POLK DR, WHARTON, NJ, 07885
Jefferson Village 96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,..., Yorktown Heights, NY 10598
$479,000

2 beds

|

2 baths

|

1,050 sq ft

|

Condo

96 MOLLY PITCHER LN H, YORKTOWN HEIGHTS,...
Community: Jefferson Village
Horizons at Mount Arlington 7 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 078..., Mount Arlington, NJ 07856
$445,000

2 beds

|

2 baths

|

Condo

7 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 078...
Clove Hill Manor 11 FAIRCHILD LN, SUSSEX, NJ, 07461, Sussex, NJ 07461
$476,200

2 beds

|

4 baths

|

2,235 sq ft

11 FAIRCHILD LN, SUSSEX, NJ, 07461
Community: Clove Hill Manor
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Village at Fox Crossing 3813 BELCOURT DR, FORKS TWP, PA, 18040, Forks Twp, PA 18040
$255,000

2 beds

|

2 baths

|

1,302 sq ft

|

Detached

3813 BELCOURT DR, FORKS TWP, PA, 18040
The Retreat at Carmel 14 LANGDON GROVE, CARMEL, NY, 10512, Carmel, NY 10512
$699,900

3 beds

|

3 baths

|

3,000 sq ft

|

Condo

14 LANGDON GROVE, CARMEL, NY, 10512
Greenbriar at Fox Ridge 7113 POLK DR, WHARTON, NJ, 07885, Wharton, NJ 07885
$479,900

2 beds

|

3 baths

|

1,568 sq ft

7113 POLK DR, WHARTON, NJ, 07885
Fox Hills 2201 FRANKLIN LN, ROCKAWAY BORO, NJ, 078..., Rockaway Boro, NJ 07866
$317,500

1 beds

|

2 baths

|

915 sq ft

2201 FRANKLIN LN, ROCKAWAY BORO, NJ, 078...
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.
Heritage Hills 55 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$675,000

2 beds

|

2 baths

|

1,500 sq ft

|

Condo

55 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Want to learn more about 55+ rental communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Heritage Hills 443 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$625,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

443 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Glassbury Court at Hunterbrook 2279 DALTON DR, CORTLANDT MANOR, NY, 105..., Cortlandt Manor, NY 10567
$925,000

2 beds

|

4 baths

|

3,500 sq ft

|

Condo

2279 DALTON DR, CORTLANDT MANOR, NY, 105...
Bald Eagle Commons 7306 RICHMOND RD # 306, WEST MILFORD, NJ..., West Milford, NJ 07480
$249,000

2 beds

|

2 baths

7306 RICHMOND RD # 306, WEST MILFORD, NJ...
Community: Bald Eagle Commons
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Heritage Hills 59 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589
$675,000

3 beds

|

2 baths

|

1,689 sq ft

|

Condo

59 HERITAGE HLS A, SOMERS, NY, 10589
Community: Heritage Hills
Wanaque Reserve 4203 WARRENS WAY # 203, WANAQUE, NJ, 074..., Wanaque, NJ 07465
$454,900

2 beds

|

2 baths

|

1,768 sq ft

4203 WARRENS WAY # 203, WANAQUE, NJ, 074...
Community: Wanaque Reserve

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