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

101 communities 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 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
$400ks - $900ks
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
Greenbriar at Fox Ridge
$300ks - $500ks
Greenbriar at Fox Ridge, Rockaway, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2018 | 336 homes
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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
HarborView
$600ks - $1Ms
HarborView, Port Washington, NY
Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes
Clove Hill Manor
$200ks - $300ks
Clove Hill Manor, Wantage, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2007 | 117 homes
Rivington
$300ks - $900ks
Rivington, Danbury, CT
New and Resale | Age-targeted | Built 2006 - present | 1,050 homes
Four Seasons at Bridgewat...
$300ks - $400ks
Four Seasons at Bridgewat..., Bridgewater, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 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
Meadowbrook Pointe Athlet...
$700ks - $1Ms
Meadowbrook Pointe Athlet..., Westbury, NY
Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 homes
The Meadows at Panther Va...
$300ks - $400ks
The Meadows at Panther Va..., Hackettstown, NJ
Resale Only | Age-targeted | Built 2010 - 2021 | 312 homes
2.5 rating (2 reviews) Brookfield Estates
$300ks
Brookfield Estates, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 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
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Questions? Call us: (845) 479-5674
Riverview Estates Active ...
$500ks - $600ks
Riverview Estates Active ..., Easton, PA
Resale Only | 55+ age-restricted | Built 2005 - present | 92 homes
5 rating (1 reviews) Warwick Grove
$400ks - $600ks
Warwick Grove, Warwick, NY
New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes
Overlook
$600ks - $900ks
Overlook, Carmel, NY
New Construction | 55+ age-restricted | 300 homes
Four Seasons at Wayne
$300ks - $400ks
Four Seasons at Wayne, Wayne, NJ
Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 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.
Nolan's Ridge
$400ks - $700ks
Nolan's Ridge, Mount Arlington, NJ
Resale Only | 55+ age-restricted | Built 2008 - 2014 | 156 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
Kimbolton
$900ks - $1Ms
Kimbolton, Far Hills, NJ
New Construction | 55+ age-restricted | Built 2024 - present | 105 homes
Parkview Crossings at Woo...
$300ks - $400ks
Parkview Crossings at Woo..., Woodbridge, NJ
Resale Only | 55+ age-restricted | Built 2005 - 2007 | 85 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
Glenmoor
$300ks - $400ks
Glenmoor, Easton, PA
Resale Only | 55+ age-restricted | Built 2004 - 2008 | 182 homes
Del Webb Florham Park
$600ks - $1Ms
Del Webb Florham Park, Florham Park, NJ
Resale Only | 55+ age-restricted | Built 2018 - 2022 | 242 homes
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Questions? Call us: (845) 479-5674
Bear's Cove
$800ks - $900ks
Bear's Cove, Ramsey, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 104 homes
The Savannah
$600ks - $700ks
The Savannah, Westfield, NJ
Resale Only | 55+ age-restricted | Built 2009 - 2009 | 35 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
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 Ridgemont
$800ks - $1Ms
Four Seasons at Ridgemont, Montvale, NJ
Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 homes
Dutchgate
$300ks - $500ks
Dutchgate, Valley Stream, NY
Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes
Brookfield Glen
$100ks - $200ks
Brookfield Glen, Belvidere, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 124 homes
Melrose at Chatham
$1Ms
Melrose at Chatham, Chatham, NJ
Resale Only | 55+ age-restricted | Built 2004 - 2005 | 19 homes
Reserve at Hawk Pointe
$400ks - $500ks
Reserve at Hawk Pointe, Washington, NJ
Resale Only | 55+ age-restricted | Built 2003 - 2006 | 120 homes
Hawk Pointe
$300ks - $500ks
Hawk Pointe, Washington, NJ
New and Resale | 55+ age-restricted | Built 2019 - present | 85 homes
Regency at Readington
$600ks - $700ks
Regency at Readington, Readington Township, NJ
Resale Only | 55+ age-restricted | Built 2014 - 2019 | 209 homes
Woodcrest at Jacobs Hill
$200ks - $300ks
Woodcrest at Jacobs Hill, Cortlandt, NY
Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
5 rating (1 reviews) Delaware Crossing
$200ks - $300ks
Delaware Crossing, Lopatcong, NJ
Resale Only | 55+ age-restricted | Built 2006 - 2014 | 158 homes
Campagna
$300ks - $400ks
Campagna, Montville Township, NJ
Resale Only | 55+ age-restricted | Built 1980 - 1986 | 136 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 351 VICTORIA DR, BRIDGEWATER TWP., NJ, 0..., Bridgewater Twp., NJ 08807
$439,000

2 beds

|

2 baths

|

1,155 sq ft

351 VICTORIA DR, BRIDGEWATER TWP., NJ, 0...
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
New Nolan's Ridge 19 ZACHARY WAY, MOUNT ARLINGTON BORO, NJ..., Mount Arlington Boro, NJ 07856
$465,000

2 beds

|

2 baths

19 ZACHARY WAY, MOUNT ARLINGTON BORO, NJ...
Community: Nolan's Ridge
New Greenbriar at Fox Ridge 4309 HOOVER LN 309, ROCKAWAY TWP., NJ, 0..., Rockaway Twp., NJ 07885
$479,000

2 beds

|

3 baths

4309 HOOVER LN 309, ROCKAWAY TWP., NJ, 0...
New Parkview Crossings at Woodbridge 323 REGENCY PL, WOODBRIDGE PROPER, NJ, 0..., Woodbridge Proper, NJ 07095
$449,900

2 beds

|

2 baths

|

1,605 sq ft

|

Condo

323 REGENCY PL, WOODBRIDGE PROPER, NJ, 0...
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
New Heritage Hills 154 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$525,000

2 beds

|

2 baths

|

1,396 sq ft

|

Condo

154 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
New The Savannah 111 PROSPECT ST 4C, WESTFIELD TOWN, NJ, ..., Westfield Town, NJ 07090
$1,199,000

2 beds

|

3 baths

|

2,615 sq ft

111 PROSPECT ST 4C, WESTFIELD TOWN, NJ, ...
Community: The Savannah
New Jefferson Village 45 JEFFERSON OVAL G, YORKTOWN, NY, 10598, Yorktown, NY 10598
$429,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

45 JEFFERSON OVAL G, YORKTOWN, NY, 10598
Community: Jefferson Village
New Heritage Hills 446 HERITAGE HLS D, SOMERS, NY, 10589, Somers, NY 10589
$679,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

446 HERITAGE HLS D, SOMERS, NY, 10589
Community: Heritage Hills
New Rivington 11 MERCY ST 11, DANBURY, CT, 06810, Danbury, CT 06810
$600,000

2 beds

|

4 baths

|

1,572 sq ft

|

Condo

11 MERCY ST 11, DANBURY, CT, 06810
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.
New Four Seasons at Bridgewater 151 VICTORIA DR, BRIDGEWATER TWP., NJ, 0..., Bridgewater Twp., NJ 08807
$426,900

2 beds

|

2 baths

151 VICTORIA DR, BRIDGEWATER TWP., NJ, 0...
New Jefferson Village 18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598
$340,000

2 beds

|

1 baths

|

1,000 sq ft

|

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598
Community: Jefferson Village
New Four Seasons at Bridgewater 363 VICTORIA DR, BRIDGEWATER TWP., NJ, 0..., Bridgewater Twp., NJ 08807
$524,900

2 beds

|

2 baths

|

1,491 sq ft

363 VICTORIA DR, BRIDGEWATER TWP., NJ, 0...
New Fox Hills 1115 HAMILTON DR, ROCKAWAY TWP., NJ, 078..., Rockaway Twp., NJ 07866
$425,000

2 beds

|

2 baths

1115 HAMILTON DR, ROCKAWAY TWP., NJ, 078...
Community: Fox Hills
New Overlook 2011 SUMMIT LOOP 86, CARMEL, NY, 10512, Carmel, NY 10512
$936,000

2 beds

|

3 baths

|

2,873 sq ft

|

Condo

2011 SUMMIT LOOP 86, CARMEL, NY, 10512
Community: Overlook
New Overlook 2037 SUMMIT LOOP 92, CARMEL, NY, 10512, Carmel, NY 10512
$899,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2037 SUMMIT LOOP 92, CARMEL, NY, 10512
Community: Overlook
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
New Overlook 2055 SUMMIT LOOP 95, CARMEL, NY, 10512, Carmel, NY 10512
$905,000

2 beds

|

2 baths

|

2,102 sq ft

|

Condo

2055 SUMMIT LOOP 95, CARMEL, NY, 10512
Community: Overlook
New Bald Eagle Commons 1409 RICHMOND RD 409, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480
$229,000

2 beds

|

1 baths

1409 RICHMOND RD 409, WEST MILFORD TWP.,...
Community: Bald Eagle Commons
New HarborView 100 HARBOR VIEW DR 651, NORTH HEMPSTEAD,..., North Hempstead, NY 11050
$848,000

2 beds

|

3 baths

|

1,363 sq ft

|

Condo

100 HARBOR VIEW DR 651, NORTH HEMPSTEAD,...
Community: HarborView
New Bear's Cove 107 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446
$1,199,000

3 beds

|

3 baths

|

Townhouse

107 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.
New Del Webb Florham Park 1 VANDERBILT BLVD 303, FLORHAM PARK BORO..., Florham Park Boro, NJ 07932
$935,000

2 beds

|

2 baths

|

1,388 sq ft

1 VANDERBILT BLVD 303, FLORHAM PARK BORO...
New Greenbriar at Fox Ridge 4315 HOOVER LN, ROCKAWAY TWP., NJ, 07885, Rockaway Twp., NJ 07885
$450,000

2 beds

|

3 baths

4315 HOOVER LN, ROCKAWAY TWP., NJ, 07885
New Horizons at Mount Arlington 53 RIDGEVIEW LN, MOUNT ARLINGTON BORO, N..., Mount Arlington Boro, NJ 07856
$439,900

2 beds

|

2 baths

53 RIDGEVIEW LN, MOUNT ARLINGTON BORO, N...
Four Seasons at Ridgemont 410 FOUR SEASONS LN, MONTVALE, NJ, 07645, Montvale, NJ 07645
$924,900

2 beds

|

2 baths

|

Condo

410 FOUR SEASONS LN, MONTVALE, NJ, 07645
Bald Eagle Commons 4 RICHMOND RD 215, WEST MILFORD, NJ, 074..., West Milford, NJ 07480
$250,000

2 beds

|

2 baths

|

Condo

4 RICHMOND RD 215, WEST MILFORD, NJ, 074...
Community: Bald Eagle Commons
Heritage Hills 351 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589
$629,900

2 beds

|

2 baths

|

1,484 sq ft

|

Condo

351 HERITAGE HLS B, SOMERS, NY, 10589
Community: Heritage Hills
Glenmoor 40 GLENMOOR CIR, PALMER TWP, PA, 18045, Palmer Twp, PA 18045
$390,000

2 beds

|

2 baths

|

1,524 sq ft

|

Semi Detached

40 GLENMOOR CIR, PALMER TWP, PA, 18045
Community: Glenmoor
Want to learn more about 55+ communities in Middletown? 55places can help!
Questions? Call us: (845) 479-5674
Heritage Hills 606 HERITAGE HLS F, SOMERS, NY, 10589, Somers, NY 10589
$874,900

2 beds

|

2 baths

|

1,860 sq ft

|

Condo

606 HERITAGE HLS F, SOMERS, NY, 10589
Community: Heritage Hills
HarborView 95 W OVERLOOK, NORTH HEMPSTEAD, NY, 1105..., North Hempstead, NY 11050
$2,100,000

3 beds

|

3 baths

|

3,760 sq ft

|

Condo

95 W OVERLOOK, NORTH HEMPSTEAD, NY, 1105...
Community: HarborView
Bald Eagle Commons 4 RICHMOND RD 215, WEST MILFORD TWP., NJ..., West Milford Twp., NJ 07480
$250,000

2 beds

|

2 baths

4 RICHMOND RD 215, WEST MILFORD TWP., 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.
Meadowbrook Pointe Athletic Club & Spa 103 ROOSEVELT WAY, HEMPSTEAD, NY, 11590, Hempstead, NY 11590
$1,169,000

2 beds

|

2 baths

|

2,036 sq ft

|

Condo

103 ROOSEVELT WAY, HEMPSTEAD, NY, 11590
Fox Hills 1213 CLINTON LN, ROCKAWAY TWP., NJ, 0786..., Rockaway Twp., NJ 07866
$469,000

2 beds

|

2 baths

1213 CLINTON LN, ROCKAWAY TWP., NJ, 0786...
Community: Fox Hills
Delaware Crossing 418 EDWARD ST, LOPATCONG TWP., NJ, 08865, Lopatcong Twp., NJ 08865
$465,000

2 beds

|

3 baths

|

2,437 sq ft

418 EDWARD ST, LOPATCONG TWP., NJ, 08865
Community: Delaware Crossing
Jefferson Village 52 JEFFERSON OVAL A, YORKTOWN, NY, 10598, Yorktown, NY 10598
$450,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

52 JEFFERSON OVAL A, YORKTOWN, NY, 10598
Community: Jefferson Village
Jefferson Village 27 WALDEN CT F, YORKTOWN, NY, 10598, Yorktown, NY 10598
$399,000

2 beds

|

1 baths

|

925 sq ft

|

Condo

27 WALDEN CT F, YORKTOWN, NY, 10598
Community: Jefferson Village
Melrose at Chatham 6 MELROSE LN, CHATHAM TWP., NJ, 07935, Chatham Twp., NJ 07935
$1,495,000

4 beds

|

4 baths

6 MELROSE LN, CHATHAM TWP., NJ, 07935
Community: Melrose at Chatham
Clove Hill Manor 33 SPRING HOLLOW RD, WANTAGE TWP., NJ, 0..., Wantage Twp., NJ 07461
$450,000

3 beds

|

3 baths

33 SPRING HOLLOW RD, WANTAGE TWP., NJ, 0...
Community: Clove Hill Manor
Wanaque Reserve 5203 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465
$349,000

2 beds

|

2 baths

|

1,768 sq ft

5203 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
The Meadows at Panther Valley 6 ALEXANDERS RD, ALLAMUCHY TWP., NJ, 078..., Allamuchy Twp., NJ 07840
$525,000

3 beds

|

3 baths

6 ALEXANDERS RD, ALLAMUCHY TWP., NJ, 078...
Wildflowers at Wallkill 6 CYPRUS DR, WALLKILL, NY, 10940, Wallkill, NY 10940
$549,900

2 beds

|

3 baths

|

2,454 sq ft

|

House

6 CYPRUS DR, WALLKILL, NY, 10940
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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