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

181 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

3 rating (2 reviews)

Heritage Hills

$400ks - $900ks

Heritage Hills, Somers, NY

Resale Only | Age-targeted | Built 1974 - 2006 | 2,600 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

Bald Eagle Commons

$100ks - $300ks

Bald Eagle Commons, West Milford, NJ

Resale Only | 55+ age-restricted | Built 1995 - 2005 | 463 homes

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 homes

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Greenbriar at Fox Ridge

$300ks - $500ks

Greenbriar at Fox Ridge, Rockaway, NJ

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 336 homes

Fox Hills

$300ks - $600ks

Fox Hills, Rockaway, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2003 | 672 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)

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

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1 rating (1 reviews)

Brookfield Estates

$300ks

Brookfield Estates, Belvidere, NJ

Resale Only | 55+ age-restricted | Built 1999 - 2002 | 274 homes

5 rating (1 reviews)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

New and Resale | 55+ age-restricted | Built 2004 - present | 215 homes

Rivington

$300ks - $900ks

Rivington, Danbury, CT

New and Resale | Age-targeted | Built 2006 - present | 1,050 homes

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

Resale Only | 55+ age-restricted | Built 2008 - 2020 | 164 homes

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Questions? Call us: (845) 479-5674

Fox Crest

$300ks - $600ks

Fox Crest, Rockaway, NJ

New Construction | 55+ age-restricted | Built 2020 - present | 41 homes

Four Seasons at Bridgewat...

$300ks - $400ks

Four Seasons at Bridgewat..., Bridgewater, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2010 | 154 homes

The Pointe

$300ks - $600ks

The Pointe, Livingston, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2007 | 180 homes

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

Resale Only | 55+ age-restricted | Built 2002 - 2004 | 270 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 homes

Horizons at Mount Arlingt...

$400ks

Horizons at Mount Arlingt..., Mount Arlington, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2004 | 144 homes

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 Wayne

$300ks - $400ks

Four Seasons at Wayne, Wayne, NJ

Resale Only | 55+ age-restricted | Built 1999 - 2001 | 230 homes

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5 rating (2 reviews)

Blackburne Farm Townhomes

$400ks

Blackburne Farm Townhomes, Campbell Hall, NY

New Construction | 55+ age-restricted | Built 2019 - present | 29 homes

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

Resale Only | 55+ age-restricted | Built 2006 - 2017 | 283 homes

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

New Construction | 55+ age-restricted | Built 2019 - present | 72 homes

Winthrop Court

$400ks - $600ks

Winthrop Court, Clifton, NJ

Resale Only | 55+ age-restricted | Built 2000 - 2010 | 270 homes

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

Resale Only | 55+ age-restricted | Built 2015 - 2017 | 112 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

Clove Hill Manor

$200ks - $300ks

Clove Hill Manor, Wantage, NJ

Resale Only | 55+ age-restricted | Built 2003 - 2007 | 117 homes

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

Resale Only | 55+ age-restricted | Built 2015 - 2016 | 720 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

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

Lakeside Villas

$400ks - $500ks

Lakeside Villas, Watchung, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2020 | 42 homes

Four Seasons at Troy Hill...

$500ks

Four Seasons at Troy Hill..., Parsippany, NJ

Resale Only | 55+ age-restricted | Built 2007 - 2007 | 46 homes

Riverview Estates Active ...

$500ks - $600ks

Riverview Estates Active ..., Easton, PA

Resale Only | 55+ age-restricted | Built 2005 - present | 92 homes

5 rating (1 reviews)

Delaware Crossing

$200ks - $300ks

Delaware Crossing, Lopatcong, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 158 homes

Regency at Flanders

$400ks - $900ks

Regency at Flanders, Flanders, NJ

Resale Only | 55+ age-restricted | Built 2016 - 2022 | 275 homes

The Village at Fox Crossi...

$200ks - $300ks

The Village at Fox Crossi..., Easton, PA

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 135 homes

Nolan's Ridge

$400ks - $700ks

Nolan's Ridge, Mount Arlington, NJ

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 156 homes

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Questions? Call us: (845) 479-5674

Meadowbrooke Pointe East ...

$500ks - $600ks

Meadowbrooke Pointe East ..., East Meadow, NY

New Construction | 62+ age-restricted | Built 2019 - present | 104 homes

Villas at Seminary Hill

$200ks - $300ks

Villas at Seminary Hill, Carmel, NY

New Construction | 55+ age-restricted | Built 2018 - present | 50 homes

1 2...3

New Brookfield Estates

107 KENSINGTON CIR, WHITE TWP., NJ, 0782..., White Twp., NJ 07823

$470,000

2 beds

2 baths

1,662 sq ft

107 KENSINGTON CIR, WHITE TWP., NJ, 0782...

Community: Brookfield Estates

New Heritage Hills

612 HERITAGE HLS A, SOMERS, NY, 10589, Somers, NY 10589

$649,000

2 beds

2 baths

1,483 sq ft

Condo

612 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

New Regency at Flanders

56 DRAKE WAY, MOUNT OLIVE TWP., NJ, 0783..., Mount Olive Twp., NJ 07836

$850,000

2 beds

2 baths

56 DRAKE WAY, MOUNT OLIVE TWP., NJ, 0783...

Community: Regency at Flanders

New Bald Eagle Commons

6116 RICHMOND RD 116, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480

$250,000

2 beds

1 baths

957 sq ft

6116 RICHMOND RD 116, WEST MILFORD TWP.,...

Community: Bald Eagle Commons

New The Pointe

1403 POINTE GATE DR, LIVINGSTON, NJ, 070..., Livingston, NJ 07039

$450,000

2 beds

2 baths

Condo

1403 POINTE GATE DR, LIVINGSTON, NJ, 070...

Community: The Pointe

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New Heritage Hills

272 HERITAGE HLS C, SOMERS, NY, 10589, Somers, NY 10589

$569,900

2 beds

2 baths

1,500 sq ft

Condo

272 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

New Greenbriar at Fox Ridge

5107 VETERANS DR, ROCKAWAY TWP., NJ, 078..., Rockaway Twp., NJ 07885

$450,000

2 beds

3 baths

5107 VETERANS DR, ROCKAWAY TWP., NJ, 078...

Community: Greenbriar at Fox Ridge

New Four Seasons at Troy Hills

24 HOPKINS CT, PARSIPPANY-TROY HILLS TWP..., Parsippany-troy Hills Twp., NJ 07054

$650,000

3 beds

3 baths

2,175 sq ft

24 HOPKINS CT, PARSIPPANY-TROY HILLS TWP...

Community: Four Seasons at Troy Hills

New Four Seasons at Wayne

703 FOUR SEASONS DR, WAYNE, NJ, 07470, Wayne, NJ 07470

$510,000

2 beds

2 baths

Condo

703 FOUR SEASONS DR, WAYNE, NJ, 07470

Community: Four Seasons at Wayne

New Four Seasons at Wayne

703 FOUR SEASONS DR, WAYNE TWP., NJ, 074..., Wayne Twp., NJ 07470

$510,000

2 beds

2 baths

703 FOUR SEASONS DR, WAYNE TWP., NJ, 074...

Community: Four Seasons at Wayne

New Jefferson Village

119 VILLAGE RD H, YORKTOWN, NY, 10598, Yorktown, NY 10598

$439,000

2 beds

2 baths

1,100 sq ft

Condo

119 VILLAGE RD H, YORKTOWN, NY, 10598

Community: Jefferson Village

New Heritage Hills

725 HERITAGE HLS, SOMERS, NY, 10589, Somers, NY 10589

$774,900

2 beds

2 baths

1,526 sq ft

Condo

725 HERITAGE HLS, SOMERS, NY, 10589

Community: Heritage Hills

New HarborView

626 VILLAGE GRN, NORTH HEMPSTEAD, NY, 11..., North Hempstead, NY 11050

$1,199,000

3 beds

3 baths

2,424 sq ft

Condo

626 VILLAGE GRN, NORTH HEMPSTEAD, NY, 11...

Community: HarborView

Want to learn more about 55+ communities in Middletown? 55places can help!

Questions? Call us: (845) 479-5674

New Nolan's Ridge

9 ZACHARY WAY, MOUNT ARLINGTON BORO, NJ,..., Mount Arlington Boro, NJ 07856

$495,000

2 beds

2 baths

9 ZACHARY WAY, MOUNT ARLINGTON BORO, NJ,...

Community: Nolan's Ridge

New Glenmoor

158 GLENMOOR CIR, EASTON, PA, 18045, Easton, PA 18045

$559,900

3 beds

4 baths

2,792 sq ft

Condo

158 GLENMOOR CIR, EASTON, PA, 18045

Community: Glenmoor

New Jefferson Village

129 COLUMBIA CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$469,999

2 beds

2 baths

1,100 sq ft

Condo

129 COLUMBIA CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

New The Pointe

1403 POINTE GATE DR, LIVINGSTON TWP., NJ..., Livingston Twp., NJ 07039

$450,000

2 beds

2 baths

1403 POINTE GATE DR, LIVINGSTON TWP., NJ...

Community: The Pointe

New Four Seasons at Great Notch Spa and Club

5 SLATE CT, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424

$615,000

2 beds

2 baths

1,466 sq ft

5 SLATE CT, WOODLAND PARK, NJ, 07424

Community: Four Seasons at Great Notch Spa and Club

New Overlook

2079 SUMMIT LOOP 103, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

1,948 sq ft

Condo

2079 SUMMIT LOOP 103, CARMEL, NY, 10512

Community: Overlook

Four Seasons at Great Notch Spa and Club

5 SLATE CT A3, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424

$615,000

2 beds

2 baths

Condo

5 SLATE CT A3, WOODLAND PARK, NJ, 07424

Community: Four Seasons at Great Notch Spa and Club

Glenmoor

$369,000

2 beds

2 baths

1,597 sq ft

Semi Detached

19 GLENMOOR CIR, EASTON, PA, 18045

Community: Glenmoor

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Winthrop Court

1107 WICKHAM TER 374, CLIFTON, NJ, 07013, Clifton, NJ 07013

$559,000

2 beds

2 baths

Condo

1107 WICKHAM TER 374, CLIFTON, NJ, 07013

Community: Winthrop Court

The Village at Fox Crossing

3813 BELCOURT RD, FORKS TWP, PA, 18040, Forks Twp, PA 18040

$250,000

2 beds

2 baths

1,302 sq ft

Detached

3813 BELCOURT RD, FORKS TWP, PA, 18040

Community: The Village at Fox Crossing

Winthrop Court

9210 RAVENSCROFT RD 627, CLIFTON, NJ, 07..., Clifton, NJ 07013

$585,000

2 beds

2 baths

Condo

9210 RAVENSCROFT RD 627, CLIFTON, NJ, 07...

Community: Winthrop Court

Winthrop Court

9210 RAVENSCROFT RD, CLIFTON CITY, NJ, 0..., Clifton City, NJ 07013

$585,000

2 beds

2 baths

1,871 sq ft

9210 RAVENSCROFT RD, CLIFTON CITY, NJ, 0...

Community: Winthrop Court

Wildflowers at Wallkill

10 CYPRUS DR, MIDDLETOWN, NY, 10940, Middletown, NY 10940

$489,999

2 beds

2 baths

1,612 sq ft

House

10 CYPRUS DR, MIDDLETOWN, NY, 10940

Community: Wildflowers at Wallkill

Lakeside Villas

8 SCHMIDT CIR, WATCHUNG BORO, NJ, 07069, Watchung Boro, NJ 07069

$849,500

2 beds

3 baths

8 SCHMIDT CIR, WATCHUNG BORO, NJ, 07069

Community: Lakeside Villas

Heritage Hills

29 HERITAGE HLS 29D, SOMERS, NY, 10589, Somers, NY 10589

$495,000

2 beds

3 baths

1,340 sq ft

Condo

29 HERITAGE HLS 29D, SOMERS, NY, 10589

Community: Heritage Hills

The Seasons at Seaford

56 SPRING DR, HEMPSTEAD, NY, 11783, Hempstead, NY 11783

$820,000

2 beds

3 baths

1,034 sq ft

Condo

56 SPRING DR, HEMPSTEAD, NY, 11783

Community: The Seasons at Seaford

Regency at Flanders

4 VIRGIL LN, MOUNT OLIVE TWP., NJ, 07836, Mount Olive Twp., NJ 07836

$929,000

4 beds

3 baths

4 VIRGIL LN, MOUNT OLIVE TWP., NJ, 07836

Community: Regency at Flanders

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Bald Eagle Commons

5301 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480

$269,900

2 beds

2 baths

5301 RICHMOND RD, WEST MILFORD, NJ, 0748...

Community: Bald Eagle Commons

Bald Eagle Commons

5320 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480

$225,000

1 beds

1 baths

Condo

5320 RICHMOND RD, WEST MILFORD, NJ, 0748...

Community: Bald Eagle Commons

Bald Eagle Commons

5320 RICHMOND RD 320, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480

$225,000

1 beds

1 baths

655 sq ft

5320 RICHMOND RD 320, WEST MILFORD TWP.,...

Community: Bald Eagle Commons

Breton Hills

401 BRETON WAY, GLEN COVE, NY, 11542, Glen Cove, NY 11542

$699,999

2 beds

2 baths

1,300 sq ft

Condo

401 BRETON WAY, GLEN COVE, NY, 11542

Community: Breton Hills

Four Seasons at Bridgewater

373 VICTORIA DR, BRIDGEWATER TWP., NJ, 0..., Bridgewater Twp., NJ 08807

$469,999

2 beds

2 baths

1,200 sq ft

373 VICTORIA DR, BRIDGEWATER TWP., NJ, 0...

Community: Four Seasons at Bridgewater

Bald Eagle Commons

4 RICHMOND RD 215, WEST MILFORD, NJ, 074..., West Milford, NJ 07480

$260,000

2 beds

2 baths

Condo

4 RICHMOND RD 215, WEST MILFORD, NJ, 074...

Community: Bald Eagle Commons

Wanaque Reserve

1118 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$569,000

2 beds

2 baths

1118 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

Greenbriar at Fox Ridge

5211 VETERANS DR, ROCKAWAY TWP., NJ, 078..., Rockaway Twp., NJ 07866

$342,000

1 beds

2 baths

5211 VETERANS DR, ROCKAWAY TWP., NJ, 078...

Community: Greenbriar at Fox Ridge

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Bald Eagle Commons

5301 RICHMOND RD 301, WEST MILFORD TWP.,..., West Milford Twp., NJ 07480

$269,900

2 beds

2 baths

5301 RICHMOND RD 301, WEST MILFORD TWP.,...

Community: Bald Eagle Commons

Jefferson Village

10 REGENTS PL D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$240,000

1 baths

550 sq ft

Condo

10 REGENTS PL D, YORKTOWN, NY, 10598

Community: Jefferson Village

1 2 3 4…5

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Middletown?

The smallest 55+ community in Middletown has 283 homes, the largest has 283 homes, and the average community consists of 283 homes.

Are there gated 55+ communities in Middletown?

Yes, there is gated 55+ community in Middletown. The only 55+ community in Middletown is gated. For instance, Wildflowers at Wallkill is a gated community with 283 homes.

How long do listings in 55+ communities in Middletown typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ community in Middletown stay on the market for around 376 days. The average price of homes for sale in this community is approximately $510,000, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Wildflowers at Wallkill average around $510,000.

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181 homes

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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
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Middletown, NY 55+ active adult communities & homes for sale

95 communities near Middletown

181 homes near Middletown

2 beds

2 baths

1,662 sq ft

2 beds

2 baths

1,483 sq ft

Condo

2 beds

2 baths

2 beds

1 baths

957 sq ft

2 beds

2 baths

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

3 baths

3 beds

3 baths

2,175 sq ft

2 beds

2 baths

Condo

2 beds

2 baths

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

1,526 sq ft

Condo

3 beds

3 baths

2,424 sq ft

Condo

2 beds

2 baths

3 beds

4 baths

2,792 sq ft

Condo

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

2 beds

2 baths

1,466 sq ft

2 beds

2 baths

1,948 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

1,597 sq ft

Semi Detached

2 beds

2 baths

Condo

2 beds

2 baths

1,302 sq ft

Detached

2 beds

2 baths

Condo