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

196 homes 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

3 rating (2 reviews)

Heritage Hills

$500ks - $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

4 rating (1 reviews)

Jefferson Village

$100ks - $500ks

Jefferson Village, Yorktown Heights, NY

Resale Only | 55+ age-restricted | Built 1967 - 1982 | 1,000 homes

Greenbriar at Fox Ridge

$300ks - $500ks

Greenbriar at Fox Ridge, Rockaway, NJ

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

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

Questions? Call us: (845) 479-5674

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

Four Seasons at Bridgewat...

$300ks - $400ks

Four Seasons at Bridgewat..., Bridgewater, NJ

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

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2.5 rating (2 reviews)

Brookfield Estates

$300ks

Brookfield Estates, Belvidere, NJ

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

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 755 homes

Peapack Crossing

$1Ms

Peapack Crossing, Peapack-Gladstone, NJ

New Construction | Age-targeted | Built 2026 - present | 66 homes

Riverview Estates Active ...

$500ks - $600ks

Riverview Estates Active ..., Easton, PA

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

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

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

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

Questions? Call us: (845) 479-5674

Overlook

$600ks - $900ks

Overlook, Carmel, NY

New Construction | 55+ age-restricted | 300 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

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

Four Seasons at Wayne

$300ks - $400ks

Four Seasons at Wayne, Wayne, NJ

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

Bear's Cove

$800ks - $900ks

Bear's Cove, Ramsey, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 104 homes

Kimbolton

$900ks - $1Ms

Kimbolton, Far Hills, NJ

New Construction | 55+ age-restricted | Built 2024 - present | 105 homes

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Nolan's Ridge

$400ks - $700ks

Nolan's Ridge, Mount Arlington, NJ

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

Legacy at Morgan Hill

$400ks - $500ks

Legacy at Morgan Hill, Easton, PA

Resale Only | 55+ age-restricted | Built 2006 - 2013 | 127 homes

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

Questions? Call us: (845) 479-5674

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

The Highlands at Glenmoor

$300ks - $400ks

The Highlands at Glenmoor, Easton, PA

Resale Only | 55+ age-restricted | Built 2004 - 2007 | 251 homes

Woodcrest at Jacobs Hill

$200ks - $300ks

Woodcrest at Jacobs Hill, Cortlandt, NY

Resale Only | 55+ age-restricted | Built 2005 - 2006 | 58 homes

Regency at Wappinger

$500ks

Regency at Wappinger, Wappingers Falls, NY

Resale Only | 55+ age-restricted | Built 2014 - 2020 | 225 homes

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

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

The Cottages at Wire Mill

$1Ms

The Cottages at Wire Mill, Stamford, CT

New Construction | 55+ age-restricted | Built 2026 - present | 9 homes

Reserve at Hawk Pointe

$400ks - $500ks

Reserve at Hawk Pointe, Washington, NJ

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 120 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

Regency at Readington

$600ks - $700ks

Regency at Readington, Readington Township, NJ

Resale Only | 55+ age-restricted | Built 2014 - 2019 | 209 homes

Four Seasons at Ridgemont

$800ks - $1Ms

Four Seasons at Ridgemont, Montvale, NJ

Resale Only | 55+ age-restricted | Built 2011 - 2014 | 108 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

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

Questions? Call us: (845) 479-5674

Traditions of America at ...

$500ks - $600ks

Traditions of America at ..., Bethlehem, PA

Resale Only | 55+ age-restricted | Built 2019 - present | 229 homes

Glenmoor

$300ks - $400ks

Glenmoor, Easton, PA

Resale Only | 55+ age-restricted | Built 2004 - 2008 | 182 homes

1 2...3

Four Seasons at Bridgewater

373 VICTORIA DR, BRIDGEWATER, NJ, 08807, Bridgewater, NJ 08807

$499,900

2 beds

2 baths

1,140 sq ft

Townhouse,Condominium

373 VICTORIA DR, BRIDGEWATER, NJ, 08807

Community: Four Seasons at Bridgewater

Four Seasons at Bridgewater

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

$499,900

2 beds

2 baths

1,200 sq ft

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

Community: Four Seasons at Bridgewater

Brookfield Estates

10 STAFFORD LN, WHITE TWP., NJ, 07823, White Twp., NJ 07823

$439,000

2 beds

2 baths

10 STAFFORD LN, WHITE TWP., NJ, 07823

Community: Brookfield Estates

Jefferson Village

39 SUSSEX DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$359,000

2 beds

2 baths

1,000 sq ft

Condo

39 SUSSEX DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

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

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

Questions? Call us: (845) 479-5674

New Four Seasons at Great Notch Spa and Club

59 QUARRY DR 4206, WOODLAND PARK, NJ, 07..., Woodland Park, NJ 07424

$939,900

2 beds

3 baths

Condo

59 QUARRY DR 4206, WOODLAND PARK, NJ, 07...

Community: Four Seasons at Great Notch Spa and Club

New Four Seasons at Great Notch Spa and Club

59 QUARRY DR, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424

$939,900

2 beds

3 baths

59 QUARRY DR, WOODLAND PARK, NJ, 07424

Community: Four Seasons at Great Notch Spa and Club

New Regency at Fishkill

231 REGENCY DR, FISHKILL, NY, 12524, Fishkill, NY 12524

$489,900

1 beds

2 baths

1,499 sq ft

Condo

231 REGENCY DR, FISHKILL, NY, 12524

Community: Regency at Fishkill

New Heritage Hills

763 HERITAGE HILLS DR C, SOMERS, NY, 105..., Somers, NY 10589

$849,000

3 beds

2 baths

1,909 sq ft

Condo

763 HERITAGE HILLS DR C, SOMERS, NY, 105...

Community: Heritage Hills

New Dawson Brook

2 PAR CT, RANDOLPH TWP., NJ, 07869, Randolph Twp., NJ 07869

$1,000,000

3 beds

4 baths

2,672 sq ft

2 PAR CT, RANDOLPH TWP., NJ, 07869

Community: Dawson Brook

New Jefferson Village

160 CARRIAGE CT D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$359,000

1 beds

1 baths

953 sq ft

Condo

160 CARRIAGE CT D, YORKTOWN, NY, 10598

Community: Jefferson Village

New Fox Hills

1301 HAMILTON DR 1303, ROCKAWAY TWP., NJ..., Rockaway Twp., NJ 07866

$325,000

1 beds

2 baths

896 sq ft

1301 HAMILTON DR 1303, ROCKAWAY TWP., NJ...

Community: Fox Hills

New Fox Hills

3203 CLEVELAND LN, ROCKAWAY TWP., NJ, 07..., Rockaway Twp., NJ 07866

$479,900

2 beds

2 baths

3203 CLEVELAND LN, ROCKAWAY TWP., NJ, 07...

Community: Fox Hills

New Four Seasons at Wayne

1313 FOUR SEASONS DR, WAYNE, NJ, 07470, Wayne, NJ 07470

$569,000

2 beds

3109 POINTE GATE DR, LIVINGSTON TWP., NJ..., Livingston Twp., NJ 07039

$649,900

2 beds

3 baths

3109 POINTE GATE DR, LIVINGSTON TWP., NJ...

Community: The Pointe

New Wanaque Reserve

8403 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$439,000

2 beds

2 baths

8403 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

New Rivington

1 RIVINGTON WAY 306, DANBURY, CT, 06810, Danbury, CT 06810

$565,000

$799,800

2 beds

2 baths

1,889 sq ft

Condo

6201 FRED ILL JR CT, ORANGETOWN, NY, 109...

Community: The Hollows at Blue Hill

Four Seasons at The Promenade

17 LARA PL, WARREN TWP., NJ, 07059, Warren Twp., NJ 07059

$495,000

2 beds

2 baths

1,134 sq ft

17 LARA PL, WARREN TWP., NJ, 07059

Community: Four Seasons at The Promenade

Reserve at Hawk Pointe

31 FALCON WAY, WASHINGTON TWP., NJ, 0788..., Washington Twp., NJ 07882

$629,900

3 beds

2 baths

31 FALCON WAY, WASHINGTON TWP., NJ, 0788...

Community: Reserve at Hawk Pointe

The Seasons at East Meadow

180 SPRING DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$725,000

2 beds

3 baths

1,030 sq ft

Condo

180 SPRING DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

Wanaque Reserve

5111 WARRENS WAY 11, WANAQUE BORO, NJ, 0..., Wanaque Boro, NJ 07465

$459,900

2 beds

2 baths

1,768 sq ft

5111 WARRENS WAY 11, WANAQUE BORO, NJ, 0...

Community: Wanaque Reserve

Brookfield Estates

38 VICTORIA DR, WHITE TWP., NJ, 07823, White Twp., NJ 07823

$524,900

3 beds

2 baths

2,060 sq ft

38 VICTORIA DR, WHITE TWP., NJ, 07823

Community: Brookfield Estates

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

Questions? Call us: (845) 479-5674

Fox Hills

1108 BUSH CIR, ROCKAWAY TWP., NJ, 07866, Rockaway Twp., NJ 07866

$350,000

1 beds

2 baths

1108 BUSH CIR, ROCKAWAY TWP., NJ, 07866

Community: Fox Hills

Legacy at Morgan Hill

870 E HOMESTEAD LN, WILLIAMS TWP, PA, 18..., Williams Twp, PA 18042

$625,000

3 beds

3 baths

3,728 sq ft

Detached

870 E HOMESTEAD LN, WILLIAMS TWP, PA, 18...

Community: Legacy at Morgan Hill

Wildflowers at Wallkill

24 LILAC ST, MIDDLETOWN, NY, 10940, Middletown, NY 10940

$499,900

2 beds

2 baths

1,473 sq ft

House

24 LILAC ST, MIDDLETOWN, NY, 10940

Community: Wildflowers at Wallkill

Dutchgate

1003 WILLOW LN, HEMPSTEAD, NY, 11580, Hempstead, NY 11580

$535,000

2 beds

2 baths

941 sq ft

Condo

1003 WILLOW LN, HEMPSTEAD, NY, 11580

Community: Dutchgate

Heritage Hills

$539,000

1 beds

2 baths

967 sq ft

Condo

593 HERITAGE HILLS DR C, SOMERS, NY, 105...

Community: Heritage Hills

Rivington

19 ORWICH CT 19, DANBURY, CT, 06810, Danbury, CT 06810

$669,900

3 beds

4 baths

1,572 sq ft

Condo

19 ORWICH CT 19, DANBURY, CT, 06810

Community: Rivington

Bald Eagle Commons

9225 RICHMOND RD 225, WEST MILFORD, NJ, ..., West Milford, NJ 07480

$334,900

2 beds

4308 CLEVELAND LN, ROCKAWAY TWP., NJ, 07..., Rockaway Twp., NJ 07866

$340,000

1 beds

2 baths

4308 CLEVELAND LN, ROCKAWAY TWP., NJ, 07...

Community: Fox Hills

Regency at Wappinger

63 FARMINGTON RD, WAPPINGER, NY, 12590, Wappinger, NY 12590

$854,500

3 beds

3 baths

2,944 sq ft

Condo

63 FARMINGTON RD, WAPPINGER, NY, 12590

Community: Regency at Wappinger

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 447 days. The average price of homes for sale in this community is approximately $523,306, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Wildflowers at Wallkill average around $523,306.

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196 homes

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REIN updates its listings on a daily basis. Data last updated: Oct 09, 2026.
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Middletown, NY 55+ active adult communities & homes for sale

101 communities near Middletown

196 homes near Middletown

2 beds

2 baths

1,140 sq ft

Townhouse,Condominium

2 beds

2 baths

1,200 sq ft

2 beds

2 baths

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,408 sq ft

2 beds

3 baths

Condo

2 beds

3 baths

1 beds

2 baths

1,499 sq ft

Condo

3 beds

2 baths

1,909 sq ft

Condo

3 beds

4 baths

2,672 sq ft

1 beds

1 baths

953 sq ft

Condo

1 beds

2 baths

896 sq ft

2 beds

2 baths

2 beds

2 baths

Townhouse

2 beds

2 baths

2 beds

2 baths

2 beds

3 baths

2 beds

2 baths

2 beds

2 baths

1,549 sq ft

Condo

2 beds

2 baths

Townhouse

2 beds

2 baths

1,754 sq ft

2 beds

2 baths

1,889 sq ft

Condo

2 beds

2 baths

1,134 sq ft

3 beds

2 baths

2 beds

3 baths

1,030 sq ft

Condo

2 beds

2 baths