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

220 homes near Middletown

Sort by:

Relevance

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

$400ks - $800ks

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

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

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

Fox Hills

$300ks - $600ks

Fox Hills, Rockaway, NJ

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

Traditions of America at ...

$500ks - $600ks

Traditions of America at ..., Bethlehem, PA

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

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.

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

Greenbriar at Fox Ridge

$300ks - $500ks

Greenbriar at Fox Ridge, Rockaway, NJ

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

Lakeside Villas

$400ks - $500ks

Lakeside Villas, Watchung, NJ

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

Apple Ridge

$500ks - $1Ms

Apple Ridge, Mahwah, NJ

Resale Only | Age-targeted | Built 1977 - 1991 | 276 homes

Clove Hill Manor

$200ks - $300ks

Clove Hill Manor, Wantage, NJ

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

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

Questions? Call us: (845) 479-5674

5 rating (1 reviews)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Riverview Estates Active ...

$500ks - $600ks

Riverview Estates Active ..., Easton, PA

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

Four Seasons at Bridgewat...

$300ks - $400ks

Four Seasons at Bridgewat..., Bridgewater, NJ

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

The Views at Pomona

$200ks - $400ks

The Views at Pomona, Pomona, NY

Resale Only | 55+ age-restricted | Built 2011 - 2011 | 56 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

Kimbolton

$900ks - $1Ms

Kimbolton, Far Hills, NJ

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

Del Webb Florham Park

$600ks - $1Ms

Del Webb Florham Park, Florham Park, NJ

Resale Only | 55+ age-restricted | Built 2018 - 2022 | 242 homes

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

Questions? Call us: (845) 479-5674

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

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

Glenmoor

$300ks - $400ks

Glenmoor, Easton, PA

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

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

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

Horizons at Mount Arlingt...

$400ks

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

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

$600ks - $700ks

Regency at Readington, Readington Township, NJ

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

Nolan's Ridge

$400ks - $700ks

Nolan's Ridge, Mount Arlington, NJ

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

Resale Only | 55+ age-restricted | Built 2008 - 2018 | 312 homes

5 rating (1 reviews)

Delaware Crossing

$200ks - $300ks

Delaware Crossing, Lopatcong, NJ

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

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

Questions? Call us: (845) 479-5674

Venue at The American

$600ks - $900ks

Venue at The American, Morris Plains, NJ

New and Resale | 55+ age-restricted | Built 2021 - present | 156 homes

Bear's Cove

$800ks - $900ks

Bear's Cove, Ramsey, NJ

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

1 2...3

Bald Eagle Commons

12 LAFAYETTE ST, WEST MILFORD TWP., NJ, ..., West Milford Twp., NJ 07480

$558,000

3 beds

3 baths

2,372 sq ft

12 LAFAYETTE ST, WEST MILFORD TWP., NJ, ...

Community: Bald Eagle Commons

Bear's Cove

99 WINDSOR LN, RAMSEY, NJ, 07446, Ramsey, NJ 07446

$1,175,000

3 beds

3 baths

Townhouse

99 WINDSOR LN, RAMSEY, NJ, 07446

Community: Bear's Cove

Del Webb Florham Park

2 VANDERBILT BLVD 403, FLORHAM PARK BORO..., Florham Park Boro, NJ 07932

$899,000

2 beds

2 baths

2 VANDERBILT BLVD 403, FLORHAM PARK BORO...

Community: Del Webb Florham Park

Woodcrest at Jacobs Hill

1104 JACOBS HILL RD, CORTLANDT, NY, 1056..., Cortlandt, NY 10567

$389,000

2 beds

2 baths

1,145 sq ft

House

1104 JACOBS HILL RD, CORTLANDT, NY, 1056...

Community: Woodcrest at Jacobs Hill

Bald Eagle Commons

162 RICHMOND RD, WEST MILFORD, NJ, 07480, West Milford, NJ 07480

$529,000

3 beds

4 baths

Townhouse

162 RICHMOND RD, WEST MILFORD, NJ, 07480

Community: Bald Eagle Commons

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

Questions? Call us: (845) 479-5674

Bald Eagle Commons

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

$529,000

3 beds

4 baths

162 RICHMOND RD, WEST MILFORD TWP., NJ, ...

Community: Bald Eagle Commons

The Savannah

111 PROSPECT ST 4A, WESTFIELD TOWN, NJ, ..., Westfield Town, NJ 07090

$1,599,000

2 beds

3 baths

111 PROSPECT ST 4A, WESTFIELD TOWN, NJ, ...

Community: The Savannah

Heritage Hills

220 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$699,000

3 beds

2 baths

1,689 sq ft

Condo

220 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

The Seasons at East Meadow

421 AUTUMN DR, HEMPSTEAD, NY, 11554, Hempstead, NY 11554

$635,000

2 beds

2 baths

1,272 sq ft

Condo

421 AUTUMN DR, HEMPSTEAD, NY, 11554

Community: The Seasons at East Meadow

Venue at The American

22 KELSCH DR, MORRIS PLAINS BORO, NJ, 07..., Morris Plains Boro, NJ 07950

$1,095,000

3 beds

3 baths

22 KELSCH DR, MORRIS PLAINS BORO, NJ, 07...

Community: Venue at The American

Apple Ridge

239 WESTERVELT LN, MAHWAH TWP., NJ, 0743..., Mahwah Twp., NJ 07430

$950,000

3 beds

4 baths

2,966 sq ft

239 WESTERVELT LN, MAHWAH TWP., NJ, 0743...

Community: Apple Ridge

Rivington

424 CENTER MEADOW LN 424, DANBURY, CT, 0..., Danbury, CT 06810

$479,900

2 beds

2 baths

1,258 sq ft

Condo

424 CENTER MEADOW LN 424, DANBURY, CT, 0...

Community: Rivington

Kimbolton

1 VOORHEES CT, FAR HILLS BORO, NJ, 07931, Far Hills Boro, NJ 07931

$1,665,703

4 beds

5 baths

4,225 sq ft

1 VOORHEES CT, FAR HILLS BORO, NJ, 07931

Community: Kimbolton

Greenbriar at Fox Ridge

6102 VETERANS DR, ROCKAWAY TOWNSHIP, NJ,..., Rockaway Township, NJ 07885

$468,000

2 beds

3 baths

Townhouse

6102 VETERANS DR, ROCKAWAY TOWNSHIP, NJ,...

Community: Greenbriar at Fox Ridge

Apple Ridge

239 WESTERVELT LN, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$950,000

3 beds

4 baths

Townhouse

239 WESTERVELT LN, MAHWAH, NJ, 07430

Community: Apple Ridge

Heritage Hills

88 HERITAGE HLS B, SOMERS, NY, 10589, Somers, NY 10589

$699,000

2 beds

3 baths

1,585 sq ft

Condo

88 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (845) 479-5674

Jefferson Village

196 LONG HILL DR B, YORKTOWN, NY, 10598, Yorktown, NY 10598

$675,000

2 beds

2 baths

1,550 sq ft

Condo

196 LONG HILL DR B, YORKTOWN, NY, 10598

Community: Jefferson Village

Fox Hills

4210 CLEVELAND LN 210, ROCKAWAY TWP., NJ..., Rockaway Twp., NJ 07866

3 baths

8 SCHMIDT CIR, WATCHUNG BORO, NJ, 07069

Community: Lakeside Villas

Wildflowers at Wallkill

111 JASMINE DR, MIDDLETOWN, NY, 10940, Middletown, NY 10940

$505,000

2 beds

2 baths

1,473 sq ft

House

111 JASMINE DR, MIDDLETOWN, NY, 10940

Community: Wildflowers at Wallkill

Apple Ridge

89 FISHER RD, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$990,000

3 beds

3 baths

Townhouse

89 FISHER RD, MAHWAH, NJ, 07430

Community: Apple Ridge

Apple Ridge

89 FISHER RD, MAHWAH TWP., NJ, 07430, Mahwah Twp., NJ 07430

$990,000

3 beds

3 baths

2,112 sq ft

89 FISHER RD, MAHWAH TWP., NJ, 07430

Community: Apple Ridge

Jefferson Village

20 HASTINGS CT A, YORKTOWN, NY, 10598, Yorktown, NY 10598

$345,000

1 beds

1 baths

800 sq ft

Condo

20 HASTINGS CT A, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (845) 479-5674

Rivington

215 CENTER MEADOW LN 215, DANBURY, CT, 0..., Danbury, CT 06810

$499,000

2 beds

2 baths

1,258 sq ft

Condo

215 CENTER MEADOW LN 215, DANBURY, CT, 0...

Community: Rivington

The Meadows at Panther Valley

51 JUNEGRASS WAY, ALLAMUCHY TWP., NJ, 07..., Allamuchy Twp., NJ 07840

$564,900

3 beds

3 baths

1,814 sq ft

51 JUNEGRASS WAY, ALLAMUCHY TWP., NJ, 07...

Community: The Meadows at Panther Valley

Overlook

2040 SUMMIT LOOP 57, CARMEL, NY, 10512, Carmel, NY 10512

$899,000

2 beds

2 baths

1,948 sq ft

Condo

2040 SUMMIT LOOP 57, CARMEL, NY, 10512

Community: Overlook

Del Webb Florham Park

1 VANDERBILT BLVD 303, FLORHAM PARK BORO..., Florham Park Boro, NJ 07932

3 beds

2 baths

Condo

13 WHITNEY AVE 402, MORRIS PLAINS BOROUG...

Community: Venue at The American

Reserve at Hawk Pointe

14 KESTREL CT, WASHINGTON TWP., NJ, 0788..., Washington Twp., NJ 07882

$529,000

3 beds

3 baths

2,547 sq ft

14 KESTREL CT, WASHINGTON TWP., NJ, 0788...

Community: Reserve at Hawk Pointe

Cindy Certified

4912 RESTON DR, FORKS TWP, PA, 18040, Forks Twp, PA 18040

$670,000

3 beds

2 baths

1,936 sq ft

Detached

4912 RESTON DR, FORKS TWP, PA, 18040

The Views at Pomona

1309 VIEWS WAY, RAMAPO, NY, 10970, Ramapo, NY 10970

$399,000

2 beds

2 baths

1,245 sq ft

Condo

1309 VIEWS WAY, RAMAPO, NY, 10970

Community: The Views at Pomona

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

Questions? Call us: (845) 479-5674

The Retreat at Carmel

8 ATKINS CT, CARMEL, NY, 10512, Carmel, NY 10512

$690,000

2 beds

3 baths

2,148 sq ft

Condo

8 ATKINS CT, CARMEL, NY, 10512

Community: The Retreat at Carmel

Wanaque Reserve

2202 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$344,900

2 beds

2 baths

2202 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

1 2 3 4 5…6

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.

Want more information about active adult communities around Middletown?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Middletown?

Call us: (845) 479-5674

220 homes

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Aug 25, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

98 communities near Middletown

220 homes near Middletown

3 beds

3 baths

2,372 sq ft

3 beds

3 baths

Townhouse

2 beds

2 baths

2 beds

2 baths

1,145 sq ft

House

3 beds

4 baths

Townhouse

3 beds

4 baths

2 beds

3 baths

3 beds

2 baths

1,689 sq ft

Condo

2 beds

2 baths

1,272 sq ft

Condo

3 beds

3 baths

3 beds

4 baths

2,966 sq ft

2 beds

2 baths

1,258 sq ft

Condo

4 beds

5 baths

4,225 sq ft

2 beds

3 baths

Townhouse

3 beds

4 baths

Townhouse

2 beds

3 baths

1,585 sq ft

Condo

2 beds

2 baths

1,550 sq ft

Condo

2 beds

2 baths

2 beds

2 baths

1,000 sq ft

Condo

2 beds

2 baths

1,265 sq ft

Condo

2 beds

2 baths

1,500 sq ft

Condo

2 beds

2 baths

1,200 sq ft

Condo

2 beds

3 baths

2 beds

2 baths

1,473 sq ft

House