Middletown, NY 55+ active adult communities & homes for sale - Page 4

148 homes near Middletown

Sort by:

Relevance

3 rating (2 reviews)

Heritage Hills

$400ks - $1Ms

Heritage Hills, Somers, NY

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

4.8 rating (4 reviews)

Wanaque Reserve

$300ks - $500ks

Wanaque Reserve, Wanaque, NJ

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

Bald Eagle Commons

$100ks - $300ks

Bald Eagle Commons, West Milford, NJ

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

Greenbriar at Fox Ridge

$300ks - $500ks

Greenbriar at Fox Ridge, Rockaway, NJ

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

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Fox Hills

$300ks - $400ks

Fox Hills, Rockaway, NJ

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

5 rating (1 reviews)

Warwick Grove

$400ks - $600ks

Warwick Grove, Warwick, NY

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

Regency at Flanders

$300ks - $900ks

Regency at Flanders, Flanders, NJ

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

Traditions of America at ...

$500ks - $600ks

Traditions of America at ..., Bethlehem, PA

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

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

Questions? Call us: (845) 479-5674

Four Seasons at Wayne

$300ks - $400ks

Four Seasons at Wayne, Wayne, NJ

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

Rivington

$300ks - $900ks

Rivington, Danbury, CT

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

5 rating (2 reviews)

Blackburne Farm Townhomes

$400ks

Blackburne Farm Townhomes, Campbell Hall, NY

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

Clove Hill Manor

$200ks - $300ks

Clove Hill Manor, Wantage, NJ

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

1 rating (1 reviews)

Brookfield Estates

$300ks

Brookfield Estates, Belvidere, NJ

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

Riverview Estates Active ...

$500ks - $600ks

Riverview Estates Active ..., Easton, PA

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

5 rating (1 reviews)

The Village at Upstream F...

$100ks - $200ks

The Village at Upstream F..., Easton, PA

Resale Only | 55+ age-restricted | Built 2002 - 2009 | 124 homes

The Seasons at Seaford

$600ks

The Seasons at Seaford, Seaford, NY

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

HarborView

$600ks - $800ks

HarborView, Port Washington, NY

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

Reserve at Hawk Pointe

$400ks - $500ks

Reserve at Hawk Pointe, Washington, NJ

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

Brookfield Glen

$100ks - $200ks

Brookfield Glen, Belvidere, NJ

Resale Only | 55+ age-restricted | Built 2003 - 2006 | 124 homes

The Commons at Mendham

$300ks - $600ks

The Commons at Mendham, Mendham, NJ

Resale Only | Age-targeted | Built 1978 - 1985 | 330 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

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

Questions? Call us: (845) 479-5674

Kimbolton

$900ks - $1Ms

Kimbolton, Far Hills, NJ

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

5 rating (1 reviews)

Paris Square

$600ks - $900ks

Paris Square, Northvale, NJ

New and Resale | 55+ age-restricted | Built 2000 - present | 88 homes

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

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

Regency at Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

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

Wildflowers at Wallkill

$400ks - $500ks

Wildflowers at Wallkill, Middletown, NY

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

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

Questions? Call us: (845) 479-5674

Knickerbocker Bay Club

$700ks - $3Ms

Knickerbocker Bay Club, Port Washington, NY

New and Resale | 55+ age-restricted | Built 2014 - present | 32 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

1 2...3

Overlook

2088 SUMMIT LOOP # 79, CARMEL, NY, 10512, Carmel, NY 10512

$849,000

2 beds

4 baths

2,711 sq ft

Condo

2088 SUMMIT LOOP # 79, CARMEL, NY, 10512

Community: Overlook

Fox Hills

2210 JOHNSON DR, ROCKAWAY BORO, NJ, 0786..., Rockaway Boro, NJ 07866

$500,000

2 beds

2 baths

1,837 sq ft

2210 JOHNSON DR, ROCKAWAY BORO, NJ, 0786...

Community: Fox Hills

Greenbriar at Fox Ridge

7311 POLK DR, ROCKAWAY TWP., NJ, 07866, Rockaway Twp., NJ 07866

$559,000

2 beds

2 baths

7311 POLK DR, ROCKAWAY TWP., NJ, 07866

Community: Greenbriar at Fox Ridge

Riverview Estates Active Adult

868 VENETO CT # 66, EASTON, PA, 18040, Easton, PA 18040

$544,900

2 beds

3 baths

Condo

868 VENETO CT # 66, EASTON, PA, 18040

Community: Riverview Estates Active Adult

Horizons at Mount Arlington

29 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07..., Mount Arlington, NJ 07856

$478,888

2 beds

2 baths

1,840 sq ft

29 RIDGEVIEW LN, MOUNT ARLINGTON, NJ, 07...

Community: Horizons at Mount Arlington

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

Questions? Call us: (845) 479-5674

The Commons at Mendham

16 GALWAY DR, MENDHAM BORO, NJ, 07945, Mendham Boro, NJ 07945

$734,000

3 beds

3 baths

2,292 sq ft

16 GALWAY DR, MENDHAM BORO, NJ, 07945

Community: The Commons at Mendham

Greenbriar at Fox Ridge

5307 VETERANS DR, WHARTON, NJ, 07885, Wharton, NJ 07885

$469,000

2 beds

3 baths

5307 VETERANS DR, WHARTON, NJ, 07885

Community: Greenbriar at Fox Ridge

Heritage Hills

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

$596,000

2 beds

2 baths

1,428 sq ft

Condo

348 HERITAGE HLS A, SOMERS, NY, 10589

Community: Heritage Hills

Wanaque Reserve

9116 WARRENS WAY # 116, WANAQUE, NJ, 074..., Wanaque, NJ 07465

$429,000

2 beds

2 baths

9116 WARRENS WAY # 116, WANAQUE, NJ, 074...

Community: Wanaque Reserve

Heritage Hills

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

$1,100,000

3 beds

2 baths

1,905 sq ft

Condo

593 HERITAGE HLS B, SOMERS, NY, 10589

Community: Heritage Hills

Fox Hills

1111 CLINTON LN # 111, ROCKAWAY BORO, NJ..., Rockaway Boro, NJ 07866

$475,000

2 beds

2 baths

1,782 sq ft

1111 CLINTON LN # 111, ROCKAWAY BORO, NJ...

Community: Fox Hills

Reserve at Hawk Pointe

11 SHARP SHINNED CT, WASHINGTON TWP., NJ..., Washington Twp., NJ 07882

$539,000

3 beds

3 baths

11 SHARP SHINNED CT, WASHINGTON TWP., NJ...

Community: Reserve at Hawk Pointe

Breton Hills

704 BRETON WAY # 704, GLEN COVE, NY, 115..., Glen Cove, NY 11542

$649,000

2 beds

2 baths

1,440 sq ft

Condo

704 BRETON WAY # 704, GLEN COVE, NY, 115...

Community: Breton Hills

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

Questions? Call us: (845) 479-5674

Traditions of America at Green Pond

3801 LOYAL LN, EASTON, PA, 18045, Easton, PA 18045

$842,000

3 beds

3 baths

3,021 sq ft

3801 LOYAL LN, EASTON, PA, 18045

Community: Traditions of America at Green Pond

Jefferson Village

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N..., Yorktown Heights, NY 10598

$375,000

2 beds

2 baths

1,100 sq ft

Condo

45 JEFFERSON OVAL D, YORKTOWN HEIGHTS, N...

Community: Jefferson Village

Wanaque Reserve

5201 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465

$435,000

2 beds

2 baths

Condo

5201 WARRENS WAY, WANAQUE, NJ, 07465

Community: Wanaque Reserve

Bald Eagle Commons

7308 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480

$279,000

2 beds

2 baths

Condo

7308 RICHMOND RD, WEST MILFORD, NJ, 0748...

Community: Bald Eagle Commons

Wanaque Reserve

8415 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465

$476,000

2 beds

2 baths

Condo

8415 WARRENS WAY, WANAQUE, NJ, 07465

Community: Wanaque Reserve

Glassbury Court at Cold Spring

43 YESTERDAY DR, COLD SPRING, NY, 10516, Cold Spring, NY 10516

$700,000

2 beds

3 baths

2,620 sq ft

Condo

43 YESTERDAY DR, COLD SPRING, NY, 10516

Community: Glassbury Court at Cold Spring

Wanaque Reserve

7414 WARRENS WAY DEEDED PARKING, WANAQUE..., Wanaque, NJ 07465

$442,000

2 beds

2 baths

Condo

7414 WARRENS WAY DEEDED PARKING, WANAQUE...

Community: Wanaque Reserve

Bald Eagle Commons

9302 RICHMOND RD, WEST MILFORD, NJ, 0748..., West Milford, NJ 07480

$264,000

2 beds

2 baths

Condo

9302 RICHMOND RD, WEST MILFORD, NJ, 0748...

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

2 RICHMOND RD 210, WEST MILFORD, NJ, 074..., West Milford, NJ 07480

$264,900

2 beds

2 baths

Condo

2 RICHMOND RD 210, WEST MILFORD, NJ, 074...

Community: Bald Eagle Commons

Riverview Estates Active Adult

868 VENETO CT # 66, FORKS TWP, PA, 18040, Forks Twp, PA 18040

$544,900

2 beds

3 baths

1,966 sq ft

Townhouse

868 VENETO CT # 66, FORKS TWP, PA, 18040

Community: Riverview Estates Active Adult

Warwick Grove

2 SLY ST, WARWICK (TOWN), NY, 10990, Warwick (town), NY 10990

$849,000

2 beds

3 baths

2,256 sq ft

House

2 SLY ST, WARWICK (TOWN), NY, 10990

Community: Warwick Grove

Winthrop Court

8205 HARCOURT RD # 8205, CLIFTON, NJ, 07..., Clifton, NJ 07013

$499,000

2 beds

2 baths

Condo

8205 HARCOURT RD # 8205, CLIFTON, NJ, 07...

Community: Winthrop Court

Brookfield Glen

$264,900

2 beds

2 baths

1,179 sq ft

6015 BROOKFIELD GLEN DR # 15, BELVIDERE,...

Community: Brookfield Glen

HarborView

$648,000

1 beds

2 baths

1,161 sq ft

Condo

100 HARBOR VIEW DR 423, PORT WASHINGTON,...

Community: HarborView

Sterling Mist

72 SCHINDLER CT, PARSIPPANY, NJ, 07054, Parsippany, NJ 07054

$779,000

7 beds

6 baths

Townhouse

72 SCHINDLER CT, PARSIPPANY, NJ, 07054

Community: Sterling Mist

1 2 3 4

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.

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 [email protected]. 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

148 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: Feb 24, 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 4

95 communities near Middletown

148 homes near Middletown

2 beds

4 baths

2,711 sq ft

Condo

2 beds

2 baths

1,837 sq ft

2 beds

2 baths

2 beds

3 baths

Condo

2 beds

2 baths

1,840 sq ft

3 beds

3 baths

2,292 sq ft

2 beds

3 baths

2 beds

2 baths

1,428 sq ft

Condo

2 beds

2 baths

3 beds

2 baths

1,905 sq ft

Condo

2 beds

2 baths

1,782 sq ft

3 beds

3 baths

2 beds

2 baths

1,440 sq ft

Condo

3 beds

3 baths

3,021 sq ft

2 beds

2 baths

1,100 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

Condo

2 beds

2 baths

Condo

2 beds

3 baths

2,620 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

Condo

2 beds

2 baths

Condo

2 beds

3 baths

1,966 sq ft

Townhouse

2 beds

3 baths

2,256 sq ft

House

2 beds