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

192 homes near Middletown

Sort by:

Relevance

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

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

- $800ks

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

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

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 Fishkill

$300ks - $400ks

Regency at Fishkill, Fishkill, NY

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

The Highlands at Glenmoor

$300ks - $400ks

The Highlands at Glenmoor, Easton, PA

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

Greenbriar at Fox Ridge

$300ks - $500ks

Greenbriar at Fox Ridge, Rockaway, NJ

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

Reserve at Hawk Pointe

$400ks - $500ks

Reserve at Hawk Pointe, Washington, NJ

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

Lakeside Villas

$400ks - $500ks

Lakeside Villas, Watchung, NJ

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

Fox Crest

$300ks - $600ks

Fox Crest, Rockaway, NJ

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

Nolan's Ridge

$400ks - $700ks

Nolan's Ridge, Mount Arlington, NJ

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

Apple Ridge

$500ks - $1Ms

Apple Ridge, Mahwah, NJ

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

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

Questions? Call us: (845) 479-5674

Breton Hills

$500ks

Breton Hills, Glen Cove, NY

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

Horizons at Mount Arlingt...

$400ks

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

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

Meadowbrook Pointe Athlet...

$700ks - $1Ms

Meadowbrook Pointe Athlet..., Westbury, NY

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

Clove Hill Manor

$200ks - $300ks

Clove Hill Manor, Wantage, NJ

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

$600ks

The Seasons at Seaford, Seaford, NY

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

HarborView

$600ks - $1Ms

HarborView, Port Washington, NY

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

The Retreat at Carmel

$300ks - $800ks

The Retreat at Carmel, Carmel, NY

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

1 rating (1 reviews)

Brookfield Estates

$300ks

Brookfield Estates, Belvidere, NJ

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

Enclave at Shackamaxon

$1Ms

Enclave at Shackamaxon, Scotch Plains, NJ

Resale Only | 55+ age-restricted | Built 2016 - 2018 | 56 homes

Brookfield Glen

$100ks - $200ks

Brookfield Glen, Belvidere, NJ

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

Regency at Flanders

$800ks

Regency at Flanders, Flanders, NJ

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

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)

Paris Square

$500ks - $700ks

Paris Square, Northvale, NJ

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

Dutchgate

$300ks - $500ks

Dutchgate, Valley Stream, NY

Resale Only | 55+ age-restricted | Built 2009 - 2015 | 348 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 The Prome...

$700ks - $1Ms

Four Seasons at The Prome..., Warren, NJ

Resale Only | 55+ age-restricted | Built 2007 - 2014 | 208 homes

Four Seasons at Bridgewat...

$300ks - $400ks

Four Seasons at Bridgewat..., Bridgewater, NJ

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

Riverview Estates Active ...

$500ks - $600ks

Riverview Estates Active ..., Easton, PA

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

Regency at Denville

$700ks - $800ks

Regency at Denville, Denville, NJ

Resale Only | 55+ age-restricted | Built 2004 - 2009 | 140 homes

1 2...3

Nolan's Ridge

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

$479,900

2 beds

2 baths

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

Community: Nolan's Ridge

Glenmoor

$549,900

3 beds

4 baths

2,792 sq ft

Condo

158 GLENMOOR CIR, EASTON, PA, 18045

Community: Glenmoor

Overlook

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

$849,000

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

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

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

Questions? Call us: (845) 479-5674

The Village at Fox Crossing

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

$244,900

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

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

Regency at Flanders

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

$899,000

4 beds

3 baths

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

Community: Regency at Flanders

Bald Eagle Commons

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

$205,000

1 beds

1 baths

Condo

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

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

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

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

Bald Eagle Commons

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

$260,000

2 beds

2 baths

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

Community: Bald Eagle Commons

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

Questions? Call us: (845) 479-5674

Reserve at Hawk Pointe

35 SPARROWHAWK ST, WASHINGTON TWP., NJ, ..., Washington Twp., NJ 07882

$580,000

2 beds

3 baths

1,910 sq ft

35 SPARROWHAWK ST, WASHINGTON TWP., NJ, ...

Community: Reserve at Hawk Pointe

Fox Hills

2304 CLINTON LN, ROCKAWAY TWP., NJ, 0786..., Rockaway Twp., NJ 07866

$479,000

2 beds

2 baths

1,837 sq ft

2304 CLINTON LN, ROCKAWAY TWP., NJ, 0786...

Community: Fox Hills

Rivington

131 WINDING RIDGE WAY 131, DANBURY, CT, ..., Danbury, CT 06810

$750,000

3 beds

3 baths

1,592 sq ft

Condo

131 WINDING RIDGE WAY 131, DANBURY, CT, ...

Community: Rivington

Apple Ridge

37 NIAGARA DR 37, MAHWAH, NJ, 07430, Mahwah, NJ 07430

$760,000

2 beds

3 baths

Townhouse

37 NIAGARA DR 37, MAHWAH, NJ, 07430

Community: Apple Ridge

Four Seasons at Cedar Grove

1209 HOLLY LN 141, CEDAR GROVE, NJ, 0700..., Cedar Grove, NJ 07009

$750,000

2 beds

2 baths

Condo

1209 HOLLY LN 141, CEDAR GROVE, NJ, 0700...

Community: Four Seasons at Cedar Grove

Jefferson Village

59 KIRBY CLOSE D, YORKTOWN, NY, 10598, Yorktown, NY 10598

$375,000

2 beds

2 baths

910 sq ft

Condo

59 KIRBY CLOSE D, YORKTOWN, NY, 10598

Community: Jefferson Village

Hawk Pointe

18 SPARROWHAWK ST, WASHINGTON TWP., NJ, ..., Washington Twp., NJ 07882

$565,000

2 beds

4 baths

18 SPARROWHAWK ST, WASHINGTON TWP., NJ, ...

Community: Hawk Pointe

Heritage Hills

$875,000

2 beds

2 baths

1,663 sq ft

Condo

415 HERITAGE HILLS DR D, SOMERS, NY, 105...

Community: Heritage Hills

Fox Hills

2205 CLINTON LN, ROCKAWAY TWP., NJ, 0786..., Rockaway Twp., NJ 07866

$474,000

2 beds

2 baths

2205 CLINTON LN, ROCKAWAY TWP., NJ, 0786...

Community: Fox Hills

Apple Ridge

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

$899,999

3 beds

3 baths

Townhouse

89 FISHER RD, MAHWAH, NJ, 07430

Community: Apple Ridge

Jefferson Village

18L HASTINGS CT, YORKTOWN, NY, 10598, Yorktown, NY 10598

$385,000

2 beds

1 baths

1,000 sq ft

Condo

18L HASTINGS CT, YORKTOWN, NY, 10598

Community: Jefferson Village

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

Questions? Call us: (845) 479-5674

Four Seasons at Great Notch Spa and Club

8 QUARTZ WAY, WOODLAND PARK, NJ, 07424, Woodland Park, NJ 07424

$800,000

2 beds

2 baths

Townhouse

8 QUARTZ WAY, WOODLAND PARK, NJ, 07424

Community: Four Seasons at Great Notch Spa and Club

Wanaque Reserve

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

$410,000

2 beds

2 baths

Condo

5201 WARRENS WAY, WANAQUE, NJ, 07465

Community: Wanaque Reserve

Brookfield Estates

95 KENSINGTON CIR, WHITE TWP., NJ, 07823, White Twp., NJ 07823

$410,000

2 beds

2 baths

1,562 sq ft

95 KENSINGTON CIR, WHITE TWP., NJ, 07823

Community: Brookfield Estates

Rivington

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

$489,900

2 beds

2 baths

1,258 sq ft

Condo

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

Community: Rivington

Wanaque Reserve

2217 WARRENS WAY, WANAQUE, NJ, 07465, Wanaque, NJ 07465

$425,000

2 beds

2 baths

Condo

2217 WARRENS WAY, WANAQUE, NJ, 07465

Community: Wanaque Reserve

Wanaque Reserve

2217 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$425,000

2 beds

2 baths

2217 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

Wanaque Reserve

5402 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$409,700

2 beds

2 baths

1,768 sq ft

5402 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

Paris Square

5201 RIO VISTA LN, NORTHVALE, NJ, 07647, Northvale, NJ 07647

$735,000

2 beds

2 baths

Condo

5201 RIO VISTA LN, NORTHVALE, NJ, 07647

Community: Paris Square

Overlook

3004 EASTVIEW DR 105, CARMEL, NY, 10512, Carmel, NY 10512

$737,000

2 beds

3 baths

2,040 sq ft

Condo

3004 EASTVIEW DR 105, CARMEL, NY, 10512

Community: Overlook

Wanaque Reserve

5203 WARRENS WAY, WANAQUE BORO, NJ, 0746..., Wanaque Boro, NJ 07465

$399,000

2 beds

2 baths

1,768 sq ft

5203 WARRENS WAY, WANAQUE BORO, NJ, 0746...

Community: Wanaque Reserve

Heritage Hills

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

$690,000

1 beds

2 baths

1,296 sq ft

Condo

769 HERITAGE HLS C, SOMERS, NY, 10589

Community: Heritage Hills

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

Questions? Call us: (845) 479-5674

Warwick Grove

32 COWDREY ST, WARWICK (TOWN), NY, 10990, Warwick (town), NY 10990

$900,000

3 beds

3 baths

2,577 sq ft

House

32 COWDREY ST, WARWICK (TOWN), NY, 10990

Community: Warwick Grove

Four Seasons at Great Notch Spa and Club

7 GRAPHITE DR, LITTLE FALLS, NJ, 07424, Little Falls, NJ 07424

$849,900

2 beds

3 baths

7 GRAPHITE DR, LITTLE FALLS, NJ, 07424

Community: Four Seasons at Great Notch Spa and Club

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 309 days. The average price of homes for sale in this community is approximately $516,048, though prices can range widely based on the size, location, and amenities of the community. For example, homes in Wildflowers at Wallkill average around $516,048.

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

192 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: May 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 4

95 communities near Middletown

192 homes near Middletown

2 beds

2 baths

3 beds

4 baths

2,792 sq ft

Condo

2 beds

2 baths

1,948 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

Condo

2 beds

2 baths

1,302 sq ft

Detached

2 beds

2 baths

Condo

2 beds

3 baths

4 beds

3 baths

1 beds

1 baths

Condo

2 beds

2 baths

1,300 sq ft

Condo

2 beds

2 baths

Condo

2 beds

2 baths

2 beds

2 baths

1 baths

550 sq ft

Condo

2 beds

2 baths

2 beds

3 baths

1,910 sq ft

2 beds

2 baths

1,837 sq ft

3 beds

3 baths

1,592 sq ft

Condo

2 beds

3 baths

Townhouse

2 beds

2 baths

Condo

2 beds

2 baths

910 sq ft

Condo

2 beds

4 baths

2 beds

2 baths

1,663 sq ft

Condo

2 beds

2 baths

3 beds

3 baths

Townhouse