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

19 communities near Middletown

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Traditions at Whitehall

$400ks - $500ks

Traditions at Whitehall, Middletown, DE

New Construction | 55+ age-restricted | Built 2019 - present | 250 homes

The Villas at The Preserv...

$400ks

The Villas at The Preserv..., Townsend, DE

New Construction | 55+ age-restricted | Built 2017 - present | 144 homes

Four Seasons at Baymont F...

$400ks - $500ks

Four Seasons at Baymont F..., Middletown, DE

New Construction | Age-targeted | Built 2019 - present | 288 homes

Venue at Winchelsea

$400ks - $600ks

Venue at Winchelsea, Middletown, DE

New Construction | 55+ age-restricted | Built 2024 - present | 336 homes

The Cascades

$400ks - $500ks

The Cascades, Newark, DE

New Construction | 55+ age-restricted | Built 2021 - present | 113 homes

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

Questions? Call us: (302) 279-7380

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Ashland

$300ks - $400ks

Ashland, Smyrna, DE

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 150 homes

2.4 rating (5 reviews)

Legacy at The Village of ...

$400ks

Legacy at The Village of ..., Newark, DE

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 194 homes

3 rating (2 reviews)

Spring Arbor

$300ks - $500ks

Spring Arbor, Middletown, DE

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 317 homes

5 rating (1 reviews)

Springmill

$300ks - $400ks

Springmill, Middletown, DE

Resale Only | 55+ age-restricted | Built 2000 - 2007 | 362 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.

Crossings at Christiana

$200ks

Crossings at Christiana, Bear, DE

Resale Only | 55+ age-restricted | Built 2003 - 2011 | 140 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Riverbend

$400ks

Riverbend, New Castle, DE

New Construction | 55+ age-restricted | Built 2021 - present | 200 homes

Whispering Woods

$300ks - $400ks

Whispering Woods, Middletown, DE

New and Resale | 55+ age-restricted | Built 2017 - present | 178 homes

4 rating (1 reviews)

Village of Fountainview

$100ks - $200ks

Village of Fountainview, Newark, DE

Resale Only | 55+ age-restricted | Built 2007 - 2019 | 124 homes

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Questions? Call us: (302) 279-7380

Legacy at The Preserve at...

$400ks - $500ks

Legacy at The Preserve at..., Middletown, DE

New and Resale | 55+ age-restricted | Built 2016 - present | 205 homes

Village of Long Creek

$400ks

Village of Long Creek, Newark, DE

Resale Only | 55+ age-restricted | Built 2007 - 2016 | 100 homes

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

Questions? Call us: (302) 279-7380

The Ponds at Bayberry

$300ks - $500ks

The Ponds at Bayberry, Middletown, DE

New and Resale | 55+ age-restricted | Built 2015 - present | 572 homes

Parks Edge at Bayberry

$400ks - $600ks

Parks Edge at Bayberry, Middletown, DE

New Construction | 55+ age-restricted | Built 2022 - present | 210 homes

Four Seasons at Silver Ma...

$400ks - $500ks

Four Seasons at Silver Ma..., Middletown, DE

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 299 homes

Village of Red Lion Creek

$200ks - $300ks

Village of Red Lion Creek, Bear, DE

Resale Only | 55+ age-restricted | Built 2002 - 2005 | 85 homes

New Village of Long Creek

55 DEVALINDER DR, NEWARK, DE, 19702, Newark, DE 19702

$504,900

2 beds

2 baths

1,950 sq ft

55 DEVALINDER DR, NEWARK, DE, 19702

Community: Village of Long Creek

New Legacy at The Village of Fox Meadow

218 ANITA CT, NEWARK, DE, 19702, Newark, DE 19702

$415,000

3 beds

3 baths

2,025 sq ft

218 ANITA CT, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

New Four Seasons at Baymont Farms

19 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1..., Middletown, DE 19709

$580,400

3 beds

3 baths

2,378 sq ft

19 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1...

Community: Four Seasons at Baymont Farms

New Spring Arbor

79 LATTICE LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$499,000

2 beds

2 baths

2,275 sq ft

79 LATTICE LN, MIDDLETOWN, DE, 19709

Community: Spring Arbor

The Cascades

1001 SHANNON FALLS DR, NEWARK, DE, 19702, Newark, DE 19702

$539,900

3 beds

2 baths

2,050 sq ft

1001 SHANNON FALLS DR, NEWARK, DE, 19702

Community: The Cascades

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

Questions? Call us: (302) 279-7380

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Venue at Winchelsea

2220 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$559,775

3 beds

3 baths

3,397 sq ft

2220 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

Venue at Winchelsea

2243 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$474,809

3 beds

3 baths

2,443 sq ft

2243 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

Four Seasons at Baymont Farms

15 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1..., Middletown, DE 19709

$504,400

2 beds

2 baths

1,780 sq ft

15 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1...

Community: Four Seasons at Baymont Farms

Whispering Woods

$423,000

2 beds

2 baths

1,275 sq ft

1428 WHISPERING WOODS RD, MIDDLETOWN, DE...

Community: Whispering Woods

Four Seasons at Silver Maple

137 SILVER MAPLE RD, MIDDLETOWN, DE, 197..., Middletown, DE 19709

$519,900

3 beds

2 baths

1,625 sq ft

137 SILVER MAPLE RD, MIDDLETOWN, DE, 197...

Community: Four Seasons at Silver Maple

Four Seasons at Baymont Farms

507 CHERRY BARK RD, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$615,000

3 beds

3 baths

2,700 sq ft

507 CHERRY BARK RD, MIDDLETOWN, DE, 1970...

Community: Four Seasons at Baymont Farms

Four Seasons at Baymont Farms

505 CHERRY BARK RD, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$565,000

3 beds

3 baths

2,650 sq ft

505 CHERRY BARK RD, MIDDLETOWN, DE, 1970...

Community: Four Seasons at Baymont Farms

Spring Arbor

264 TRELLIS LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$425,000

2 beds

2 baths

1,800 sq ft

264 TRELLIS LN, MIDDLETOWN, DE, 19709

Community: Spring Arbor

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Questions? Call us: (302) 279-7380

Traditions at Whitehall

240 BALDY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$625,000

3 beds

2 baths

2,725 sq ft

240 BALDY LN, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

Crossings at Christiana

238 GLADSTONE WAY, BEAR, DE, 19701, Bear, DE 19701

$330,000

2 beds

2 baths

1,400 sq ft

238 GLADSTONE WAY, BEAR, DE, 19701

Community: Crossings at Christiana

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

Questions? Call us: (302) 279-7380

The Ponds at Bayberry

4533 CAGNEY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$725,000

4 beds

3 baths

3,375 sq ft

4533 CAGNEY LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

Venue at Winchelsea

3114 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$349,642

3 beds

2 baths

2,669 sq ft

3114 PETT LEVEL DR, MIDDLETOWN, DE, 1970...

Community: Venue at Winchelsea

Parks Edge at Bayberry

3016 BARBER LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$615,000

2 beds

2 baths

1,866 sq ft

3016 BARBER LN, MIDDLETOWN, DE, 19709

Community: Parks Edge at Bayberry

Riverbend

219 HERON CIR, NEW CASTLE, DE, 19720, New Castle, DE 19720

$495,000

3 beds

3 baths

2,375 sq ft

219 HERON CIR, NEW CASTLE, DE, 19720

Community: Riverbend

Venue at Winchelsea

2311 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$479,890

3 beds

3 baths

2,443 sq ft

2311 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

The Villas at The Preserve at Robinson Farms

929 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734

$595,000

3 beds

4 baths

4,607 sq ft

929 ROBINSON RD, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

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

Questions? Call us: (302) 279-7380

The Cascades

676 MAYFIELD FALLS DR, NEWARK, DE, 19702, Newark, DE 19702

$495,000

2 beds

2 baths

1,764 sq ft

676 MAYFIELD FALLS DR, NEWARK, DE, 19702

Community: The Cascades

Ashland

26 CYCLOPS TRL, SMYRNA, DE, 19977, Smyrna, DE 19977

$425,000

3 beds

3 baths

1,848 sq ft

26 CYCLOPS TRL, SMYRNA, DE, 19977

Community: Ashland

Crossings at Christiana

244 GLADSTONE WAY, BEAR, DE, 19701, Bear, DE 19701

$362,500

2 beds

2 baths

1,400 sq ft

244 GLADSTONE WAY, BEAR, DE, 19701

Community: Crossings at Christiana

Traditions at Whitehall

234 BALDY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$719,900

3 beds

3 baths

2,725 sq ft

234 BALDY LN, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

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Questions? Call us: (302) 279-7380

Four Seasons at Baymont Farms

114 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$720,000

4 beds

4 baths

2,595 sq ft

114 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19...

Community: Four Seasons at Baymont Farms

Legacy at The Preserve at Deep Creek

230 ANGLESEY DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$584,900

2 beds

3 baths

2,475 sq ft

230 ANGLESEY DR, MIDDLETOWN, DE, 19709

Community: Legacy at The Preserve at Deep Creek

Ashland

28 PEGASUS LN, SMYRNA, DE, 19977, Smyrna, DE 19977

$429,900

2 beds

2 baths

1,720 sq ft

28 PEGASUS LN, SMYRNA, DE, 19977

Community: Ashland

Spring Arbor

148 GAZEBO LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$479,900

3 beds

2 baths

1,650 sq ft

148 GAZEBO LN, MIDDLETOWN, DE, 19709

Community: Spring Arbor

Venue at Winchelsea

3027 IVYHOUSE LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$564,495

3 beds

3 baths

2,356 sq ft

3027 IVYHOUSE LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

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Questions? Call us: (302) 279-7380

Springmill

304 DAY LILLY WAY, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$420,000

2 beds

2 baths

1,500 sq ft

304 DAY LILLY WAY, MIDDLETOWN, DE, 19709

Community: Springmill

Legacy at The Village of Fox Meadow

433 PIERCE RUN, NEWARK, DE, 19702, Newark, DE 19702

$429,000

3 beds

4 baths

2,625 sq ft

433 PIERCE RUN, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

Traditions at Whitehall

204 BALDY LN ALRICH, MIDDLETOWN, DE, 197..., Middletown, DE 19709

$425,000

2 beds

3 baths

1,794 sq ft

204 BALDY LN ALRICH, MIDDLETOWN, DE, 197...

Community: Traditions at Whitehall

Traditions at Whitehall

314 CHAROLAIS ST ASHTON, MIDDLETOWN, DE,..., Middletown, DE 19709

$456,000

2 beds

3 baths

1,794 sq ft

314 CHAROLAIS ST ASHTON, MIDDLETOWN, DE,...

Community: Traditions at Whitehall

Traditions at Whitehall

204 BALDY LN ANNANDALE, MIDDLETOWN, DE, ..., Middletown, DE 19709

$425,000

2 beds

3 baths

1,794 sq ft

204 BALDY LN ANNANDALE, MIDDLETOWN, DE, ...

Community: Traditions at Whitehall

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

Questions? Call us: (302) 279-7380

Springmill

561 WHISPERING TRL, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$351,900

2 beds

2 baths

1,650 sq ft

561 WHISPERING TRL, MIDDLETOWN, DE, 1970...

Community: Springmill

The Ponds at Bayberry

624 VIVALDI DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$609,999

3 beds

2 baths

2,050 sq ft

624 VIVALDI DR, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

The Villas at The Preserve at Robinson Farms

1063 ROBINSON RD WHITFIELD PLAN, TOWNSEN..., Townsend, DE 19734

$494,900

3 beds

2 baths

2,826 sq ft

1063 ROBINSON RD WHITFIELD PLAN, TOWNSEN...

Community: The Villas at The Preserve at Robinson Farms

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The Villas at The Preserve at Robinson Farms

1065 ROBINSON RD WHITFIELD RANCH PLAN, T..., Townsend, DE 19734

$473,900

3 beds

2 baths

2,449 sq ft

1065 ROBINSON RD WHITFIELD RANCH PLAN, T...

Community: The Villas at The Preserve at Robinson Farms

The Villas at The Preserve at Robinson Farms

1067 ROBINSON RD LAKELAND PLAN, TOWNSEND..., Townsend, DE 19734

$467,900

3 beds

2 baths

2,534 sq ft

1067 ROBINSON RD LAKELAND PLAN, TOWNSEND...

Community: The Villas at The Preserve at Robinson Farms

Frequently Asked Questions

What size 55+ communities are there in Middletown?

In Middletown, there are no large communities, 1 medium community with 500-1000 homes, and 8 small communities with less than 500 homes.

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

The smallest 55+ communities in Middletown has 178 homes, the largest has 572 homes, and the average communities consists of 311 homes.

Are there new 55+ homes available in Middletown?

Yes, there are new 55+ homes available in Middletown. The most recent communities started in Middletown include Venue at Winchelsea, Four Seasons at Baymont Farms, Traditions at Whitehall. There are also 6 communities in Middletown that offer new construction homes, including Legacy at The Preserve at Deep Creek, Venue at Winchelsea, Whispering Woods.

Are there gated 55+ communities in Middletown?

Yes, there are gated 55+ communities in Middletown. Approximately 22.2% of 55+ communities in the area are gated. For instance, Four Seasons at Silver Maple is a gated communities with 299 homes, and Four Seasons at Baymont Farms is another gated communities with 288 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+ communities in Middletown stay on the market for around 569 days. The average price of homes for sale in these communities is approximately $515,302, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in The Ponds at Bayberry average around $569,900, while homes in Whispering Woods average around $508,481.

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19 communities

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

19 communities near Middletown

58 homes near Middletown

2 beds

2 baths

1,950 sq ft

3 beds

3 baths

2,025 sq ft

3 beds

3 baths

2,378 sq ft

2 beds

2 baths

2,275 sq ft

3 beds

2 baths

2,050 sq ft

3 beds

3 baths

3,397 sq ft

3 beds

3 baths

2,443 sq ft

2 beds

2 baths

1,780 sq ft

2 beds

2 baths

1,275 sq ft

3 beds

2 baths

1,625 sq ft

3 beds

3 baths

2,700 sq ft

3 beds

3 baths

2,650 sq ft

2 beds

2 baths

1,800 sq ft

3 beds

2 baths

2,725 sq ft

2 beds

2 baths

1,400 sq ft

4 beds

3 baths

3,375 sq ft

3 beds

2 baths

2,669 sq ft

2 beds

2 baths

1,866 sq ft

3 beds

3 baths

2,375 sq ft

3 beds

3 baths

2,443 sq ft

3 beds

4 baths

4,607 sq ft

2 beds

2 baths

1,764 sq ft

3 beds

3 baths

1,848 sq ft

2 beds

2 baths

1,400 sq ft

3 beds

3 baths

2,725 sq ft

4 beds

4 baths