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

19 communities near Middletown

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Traditions at Whitehall

$400Ks - $700Ks

Traditions at Whitehall, Middletown, DE

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

The Villas at The Preserv...

$400Ks - $500Ks

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

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

Venue at Winchelsea

$300Ks - $500Ks

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

Ashland

$300Ks - $400Ks

Ashland, Smyrna, DE

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

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Questions? Call us: (302) 279-7380

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Parks Edge at Bayberry

$500Ks - $600Ks

Parks Edge at Bayberry, Middletown, DE

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

5 rating (1 reviews)

Springmill

$300Ks - $400Ks

Springmill, Middletown, DE

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

4 rating (1 reviews)

Village of Fountainview

$100Ks - $200Ks

Village of Fountainview, Newark, DE

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

Four Seasons at Baymont F...

$500Ks - $600Ks

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

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

The Ponds at Bayberry

$500Ks - $600Ks

The Ponds at Bayberry, Middletown, DE

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

Village of Long Creek

$400Ks

Village of Long Creek, Newark, DE

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

Legacy at The Preserve at...

$500Ks - $600Ks

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

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

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Questions? Call us: (302) 279-7380

Crossings at Christiana

$200Ks - $300Ks

Crossings at Christiana, Bear, DE

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

Riverbend

$400Ks - $500Ks

Riverbend, New Castle, DE

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

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

Questions? Call us: (302) 279-7380

3 rating (2 reviews)

Spring Arbor

$400Ks

Spring Arbor, Middletown, DE

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

Whispering Woods

$400Ks

Whispering Woods, Middletown, DE

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

Village of Red Lion Creek

$300Ks

Village of Red Lion Creek, Bear, DE

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

Four Seasons at Silver Ma...

$500Ks

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

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

New Traditions at Whitehall

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

$735,000

3 beds

3 baths

2,725 sq ft

234 BALDY LN, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

Ashland

125 E CLARENDON DR, SMYRNA, DE, 19977, Smyrna, DE 19977

$344,900

2 beds

2 baths

1,466 sq ft

125 E CLARENDON DR, SMYRNA, DE, 19977

Community: Ashland

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

$599,900

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

$445,900

2 beds

2 baths

1,720 sq ft

28 PEGASUS LN, SMYRNA, DE, 19977

Community: Ashland

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

Questions? Call us: (302) 279-7380

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Questions? Call us: (302) 279-7380

Venue at Winchelsea

2303 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$475,509

3 beds

3 baths

2,443 sq ft

2303 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

Spring Arbor

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

$490,000

3 beds

2 baths

1,650 sq ft

148 GAZEBO LN, MIDDLETOWN, DE, 19709

Community: Spring Arbor

Venue at Winchelsea

2228 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$509,900

3 beds

3 baths

3,397 sq ft

2228 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

Venue at Winchelsea

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

$559,495

3 beds

3 baths

2,356 sq ft

3027 IVYHOUSE LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Springmill

304 DAYLILLY WAY, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$420,000

2 beds

2 baths

1,500 sq ft

304 DAYLILLY WAY, MIDDLETOWN, DE, 19709

Community: Springmill

Village of Fountainview

1000 FOUNTAINVIEW CIR 311, NEWARK, DE, 1..., Newark, DE 19713

$190,000

2 beds

2 baths

820 sq ft

Condo

1000 FOUNTAINVIEW CIR 311, NEWARK, DE, 1...

Community: Village of Fountainview

The Villas at The Preserve at Robinson Farms

1143 KAYLA LN, TOWNSEND, DE, 19734, Townsend, DE 19734

$479,900

3 beds

2 baths

1,850 sq ft

1143 KAYLA LN, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

Legacy at The Village of Fox Meadow

325 PIERCE RUN, NEWARK, DE, 19702, Newark, DE 19702

$400,000

4 beds

3 baths

2,200 sq ft

325 PIERCE RUN, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

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Questions? Call us: (302) 279-7380

Village of Long Creek

121 DEVALINDER DR, NEWARK, DE, 19702, Newark, DE 19702

$569,000

3 beds

3 baths

3,050 sq ft

121 DEVALINDER DR, NEWARK, DE, 19702

Community: Village of Long Creek

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

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Questions? Call us: (302) 279-7380

Venue at Winchelsea

3029 IVYHOUSE LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$538,793

3 beds

2 baths

2,065 sq ft

3029 IVYHOUSE LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Venue at Winchelsea

3134 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$364,800

5 beds

2 baths

2,669 sq ft

3134 PETT LEVEL DR, MIDDLETOWN, DE, 1970...

Community: Venue at Winchelsea

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

Springmill

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

$361,900

2 beds

2 baths

1,650 sq ft

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

Community: Springmill

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Questions? Call us: (302) 279-7380

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

Parks Edge at Bayberry

3032 BARBER LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$699,000

3 beds

2 baths

3032 BARBER LN, MIDDLETOWN, DE, 19709

Community: Parks Edge at Bayberry

Crossings at Christiana

221 GLADSTONE WAY, BEAR, DE, 19701, Bear, DE 19701

$320,000

2 beds

2 baths

1,425 sq ft

221 GLADSTONE WAY, BEAR, DE, 19701

Community: Crossings at Christiana

Legacy at The Village of Fox Meadow

361 PIERCE RUN, NEWARK, DE, 19702, Newark, DE 19702

$450,000

3 beds

3 baths

2,200 sq ft

361 PIERCE RUN, NEWARK, DE, 19702

2,004 sq ft

1071 ROBINSON RD DELRAY PLAN, TOWNSEND, ...

Community: The Villas at The Preserve at Robinson Farms

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Spring Arbor

149 GAZEBO LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$410,000

2 beds

2 baths

1,825 sq ft

149 GAZEBO LN, MIDDLETOWN, DE, 19709

Community: Spring Arbor

The Cascades

511 DAVIS FALLS DR, NEWARK, DE, 19702, Newark, DE 19702

$539,900

2 beds

2 baths

1,900 sq ft

511 DAVIS FALLS DR, NEWARK, DE, 19702

Community: The Cascades

Four Seasons at Baymont Farms

798 HONEY LOCUST RD, MIDDLETOWN, DE, 197..., Middletown, DE 19709

$610,000

3 beds

3 baths

1,875 sq ft

798 HONEY LOCUST RD, MIDDLETOWN, DE, 197...

Community: Four Seasons at Baymont Farms

Village of Fountainview

3000 FOUNTAINVIEW CIR # 3411, NEWARK, DE..., Newark, DE 19713

$219,900

2 beds

2 baths

825 sq ft

Condo

3000 FOUNTAINVIEW CIR # 3411, NEWARK, DE...

Community: Village of Fountainview

The Cascades

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

$499,000

2 beds

2 baths

1,875 sq ft

663 MAYFIELD FALLS DR, NEWARK, DE, 19702

Community: The Cascades

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The Ponds at Bayberry

4116 LAUGHTON LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$579,000

4 beds

3 baths

2,650 sq ft

4116 LAUGHTON LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

Parks Edge at Bayberry

3037 BARBER LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$528,900

2 beds

2 baths

1,800 sq ft

3037 BARBER LN, MIDDLETOWN, DE, 19709

Community: Parks Edge at Bayberry

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

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Questions? Call us: (302) 279-7380

Ashland

2 CYCLOPS TRL, SMYRNA, DE, 19977, Smyrna, DE 19977

$459,000

2 beds

2 baths

1,612 sq ft

2 CYCLOPS TRL, SMYRNA, DE, 19977

Community: Ashland

Traditions at Whitehall

548 LONGHORN LOOP LOT 33 CHELSEA, MIDDLE..., Middletown, DE 19709

$688,893

3 beds

2 baths

2,296 sq ft

548 LONGHORN LOOP LOT 33 CHELSEA, MIDDLE...

Community: Traditions at Whitehall

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

53 homes near Middletown

3 beds

3 baths

2,725 sq ft

2 beds

2 baths

1,466 sq ft

4 beds

4 baths

2,595 sq ft

2 beds

3 baths

2,475 sq ft

2 beds

2 baths

1,720 sq ft

3 beds

3 baths

2,443 sq ft

3 beds

2 baths

1,650 sq ft

3 beds

3 baths

3,397 sq ft

3 beds

3 baths

2,356 sq ft

2 beds

2 baths

1,500 sq ft

2 beds

2 baths

820 sq ft

Condo

3 beds

2 baths

1,850 sq ft

4 beds

3 baths

2,200 sq ft

3 beds

3 baths

3,050 sq ft

3 beds

4 baths

2,625 sq ft

3 beds

2 baths

2,065 sq ft

5 beds

2 baths

2,669 sq ft

2 beds

3 baths

1,794 sq ft

2 beds

3 baths

1,794 sq ft

2 beds

3 baths

1,794 sq ft

2 beds

2 baths

1,650 sq ft

3 beds

2 baths

2,050 sq ft

3 beds

2 baths

2 beds

2 baths

1,425 sq ft

3 beds

3 baths

2,200 sq ft

3 beds

2 baths