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

16 communities near Middletown

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The Ponds at Bayberry

$500Ks - $600Ks

The Ponds at Bayberry, Middletown, DE

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

5 rating (1 reviews)

Springmill

$400Ks - $400Ks

Springmill, Middletown, DE

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

No reviews yet

Venue at Winchelsea

$400Ks - $500Ks

Venue at Winchelsea, Middletown, DE

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

3 rating (2 reviews)

Spring Arbor

$400Ks - $400Ks

Spring Arbor, Middletown, DE

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

No reviews yet

Four Seasons at Silver Ma...

$500Ks - $500Ks

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

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

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

Questions? Call us: (302) 279-7380

No reviews yet

Four Seasons at Baymont F...

$500Ks - $700Ks

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

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

No reviews yet

Traditions at Whitehall

$400Ks - $600Ks

Traditions at Whitehall, Middletown, DE

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

No reviews yet

Legacy at The Preserve at...

$500Ks - $700Ks

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

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

No reviews yet

Whispering Woods

$400Ks - $400Ks

Whispering Woods, Middletown, DE

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

2.4 rating (5 reviews)

Legacy at The Village of ...

$400Ks - $400Ks

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

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

No reviews yet

The Villas at The Preserv...

$400Ks - $500Ks

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

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

No reviews yet

Crossings at Christiana

$200Ks - $300Ks

Crossings at Christiana, Bear, DE

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

No reviews yet

Village of Fountainview

$100Ks - $200Ks

Village of Fountainview, Newark, DE

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

No reviews yet

The Cascades

$500Ks - $500Ks

The Cascades, Newark, DE

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

No reviews yet

Village of Long Creek

$400Ks - $400Ks

Village of Long Creek, Newark, DE

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

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

Questions? Call us: (302) 279-7380

No reviews yet

Village of Red Lion Creek

$300Ks - $300Ks

Village of Red Lion Creek, Bear, DE

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

Springmill

$480,000

2 beds

2 baths

3,450 sq ft

56 SPRINGMILL DR, MIDDLETOWN, DE, 19709

Community: Springmill

Springmill

$475,000

2 beds

2 baths

2,100 sq ft

102 SPRINGMILL DR, 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

New Venue at Winchelsea

3126 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$495,700

3 beds

3 baths

2,443 sq ft

3126 PETT LEVEL DR, MIDDLETOWN, DE, 1970...

Community: Venue at Winchelsea

Spring Arbor

$490,000

2 beds

2 baths

1,750 sq ft

47 SPRING ARBOR DR, MIDDLETOWN, DE, 1970...

Community: Spring Arbor

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

Questions? Call us: (302) 279-7380

Venue at Winchelsea

2816 ARMOURY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$565,590

3 beds

3 baths

3,397 sq ft

2816 ARMOURY LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Venue at Winchelsea

3031 IVYHOUSE LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$579,000

3 beds

3 baths

3,269 sq ft

3031 IVYHOUSE LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Traditions at Whitehall

222 BALDY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$600,000

3 beds

3 baths

2,305 sq ft

222 BALDY LN, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

Whispering Woods

$445,000

2 beds

2 baths

1,875 sq ft

1415 WHISPERING WOODS RD, MIDDLETOWN, DE...

Community: Whispering Woods

Springmill

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

$479,900

2 beds

3 baths

2,200 sq ft

577 WHISPERING TRL, MIDDLETOWN, DE, 1970...

Community: Springmill

Venue at Winchelsea

3128 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$400,800

5 beds

2 baths

2,669 sq ft

3128 PETT LEVEL DR, MIDDLETOWN, DE, 1970...

Community: Venue at Winchelsea

The Villas at The Preserve at Robinson Farms

1113 KAYLA LN, TOWNSEND, DE, 19734, Townsend, DE 19734

$474,900

3 beds

3 baths

2,075 sq ft

1113 KAYLA LN, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

Legacy at The Village of Fox Meadow

212 ANITA CT, NEWARK, DE, 19702, Newark, DE 19702

$439,900

3 beds

3 baths

2,025 sq ft

212 ANITA CT, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

Four Seasons at Baymont Farms

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

$600,000

4 beds

3 baths

2,650 sq ft

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

Community: Four Seasons at Baymont Farms

The Ponds at Bayberry

650 VIVALDI DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$660,000

4 beds

3 baths

3,000 sq ft

Condo

650 VIVALDI DR, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

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

Questions? Call us: (302) 279-7380

Legacy at The Preserve at Deep Creek

1613 ELLINOR CT, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$599,900

3 beds

3 baths

2,797 sq ft

1613 ELLINOR CT, MIDDLETOWN, DE, 19709

Community: Legacy at The Preserve at Deep Creek

Four Seasons at Baymont Farms

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

$755,000

4 beds

4 baths

4,155 sq ft

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

Community: Four Seasons at Baymont Farms

The Ponds at Bayberry

4513 CAGNEY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$575,000

2 beds

2 baths

1,825 sq ft

4513 CAGNEY LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

The Villas at The Preserve at Robinson Farms

1019 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734

$474,900

3 beds

2 baths

1,637 sq ft

1019 ROBINSON RD, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

The Villas at The Preserve at Robinson Farms

1020 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734

$519,900

2 beds

2 baths

1020 ROBINSON RD, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

The Villas at The Preserve at Robinson Farms

1064 ROBINSON RD LAKELAND PLAN, TOWNSEND..., Townsend, DE 19734

$477,900

3 beds

2 baths

1,913 sq ft

1064 ROBINSON RD LAKELAND PLAN, TOWNSEND...

Community: The Villas at The Preserve at Robinson Farms

The Cascades

715 STAIRWAY FALLS RD, NEWARK, DE, 19702, Newark, DE 19702

$580,978

3 beds

3 baths

2,285 sq ft

715 STAIRWAY FALLS RD, NEWARK, DE, 19702

Community: The Cascades

The Villas at The Preserve at Robinson Farms

1027 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734

$526,017

2 beds

2 baths

1,637 sq ft

1027 ROBINSON RD, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

Legacy at The Village of Fox Meadow

246 ANITA CT, NEWARK, DE, 19702, Newark, DE 19702

$474,900

3 beds

4 baths

2,225 sq ft

246 ANITA CT, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

The Ponds at Bayberry

4602 BOGART LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$579,000

3 beds

2 baths

1,875 sq ft

4602 BOGART LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

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

Questions? Call us: (302) 279-7380

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

The Cascades

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

$515,000

2 beds

2 baths

1,950 sq ft

632 MAYFIELD FALLS DR, NEWARK, DE, 19702

Community: The Cascades

Whispering Woods

$454,900

2 beds

2 baths

2,025 sq ft

1429 WHISPERING WOODS RD, MIDDLETOWN, DE...

Community: Whispering Woods

Legacy at The Village of Fox Meadow

339 PIERCE RUN, NEWARK, DE, 19702, Newark, DE 19702

$489,000

4 beds

4 baths

3,558 sq ft

339 PIERCE RUN, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

Springmill

636 POETS WAY, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$469,900

3 beds

2 baths

2,225 sq ft

636 POETS WAY, MIDDLETOWN, DE, 19709

Community: Springmill

Traditions at Whitehall

1102 HIGHLAND ST, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$504,900

2 beds

3 baths

1,794 sq ft

1102 HIGHLAND ST, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

Traditions at Whitehall

1104 HIGHLAND ST, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$449,500

2 beds

3 baths

1,794 sq ft

1104 HIGHLAND ST, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

Springmill

343 DAYLILLY WAY, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$465,000

2 beds

3 baths

2,200 sq ft

343 DAYLILLY WAY, MIDDLETOWN, DE, 19709

Community: Springmill

The Villas at The Preserve at Robinson Farms

1068 ROBINSON RD DELRAY PLAN, TOWNSEND, ..., Townsend, DE 19734

$449,900

3 beds

2 baths

1,452 sq ft

1068 ROBINSON RD DELRAY PLAN, TOWNSEND, ...

Community: The Villas at The Preserve at Robinson Farms

The Villas at The Preserve at Robinson Farms

1066 ROBINSON RD PEMBROOK PLAN, TOWNSEND..., Townsend, DE 19734

$462,900

3 beds

2 baths

1,637 sq ft

1066 ROBINSON RD PEMBROOK PLAN, TOWNSEND...

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 Villas at The Preserve at Robinson Farms

1062 ROBINSON RD WHITFIELD RANCH PLAN, T..., Townsend, DE 19734

$483,900

3 beds

2 baths

1,863 sq ft

1062 ROBINSON RD WHITFIELD RANCH PLAN, T...

Community: The Villas at The Preserve at Robinson Farms

The Villas at The Preserve at Robinson Farms

1060 ROBINSON RD WHITFIELD PLAN, TOWNSEN..., Townsend, DE 19734

$504,900

3 beds

2 baths

2,240 sq ft

1060 ROBINSON RD WHITFIELD PLAN, TOWNSEN...

Community: The Villas at The Preserve at Robinson Farms

Four Seasons at Baymont Farms

411 PAPER BIRCH ST, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$739,000

4 beds

4 baths

2,378 sq ft

411 PAPER BIRCH ST, MIDDLETOWN, DE, 1970...

Community: Four Seasons at Baymont Farms

Springmill

$425,000

2 beds

2 baths

1,875 sq ft

51 SPRINGMILL DR, MIDDLETOWN, DE, 19709

Community: Springmill

Village of Fountainview

3000 FOUNTAINVIEW CIR # 3107, NEWARK, DE..., Newark, DE 19713

$220,000

2 beds

2 baths

1,075 sq ft

Condo

3000 FOUNTAINVIEW CIR # 3107, NEWARK, DE...

Community: Village of Fountainview

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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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Want to learn more about 55+ communities in Middletown?

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16 communities near Middletown

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

16 communities near Middletown

62 homes near Middletown

2 beds

2 baths

3,450 sq ft

2 beds

2 baths

2,100 sq ft

3 beds

4 baths

2,625 sq ft

3 beds

3 baths

2,443 sq ft

2 beds

2 baths

1,750 sq ft

3 beds

3 baths

3,397 sq ft

3 beds

3 baths

3,269 sq ft

3 beds

3 baths

2,305 sq ft

2 beds

2 baths

1,875 sq ft

2 beds

3 baths

2,200 sq ft

5 beds

2 baths

2,669 sq ft

3 beds

3 baths

2,075 sq ft

3 beds

3 baths

2,025 sq ft

4 beds

3 baths

2,650 sq ft

4 beds

3 baths

3,000 sq ft

Condo

3 beds

3 baths

2,797 sq ft

4 beds

4 baths

4,155 sq ft

2 beds

2 baths

1,825 sq ft

3 beds

2 baths

1,637 sq ft

2 beds

2 baths

3 beds

2 baths

1,913 sq ft

3 beds

3 baths

2,285 sq ft

2 beds

2 baths

1,637 sq ft

3 beds

4 baths

2,225 sq ft

3 beds

2 baths

1,875 sq ft

3 beds

2 baths