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

Ashland

$300ks - $400ks

Ashland, Smyrna, DE

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

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

Questions? Call us: (302) 279-7380

Venue at Winchelsea

$400ks - $600ks

Venue at Winchelsea, Middletown, DE

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

The Ponds at Bayberry

$300ks - $500ks

The Ponds at Bayberry, Middletown, DE

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

3 rating (2 reviews)

Spring Arbor

$300ks - $500ks

Spring Arbor, Middletown, DE

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

The Cascades

$400ks - $500ks

The Cascades, Newark, DE

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

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Whispering Woods

$300ks - $400ks

Whispering Woods, Middletown, DE

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

Crossings at Christiana

$200ks

Crossings at Christiana, Bear, DE

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

Village of Long Creek

$400ks

Village of Long Creek, Newark, DE

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

5 rating (1 reviews)

Springmill

$300ks - $400ks

Springmill, Middletown, DE

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

Parks Edge at Bayberry

$400ks - $600ks

Parks Edge at Bayberry, Middletown, DE

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

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

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 Red Lion Creek

$200ks - $300ks

Village of Red Lion Creek, Bear, DE

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

Riverbend

$400ks

Riverbend, New Castle, DE

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

New Village of Fountainview

1000 FOUNTAINVIEW CIR 407, NEWARK, DE, 1..., Newark, DE 19713

$202,500

2 beds

2 baths

1,067 sq ft

Condo

1000 FOUNTAINVIEW CIR 407, NEWARK, DE, 1...

Community: Village of Fountainview

New Village of Fountainview

2000 FOUNTAINVIEW CIR 2108, NEWARK, DE, ..., Newark, DE 19713

$209,900

2 beds

2 baths

1,075 sq ft

Condo

2000 FOUNTAINVIEW CIR 2108, NEWARK, DE, ...

Community: Village of Fountainview

The Cascades

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

$518,000

2 beds

2 baths

1,900 sq ft

511 DAVIS FALLS DR, NEWARK, DE, 19702

Community: The Cascades

Four Seasons at Silver Maple

239 SILKY DOGWOOD LN, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$569,000

3 beds

2 baths

2,325 sq ft

239 SILKY DOGWOOD LN, MIDDLETOWN, DE, 19...

Community: Four Seasons at Silver Maple

Spring Arbor

623 GARDEN GATE DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$495,000

2 beds

2 baths

1,775 sq ft

623 GARDEN GATE DR, MIDDLETOWN, DE, 1970...

Community: Spring Arbor

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Questions? Call us: (302) 279-7380

Four Seasons at Silver Maple

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

$579,900

3 beds

2 baths

3,558 sq ft

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

Community: Four Seasons at Silver Maple

Four Seasons at Silver Maple

614 RED MAPLE RD, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$550,000

3 beds

2 baths

2,478 sq ft

614 RED MAPLE RD, MIDDLETOWN, DE, 19709

Community: Four Seasons at Silver Maple

Legacy at The Preserve at Deep Creek

272 ANGLESEY DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$549,999

3 beds

3 baths

3,303 sq ft

272 ANGLESEY DR, MIDDLETOWN, DE, 19709

Community: Legacy at The Preserve at Deep Creek

Springmill

100 DAWN CT, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$395,000

2 beds

2 baths

1,595 sq ft

100 DAWN CT, MIDDLETOWN, DE, 19709

Community: Springmill

The Ponds at Bayberry

4534 CAGNEY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$600,000

4 beds

3 baths

3,025 sq ft

4534 CAGNEY LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

The Cascades

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

$519,995

3 beds

2 baths

1,904 sq ft

678 MAYFIELD FALLS DR, NEWARK, DE, 19702

Community: The Cascades

Venue at Winchelsea

3034 IVYHOUSE LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$595,000

3 beds

4 baths

2,151 sq ft

3034 IVYHOUSE LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Four Seasons at Baymont Farms

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

$639,990

3 beds

4 baths

2,441 sq ft

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

Community: Four Seasons at Baymont Farms

Four Seasons at Baymont Farms

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

$624,900

3 beds

3 baths

1,859 sq ft

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

Community: Four Seasons at Baymont Farms

Venue at Winchelsea

3314 ROOKERY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$593,250

3 beds

4 baths

2,151 sq ft

3314 ROOKERY LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Venue at Winchelsea

3315 ROOKERY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$579,250

3 beds

3 baths

2,065 sq ft

3315 ROOKERY LN, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

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Questions? Call us: (302) 279-7380

Venue at Winchelsea

2213 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$442,509

3 beds

3 baths

2,443 sq ft

2213 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

The Ponds at Bayberry

4200 CROSBY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$689,900

4 beds

3 baths

2,700 sq ft

4200 CROSBY LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

Ashland

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

$392,000

2 beds

2 baths

1,796 sq ft

145 E CLARENDON DR, SMYRNA, DE, 19977

Community: Ashland

Whispering Woods

$423,000

2 beds

2 baths

1,275 sq ft

1428 WHISPERING WOODS RD, MIDDLETOWN, DE...

Community: Whispering Woods

Four Seasons at Baymont Farms

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

$675,000

4 beds

4 baths

2,525 sq ft

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

Community: Four Seasons at Baymont Farms

Whispering Woods

529 CONTEMPLATION WAY, MIDDLETOWN, DE, 1..., Middletown, DE 19709

$569,900

3 beds

3 baths

2,375 sq ft

529 CONTEMPLATION WAY, MIDDLETOWN, DE, 1...

Community: Whispering Woods

Village of Fountainview

2000 FOUNTAINVIEW CIR 114, NEWARK, DE, 1..., Newark, DE 19713

$209,500

2 beds

2 baths

1,034 sq ft

Condo

2000 FOUNTAINVIEW CIR 114, NEWARK, DE, 1...

Community: Village of Fountainview

Crossings at Christiana

428 SWEETMAN DR, BEAR, DE, 19701, Bear, DE 19701

$319,900

2 beds

2 baths

1,425 sq ft

428 SWEETMAN DR, BEAR, DE, 19701

Community: Crossings at Christiana

Springmill

$410,000

2 beds

2 baths

1,783 sq ft

25 SPRINGMILL DR, MIDDLETOWN, DE, 19709

Community: Springmill

Parks Edge at Bayberry

2817 BERNSTEIN CIR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$621,619

2 beds

2 baths

2817 BERNSTEIN CIR, MIDDLETOWN, DE, 1970...

Community: Parks Edge at Bayberry

Traditions at Whitehall

216 BALDY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$669,900

3 beds

2 baths

2,925 sq ft

216 BALDY LN, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

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

Questions? Call us: (302) 279-7380

Village of Fountainview

1000 FOUNTAINVIEW CIR 1306, NEWARK, DE, ..., Newark, DE 19713

$190,000

2 beds

2 baths

Condo

1000 FOUNTAINVIEW CIR 1306, NEWARK, DE, ...

Community: Village of Fountainview

Four Seasons at Silver Maple

1502 ARROWOOD CT, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$509,900

2 beds

2 baths

1,925 sq ft

1502 ARROWOOD CT, MIDDLETOWN, DE, 19709

Community: Four Seasons at Silver Maple

Village of Fountainview

2000 FOUNTAINVIEW CIR 2106, NEWARK, DE, ..., Newark, DE 19713

$179,900

1 beds

1 baths

650 sq ft

2000 FOUNTAINVIEW CIR 2106, NEWARK, DE, ...

Community: Village of Fountainview

Ashland

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

$409,900

2 beds

2 baths

1,720 sq ft

28 PEGASUS LN, SMYRNA, DE, 19977

Community: Ashland

Whispering Woods

$495,000

2 beds

2 baths

1,675 sq ft

1426 WHISPERING WOODS RD, MIDDLETOWN, DE...

Community: Whispering Woods

Four Seasons at Baymont Farms

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

$639,990

3 beds

3 baths

2,080 sq ft

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

Community: Four Seasons at Baymont Farms

Legacy at The Village of Fox Meadow

224 ANITA CT, NEWARK, DE, 19702, Newark, DE 19702

$439,900

3 beds

4 baths

3,118 sq ft

224 ANITA CT, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

Traditions at Whitehall

130 BURLINA BLVD, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$590,000

2 beds

3 baths

2,275 sq ft

130 BURLINA BLVD, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

The Villas at The Preserve at Robinson Farms

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

$530,000

3 beds

4 baths

3,350 sq ft

929 ROBINSON RD, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

The Cascades

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

$523,900

3 beds

2 baths

2,075 sq ft

651 MAYFIELD FALLS DR, NEWARK, DE, 19702

Community: The Cascades

Four Seasons at Baymont Farms

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

$569,000

2 beds

2 baths

1,825 sq ft

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

Community: Four Seasons at Baymont Farms

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

Questions? Call us: (302) 279-7380

The Ponds at Bayberry

2753 VAN CLIBURN CIR, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$589,000

3 beds

3 baths

3,750 sq ft

2753 VAN CLIBURN CIR, MIDDLETOWN, DE, 19...

Community: The Ponds at Bayberry

The Cascades

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

$490,000

2 beds

2 baths

1,900 sq ft

672 MAYFIELD FALLS DR, NEWARK, DE, 19702

Community: The Cascades

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 9 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 301 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, Parks Edge at Bayberry, Four Seasons at Baymont Farms. There are also 7 communities in Middletown that offer new construction homes, including Whispering Woods, Legacy at The Preserve at Deep Creek, Four Seasons at Baymont Farms.

Are there gated 55+ communities in Middletown?

Yes, there are gated 55+ communities in Middletown. Approximately 20.0% 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 516 days. The average price of homes for sale in these communities is approximately $510,646, 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 Parks Edge at Bayberry average around $538,900.

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19 communities

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

19 communities near Middletown

72 homes near Middletown

2 beds

2 baths

1,067 sq ft

Condo

2 beds

2 baths

1,075 sq ft

Condo

2 beds

2 baths

1,900 sq ft

3 beds

2 baths

2,325 sq ft

2 beds

2 baths

1,775 sq ft

3 beds

2 baths

3,558 sq ft

3 beds

2 baths

2,478 sq ft

3 beds

3 baths

3,303 sq ft

2 beds

2 baths

1,595 sq ft

4 beds

3 baths

3,025 sq ft

3 beds

2 baths

1,904 sq ft

3 beds

4 baths

2,151 sq ft

3 beds

4 baths

2,441 sq ft

3 beds

3 baths

1,859 sq ft

3 beds

4 baths

2,151 sq ft

3 beds

3 baths

2,065 sq ft

3 beds

3 baths

2,443 sq ft

4 beds

3 baths

2,700 sq ft

2 beds

2 baths

1,796 sq ft

2 beds

2 baths

1,275 sq ft

4 beds

4 baths

2,525 sq ft

3 beds

3 baths

2,375 sq ft

2 beds

2 baths

1,034 sq ft

Condo

2 beds

2 baths

1,425 sq ft

2 beds

2 baths