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

5 rating (1 reviews)

Springmill

$300ks - $400ks

Springmill, Middletown, DE

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

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

Questions? Call us: (302) 279-7380

Crossings at Christiana

$200ks

Crossings at Christiana, Bear, DE

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

The Cascades

$400ks - $500ks

The Cascades, Newark, DE

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

3 rating (2 reviews)

Spring Arbor

$300ks - $500ks

Spring Arbor, Middletown, DE

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

The Ponds at Bayberry

$300ks - $500ks

The Ponds at Bayberry, Middletown, DE

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

Venue at Winchelsea

$400ks - $600ks

Venue at Winchelsea, Middletown, DE

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

Whispering Woods

$300ks - $400ks

Whispering Woods, Middletown, DE

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

4 rating (1 reviews)

Village of Fountainview

$100ks - $200ks

Village of Fountainview, Newark, DE

Resale Only | 55+ age-restricted | Built 2007 - 2019 | 124 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+ communities in Middletown? 55places can help!

Questions? Call us: (302) 279-7380

Village of Red Lion Creek

$200ks - $300ks

Village of Red Lion Creek, Bear, DE

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

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

Riverbend

$400ks

Riverbend, New Castle, DE

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

New Crossings at Christiana

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

$329,900

2 beds

2 baths

1,425 sq ft

428 SWEETMAN DR, BEAR, DE, 19701

Community: Crossings at Christiana

New Springmill

25 SPRINGMILL DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$410,000

2 beds

2 baths

1,783 sq ft

25 SPRINGMILL DR, MIDDLETOWN, DE, 19709

Community: Springmill

New Springmill

101 SPRINGMILL DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$474,900

2 beds

2 baths

2,550 sq ft

101 SPRINGMILL DR, MIDDLETOWN, DE, 19709

Community: Springmill

Four Seasons at Baymont Farms

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

$670,000

4 beds

3 baths

2,375 sq ft

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

Community: Four Seasons at Baymont Farms

Legacy at The Village of Fox Meadow

341 PIERCE RUN, NEWARK, DE, 19702, Newark, DE 19702

$450,000

3 beds

3 baths

2,872 sq ft

341 PIERCE RUN, NEWARK, DE, 19702

Community: Legacy at The Village of Fox Meadow

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Questions? Call us: (302) 279-7380

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

$685,000

3 beds

2 baths

2,925 sq ft

216 BALDY LN, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

Four Seasons at Silver Maple

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

$519,999

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

$185,000

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

Springmill

406 MORNING GLORY LN, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$476,000

2 beds

2 baths

2,375 sq ft

406 MORNING GLORY LN, MIDDLETOWN, DE, 19...

Community: Springmill

Whispering Woods

$499,000

2 beds

2 baths

1,675 sq ft

1426 WHISPERING WOODS RD, MIDDLETOWN, DE...

Community: Whispering Woods

Venue at Winchelsea

2239 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$439,250

3 beds

3 baths

2,443 sq ft

2239 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

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

$450,000

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

$595,000

2 beds

3 baths

2,275 sq ft

130 BURLINA BLVD, MIDDLETOWN, DE, 19709

Community: Traditions at Whitehall

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Questions? Call us: (302) 279-7380

Springmill

228 PATIENCE WAY, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$424,900

2 beds

2 baths

2,225 sq ft

228 PATIENCE WAY, MIDDLETOWN, DE, 19709

Community: Springmill

The Villas at The Preserve at Robinson Farms

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

$540,000

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

The Cascades

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

$495,000

2 beds

2 baths

1,900 sq ft

672 MAYFIELD FALLS DR, NEWARK, DE, 19702

Community: The Cascades

Venue at Winchelsea

2251 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$362,800

5 beds

2 baths

2,669 sq ft

2251 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...

Community: Venue at Winchelsea

The Ponds at Bayberry

4007 HESTON LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$540,000

3 beds

2 baths

2,050 sq ft

4007 HESTON LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

Springmill

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

$430,000

2 beds

2 baths

2,200 sq ft

506 WHISPERING TRL, MIDDLETOWN, DE, 1970...

Community: Springmill

Spring Arbor

400 TOPIARY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$469,900

2 beds

2 baths

2,100 sq ft

400 TOPIARY LN, MIDDLETOWN, DE, 19709

Community: Spring Arbor

Springmill

107 DAWN CT, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$385,000

2 beds

2 baths

2,225 sq ft

107 DAWN CT, MIDDLETOWN, DE, 19709

Community: Springmill

Crossings at Christiana

623 KENDALL DR, BEAR, DE, 19701, Bear, DE 19701

$360,000

2 beds

2 baths

1,300 sq ft

623 KENDALL DR, BEAR, DE, 19701

Community: Crossings at Christiana

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

1003 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734

$541,197

$245,000

3 beds

2 baths

1,500 sq ft

Condo

1000 FOUNTAINVIEW CIR 1301, NEWARK, DE, ...

Community: Village of Fountainview

Four Seasons at Silver Maple

420 WINTERBERRY DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$560,000

3 beds

3 baths

3,100 sq ft

420 WINTERBERRY DR, MIDDLETOWN, DE, 1970...

Community: Four Seasons at Silver Maple

Ashland

25 CYCLOPS TRL, SMYRNA, DE, 19977, Smyrna, DE 19977

$398,900

2 beds

2 baths

1,612 sq ft

25 CYCLOPS TRL, SMYRNA, DE, 19977

Community: Ashland

The Ponds at Bayberry

4605 BOGART LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$780,000

5 beds

4 baths

5,325 sq ft

4605 BOGART LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

Village of Long Creek

29 DEVALINDER DR, NEWARK, DE, 19702, Newark, DE 19702

$489,900

2 beds

2 baths

1,875 sq ft

29 DEVALINDER DR, NEWARK, DE, 19702

Community: Village of Long Creek

Traditions at Whitehall

264 BALDY LN 157 BLOOMFIELD MODEL, MIDDL..., Middletown, DE 19709

$639,999

2 beds

3 baths

2,053 sq ft

264 BALDY LN 157 BLOOMFIELD MODEL, MIDDL...

Community: Traditions at Whitehall

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

Questions? Call us: (302) 279-7380

Four Seasons at Baymont Farms

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

$629,990

3 beds

3 baths

1,859 sq ft

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

Community: Four Seasons at Baymont Farms

Four Seasons at Baymont Farms

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

$599,990

3 beds

4 baths

2,441 sq ft

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

Community: Four Seasons at Baymont 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 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

70 homes near Middletown

2 beds

2 baths

1,425 sq ft

2 beds

2 baths

1,783 sq ft

2 beds

2 baths

2,550 sq ft

4 beds

3 baths

2,375 sq ft

3 beds

3 baths

2,872 sq ft

2 beds

2 baths

3 beds

2 baths

2,925 sq ft

2 beds

2 baths

1,925 sq ft

1 beds

1 baths

650 sq ft

2 beds

2 baths

1,720 sq ft

2 beds

2 baths

2,375 sq ft

2 beds

2 baths

1,675 sq ft

3 beds

3 baths

2,443 sq ft

3 beds

3 baths

2,080 sq ft

3 beds

4 baths

3,118 sq ft

2 beds

3 baths

2,275 sq ft

2 beds

2 baths

2,225 sq ft

3 beds

4 baths

3,350 sq ft

3 beds

2 baths

2,075 sq ft

2 beds

2 baths

1,825 sq ft

2 beds

2 baths

1,900 sq ft

5 beds

2 baths

2,669 sq ft

3 beds

2 baths

2,050 sq ft

2 beds

2 baths

2,200 sq ft

2 beds

2 baths

2,100 sq ft

2 beds

2 baths

2,225 sq ft