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 - $600Ks

Venue at Winchelsea, Middletown, DE

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

3 rating (2 reviews)

Spring Arbor

$300Ks - $300Ks

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 - $600Ks

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

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

No reviews yet

Whispering Woods

$500Ks - $500Ks

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

$400Ks - $400Ks

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

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

$475,000

3 beds

2 baths

2,150 sq ft

574 WHISPERING TRL, MIDDLETOWN, DE, 1970...

Community: Springmill

The Villas at The Preserve at Robinson Farms

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

$482,670

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

$549,800

2 beds

2 baths

2,073 sq ft

1020 ROBINSON RD, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

The Ponds at Bayberry

2704 VAN CLIBURN CIR, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$630,000

5 beds

3 baths

3,975 sq ft

2704 VAN CLIBURN CIR, MIDDLETOWN, DE, 19...

Community: The Ponds at Bayberry

Venue at Winchelsea

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

$400,800

5 beds

2 baths

2,669 sq ft

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

Community: Venue at Winchelsea

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Venue at Winchelsea

3112 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$499,000

3 beds

3 baths

2,443 sq ft

3112 PETT LEVEL DR, MIDDLETOWN, DE, 1970...

Community: Venue at Winchelsea

Venue at Winchelsea

2661 FAIRLIGHT DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$544,900

2 beds

3 baths

2,972 sq ft

2661 FAIRLIGHT DR, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Venue at Winchelsea

2659 FAIRLIGHT DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$539,990

3 beds

2 baths

2,151 sq ft

2659 FAIRLIGHT DR, MIDDLETOWN, DE, 19709

Community: Venue at Winchelsea

Venue at Winchelsea

2907 CORDWAINERS LN, MIDDLETOWN, DE, 197..., Middletown, DE 19709

$525,498

3 beds

4 baths

3,397 sq ft

2907 CORDWAINERS LN, MIDDLETOWN, DE, 197...

Community: Venue at Winchelsea

Village of Fountainview

3000 FOUNTAINVIEW CIR 202, NEWARK, DE, 1..., Newark, DE 19713

$239,900

3 beds

2 baths

1,500 sq ft

3000 FOUNTAINVIEW CIR 202, NEWARK, DE, 1...

Community: Village of Fountainview

The Villas at The Preserve at Robinson Farms

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

$525,000

3 beds

2 baths

1,850 sq ft

1143 KAYLA LN, TOWNSEND, DE, 19734

Community: The Villas at The Preserve at Robinson Farms

New Legacy at The Preserve at Deep Creek

277 ANGLESEY DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$499,900

2 beds

3 baths

2,325 sq ft

277 ANGLESEY DR, MIDDLETOWN, DE, 19709

Community: Legacy at The Preserve at Deep Creek

Traditions at Whitehall

204 BALDY LN CAYOT, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$579,000

3 beds

2 baths

2,004 sq ft

204 BALDY LN CAYOT, MIDDLETOWN, DE, 1970...

Community: Traditions at Whitehall

The Ponds at Bayberry

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

$585,000

3 beds

2 baths

1,875 sq ft

4602 BOGART LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

Village of Fountainview

3000 FOUNTAINVIEW CIR # 3311, NEWARK, DE..., Newark, DE 19713

$205,000

2 beds

2 baths

825 sq ft

Condo

3000 FOUNTAINVIEW CIR # 3311, NEWARK, DE...

Community: Village of Fountainview

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

Questions? Call us: (302) 279-7380

The Cascades

802 HORSESHOE FALLS DR, NEWARK, DE, 1970..., Newark, DE 19702

$515,000

2 beds

2 baths

1,900 sq ft

802 HORSESHOE FALLS DR, NEWARK, DE, 1970...

Community: The Cascades

Village of Fountainview

5 FOUNTAINVIEW DR # 23, NEWARK, DE, 1971..., Newark, DE 19713

$269,000

2 beds

2 baths

1,350 sq ft

Condo

5 FOUNTAINVIEW DR # 23, NEWARK, DE, 1971...

Community: Village of Fountainview

Springmill

$447,000

2 beds

2 baths

1,875 sq ft

51 SPRINGMILL DR, MIDDLETOWN, DE, 19709

Community: Springmill

Four Seasons at Baymont Farms

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

$559,000

3 beds

2 baths

1,850 sq ft

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

Community: Four Seasons at Baymont Farms

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

Village of Fountainview

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

$225,000

2 beds

2 baths

1,075 sq ft

Condo

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

Community: Village of Fountainview

Crossings at Christiana

303 BAKER DR, BEAR, DE, 19701, Bear, DE 19701

$309,900

2 beds

2 baths

1,425 sq ft

303 BAKER DR, BEAR, DE, 19701

Community: Crossings at Christiana

Village of Fountainview

3000 FOUNTAINVIEW CIR # 3113, NEWARK, DE..., Newark, DE 19713

$205,000

2 beds

2 baths

1,025 sq ft

Condo

3000 FOUNTAINVIEW CIR # 3113, NEWARK, DE...

Community: Village of Fountainview

Springmill

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

$435,000

2 beds

2 baths

1,900 sq ft

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

Community: Springmill

Traditions at Whitehall

414 HIGHLAND ST 138, MIDDLETOWN, DE, 197..., Middletown, DE 19709

$449,500

2 beds

3 baths

1,794 sq ft

414 HIGHLAND ST 138, MIDDLETOWN, DE, 197...

Community: Traditions at Whitehall

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Questions? Call us: (302) 279-7380

Springmill

$485,000

2 beds

3 baths

2,350 sq ft

66 SPRINGMILL DR, MIDDLETOWN, DE, 19709

Community: Springmill

Village of Fountainview

1000 FOUNTAINVIEW CIR # 1212, NEWARK, DE..., Newark, DE 19713

$189,900

2 beds

2 baths

825 sq ft

Condo

1000 FOUNTAINVIEW CIR # 1212, NEWARK, DE...

Community: Village of Fountainview

Village of Fountainview

19 FOUNTAINVIEW DR, NEWARK, DE, 19713, Newark, DE 19713

$278,500

2 beds

3 baths

1,655 sq ft

19 FOUNTAINVIEW DR, NEWARK, DE, 19713

Community: Village of Fountainview

Springmill

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

$484,900

2 beds

3 baths

2,200 sq ft

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

Community: Springmill

The Cascades

819 HORSESHOE FALLS DR, NEWARK, DE, 1970..., Newark, DE 19702

$499,000

2 beds

2 baths

1,728 sq ft

819 HORSESHOE FALLS DR, NEWARK, DE, 1970...

Community: The Cascades

The Cascades

825 HORSESHOE FALLS DR, NEWARK, DE, 1970..., Newark, DE 19702

$498,480

2 beds

2 baths

1,778 sq ft

825 HORSESHOE FALLS DR, NEWARK, DE, 1970...

Community: The Cascades

Whispering Woods

108 SERENITY CIR, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$528,000

3 beds

3 baths

2,425 sq ft

108 SERENITY CIR, MIDDLETOWN, DE, 19709

Community: Whispering Woods

Village of Fountainview

1000 FOUNTAINVIEW CIR APT 304, NEWARK, D..., Newark, DE 19713

$222,000

2 beds

2 baths

1,025 sq ft

1000 FOUNTAINVIEW CIR APT 304, NEWARK, D...

Community: Village of Fountainview

Whispering Woods

$459,900

2 beds

2 baths

2,025 sq ft

1429 WHISPERING WOODS RD, MIDDLETOWN, DE...

Community: Whispering Woods

Traditions at Whitehall

204 BALDY LN CHELSEA, MIDDLETOWN, DE, 19..., Middletown, DE 19709

$599,000

3 beds

2 baths

2,296 sq ft

204 BALDY LN CHELSEA, MIDDLETOWN, DE, 19...

Community: Traditions at Whitehall

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

Questions? Call us: (302) 279-7380

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

Village of Fountainview

3000 FOUNTAINVIEW CIR APT 116, NEWARK, D..., Newark, DE 19713

$240,000

3 beds

2 baths

1,500 sq ft

Condo

3000 FOUNTAINVIEW CIR APT 116, NEWARK, D...

Community: Village of Fountainview

Four Seasons at Baymont Farms

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

$570,000

2 beds

2 baths

1,825 sq ft

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

Community: Four Seasons at Baymont Farms

Village of Fountainview

1000 FOUNTAINVIEW CIR APT 206, NEWARK, D..., Newark, DE 19713

$185,000

2 beds

2 baths

825 sq ft

Condo

1000 FOUNTAINVIEW CIR APT 206, NEWARK, D...

Community: Village of Fountainview

Crossings at Christiana

515 ABRAMS CT, BEAR, DE, 19701, Bear, DE 19701

$299,000

2 beds

2 baths

1,325 sq ft

Condo

515 ABRAMS CT, BEAR, DE, 19701

Community: Crossings at Christiana

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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 The Ponds at Bayberry, Whispering Woods, Four Seasons at Baymont Farms.

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 248 days. The average price of homes for sale in these communities is approximately $530,260, 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 $639,677, while homes in Four Seasons at Silver Maple average around $515,000.

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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

59 homes near Middletown

3 beds

2 baths

2,150 sq ft

3 beds

2 baths

1,637 sq ft

2 beds

2 baths

2,073 sq ft

5 beds

3 baths

3,975 sq ft

5 beds

2 baths

2,669 sq ft

3 beds

3 baths

2,443 sq ft

2 beds

3 baths

2,972 sq ft

3 beds

2 baths

2,151 sq ft

3 beds

4 baths

3,397 sq ft

3 beds

2 baths

1,500 sq ft

3 beds

2 baths

1,850 sq ft

2 beds

3 baths

2,325 sq ft

3 beds

2 baths

2,004 sq ft

3 beds

2 baths

1,875 sq ft

2 beds

2 baths

825 sq ft

Condo

2 beds

2 baths

1,900 sq ft

2 beds

2 baths

1,350 sq ft

Condo

2 beds

2 baths

1,875 sq ft

3 beds

2 baths

1,850 sq ft

4 beds

4 baths

4,155 sq ft

2 beds

2 baths

1,075 sq ft

Condo

2 beds

2 baths

1,425 sq ft

2 beds

2 baths

1,025 sq ft

Condo

2 beds

2 baths

1,900 sq ft

2 beds