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Middletown, DE 55+ active adult communities & homes for sale
19 communities near Middletown
64 homes near Middletown
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$500Ks
- $500Ks
The Ponds at Bayberry, Middletown, DE
New and Resale
|
55+ age-restricted
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Built 2015 - present
|
572 homes
5 rating (1 reviews)
![Springmill]()
$400Ks
- $400Ks
Springmill, Middletown, DE
Resale Only
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55+ age-restricted
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Built 2000 - 2007
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362 homes
$400Ks
- $500Ks
Venue at Winchelsea, Middletown, DE
New Construction
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55+ age-restricted
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Built 2024 - present
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336 homes
3 rating (2 reviews)
![Spring Arbor]()
$400Ks
- $400Ks
Spring Arbor, Middletown, DE
Resale Only
|
55+ age-restricted
|
Built 2007 - 2018
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317 homes
$500Ks
- $500Ks
Four Seasons at Silver Ma..., Middletown, DE
Resale Only
|
55+ age-restricted
|
Built 2011 - 2017
|
299 homes
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$500Ks
- $700Ks
Four Seasons at Baymont F..., Middletown, DE
New Construction
|
Age-targeted
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Built 2019 - present
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288 homes
$400Ks
- $600Ks
Traditions at Whitehall, Middletown, DE
New Construction
|
55+ age-restricted
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Built 2019 - present
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250 homes
$500Ks
- $600Ks
Parks Edge at Bayberry, Middletown, DE
New Construction
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55+ age-restricted
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Built 2022 - present
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210 homes
$500Ks
- $600Ks
Legacy at The Preserve at..., Middletown, DE
New and Resale
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55+ age-restricted
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Built 2016 - present
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205 homes
$400Ks
- $400Ks
Whispering Woods, Middletown, DE
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
178 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.
$400Ks
- $500Ks
Riverbend, New Castle, DE
New Construction
|
55+ age-restricted
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Built 2021 - present
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200 homes
2.4 rating (5 reviews)
![Legacy at The Village of ...]()
$400Ks
- $400Ks
Legacy at The Village of ..., Newark, DE
Resale Only
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55+ age-restricted
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Built 2008 - 2014
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194 homes
$300Ks
- $400Ks
Ashland, Smyrna, DE
Resale Only
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55+ age-restricted
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Built 2016 - 2020
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150 homes
$400Ks
- $500Ks
The Villas at The Preserv..., Townsend, DE
New Construction
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55+ age-restricted
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Built 2017 - present
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144 homes
$200Ks
- $300Ks
Crossings at Christiana, Bear, DE
Resale Only
|
55+ age-restricted
|
Built 2003 - 2011
|
140 homes
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Questions? Call us:
(302) 279-7380
4 rating (1 reviews)
![Village of Fountainview]()
$200Ks
- $200Ks
Village of Fountainview, Newark, DE
Resale Only
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55+ age-restricted
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Built 2007 - 2019
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124 homes
$500Ks
- $500Ks
The Cascades, Newark, DE
New Construction
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55+ age-restricted
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Built 2021 - present
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113 homes
$400Ks
- $400Ks
Village of Long Creek, Newark, DE
Resale Only
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55+ age-restricted
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Built 2007 - 2016
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100 homes
Legacy at The Village of Fox Meadow
![339 PIERCE RUN, NEWARK, DE, 19702, Newark, DE 19702]()
4 beds
|4 baths
|3,558 sq ft
339 PIERCE RUN, NEWARK, DE, 19702
Community: Legacy at The Village of Fox Meadow
MLS DENC2087250 • Crown Homes Real Estate, Melvin...
Village of Fountainview
![5 FOUNTAINVIEW DR # 23, NEWARK, DE, 1971..., Newark, DE 19713]()
2 beds
|2 baths
|1,350 sq ft
|Condo
5 FOUNTAINVIEW DR # 23, NEWARK, DE, 1971...
Community: Village of Fountainview
MLS DENC2083560 • Long & Foster Real Estate, Inc....
New
The Villas at The Preserve at Robinson Farms
![1063 ROBINSON RD WHITFIELD PLAN, TOWNSEN..., Townsend, DE 19734]()
3 beds
|2 baths
|2,826 sq ft
1063 ROBINSON RD WHITFIELD PLAN, TOWNSEN...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2093264 • Mark L Handler Real Estate, Mar...
New
The Villas at The Preserve at Robinson Farms
![1065 ROBINSON RD WHITFIELD RANCH PLAN, T..., Townsend, DE 19734]()
3 beds
|2 baths
|2,449 sq ft
1065 ROBINSON RD WHITFIELD RANCH PLAN, T...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2093262 • Mark L Handler Real Estate, Mar...
New
The Villas at The Preserve at Robinson Farms
![1067 ROBINSON RD LAKELAND PLAN, TOWNSEND..., Townsend, DE 19734]()
3 beds
|2 baths
|2,534 sq ft
1067 ROBINSON RD LAKELAND PLAN, TOWNSEND...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2093260 • Mark L Handler Real Estate, Mar...
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New
The Villas at The Preserve at Robinson Farms
![1069 ROBINSON RD PEMBROOK PLAN, TOWNSEND..., Townsend, DE 19734]()
3 beds
|2 baths
|2,439 sq ft
1069 ROBINSON RD PEMBROOK PLAN, TOWNSEND...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2093254 • Mark L Handler Real Estate, Mar...
New
The Villas at The Preserve at Robinson Farms
![1071 ROBINSON RD DELRAY PLAN, TOWNSEND, ..., Townsend, DE 19734]()
3 beds
|2 baths
|2,004 sq ft
1071 ROBINSON RD DELRAY PLAN, TOWNSEND, ...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2093252 • Mark L Handler Real Estate, Mar...
The Ponds at Bayberry
![4116 LAUGHTON LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|3 baths
|2,650 sq ft
4116 LAUGHTON LN, MIDDLETOWN, DE, 19709
Community: The Ponds at Bayberry
MLS DENC2091776 • BHHS Fox & Roach - Hockessin, A...
Four Seasons at Baymont Farms
![798 HONEY LOCUST RD, MIDDLETOWN, DE, 197..., Middletown, DE 19709]()
3 beds
|3 baths
|1,875 sq ft
798 HONEY LOCUST RD, MIDDLETOWN, DE, 197...
Community: Four Seasons at Baymont Farms
MLS DENC2092652 • RE/MAX 1st Choice - Middletown,...
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 Farms
![114 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19..., Middletown, DE 19709]()
4 beds
|4 baths
|4,155 sq ft
114 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19...
Community: Four Seasons at Baymont Farms
MLS DENC2074562 • EXP Realty, LLC, Mahassein John...
The Villas at The Preserve at Robinson Farms
![1060 ROBINSON RD WHITFIELD PLAN, TOWNSEN..., Townsend, DE 19734]()
3 beds
|2 baths
|2,826 sq ft
1060 ROBINSON RD WHITFIELD PLAN, TOWNSEN...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2082670 • Mark L Handler Real Estate, Mar...
The Villas at The Preserve at Robinson Farms
![1064 ROBINSON RD LAKELAND PLAN, TOWNSEND..., Townsend, DE 19734]()
3 beds
|2 baths
|2,534 sq ft
1064 ROBINSON RD LAKELAND PLAN, TOWNSEND...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2082660 • Mark L Handler Real Estate, Mar...
The Villas at The Preserve at Robinson Farms
![1068 ROBINSON RD DELRAY PLAN, TOWNSEND, ..., Townsend, DE 19734]()
3 beds
|2 baths
|2,004 sq ft
1068 ROBINSON RD DELRAY PLAN, TOWNSEND, ...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2082616 • Mark L Handler Real Estate, Mar...
The Villas at The Preserve at Robinson Farms
![1062 ROBINSON RD WHITFIELD RANCH PLAN, T..., Townsend, DE 19734]()
3 beds
|2 baths
|2,449 sq ft
1062 ROBINSON RD WHITFIELD RANCH PLAN, T...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2082666 • Mark L Handler Real Estate, Mar...
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55places can help!
Questions? Call us:
(302) 279-7380
The Villas at The Preserve at Robinson Farms
![1066 ROBINSON RD PEMBROOK PLAN, TOWNSEND..., Townsend, DE 19734]()
3 beds
|2 baths
|2,439 sq ft
1066 ROBINSON RD PEMBROOK PLAN, TOWNSEND...
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2082668 • Mark L Handler Real Estate, Mar...
Parks Edge at Bayberry
![3037 BARBER LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
2 beds
|2 baths
|1,800 sq ft
3037 BARBER LN, MIDDLETOWN, DE, 19709
Community: Parks Edge at Bayberry
MLS DENC2089864 • Active Adults Realty, Ronald A ...
Springmill
![415 MORNING GLORY LN, MIDDLETOWN, DE, 19..., Middletown, DE 19709]()
MLS DENC2090086 • Patterson-Schwartz-Middletown, ...
New
Spring Arbor
![149 GAZEBO LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
MLS DENC2093004 • Patterson-Schwartz-Hockessin, R...
The Cascades
![663 MAYFIELD FALLS DR, NEWARK, DE, 19702, Newark, DE 19702]()
MLS DENC2091220 • Real Broker, LLC, Dawn A Wilson
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.
Village of Fountainview
![3000 FOUNTAINVIEW CIR # 3411, NEWARK, DE..., Newark, DE 19713]()
2 beds
|2 baths
|825 sq ft
|Condo
3000 FOUNTAINVIEW CIR # 3411, NEWARK, DE...
Community: Village of Fountainview
MLS DENC2092366 • Luke Real Estate, Robert F Mill...
Village of Fountainview
![3000 FOUNTAINVIEW CIR # 3311, NEWARK, DE..., Newark, DE 19713]()
2 beds
|2 baths
|825 sq ft
|Condo
3000 FOUNTAINVIEW CIR # 3311, NEWARK, DE...
Community: Village of Fountainview
MLS DENC2088420 • Empower Real Estate, LLC, Benja...
Venue at Winchelsea
![2918 CORDWAINERS LN, MIDDLETOWN, DE, 197..., Middletown, DE 19709]()
2 beds
|3 baths
|3,422 sq ft
2918 CORDWAINERS LN, MIDDLETOWN, DE, 197...
Community: Venue at Winchelsea
MLS DENC2090886 • Atlantic Five Realty, David Vas...
Riverbend
![548 ARROWGRASS LN, NEW CASTLE, DE, 19720, New Castle, DE 19720]()
MLS DENC2092520 • Atlantic Five Realty, David Vas...
The Villas at The Preserve at Robinson Farms
![1143 KAYLA LN, TOWNSEND, DE, 19734, Townsend, DE 19734]()
3 beds
|2 baths
|1,850 sq ft
1143 KAYLA LN, TOWNSEND, DE, 19734
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2082854 • RE/MAX Edge, Lisa Marie
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The Cascades
![511 DAVIS FALLS DR, NEWARK, DE, 19702, Newark, DE 19702]()
MLS DENC2092916 • House of Real Estate, Bayard Wi...
Venue at Winchelsea
![3112 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709]()
3 beds
|3 baths
|2,443 sq ft
3112 PETT LEVEL DR, MIDDLETOWN, DE, 1970...
Community: Venue at Winchelsea
MLS DENC2090798 • Atlantic Five Realty, David Vas...
Village of Fountainview
![1000 FOUNTAINVIEW CIR # 1113, NEWARK, DE..., Newark, DE 19713]()
2 beds
|2 baths
|1,025 sq ft
1000 FOUNTAINVIEW CIR # 1113, NEWARK, DE...
Community: Village of Fountainview
MLS DENC2090060 • Foraker Realty Co., Brian D. Fo...
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
![3124 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709]()
3 beds
|3 baths
|2,443 sq ft
3124 PETT LEVEL DR, MIDDLETOWN, DE, 1970...
Community: Venue at Winchelsea
MLS DENC2092526 • Atlantic Five Realty, David Vas...
Venue at Winchelsea
![3502 PIPEWELL LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|3 baths
|3,397 sq ft
3502 PIPEWELL LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
MLS DENC2092064 • Atlantic Five Realty, David Vas...
The Villas at The Preserve at Robinson Farms
![1019 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734]()
3 beds
|2 baths
|1,637 sq ft
1019 ROBINSON RD, TOWNSEND, DE, 19734
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2082266 • Mark L Handler Real Estate, Mar...
The Villas at The Preserve at Robinson Farms
![1020 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734]()
3 beds
|2 baths
1020 ROBINSON RD, TOWNSEND, DE, 19734
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2073180 • Mark L Handler Real Estate, Mar...
The Villas at The Preserve at Robinson Farms
![1027 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734]()
2 beds
|2 baths
|1,637 sq ft
1027 ROBINSON RD, TOWNSEND, DE, 19734
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2086096 • Mark L Handler Real Estate, Mar...
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Venue at Winchelsea
![2674 FAIRLIGHT DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
5 beds
|2 baths
|2,669 sq ft
2674 FAIRLIGHT DR, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
MLS DENC2090434 • Atlantic Five Realty, David Vas...
Parks Edge at Bayberry
![5735 E CENTRAL PARK DR, MIDDLETOWN, DE, ..., Middletown, DE 19709]()
3 beds
|2 baths
|2,156 sq ft
5735 E CENTRAL PARK DR, MIDDLETOWN, DE, ...
Community: Parks Edge at Bayberry
MLS DENC2092406 • Blenheim Marketing LLC, Brittan...
Springmill
![102 SPRINGMILL DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
MLS DENC2087760 • Long & Foster Real Estate, Inc....
Springmill
![51 SPRINGMILL DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
MLS DENC2083796 • Long & Foster Real Estate, Inc....
Frequently Asked Questions
In Middletown, there are no large communities, 1 medium community with 500-1000 homes, and 8 small communities with less than 500 homes.
The smallest 55+ communities in Middletown has 178 homes, the largest has 572 homes, and the average communities consists of 311 homes.
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.
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.
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.
Want more information about active adult communities around Middletown?
Want to learn more about 55+ communities in Middletown?
19
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REIN updates its listings on a daily basis. Data last updated: Nov 16, 2025.
This application does not include information on all of the properties available for sale at this time.
