Call us at (302) 279-7380 to learn more about active adult communities in Middletown
Middletown, DE 55+ active adult communities & homes for sale
19 communities near Middletown
71 homes near Middletown
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$400ks
- $500ks
Traditions at Whitehall, Middletown, DE
New Construction
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55+ age-restricted
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Built 2019 - present
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250 homes
$400ks
The Villas at The Preserv..., Townsend, DE
New Construction
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55+ age-restricted
|
Built 2017 - present
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144 homes
$400ks
- $600ks
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
$400ks
- $500ks
Four Seasons at Baymont F..., Middletown, DE
New Construction
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Age-targeted
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Built 2019 - present
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288 homes
$300ks
- $400ks
Ashland, Smyrna, DE
Resale Only
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55+ age-restricted
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Built 2016 - 2020
|
150 homes
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$300ks
- $500ks
The Ponds at Bayberry, Middletown, DE
New and Resale
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55+ age-restricted
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Built 2015 - present
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572 homes
$400ks
- $500ks
Four Seasons at Silver Ma..., Middletown, DE
Resale Only
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55+ age-restricted
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Built 2011 - 2017
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299 homes
$300ks
- $400ks
Whispering Woods, Middletown, DE
New and Resale
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55+ age-restricted
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Built 2017 - present
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178 homes
3 rating (2 reviews)
![Spring Arbor]()
$300ks
- $500ks
Spring Arbor, Middletown, DE
Resale Only
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55+ age-restricted
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Built 2007 - 2018
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317 homes
$400ks
- $500ks
Legacy at The Preserve at..., Middletown, DE
New and Resale
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55+ age-restricted
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Built 2016 - present
|
205 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.
4 rating (1 reviews)
![Village of Fountainview]()
$100ks
- $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
$400ks
- $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
$200ks
Crossings at Christiana, Bear, DE
Resale Only
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55+ age-restricted
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Built 2003 - 2011
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140 homes
2.4 rating (5 reviews)
![Legacy at The Village of ...]()
$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
$400ks
- $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
5 rating (1 reviews)
![Springmill]()
$300ks
- $400ks
Springmill, Middletown, DE
Resale Only
|
55+ age-restricted
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Built 2000 - 2007
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362 homes
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(302) 279-7380
$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
$400ks
Riverbend, New Castle, DE
New Construction
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55+ age-restricted
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Built 2021 - present
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200 homes
$200ks
- $300ks
Village of Red Lion Creek, Bear, DE
Resale Only
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55+ age-restricted
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Built 2002 - 2005
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85 homes
New
The Ponds at Bayberry
![642 VIVALDI DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
4 beds
|3 baths
|2,900 sq ft
642 VIVALDI DR, MIDDLETOWN, DE, 19709
Community: The Ponds at Bayberry
MLS DENC2110610 • Patterson-Schwartz-Middletown, ... • Patterson-Schwartz-Middletown
New
Venue at Winchelsea
![2213 WINCHELSEA PKWY, MIDDLETOWN, DE, 19..., Middletown, DE 19709]()
3 beds
|3 baths
|2,443 sq ft
2213 WINCHELSEA PKWY, MIDDLETOWN, DE, 19...
Community: Venue at Winchelsea
MLS DENC2110504 • Atlantic Five Realty, David Vas... • Atlantic Five Realty
New
Venue at Winchelsea
![3305 ROOKERY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
2 beds
|3 baths
|3,292 sq ft
3305 ROOKERY LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
MLS DENC2110480 • Atlantic Five Realty, David Vas... • Atlantic Five Realty
New
Venue at Winchelsea
![3310 ROOKERY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|3 baths
|3,015 sq ft
3310 ROOKERY LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
MLS DENC2110450 • Atlantic Five Realty, David Vas... • Atlantic Five Realty
Four Seasons at Silver Maple
![631 RED MAPLE RD, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|2 baths
|1,450 sq ft
631 RED MAPLE RD, MIDDLETOWN, DE, 19709
Community: Four Seasons at Silver Maple
MLS DENC2110194 • Crown Homes Real Estate, Ashley... • Crown Homes Real Estate
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The Cascades
![1031 SHANNON FALLS DR, NEWARK, DE, 19702, Newark, DE 19702]()
MLS DENC2109976 • Active Adults Realty, Ronald Me... • Active Adults Realty
Village of Fountainview
![6 FOUNTAINVIEW DR, NEWARK, DE, 19713, Newark, DE 19713]()
2 beds
|3 baths
|1,890 sq ft
|Condo
6 FOUNTAINVIEW DR, NEWARK, DE, 19713
Community: Village of Fountainview
MLS DENC2110174 • Patterson-Schwartz-Newark, Davi... • Patterson-Schwartz-Newark
Springmill
![54 SPRINGMILL DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
MLS DENC2110058 • Patterson-Schwartz-Hockessin, P... • Patterson-Schwartz-Hockessin
Village of Fountainview
![1000 FOUNTAINVIEW CIR 1306, NEWARK, DE, ..., Newark, DE 19713]()
2 beds
|2 baths
|Condo
1000 FOUNTAINVIEW CIR 1306, NEWARK, DE, ...
Community: Village of Fountainview
MLS DENC2109750 • EXP Realty, LLC, Carol M Quattr... • EXP Realty, LLC
Venue at Winchelsea
![3307 ROOKERY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|3 baths
|2,151 sq ft
3307 ROOKERY LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
MLS DENC2109738 • Atlantic Five Realty, David Vas... • Atlantic Five Realty
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.
The Villas at The Preserve at Robinson Farms
![929 ROBINSON RD, TOWNSEND, DE, 19734, Townsend, DE 19734]()
3 beds
|4 baths
|3,350 sq ft
929 ROBINSON RD, TOWNSEND, DE, 19734
Community: The Villas at The Preserve at Robinson Farms
MLS DENC2109548 • Crown Homes Real Estate, Melvin... • Crown Homes Real Estate
Legacy at The Preserve at Deep Creek
![211 ANGLESEY DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
2 beds
|3 baths
|2,475 sq ft
211 ANGLESEY DR, MIDDLETOWN, DE, 19709
Community: Legacy at The Preserve at Deep Creek
MLS DENC2109526 • Keys & Deeds Realty, Lorie Lyn ... • Keys & Deeds Realty
Springmill
![352 DAYLILLY WAY, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
MLS DENC2104838 • Empower Real Estate, LLC, Marc ... • Empower Real Estate, LLC
Village of Red Lion Creek
![272 W RED LION DR, BEAR, DE, 19701, Bear, DE 19701]()
2 beds
|2 baths
|2,075 sq ft
272 W RED LION DR, BEAR, DE, 19701
Community: Village of Red Lion Creek
MLS DENC2108362 • Coldwell Banker Realty, Lacinda... • Coldwell Banker Realty
Venue at Winchelsea
![2638 FAIRLIGHT DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|3 baths
|2,443 sq ft
2638 FAIRLIGHT DR, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
MLS DENC2108520 • EXP Realty, LLC, Katina Geralis • EXP Realty, LLC
Crossings at Christiana
![626 KENDALL DR, BEAR, DE, 19701, Bear, DE 19701]()
MLS DENC2108876 • Crown Homes Real Estate, John R... • Crown Homes Real Estate
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Questions? Call us:
(302) 279-7380
Whispering Woods
![352 TRANQUILITY WAY, MIDDLETOWN, DE, 197..., Middletown, DE 19709]()
3 beds
|3 baths
|2,500 sq ft
352 TRANQUILITY WAY, MIDDLETOWN, DE, 197...
Community: Whispering Woods
MLS DENC2108800 • Compass, Andrea L Harrington • Compass
Venue at Winchelsea
![3164 PETT LEVEL DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709]()
3 beds
|3 baths
|2,443 sq ft
3164 PETT LEVEL DR, MIDDLETOWN, DE, 1970...
Community: Venue at Winchelsea
MLS DENC2108612 • Atlantic Five Realty, David Vas... • Atlantic Five Realty
Village of Fountainview
![1000 FOUNTAINVIEW CIR 407, NEWARK, DE, 1..., Newark, DE 19713]()
2 beds
|2 baths
|1,067 sq ft
|Condo
1000 FOUNTAINVIEW CIR 407, NEWARK, DE, 1...
Community: Village of Fountainview
MLS DENC2108306 • Patterson-Schwartz - Greenville... • Patterson-Schwartz - Greenville
Four Seasons at Silver Maple
![239 SILKY DOGWOOD LN, MIDDLETOWN, DE, 19..., Middletown, DE 19709]()
3 beds
|2 baths
|2,325 sq ft
239 SILKY DOGWOOD LN, MIDDLETOWN, DE, 19...
Community: Four Seasons at Silver Maple
MLS DENC2107742 • Crown Homes Real Estate, Corey ... • Crown Homes Real Estate
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.
Spring Arbor
![623 GARDEN GATE DR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709]()
MLS DENC2108110 • Coldwell Banker Realty, Jason P... • Coldwell Banker Realty
Four Seasons at Silver Maple
![171 SILVER MAPLE RD, MIDDLETOWN, DE, 197..., Middletown, DE 19709]()
3 beds
|2 baths
|3,558 sq ft
171 SILVER MAPLE RD, MIDDLETOWN, DE, 197...
Community: Four Seasons at Silver Maple
MLS DENC2108054 • Patterson-Schwartz-Middletown, ... • Patterson-Schwartz-Middletown
Legacy at The Preserve at Deep Creek
![272 ANGLESEY DR, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|3 baths
|3,303 sq ft
272 ANGLESEY DR, MIDDLETOWN, DE, 19709
Community: Legacy at The Preserve at Deep Creek
MLS DENC2107852 • RE/MAX Advantage Realty, Richar... • RE/MAX Advantage Realty
Springmill
![100 DAWN CT, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
MLS DENC2107936 • Patterson-Schwartz-Middletown, ... • Patterson-Schwartz-Middletown
The Ponds at Bayberry
![4534 CAGNEY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
4 beds
|3 baths
|3,025 sq ft
4534 CAGNEY LN, MIDDLETOWN, DE, 19709
Community: The Ponds at Bayberry
MLS DENC2107832 • Compass, Andrea L Harrington • Compass
The Cascades
![678 MAYFIELD FALLS DR, NEWARK, DE, 19702, Newark, DE 19702]()
MLS DENC2107724 • Patterson-Schwartz-Newark, Jenn... • Patterson-Schwartz-Newark
Venue at Winchelsea
![3034 IVYHOUSE LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|4 baths
|2,151 sq ft
3034 IVYHOUSE LN, MIDDLETOWN, DE, 19709
Community: Venue at Winchelsea
MLS DENC2107686 • Atlantic Five Realty, David Vas... • Atlantic Five Realty
Want to learn more about 55+ communities in Middletown?
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(302) 279-7380
Four Seasons at Baymont Farms
![112 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19..., Middletown, DE 19709]()
3 beds
|4 baths
|2,441 sq ft
112 AUSTRIAN PINE CT, MIDDLETOWN, DE, 19...
Community: Four Seasons at Baymont Farms
MLS DENC2107688 • Delaware Homes Inc, Barbara K H... • Delaware Homes Inc
Four Seasons at Baymont Farms
![13 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1..., Middletown, DE 19709]()
3 beds
|3 baths
|1,859 sq ft
13 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1...
Community: Four Seasons at Baymont Farms
MLS DENC2107684 • Delaware Homes Inc, Barbara K H... • Delaware Homes Inc
The Ponds at Bayberry
![4200 CROSBY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
4 beds
|3 baths
|2,700 sq ft
4200 CROSBY LN, MIDDLETOWN, DE, 19709
Community: The Ponds at Bayberry
MLS DENC2106702 • Walker Realty Group, Laura Walk... • Walker Realty Group
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.
Ashland
![145 E CLARENDON DR, SMYRNA, DE, 19977, Smyrna, DE 19977]()
MLS DEKT2048660 • Empower Real Estate, LLC, Debbi... • Empower Real Estate, LLC
Whispering Woods
![1428 WHISPERING WOODS RD, MIDDLETOWN, DE..., Middletown, DE 19709]()
2 beds
|2 baths
|1,275 sq ft
1428 WHISPERING WOODS RD, MIDDLETOWN, DE...
Community: Whispering Woods
MLS DENC2106260 • Compass, Dustin Oldfather • Compass
Four Seasons at Baymont Farms
![506 CHERRY BARK RD, MIDDLETOWN, DE, 1970..., Middletown, DE 19709]()
4 beds
|4 baths
|2,525 sq ft
506 CHERRY BARK RD, MIDDLETOWN, DE, 1970...
Community: Four Seasons at Baymont Farms
MLS DENC2106630 • Keller Williams Realty, Megan A... • Keller Williams Realty
Whispering Woods
![529 CONTEMPLATION WAY, MIDDLETOWN, DE, 1..., Middletown, DE 19709]()
3 beds
|3 baths
|2,375 sq ft
529 CONTEMPLATION WAY, MIDDLETOWN, DE, 1...
Community: Whispering Woods
MLS DENC2105858 • BHHS Fox & Roach - Hockessin, E... • BHHS Fox & Roach - Hockessin
Parks Edge at Bayberry
![2817 BERNSTEIN CIR, MIDDLETOWN, DE, 1970..., Middletown, DE 19709]()
MLS DENC2106040 • Blenheim Marketing LLC, Brittan... • Blenheim Marketing LLC
Traditions at Whitehall
![216 BALDY LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
3 beds
|2 baths
|2,925 sq ft
216 BALDY LN, MIDDLETOWN, DE, 19709
Community: Traditions at Whitehall
MLS DENC2105896 • Patterson-Schwartz-Hockessin, J... • Patterson-Schwartz-Hockessin
Ashland
![28 PEGASUS LN, SMYRNA, DE, 19977, Smyrna, DE 19977]()
MLS DEKT2047988 • RE/MAX Elite, Kathleen S Pennin... • RE/MAX Elite
Four Seasons at Baymont Farms
![21 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1..., Middletown, DE 19709]()
3 beds
|3 baths
|2,080 sq ft
21 GOLDEN RAINTREE CT, MIDDLETOWN, DE, 1...
Community: Four Seasons at Baymont Farms
MLS DENC2104904 • Delaware Homes Inc, Barbara K H... • Delaware Homes Inc
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Legacy at The Village of Fox Meadow
![224 ANITA CT, NEWARK, DE, 19702, Newark, DE 19702]()
3 beds
|4 baths
|3,118 sq ft
224 ANITA CT, NEWARK, DE, 19702
Community: Legacy at The Village of Fox Meadow
MLS DENC2104862 • Patterson-Schwartz-Newark, Davi... • Patterson-Schwartz-Newark
Traditions at Whitehall
![130 BURLINA BLVD, MIDDLETOWN, DE, 19709, Middletown, DE 19709]()
2 beds
|3 baths
|2,275 sq ft
130 BURLINA BLVD, MIDDLETOWN, DE, 19709
Community: Traditions at Whitehall
MLS DENC2104738 • RE/MAX Advantage Realty, Lisa M... • RE/MAX Advantage Realty
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.
Frequently Asked Questions
In Middletown, there are no large communities, 1 medium community with 500-1000 homes, and 9 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 301 homes.
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.
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.
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.
Want more information about active adult communities around Middletown?
Want to learn more about 55+ communities in Middletown?
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REIN updates its listings on a daily basis. Data last updated: Sep 05, 2026.
This application does not include information on all of the properties available for sale at this time.
