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Chesapeake, VA 55+ active adult communities & homes for sale
11 communities near Chesapeake
70 homes near Chesapeake
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$500Ks
- $600Ks
Retreat at Edinburgh Farm..., Chesapeake, VA
New Construction
|
55+ age-restricted
|
Built 2023 - present
|
102 homes
$500Ks
The Retreat at Harbour Co..., Suffolk, VA
New Construction
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55+ age-restricted
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Built 2022 - present
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101 homes
$400Ks
- $500Ks
The Retreat at Western Br..., Chesapeake, VA
New Construction
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55+ age-restricted
|
Built 2021 - present
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84 homes
$600Ks
- $700Ks
The Landings at Bennett's..., Suffolk, VA
New and Resale
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55+ age-restricted
|
Built 2020 - present
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23 homes
$400Ks
The Commons at Hunningdon..., Chesapeake, VA
Resale Only
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55+ age-restricted
|
Built 2004 - present
|
87 homes
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4.4 rating (5 reviews)
![Eagle Pointe at Cahoon Pl...]()
$400Ks
- $500Ks
Eagle Pointe at Cahoon Pl..., Chesapeake, VA
Resale Only
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55+ age-restricted
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Built 2005 - present
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501 homes
$400Ks
The Retreat at Greenbrier, Chesapeake, VA
Resale Only
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55+ age-restricted
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Built 2003 - 2015
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184 homes
5 rating (1 reviews)
![Retreat at Kemps River]()
$300Ks
- $400Ks
Retreat at Kemps River, Chesapeake, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2021
|
80 homes
Download the Ultimate 55+ Homebuying Guide
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$200Ks
- $400Ks
Legacy at Burbage Lake, Suffolk, VA
New Construction
|
55+ age-restricted
|
90 homes
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
$100Ks
- $200Ks
Monarch Walk, Chesapeake, VA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2014
|
62 homes
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New
Retreat at Edinburgh Farms
![2142 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
2 beds
|3 baths
|1,986 sq ft
|Townhome
2142 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10618144 • D R Horton Realty of Virginia, Vic...
New
The Retreat at Greenbrier
![1415 SANDCHIP TER # 127, CHESAPEAKE, VA,..., Chesapeake, VA 23320]()
4 beds
|2 baths
|1,977 sq ft
|Detached
1415 SANDCHIP TER # 127, CHESAPEAKE, VA,...
Community: The Retreat at Greenbrier
MLS 10617678 • Clearview Real Estate, Lauren Lerc...
New
The Retreat at Western Branch
![4723 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|3 baths
|2,880 sq ft
|Townhome
4723 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10618083 • BHHS RW Towne Realty, Monique McCl...
The Commons at Hunningdon Lakes
![809 MASON CT, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320]()
3 beds
|2 baths
|2,225 sq ft
|Detached
809 MASON CT, CHESAPEAKE, VA, 23320
Community: The Commons at Hunningdon Lakes
MLS 10617216 • The Bryant Group, Misty Mazzaferro
Retreat at Edinburgh Farms
![2212 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|3 baths
|2,314 sq ft
|Townhome
2212 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10617434 • D R Horton Realty of Virginia, Vic...
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The Retreat at Western Branch
![3105 LANTERN PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|2 baths
|2,653 sq ft
|Townhome
3105 LANTERN PL, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10617135 • Real Broker LLC, Maritza Arroyo
The Retreat at Western Branch
![4719 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
4719 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10617013 • BHHS RW Towne Realty, Monique McCl...
Eagle Pointe at Cahoon Plantation
![1506 HAWICK TER, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,598 sq ft
|Detached
1506 HAWICK TER, CHESAPEAKE, VA, 23322
Community: Eagle Pointe at Cahoon Plantation
MLS 10616837 • The Real Estate Group, Beth Wiegan
Eagle Pointe at Cahoon Plantation
![1144 WHITBURN TER, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|2 baths
|2,149 sq ft
|Townhome
1144 WHITBURN TER, CHESAPEAKE, VA, 23322
Community: Eagle Pointe at Cahoon Plantation
MLS 10616602 • The Real Estate Group, Beth Wiegan
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.
Sommerton
![1008 CRANBERRY DR # 88, CHESAPEAKE, VA, ..., Chesapeake, VA 23320]()
3 beds
|2 baths
|2,575 sq ft
|Townhome
1008 CRANBERRY DR # 88, CHESAPEAKE, VA, ...
Community: Sommerton
MLS 10616175 • Creed Realty, Brandi McNeil
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Retreat at Kemps River
![936 BILTMORE WAY # 37, CHESAPEAKE, VA, 2..., Chesapeake, VA 23320]()
3 beds
|3 baths
|2,112 sq ft
|Townhome
936 BILTMORE WAY # 37, CHESAPEAKE, VA, 2...
Community: Retreat at Kemps River
MLS 10616319 • Real Broker LLC, Dominique Ferguso...
The Retreat at Western Branch
![4729 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|3 baths
|2,880 sq ft
|Townhome
4729 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10616206 • BHHS RW Towne Realty, Monique McCl...
Eagle Pointe at Cahoon Plantation
![407 DUNDEE LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|3 baths
|2,378 sq ft
|Townhome
407 DUNDEE LN, CHESAPEAKE, VA, 23322
Community: Eagle Pointe at Cahoon Plantation
MLS 10616084 • The Real Estate Group, Beth Wiegan
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Retreat at Edinburgh Farms
![2000 NICOLE LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
2000 NICOLE LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10616046 • D R Horton Realty of Virginia, Vic...
The Retreat at Western Branch
![4743 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|2 baths
|2,653 sq ft
|Townhome
4743 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10614809 • BHHS RW Towne Realty, Tori Hanbury
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Retreat at Edinburgh Farms
![2001 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
2001 MUNRO LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10615674 • D R Horton Realty of Virginia, Vic...
The Retreat at Harbour Cove
![2012 ASHER DR LOT 80, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|2 baths
|1,986 sq ft
|Townhome
2012 ASHER DR LOT 80, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10615615 • BHHS RW Towne Realty, Laurie Willi...
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 Retreat at Harbour Cove
![1204 BRIANNA LN LOT 32, SUFFOLK, VA, 234..., Suffolk, VA 23435]()
3 beds
|3 baths
|2,859 sq ft
|Townhome
1204 BRIANNA LN LOT 32, SUFFOLK, VA, 234...
Community: The Retreat at Harbour Cove
MLS 10615504 • BHHS RW Towne Realty, Laurie Willi...
Retreat at Edinburgh Farms
![2009 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
2009 MUNRO LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10615574 • D R Horton Realty of Virginia, Vic...
Eagle Pointe at Cahoon Plantation
![551 DUNNING LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|2 baths
|1,760 sq ft
|Townhome
551 DUNNING LN, CHESAPEAKE, VA, 23322
Community: Eagle Pointe at Cahoon Plantation
MLS 10614732 • The Real Estate Group, Beth Wiegan
Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
Sommerton
![1072 CRANBERRY DR, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320]()
3 beds
|2 baths
|2,467 sq ft
|Townhome
1072 CRANBERRY DR, CHESAPEAKE, VA, 23320
Community: Sommerton
MLS 10614553 • CENTURY 21 Nachman Realty, Tom Pul...
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The Retreat at Western Branch
![4646 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|3 baths
|2,842 sq ft
|Townhome
4646 LONGLEAF PL, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10614629 • KW Coastal Virginia Chesapeake, Da...
Legacy at Burbage Lake
![2018 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|2 baths
|1,563 sq ft
|Townhome
2018 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10614214 • Pointe East Realty LLC, Carolyn Hu...
The Retreat at Western Branch
![4728 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|3 baths
|2,880 sq ft
|Townhome
4728 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10611933 • BHHS RW Towne Realty, Monique McCl...
Retreat at Edinburgh Farms
![2144 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|3 baths
|2,314 sq ft
|Townhome
2144 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10610914 • D R Horton Realty of Virginia, Vic...
Want to learn more about 55+ rental communities in Chesapeake?
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Questions? Call us:
(804) 568-8917
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.
Legacy at Burbage Lake
![1016 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|1,978 sq ft
|Townhome
1016 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10610060 • Pointe East Realty LLC, Carolyn Hu...
Retreat at Edinburgh Farms
![2152 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
2 beds
|2 baths
|1,462 sq ft
|Townhome
2152 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10609757 • D R Horton Realty of Virginia, Vic...
The Retreat at Harbour Cove
![2069 ASHER DR LOT 10, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,880 sq ft
|Townhome
2069 ASHER DR LOT 10, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10609622 • BHHS RW Towne Realty, Laurie Willi...
The Retreat at Greenbrier
![1439 THISTLEWOOD LN, CHESAPEAKE, VA, 233..., Chesapeake, VA 23320]()
2 beds
|2 baths
|1,727 sq ft
|Townhome
1439 THISTLEWOOD LN, CHESAPEAKE, VA, 233...
Community: The Retreat at Greenbrier
MLS 10609334 • Beach Realty United, Jamie Flowers
Legacy at Burbage Lake
![2002 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|2 baths
|1,052 sq ft
|Townhome
2002 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10609017 • Garrett Realty Partners, Adam Trip...
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Read the Ultimate 55+ Rental Guide
Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.
The Commons at Hunningdon Lakes
![817 NICHOLSON CT, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320]()
3 beds
|2 baths
|2,225 sq ft
|Townhome
817 NICHOLSON CT, CHESAPEAKE, VA, 23320
Community: The Commons at Hunningdon Lakes
MLS 10608203 • Howard Hanna Real Estate Svcs., Ro...
The Retreat at Western Branch
![4644 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
3 beds
|2 baths
|2,481 sq ft
|Townhome
4644 LONGLEAF PL, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10607679 • Brooke Madison & Associates, Kevin...
The Landings at Bennett's Creek
![119 CREEK LN, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,698 sq ft
|Detached
119 CREEK LN, SUFFOLK, VA, 23435
Community: The Landings at Bennett's Creek
MLS 10603490 • Howard Hanna Real Estate Svcs., An...
The Landings at Bennett's Creek
![201 COVE REACH, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,698 sq ft
|Detached
201 COVE REACH, SUFFOLK, VA, 23435
Community: The Landings at Bennett's Creek
MLS 10603615 • Howard Hanna Real Estate Svcs., E ...
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.
Retreat at Edinburgh Farms
![2028 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|2 baths
|2,557 sq ft
|Townhome
2028 MUNRO LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10605123 • D R Horton Realty of Virginia, Vic...
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The Retreat at Western Branch
![3505 ELAINA WAY, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|2 baths
|2,433 sq ft
|Townhome
3505 ELAINA WAY, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10607782 • BHHS RW Towne Realty, Monique McCl...
The Commons at Hunningdon Lakes
![800 MONROE CT, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320]()
3 beds
|2 baths
|2,225 sq ft
|Townhome
800 MONROE CT, CHESAPEAKE, VA, 23320
Community: The Commons at Hunningdon Lakes
MLS 10604659 • Swell Realty Co, Chris Faircloth
The Retreat at Harbour Cove
![2022 ASHER DR LOT 95, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,314 sq ft
|Townhome
2022 ASHER DR LOT 95, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10583341 • BHHS RW Towne Realty, Laurie Willi...
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The Retreat at Harbour Cove
![2092 ASHER DR LOT 52, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,859 sq ft
|Townhome
2092 ASHER DR LOT 52, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10582788 • BHHS RW Towne Realty, Laurie Willi...
The Retreat at Harbour Cove
![2071 ASHER DR LOT 11, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|2 baths
|2,557 sq ft
|Townhome
2071 ASHER DR LOT 11, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10604864 • BHHS RW Towne Realty, Summer Johns...
Frequently Asked Questions
In Chesapeake, there are no large communities, 1 medium community with 500-1000 homes, and 7 small communities with less than 500 homes.
The smallest 55+ communities in Chesapeake has 62 homes, the largest has 501 homes, and the average communities consists of 148 homes.
Yes, there are new 55+ homes available in Chesapeake. The most recent communities started in Chesapeake include Retreat at Edinburgh Farms, The Retreat at Western Branch, Retreat at Kemps River. There are also 2 communities in Chesapeake that offer new construction homes, including The Retreat at Western Branch, Retreat at Edinburgh Farms.
Yes, there are gated 55+ communities in Chesapeake. Approximately 25.0% of 55+ communities in the area are gated. For instance, Monarch Walk is a gated communities with 62 homes, and Eagle Pointe at Cahoon Plantation is another gated communities with 501 homes.
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REIN updates its listings on a daily basis. Data last updated: Feb 01, 2026.
This application does not include information on all of the properties available for sale at this time.
