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Call us at (804) 568-8917 to learn more about active adult communities in Chesapeake

Chesapeake, VA 55+ active adult communities & homes for sale - Page 3

82 homes near Chesapeake

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Retreat at Edinburgh Farm...
$400ks - $500ks
Retreat at Edinburgh Farm..., Chesapeake, VA
New Construction | 55+ age-restricted | Built 2023 - present | 102 homes
The Retreat at Western Br...
$400ks - $500ks
The Retreat at Western Br..., Chesapeake, VA
New Construction | 55+ age-restricted | Built 2021 - present | 84 homes
The Retreat at Harbour Co...
$400ks - $500ks
The Retreat at Harbour Co..., Suffolk, VA
New Construction | 55+ age-restricted | Built 2022 - present | 101 homes
4.4 rating (5 reviews) Eagle Pointe at Cahoon Pl...
$300ks - $600ks
Eagle Pointe at Cahoon Pl..., Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2005 - present | 501 homes
Legacy at Burbage Lake
$200ks - $400ks
Legacy at Burbage Lake, Suffolk, VA
New Construction | 55+ age-restricted | 90 homes
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
The Landings at Bennett's...
$500ks - $600ks
The Landings at Bennett's..., Suffolk, VA
New and Resale | 55+ age-restricted | Built 2020 - present | 23 homes
Vistas at Bennett's Creek...
$400ks - $600ks
Vistas at Bennett's Creek..., Suffolk, VA
New Construction | Age-targeted | Built 2024 - present | 49 homes
Sommerton
$400ks - $500ks
Sommerton, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 90 homes
The Retreat at Greenbrier
$400ks - $600ks
The Retreat at Greenbrier, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2003 - 2015 | 184 homes
The Commons at Hunningdon...
$200ks - $300ks
The Commons at Hunningdon..., Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2004 - present | 87 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.
Monarch Walk
$100ks - $200ks
Monarch Walk, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 62 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
The Retreat at Western Branch 4611 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$505,422

4 beds

|

3 baths

|

2,880 sq ft

|

Townhome

4611 LONGLEAF PL, CHESAPEAKE, VA, 23321
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
The Retreat at Western Branch 4730 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$537,000

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

4730 MAHOGANY RUN, CHESAPEAKE, VA, 23321
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.

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The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: May 28, 2026.
This application does not include information on all of the properties available for sale at this time.

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