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Chesapeake, VA 55+ active adult communities & homes for sale
12 communities near Chesapeake
94 homes near Chesapeake
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$400ks
- $500ks
Retreat at Edinburgh Farm..., Chesapeake, VA
New Construction
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55+ age-restricted
|
Built 2023 - present
|
102 homes
$400ks
- $500ks
The Retreat at Western Br..., Chesapeake, VA
New Construction
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55+ age-restricted
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Built 2021 - present
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84 homes
$400ks
- $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
- $600ks
Vistas at Bennett's Creek..., Suffolk, VA
New Construction
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Age-targeted
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Built 2024 - present
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49 homes
$200ks
- $400ks
Legacy at Burbage Lake, Suffolk, VA
New Construction
|
55+ age-restricted
|
90 homes
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4.4 rating (5 reviews)
![Eagle Pointe at Cahoon Pl...]()
$300ks
- $600ks
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
$500ks
- $600ks
The Landings at Bennett's..., Suffolk, VA
New and Resale
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55+ age-restricted
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Built 2020 - present
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23 homes
$400ks
- $600ks
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
$100ks
- $200ks
Monarch Walk, Chesapeake, VA
Resale Only
|
55+ age-restricted
|
Built 2007 - 2014
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62 homes
Download the Ultimate 55+ Homebuying Guide
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5 rating (1 reviews)
![Retreat at Kemps River]()
$300ks
- $400ks
Retreat at Kemps River, Chesapeake, VA
Resale Only
|
55+ age-restricted
|
Built 2017 - 2021
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80 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.
$200ks
- $300ks
The Commons at Hunningdon..., Chesapeake, VA
Resale Only
|
55+ age-restricted
|
Built 2004 - present
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87 homes
$400ks
- $500ks
Sommerton, Chesapeake, VA
Resale Only
|
55+ age-restricted
|
Built 2006 - 2017
|
90 homes
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New
The Landings at Bennett's Creek
![100 CREEK LN, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,170 sq ft
|Detached
100 CREEK LN, SUFFOLK, VA, 23435
Community: The Landings at Bennett's Creek
MLS 10628419 • BHHS RW Towne Realty, Linda Jones
New
Vistas at Bennett's Creek Quarter
![1004 BENNETTS ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|2 baths
|2,422 sq ft
|Detached
1004 BENNETTS ARCH, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10628415 • BHHS RW Towne Realty, Melissa Quee...
New
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 10627299 • BHHS RW Towne Realty, Bill Anderso...
Sommerton
![1032 CRANBERRY DR, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320]()
3 beds
|2 baths
|2,864 sq ft
|Townhome
1032 CRANBERRY DR, CHESAPEAKE, VA, 23320
Community: Sommerton
MLS 10628068 • Redfin Corporation, Richard Oliver
Monarch Walk
![3958 REX CIR, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
2 beds
|2 baths
|1,257 sq ft
|Townhome
3958 REX CIR, CHESAPEAKE, VA, 23321
Community: Monarch Walk
MLS 10627976 • The Real Estate Group, Jaine Lindo
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Retreat at Edinburgh Farms
![2206 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|3 baths
|2,642 sq ft
|Townhome
2206 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10627394 • D R Horton Realty of Virginia, Vic...
Retreat at Edinburgh Farms
![2202 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
2 beds
|2 baths
|1,462 sq ft
|Townhome
2202 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10627384 • D R Horton Realty of Virginia, Vic...
Retreat at Edinburgh Farms
![2200 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
2 beds
|2 baths
|1,462 sq ft
|Townhome
2200 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10627377 • D R Horton Realty of Virginia, Vic...
The Retreat at Harbour Cove
![2005 ASHER LOT 74 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|2 baths
|2,213 sq ft
|Townhome
2005 ASHER LOT 74 DR, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10627358 • 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.
Eagle Pointe at Cahoon Plantation
![518 DUNNING LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|2 baths
|1,758 sq ft
|Townhome
518 DUNNING LN, CHESAPEAKE, VA, 23322
Community: Eagle Pointe at Cahoon Plantation
MLS 10627314 • 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.
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 10627240 • Howard Hanna Real Estate Svcs., An...
Retreat at Kemps River
![936 BILTMORE WAY 37, CHESAPEAKE, VA, 233..., Chesapeake, VA 23320]()
3 beds
|3 baths
|2,112 sq ft
|Townhome
936 BILTMORE WAY 37, CHESAPEAKE, VA, 233...
Community: Retreat at Kemps River
MLS 10627181 • Real Broker LLC, Dominique Ferguso...
The Retreat at Greenbrier
![1526 CARROLTON WAY, CHESAPEAKE, VA, 2332..., Chesapeake, VA 23320]()
2 beds
|2 baths
|1,727 sq ft
|Townhome
1526 CARROLTON WAY, CHESAPEAKE, VA, 2332...
Community: The Retreat at Greenbrier
MLS 10625886 • BHHS RW Towne Realty, James Golden
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The Retreat at Harbour Cove
![2053 ASHER LOT 2 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,880 sq ft
|Townhome
2053 ASHER LOT 2 DR, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10626810 • BHHS RW Towne Realty, Laurie Willi...
Eagle Pointe at Cahoon Plantation
![1449 SCOONIE POINTE DR, CHESAPEAKE, VA, ..., Chesapeake, VA 23322]()
3 beds
|2 baths
|2,198 sq ft
|Townhome
1449 SCOONIE POINTE DR, CHESAPEAKE, VA, ...
Community: Eagle Pointe at Cahoon Plantation
MLS 10626787 • Creed Realty, Christine Burgdorf
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Retreat at Edinburgh Farms
![2017 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|3 baths
|2,781 sq ft
|Townhome
2017 BARTON LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10626712 • D R Horton Realty of Virginia, Vic...
The Retreat at Harbour Cove
![2092 ASHER LOT 52 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,859 sq ft
|Townhome
2092 ASHER LOT 52 DR, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10626621 • 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
![1014 LIBBY LOT 60 WAY, SUFFOLK, VA, 2343..., Suffolk, VA 23435]()
3 beds
|3 baths
|2,859 sq ft
|Townhome
1014 LIBBY LOT 60 WAY, SUFFOLK, VA, 2343...
Community: The Retreat at Harbour Cove
MLS 10626345 • BHHS RW Towne Realty, Laurie Willi...
Legacy at Burbage Lake
![2010 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|2 baths
|1,489 sq ft
|Townhome
2010 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10625954 • Pointe East Realty LLC, Christophe...
Legacy at Burbage Lake
![1014 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,015 sq ft
|Townhome
1014 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10625267 • Pointe East Realty LLC, Christophe...
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.
Legacy at Burbage Lake
![2012 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|3 baths
|1,978 sq ft
|Townhome
2012 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10625261 • Pointe East Realty LLC, Christophe...
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Legacy at Burbage Lake
![2004 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|1,930 sq ft
|Townhome
2004 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10625084 • Pointe East Realty LLC, Christophe...
The Retreat at Greenbrier
![1501 ROSEHILL DR 46, CHESAPEAKE, VA, 233..., Chesapeake, VA 23320]()
3 beds
|3 baths
|2,062 sq ft
|Townhome
1501 ROSEHILL DR 46, CHESAPEAKE, VA, 233...
Community: The Retreat at Greenbrier
MLS 10625581 • 1st Class Real Estate Flagship, Ch...
Eagle Pointe at Cahoon Plantation
![1427 HAWICK TER, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|2 baths
|1,748 sq ft
|Townhome
1427 HAWICK TER, CHESAPEAKE, VA, 23322
Community: Eagle Pointe at Cahoon Plantation
MLS 10625700 • BHHS RW Towne Realty, Catherine Un...
Legacy at Burbage Lake
![2006 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|2 baths
|1,069 sq ft
|Townhome
2006 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10625286 • Pointe East Realty LLC, Christophe...
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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
![1020 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
2 beds
|2 baths
|1,217 sq ft
|Townhome
1020 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10625279 • Pointe East Realty LLC, Christophe...
Retreat at Edinburgh Farms
![2013 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
2013 BARTON LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10625688 • D R Horton Realty of Virginia, Vic...
Vistas at Bennett's Creek Quarter
![4406 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|2 baths
|2,318 sq ft
|Detached
4406 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10625229 • BHHS RW Towne Realty, Melissa Quee...
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 10624808 • BHHS RW Towne Realty, Ryan Benton
The Retreat at Western Branch
![4620 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|3 baths
|2,842 sq ft
|Townhome
4620 LONGLEAF PL, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10624345 • GreenTree Realty Inc, Rachael Turn...
Want to learn more about 55+ communities in Chesapeake?
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Questions? Call us:
(804) 568-8917
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 Retreat at Western Branch
![3511 ELAINA WAY, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
3 beds
|2 baths
|2,555 sq ft
|Townhome
3511 ELAINA WAY, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10624247 • BHHS RW Towne Realty, Monique McCl...
The Retreat at Western Branch
![3509 ELAINA WAY, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|3 baths
|2,880 sq ft
|Townhome
3509 ELAINA WAY, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10624199 • BHHS RW Towne Realty, Monique McCl...
The Retreat at Western Branch
![3503 ELAINA WAY, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
4 beds
|3 baths
|2,880 sq ft
|Townhome
3503 ELAINA WAY, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10624186 • BHHS RW Towne Realty, Monique McCl...
The Retreat at Western Branch
![4725 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321]()
3 beds
|2 baths
|2,557 sq ft
|Townhome
4725 MAHOGANY RUN, CHESAPEAKE, VA, 23321
Community: The Retreat at Western Branch
MLS 10624181 • BHHS RW Towne Realty, Monique McCl...
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
![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 10623806 • Garrett Realty Partners, Adam Trip...
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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 10623441 • D R Horton Realty of Virginia, Vic...
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 10622864 • D R Horton Realty of Virginia, Vic...
Vistas at Bennett's Creek Quarter
![MM BENNETTS CREEK QUARTER (PALERMO 5 BED..., Suffolk, VA 23435]()
5 beds
|3 baths
|2,438 sq ft
|Detached
MM BENNETTS CREEK QUARTER (PALERMO 5 BED...
Community: Vistas at Bennett's Creek Quarter
MLS 10622743 • BHHS RW Towne Realty, Melissa Quee...
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The Retreat at Harbour Cove
![2057 ASHER LOT 4 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|2 baths
|2,557 sq ft
|Townhome
2057 ASHER LOT 4 DR, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10621213 • BHHS RW Towne Realty, Laurie Willi...
Retreat at Edinburgh Farms
![2009 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
2009 BARTON LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10620514 • D R Horton Realty of Virginia, Vic...
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.
Want more information about active adult communities around Chesapeake?
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REIN updates its listings on a daily basis. Data last updated: Apr 08, 2026.
This application does not include information on all of the properties available for sale at this time.
