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Chesapeake, VA 55+ active adult communities & homes for sale - Page 2
12 communities near Chesapeake
92 homes near Chesapeake
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$400ks
- $500ks
Retreat at Edinburgh Farm..., Chesapeake, VA
New Construction
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55+ age-restricted
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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
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55+ age-restricted
|
Built 2007 - 2014
|
62 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.
5 rating (1 reviews)
![Retreat at Kemps River]()
$300ks
- $400ks
Retreat at Kemps River, Chesapeake, VA
Resale Only
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55+ age-restricted
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Built 2017 - 2021
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80 homes
$200ks
- $300ks
The Commons at Hunningdon..., Chesapeake, VA
Resale Only
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55+ age-restricted
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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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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...
Retreat at Edinburgh Farms
![2001 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
2001 BARTON LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10620511 • D R Horton Realty of Virginia, Vic...
Eagle Pointe at Cahoon Plantation
![1436 SCOONIE POINTE DR, CHESAPEAKE, VA, ..., Chesapeake, VA 23322]()
3 beds
|2 baths
|1,748 sq ft
|Townhome
1436 SCOONIE POINTE DR, CHESAPEAKE, VA, ...
Community: Eagle Pointe at Cahoon Plantation
MLS 10620257 • Iron Valley Real Est Norfolk, Juli...
Vistas at Bennett's Creek Quarter
![MM BENNETTS CREEK QUARTER (SPINNAKER 3 B..., Suffolk, VA 23435]()
3 beds
|2 baths
|2,176 sq ft
|Detached
MM BENNETTS CREEK QUARTER (SPINNAKER 3 B...
Community: Vistas at Bennett's Creek Quarter
MLS 10619761 • BHHS RW Towne Realty, Melissa Quee...
Retreat at Edinburgh Farms
![2150 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
2 beds
|2 baths
|1,462 sq ft
|Townhome
2150 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10619576 • D R Horton Realty of Virginia, Vic...
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Retreat at Edinburgh Farms
![2213 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
2 beds
|2 baths
|1,462 sq ft
|Townhome
2213 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10619479 • D R Horton Realty of Virginia, Vic...
Retreat at Edinburgh Farms
![2217 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|3 baths
|2,642 sq ft
|Townhome
2217 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10619469 • D R Horton Realty of Virginia, Vic...
Retreat at Edinburgh Farms
![2005 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|3 baths
|2,781 sq ft
|Townhome
2005 BARTON LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10618900 • D R Horton Realty of Virginia, Vic...
Retreat at Edinburgh Farms
![2211 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
2 beds
|2 baths
|1,462 sq ft
|Townhome
2211 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10618874 • D R Horton Realty of Virginia, Vic...
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
![1103 ELAINA LOT 44 PL, SUFFOLK, VA, 2343..., Suffolk, VA 23435]()
3 beds
|3 baths
|2,859 sq ft
|Townhome
1103 ELAINA LOT 44 PL, SUFFOLK, VA, 2343...
Community: The Retreat at Harbour Cove
MLS 10618618 • BHHS RW Towne Realty, Laurie Willi...
Retreat at Edinburgh Farms
![2215 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
3 beds
|3 baths
|2,642 sq ft
|Townhome
2215 EDWIN DR, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10618622 • D R Horton Realty of Virginia, Vic...
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...
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...
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Vistas at Bennett's Creek Quarter
![4409 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|2 baths
|1,825 sq ft
|Detached
4409 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10617785 • BHHS RW Towne Realty, Melissa Quee...
Vistas at Bennett's Creek Quarter
![1021 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,066 sq ft
|Detached
1021 BENNETT'S ARCH, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10617034 • The Property Shoppe, Nora Spruill
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...
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...
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.
Vistas at Bennett's Creek Quarter
![1027 BENNETTS ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,150 sq ft
|Detached
1027 BENNETTS ARCH, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10615825 • The Property Shoppe, Nora Spruill
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
![1204 BRIANNA LOT 32 LN, SUFFOLK, VA, 234..., Suffolk, VA 23435]()
3 beds
|3 baths
|2,859 sq ft
|Townhome
1204 BRIANNA LOT 32 LN, 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...
Want to learn more about 55+ communities in Chesapeake?
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Questions? Call us:
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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...
Vistas at Bennett's Creek Quarter
![4408 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|2 baths
|2,278 sq ft
|Detached
4408 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10613808 • BHHS RW Towne Realty, Melissa Quee...
Vistas at Bennett's Creek Quarter
![1041 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,066 sq ft
|Detached
1041 BENNETT'S ARCH, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10613401 • The Property Shoppe, Nora Spruill
Vistas at Bennett's Creek Quarter
![1008 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
5 beds
|2 baths
|2,066 sq ft
|Detached
1008 BENNETT'S ARCH, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10613016 • The Property Shoppe, Samantha Spru...
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.
Vistas at Bennett's Creek Quarter
![4424 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,526 sq ft
|Detached
4424 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10612618 • The Property Shoppe, Nora Spruill
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...
Vistas at Bennett's Creek Quarter
![4412 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,806 sq ft
|Detached
4412 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10611577 • BHHS RW Towne Realty, Melissa Quee...
Vistas at Bennett's Creek Quarter
![1039 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|2 baths
|1,965 sq ft
|Detached
1039 BENNETT'S ARCH, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10610034 • The Property Shoppe, Nora Spruill
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...
Want to learn more about 55+ communities in Chesapeake?
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Questions? Call us:
(804) 568-8917
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
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...
Vistas at Bennett's Creek Quarter
![4420 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
5 beds
|3 baths
|2,598 sq ft
|Detached
4420 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10604815 • The Property Shoppe, Nora Spruill
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.
The Retreat at Harbour Cove
![2022 ASHER LOT 95 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|2,314 sq ft
|Townhome
2022 ASHER LOT 95 DR, SUFFOLK, VA, 23435
Community: The Retreat at Harbour Cove
MLS 10583341 • 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...
Vistas at Bennett's Creek Quarter
![4423 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|2 baths
|2,066 sq ft
|Detached
4423 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10606491 • The Property Shoppe, Samantha Spru...
Vistas at Bennett's Creek Quarter
![4427 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
4 beds
|3 baths
|2,150 sq ft
|Detached
4427 ABERCORN DR, SUFFOLK, VA, 23435
Community: Vistas at Bennett's Creek Quarter
MLS 10606479 • The Property Shoppe, Samantha Spru...
Want to learn more about 55+ communities in Chesapeake?
55places can help!
Questions? Call us:
(804) 568-8917
Legacy at Burbage Lake
![1008 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435]()
3 beds
|3 baths
|1,582 sq ft
|Townhome
1008 ASHWORTH WAY, SUFFOLK, VA, 23435
Community: Legacy at Burbage Lake
MLS 10606025 • Pointe East Realty LLC, Christophe...
Retreat at Edinburgh Farms
![2020 MUNRO LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322]()
4 beds
|2 baths
|2,614 sq ft
|Townhome
2020 MUNRO LN, CHESAPEAKE, VA, 23322
Community: Retreat at Edinburgh Farms
MLS 10606887 • 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?
Want to learn more about 55+ communities in Chesapeake?
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
