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

Living in Chesapeake

Chesapeake is structured as a federation of distinct boroughs. Greenbrier functions as the primary commercial and medical hub off I-64; Great Bridge wraps the historic locks on…
Chesapeake is structured as a federation of distinct boroughs. Greenbrier functions as the primary commercial and medical hub off I-64; Great Bridge wraps the historic locks on the Albemarle and Chesapeake Canal; Western Branch faces Portsmouth and Suffolk across the Elizabeth River; and Hickory and Deep Creek anchor the city's southern and western rural borders. From Greenbrier, downtown Norfolk sits roughly 20 minutes north on I-64.Ad valorem real estate taxes and senior relief programs are managed directly at the municipal level in Virginia:

  • Tax Rate: Chesapeake levies a real estate tax rate of $1.01 per $100 of assessed value (inclusive of a $0.01 mosquito control fee) billed in quarterly installments.
  • Senior Tax Relief: Authorized under Va. Code §58.1-3210, the Real Estate Tax Relief for the Elderly and Disabled provides partial or full real estate tax exemptions for qualifying senior homeowners.
  • Income & Net Worth Limits: Combined annual household income for owners and residing relatives cannot exceed $62,000, and net worth (excluding the dwelling value) is subject to city caps.
  • Application Filing: Submit applications to the Commissioner of the Revenue at 306 Cedar Road by May 15 of the taxable year. Tax installments are due September 30, December 31, March 31, and June 5.

Eagle Pointe at Cahoon Plantation is Chesapeake's premier amenity-focused 55+ address, featuring attached villas, condos, and single-family homes centered around the 10,000-square-foot Bay Club with heated indoor and outdoor pools, plus access to The Isles Golf Links layout. The Retreat at Greenbrier offers lakeside living with stocked fishing ponds and a 40-plot community garden. Monarch Walk provides a gated McQ Builders enclave featuring single-story plans, a putting green, and a fitness center. At 55places, we comprehensively profile every Chesapeake active adult neighborhood with verified pricing, real resident reviews, and direct access to trusted local 55+ real estate experts.

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12 communities 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 Harbour Co...
$400ks - $500ks
The Retreat at Harbour Co..., Suffolk, VA
New Construction | 55+ age-restricted | Built 2022 - present | 101 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 Landings at Bennett's...
$500ks - $600ks
The Landings at Bennett's..., Suffolk, VA
New and Resale | 55+ age-restricted | Built 2020 - present | 23 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
Vistas at Bennett's Creek...
$400ks - $600ks
Vistas at Bennett's Creek..., Suffolk, VA
New Construction | Age-targeted | Built 2024 - present | 49 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
The Commons at Hunningdon...
$200ks - $300ks
The Commons at Hunningdon..., Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2004 - present | 87 homes
Sommerton
$400ks - $500ks
Sommerton, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 90 homes
Monarch Walk
$100ks - $200ks
Monarch Walk, Chesapeake, VA
Resale Only | 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 | 55+ age-restricted | Built 2017 - 2021 | 80 homes
The Retreat at Greenbrier
$400ks - $600ks
The Retreat at Greenbrier, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2003 - 2015 | 184 homes
New Legacy at Burbage Lake 1010 ASHWORTH AVE, SUFFOLK, VA, 23435, Suffolk, VA 23435
$350,000

2 beds

|

2 baths

|

1,563 sq ft

|

Townhome

1010 ASHWORTH AVE, SUFFOLK, VA, 23435
New Legacy at Burbage Lake 1020 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$306,410

2 beds

|

2 baths

|

1,217 sq ft

|

Townhome

1020 ASHWORTH WAY, SUFFOLK, VA, 23435
New Eagle Pointe at Cahoon Plantation 1407 HAWICK TER, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$499,999

3 beds

|

3 baths

|

2,339 sq ft

|

Townhome

1407 HAWICK TER, CHESAPEAKE, VA, 23322
New Retreat at Edinburgh Farms 2220 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$585,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2220 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2201 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$543,740

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2201 EDWIN DR, CHESAPEAKE, VA, 23322
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
Legacy at Burbage Lake 13303 LEIGHTON WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$336,929

1 beds

|

1 baths

|

1,047 sq ft

|

Townhome

13303 LEIGHTON WAY, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 4404 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$566,740

5 beds

|

3 baths

|

3,047 sq ft

|

Detached

4404 ABERCORN DR, SUFFOLK, VA, 23435
Retreat at Edinburgh Farms 2207 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$597,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2207 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2180 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$597,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2180 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2182 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$597,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2182 EDWIN DR, CHESAPEAKE, VA, 23322
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 2172 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$563,740

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2172 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2170 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$563,740

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2170 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2160 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$563,740

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2160 EDWIN DR, CHESAPEAKE, VA, 23322
Legacy at Burbage Lake 2010 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$406,372

2 beds

|

2 baths

|

1,489 sq ft

|

Townhome

2010 ASHWORTH WAY, SUFFOLK, VA, 23435
Legacy at Burbage Lake 3006 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$309,990

2 beds

|

2 baths

|

1,069 sq ft

|

Townhome

3006 ASHWORTH WAY, SUFFOLK, VA, 23435
The Retreat at Western Branch 3106 LANTERN PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$424,900

4 beds

|

2 baths

|

2,513 sq ft

|

Townhome

3106 LANTERN PL, CHESAPEAKE, VA, 23321
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
The Landings at Bennett's Creek 100 CREEK LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$599,900

3 beds

|

3 baths

|

2,170 sq ft

|

Detached

100 CREEK LN, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1010 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$534,365

4 beds

|

2 baths

|

2,422 sq ft

|

Detached

1010 BENNETT'S ARCH, SUFFOLK, VA, 23435
The Retreat at Western Branch 4704 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$447,340

4 beds

|

3 baths

|

2,880 sq ft

|

Townhome

4704 MAHOGANY RUN, CHESAPEAKE, VA, 23321
The Retreat at Western Branch 4706 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$457,195

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

4706 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.
The Landings at Bennett's Creek 115 CREEK LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$630,000

4 beds

|

3 baths

|

2,500 sq ft

|

Detached

115 CREEK LN, SUFFOLK, VA, 23435
The Retreat at Harbour Cove 2061 ASHER LOT 6 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$533,000

4 beds

|

3 baths

|

2,859 sq ft

|

Townhome

2061 ASHER LOT 6 DR, SUFFOLK, VA, 23435
Retreat at Edinburgh Farms 2114 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$549,999

4 beds

|

3 baths

|

2,314 sq ft

|

Townhome

2114 EDWIN DR, CHESAPEAKE, VA, 23322
The Retreat at Western Branch 4613 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$447,340

4 beds

|

3 baths

|

2,880 sq ft

|

Townhome

4613 LONGLEAF PL, CHESAPEAKE, VA, 23321
The Commons at Hunningdon Lakes 808 MONROE CT, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320
$429,900

3 beds

|

2 baths

|

2,225 sq ft

|

Detached

808 MONROE CT, CHESAPEAKE, VA, 23320
Legacy at Burbage Lake 2012 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$392,769

2 beds

|

3 baths

|

1,978 sq ft

|

Townhome

2012 ASHWORTH WAY, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1025 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$595,510

4 beds

|

3 baths

|

2,498 sq ft

|

Detached

1025 BENNETT'S ARCH, SUFFOLK, VA, 23435
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
Retreat at Edinburgh Farms 2154 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$577,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2154 EDWIN DR, CHESAPEAKE, VA, 23322
The Retreat at Harbour Cove 2015 ASHER LOT 83 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$535,000

3 beds

|

3 baths

|

2,136 sq ft

|

Townhome

2015 ASHER LOT 83 DR, SUFFOLK, VA, 23435
The Landings at Bennett's Creek 110 CREEK LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$599,950

4 beds

|

3 baths

|

2,706 sq ft

|

Detached

110 CREEK LN, SUFFOLK, VA, 23435
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 420 DUNDEE LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$532,500

3 beds

|

2 baths

|

2,526 sq ft

|

Townhome

420 DUNDEE LN, CHESAPEAKE, VA, 23322
The Retreat at Western Branch 4607 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$449,900

3 beds

|

2 baths

|

2,557 sq ft

|

Townhome

4607 LONGLEAF PL, CHESAPEAKE, VA, 23321
Retreat at Edinburgh Farms 2009 BARTON LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$583,740

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

2009 BARTON LN, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2205 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$597,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2205 EDWIN DR, CHESAPEAKE, VA, 23322
The Retreat at Harbour Cove 2013 ASHER LOT 82 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$566,712

2 beds

|

3 baths

|

2,314 sq ft

|

Townhome

2013 ASHER LOT 82 DR, SUFFOLK, VA, 23435
Legacy at Burbage Lake 3010 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$329,990

2 beds

|

2 baths

|

1,563 sq ft

|

Townhome

3010 ASHWORTH WAY, SUFFOLK, VA, 23435
Retreat at Edinburgh Farms 2164 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$597,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2164 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2150 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$506,990

2 beds

|

2 baths

|

1,462 sq ft

|

Townhome

2150 EDWIN DR, CHESAPEAKE, VA, 23322
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
Sommerton 1016 BRIARS LNDG, CHESAPEAKE, VA, 23320, Chesapeake, VA 23320
$524,900

3 beds

|

2 baths

|

2,538 sq ft

|

Townhome

1016 BRIARS LNDG, CHESAPEAKE, VA, 23320
Community: Sommerton
Vistas at Bennett's Creek Quarter 1043 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$559,990

4 beds

|

3 baths

|

2,150 sq ft

|

Detached

1043 BENNETT'S ARCH, SUFFOLK, VA, 23435
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


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