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

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.

Frequently Asked Questions


14 communities near Chesapeake

Sort by:

Relevance

Relevance

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
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 Landings at Bennett's...
$500ks - $600ks
The Landings at Bennett's..., Suffolk, VA
New and Resale | 55+ age-restricted | Built 2020 - present | 23 homes
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
Legacy at Burbage Lake
$200ks - $400ks
Legacy at Burbage Lake, Suffolk, VA
New Construction | 55+ age-restricted | 90 homes
Riverfront 55+ Elevator C...
$300ks
Riverfront 55+ Elevator C..., Suffolk, VA
New Construction | 55+ age-restricted | Built 2025 - present
Sommerton
$400ks - $500ks
Sommerton, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2006 - 2017 | 90 homes
Vistas at Bennett's Creek...
$400ks - $600ks
Vistas at Bennett's Creek..., Suffolk, VA
New Construction | Age-targeted | Built 2024 - present | 49 homes
Rollingbrook Villas 55+
$300ks - $400ks
Rollingbrook Villas 55+, Suffolk, VA
New Construction | 55+ age-restricted | Built 2024 - present | 100 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.
The Commons at Hunningdon...
$200ks - $300ks
The Commons at Hunningdon..., Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2004 - present | 87 homes
Monarch Walk
$100ks - $200ks
Monarch Walk, Chesapeake, VA
Resale Only | 55+ age-restricted | Built 2007 - 2014 | 62 homes
5 rating (1 review) 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 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
New Retreat at Edinburgh Farms 2162 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$563,740

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2162 EDWIN DR, CHESAPEAKE, VA, 23322
New The Retreat at Western Branch 4702 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$457,023

4 beds

|

3 baths

|

2,880 sq ft

|

Townhome

4702 MAHOGANY RUN, CHESAPEAKE, VA, 23321
New The Retreat at Western Branch 4700 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$466,231

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

4700 MAHOGANY RUN, CHESAPEAKE, VA, 23321
New Riverfront 55+ Elevator Condos 7106 BRIDGEWAY DR 206, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$311,940

2 beds

|

2 baths

|

1,330 sq ft

|

Townhome

7106 BRIDGEWAY DR 206, SUFFOLK, VA, 2343...
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
New Monarch Walk 3907 REX CIR, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$365,000

3 beds

|

2 baths

|

1,974 sq ft

|

Townhome

3907 REX CIR, CHESAPEAKE, VA, 23321
Community: Monarch Walk
New Legacy at Burbage Lake 6104 BUTTERMERE LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$286,907

1 beds

|

1 baths

|

1,006 sq ft

|

Townhome

6104 BUTTERMERE LN, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1023 BENNETTS ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$473,965

3 beds

|

2 baths

|

1,762 sq ft

|

Detached

1023 BENNETTS ARCH, SUFFOLK, VA, 23435
The Retreat at Harbour Cove 1008 LIBBY WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$615,000

4 beds

|

3 baths

|

2,880 sq ft

|

Townhome

1008 LIBBY WAY, SUFFOLK, VA, 23435
Rollingbrook Villas 55+ 416 BRADEN LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$364,990

3 beds

|

2 baths

|

1,343 sq ft

|

Townhome

416 BRADEN 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.
The Landings at Bennett's Creek 119 CREEK LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$595,000

3 beds

|

3 baths

|

2,698 sq ft

|

Townhome

119 CREEK LN, SUFFOLK, VA, 23435
Rollingbrook Villas 55+ 215 JOY LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$399,990

2 beds

|

2 baths

|

1,527 sq ft

|

Townhome

215 JOY LN, SUFFOLK, VA, 23435
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
Eagle Pointe at Cahoon Plantation 1432 SCOONIE POINTE DR, CHESAPEAKE, VA, ..., Chesapeake, VA 23322
$449,900

3 beds

|

2 baths

|

1,785 sq ft

|

Townhome

1432 SCOONIE POINTE DR, CHESAPEAKE, VA, ...
Riverfront 55+ Elevator Condos 7102 BRIDGEWAY DR 202, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$324,430

2 beds

|

2 baths

|

1,330 sq ft

|

Townhome

7102 BRIDGEWAY DR 202, SUFFOLK, VA, 2343...
Retreat at Edinburgh Farms 2202 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$484,990

2 beds

|

2 baths

|

1,462 sq ft

|

Townhome

2202 EDWIN DR, CHESAPEAKE, VA, 23322
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
Riverfront 55+ Elevator Condos 7102 BRIDGEWAY DR 205, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$334,990

2 beds

|

2 baths

|

1,554 sq ft

|

Townhome

7102 BRIDGEWAY DR 205, SUFFOLK, VA, 2343...
The Retreat at Harbour Cove 2017 ASHER LOT 84 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$560,500

3 beds

|

3 baths

|

2,314 sq ft

|

Townhome

2017 ASHER LOT 84 DR, SUFFOLK, VA, 23435
Retreat at Edinburgh Farms 2152 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$506,990

2 beds

|

2 baths

|

1,462 sq ft

|

Townhome

2152 EDWIN DR, CHESAPEAKE, VA, 23322
Riverfront 55+ Elevator Condos 7102 BRIDGEWAY DR 101, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$334,990

2 beds

|

2 baths

|

1,554 sq ft

|

Townhome

7102 BRIDGEWAY DR 101, SUFFOLK, VA, 2343...
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 549 DUNNING LN, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$510,000

3 beds

|

2 baths

|

1,936 sq ft

|

House

549 DUNNING LN, CHESAPEAKE, VA, 23322
Eagle Pointe at Cahoon Plantation 1427 SCOONIE POINTE DR, CHESAPEAKE, VA, ..., Chesapeake, VA 23322
$399,000

3 beds

|

2 baths

|

1,742 sq ft

|

Townhome

1427 SCOONIE POINTE DR, CHESAPEAKE, VA, ...
Eagle Pointe at Cahoon Plantation 524 LINTON CIR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$535,000

3 beds

|

3 baths

|

2,409 sq ft

|

Townhome

524 LINTON CIR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2203 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$563,640

2 beds

|

3 baths

|

1,986 sq ft

|

Townhome

2203 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2226 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$585,540

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2226 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2213 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$494,890

2 beds

|

2 baths

|

1,462 sq ft

|

Townhome

2213 EDWIN DR, CHESAPEAKE, VA, 23322
Rollingbrook Villas 55+ 212 JOY LN, SUFFOLK, VA, 23435, Suffolk, VA 23435
$414,990

3 beds

|

2 baths

|

1,527 sq ft

|

Townhome

212 JOY LN, 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 2224 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$585,640

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2224 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2222 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$585,640

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2222 EDWIN DR, CHESAPEAKE, VA, 23322
Legacy at Burbage Lake 1010 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$350,000

2 beds

|

2 baths

|

1,563 sq ft

|

Townhome

1010 ASHWORTH WAY, 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.
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
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
Riverfront 55+ Elevator Condos 7102 BRIDGEWAY DR 305, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$334,990

2 beds

|

2 baths

|

1,554 sq ft

|

Townhome

7102 BRIDGEWAY DR 305, SUFFOLK, VA, 2343...
Riverfront 55+ Elevator Condos 7102 BRIDGEWAY DR 401, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$334,990

2 beds

|

2 baths

|

1,554 sq ft

|

Townhome

7102 BRIDGEWAY DR 401, SUFFOLK, VA, 2343...
Riverfront 55+ Elevator Condos 7102 BRIDGEWAY DR 206, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$324,990

2 beds

|

2 baths

|

1,330 sq ft

|

Townhome

7102 BRIDGEWAY DR 206, SUFFOLK, VA, 2343...
Retreat at Edinburgh Farms 2220 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$585,640

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
Riverfront 55+ Elevator Condos 7102 BRIDGEWAY DR 104, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$289,990

2 beds

|

2 baths

|

1,156 sq ft

|

Townhome

7102 BRIDGEWAY DR 104, SUFFOLK, VA, 2343...
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
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


Want more information about active adult communities around Chesapeake?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Chesapeake?

Call us: (804) 568-8917
14 communities
Remove Boundaries ×
Map Satellite

Reinmlsx

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: Nov 04, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top