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Chesapeake, VA 55+ active adult communities & homes for sale - Page 2

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


79 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 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
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
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
Vistas at Bennett's Creek...
$400ks - $600ks
Vistas at Bennett's Creek..., Suffolk, VA
New Construction | Age-targeted | Built 2024 - present | 49 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
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
The Retreat at Western Branch 4609 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$457,195

4 beds

|

2 baths

|

2,614 sq ft

|

Townhome

4609 LONGLEAF PL, CHESAPEAKE, VA, 23321
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
Legacy at Burbage Lake 1014 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$401,379

3 beds

|

3 baths

|

2,015 sq ft

|

Townhome

1014 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.
Vistas at Bennett's Creek Quarter 1029 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$554,950

4 beds

|

3 baths

|

2,150 sq ft

|

Detached

1029 BENNETT'S ARCH, SUFFOLK, VA, 23435
The Retreat at Harbour Cove 2019 ASHER LOT 85 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$548,664

3 beds

|

3 baths

|

2,136 sq ft

|

Townhome

2019 ASHER LOT 85 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
The Landings at Bennett's Creek 201 COVE REACH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$645,000

4 beds

|

3 baths

|

2,698 sq ft

|

Detached

201 COVE REACH, SUFFOLK, VA, 23435
The Retreat at Harbour Cove 2071 ASHER LOT 11 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$547,000

3 beds

|

2 baths

|

2,557 sq ft

|

Townhome

2071 ASHER LOT 11 DR, SUFFOLK, VA, 23435
The Retreat at Harbour Cove 2065 ASHER LOT 8 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$581,783

4 beds

|

2 baths

|

2,443 sq ft

|

Townhome

2065 ASHER LOT 8 DR, SUFFOLK, VA, 23435
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
The Retreat at Western Branch 4615 LONGLEAF PL, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$457,195

4 beds

|

2 baths

|

2,433 sq ft

|

Townhome

4615 LONGLEAF PL, CHESAPEAKE, VA, 23321
Sommerton 925 CRANBERRY DR 70, CHESAPEAKE, VA, 233..., Chesapeake, VA 23320
$509,900

4 beds

|

2 baths

|

2,364 sq ft

|

Townhome

925 CRANBERRY DR 70, CHESAPEAKE, VA, 233...
Community: Sommerton
Vistas at Bennett's Creek Quarter 1031 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$641,865

4 beds

|

3 baths

|

2,806 sq ft

|

Detached

1031 BENNETT'S ARCH, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1014 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$510,933

4 beds

|

3 baths

|

2,066 sq ft

|

Detached

1014 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.
Vistas at Bennett's Creek Quarter 1016 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$557,505

5 beds

|

3 baths

|

2,438 sq ft

|

Detached

1016 BENNETT'S ARCH, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1040 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$508,243

4 beds

|

3 baths

|

2,150 sq ft

|

Detached

1040 BENNETT'S ARCH, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1035 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$553,160

4 beds

|

3 baths

|

2,150 sq ft

|

Detached

1035 BENNETT'S ARCH, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1033 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$552,033

4 beds

|

3 baths

|

2,150 sq ft

|

Detached

1033 BENNETT'S ARCH, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1036 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$508,720

4 beds

|

3 baths

|

2,066 sq ft

|

Detached

1036 BENNETT'S ARCH, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1034 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$538,805

5 beds

|

2 baths

|

2,422 sq ft

|

Detached

1034 BENNETT'S ARCH, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 1019 BENNETT'S ARCH, SUFFOLK, VA, 23435, Suffolk, VA 23435
$562,675

3 beds

|

2 baths

|

2,176 sq ft

|

Detached

1019 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 2206 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$570,740

3 beds

|

3 baths

|

2,642 sq ft

|

Townhome

2206 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2202 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$504,990

2 beds

|

2 baths

|

1,462 sq ft

|

Townhome

2202 EDWIN DR, CHESAPEAKE, VA, 23322
Retreat at Edinburgh Farms 2200 EDWIN DR, CHESAPEAKE, VA, 23322, Chesapeake, VA 23322
$499,990

2 beds

|

2 baths

|

1,462 sq ft

|

Townhome

2200 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.
The Retreat at Harbour Cove 2005 ASHER LOT 74 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$516,475

2 beds

|

2 baths

|

2,213 sq ft

|

Townhome

2005 ASHER LOT 74 DR, SUFFOLK, VA, 23435
The Retreat at Harbour Cove 2053 ASHER LOT 2 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$529,688

3 beds

|

3 baths

|

2,880 sq ft

|

Townhome

2053 ASHER LOT 2 DR, SUFFOLK, VA, 23435
The Retreat at Harbour Cove 1014 LIBBY LOT 60 WAY, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$521,007

3 beds

|

3 baths

|

2,859 sq ft

|

Townhome

1014 LIBBY LOT 60 WAY, SUFFOLK, VA, 2343...
Legacy at Burbage Lake 2006 ASHWORTH WAY, SUFFOLK, VA, 23435, Suffolk, VA 23435
$310,719

2 beds

|

2 baths

|

1,069 sq ft

|

Townhome

2006 ASHWORTH WAY, SUFFOLK, VA, 23435
Vistas at Bennett's Creek Quarter 4406 ABERCORN DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$565,990

4 beds

|

2 baths

|

2,318 sq ft

|

Detached

4406 ABERCORN DR, SUFFOLK, VA, 23435
The Retreat at Western Branch 4725 MAHOGANY RUN, CHESAPEAKE, VA, 23321, Chesapeake, VA 23321
$454,900

3 beds

|

2 baths

|

2,557 sq ft

|

Townhome

4725 MAHOGANY RUN, CHESAPEAKE, VA, 23321
The Retreat at Harbour Cove 1103 ELAINA LOT 44 PL, SUFFOLK, VA, 2343..., Suffolk, VA 23435
$590,695

3 beds

|

3 baths

|

2,859 sq ft

|

Townhome

1103 ELAINA LOT 44 PL, SUFFOLK, VA, 2343...
The Retreat at Harbour Cove 2069 ASHER LOT 10 DR, SUFFOLK, VA, 23435, Suffolk, VA 23435
$571,826

3 beds

|

3 baths

|

2,880 sq ft

|

Townhome

2069 ASHER LOT 10 DR, SUFFOLK, VA, 23435
Want to learn more about 55+ communities in Chesapeake? 55places can help!
Questions? Call us: (804) 568-8917
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

Frequently Asked Questions


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