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Chesapeake, VA 55+ active adult communities & homes for sale
Living in Chesapeake
- 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
Yes, through meaningful municipal tax relief. Authorized by Va. Code §58.1-3210, Chesapeake's Real Estate Tax Relief for the Elderly and Disabled is available to homeowners aged 65 or older who occupy the home as their primary residence. Qualifying households must maintain a total combined income of $62,000 or less, with additional net worth restrictions excluding the primary residence. Eligible residents must file their application with the Commissioner of the Revenue by May 15 of the tax year to apply relief to the quarterly billing cycle.
Chesapeake active adults are served by both local community hospitals and major regional healthcare networks: Chesapeake Regional Medical Center: Located on Battlefield Boulevard, this acute-care hospital serves as the city's primary medical anchor and is one of the region's remaining independent community health systems. Sentara Norfolk General Hospital: Positioned roughly 20 minutes north in Norfolk, hosting the region's primary Level I trauma center and regional burn center. Surrounding Regional Facilities: Sentara Leigh Hospital (Norfolk), Bon Secours Maryview Medical Center (Portsmouth), and Sentara Obici Hospital (Suffolk) provide nearby emergency and specialty care across adjacent municipalities.
Deciding between Great Bridge and Western Branch involves balancing coastal access against traffic patterns and flood risks: Great Bridge Corridor: Offers immediate proximity to the Intracoastal Waterway, Chesapeake Arboretum, and the shortest drive to Virginia Beach. The tradeoff: Low-lying sections near the canal sit in FEMA Special Flood Hazard Areas, and coastal hurricane insurance deductibles are calculated at 1% to 5% of total dwelling coverage rather than a flat fee. Western Branch Corridor: Delivers quieter suburban living with convenient access to Suffolk retail. The tradeoff: Commutes to Norfolk require crossing the High Rise Bridge or local river tunnels, placing the nearest Level I trauma center 25 to 30 minutes away during peak hours.
In Chesapeake, there are no large communities, 1 medium community with 500-1000 homes, and 8 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 Acclaim at Greenbrier, Retreat at Edinburgh Farms, The Retreat at Western Branch. There are also 3 communities in Chesapeake that offer new construction homes, including Acclaim at Greenbrier, The Retreat at Western Branch, Retreat at Edinburgh Farms.
Yes, there are gated 55+ communities in Chesapeake. Approximately 22.2% of 55+ communities in the area are gated. For instance, Eagle Pointe at Cahoon Plantation is a gated communities with 501 homes, and Monarch Walk is another gated communities with 62 homes.
On average, listings in 55+ communities in Chesapeake stay on the market for around 32 days. The average price of homes for sale in these communities is approximately $486,284, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Eagle Pointe at Cahoon Plantation average around $517,177, while homes in The Retreat at Greenbrier average around $478,290.
12 communities near Chesapeake
72 homes near Chesapeake
Relevance
2 beds
|2 baths
|1,563 sq ft
|Townhome
2 beds
|2 baths
|1,217 sq ft
|Townhome
3 beds
|3 baths
|2,339 sq ft
|Townhome
3 beds
|3 baths
|2,642 sq ft
|Townhome
2 beds
|3 baths
|1,986 sq ft
|Townhome
1 beds
|1 baths
|1,047 sq ft
|Townhome
5 beds
|3 baths
|3,047 sq ft
|Detached
3 beds
|3 baths
|2,642 sq ft
|Townhome
3 beds
|3 baths
|2,642 sq ft
|Townhome
3 beds
|3 baths
|2,642 sq ft
|Townhome
2 beds
|3 baths
|1,986 sq ft
|Townhome
2 beds
|3 baths
|1,986 sq ft
|Townhome
2 beds
|3 baths
|1,986 sq ft
|Townhome
2 beds
|2 baths
|1,489 sq ft
|Townhome
2 beds
|2 baths
|1,069 sq ft
|Townhome
4 beds
|2 baths
|2,513 sq ft
|Townhome
3 beds
|3 baths
|2,170 sq ft
|Detached
4 beds
|2 baths
|2,422 sq ft
|Detached
4 beds
|3 baths
|2,880 sq ft
|Townhome
4 beds
|2 baths
|2,614 sq ft
|Townhome
4 beds
|3 baths
|2,500 sq ft
|Detached
4 beds
|3 baths
|2,859 sq ft
|Townhome
4 beds
|3 baths
|2,314 sq ft
|Townhome
4 beds
|3 baths
|2,880 sq ft
|Townhome
3 beds
|2 baths
|2,225 sq ft
|Detached
2 beds
|3 baths
|1,978 sq ft
|Townhome
4 beds
|3 baths
|2,498 sq ft
|Detached
3 beds
|3 baths
|2,642 sq ft
|Townhome
3 beds
|3 baths
|2,136 sq ft
|Townhome
4 beds
|3 baths
|2,706 sq ft
|Detached
3 beds
|2 baths
|2,526 sq ft
|Townhome
3 beds
|2 baths
|2,557 sq ft
|Townhome
4 beds
|2 baths
|2,614 sq ft
|Townhome
3 beds
|3 baths
|2,642 sq ft
|Townhome
2 beds
|3 baths
|2,314 sq ft
|Townhome
2 beds
|2 baths
|1,563 sq ft
|Townhome
3 beds
|3 baths
|2,642 sq ft
|Townhome
2 beds
|2 baths
|1,462 sq ft
|Townhome
3 beds
|2 baths
|2,538 sq ft
|Townhome
4 beds
|3 baths
|2,150 sq ft
|Detached
Frequently Asked Questions
In Chesapeake, there are no large communities, 1 medium community with 500-1000 homes, and 8 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 Acclaim at Greenbrier, Retreat at Edinburgh Farms, The Retreat at Western Branch. There are also 3 communities in Chesapeake that offer new construction homes, including Acclaim at Greenbrier, The Retreat at Western Branch, Retreat at Edinburgh Farms.
Yes, there are gated 55+ communities in Chesapeake. Approximately 22.2% of 55+ communities in the area are gated. For instance, Eagle Pointe at Cahoon Plantation is a gated communities with 501 homes, and Monarch Walk is another gated communities with 62 homes.
On average, listings in 55+ communities in Chesapeake stay on the market for around 32 days. The average price of homes for sale in these communities is approximately $486,284, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Eagle Pointe at Cahoon Plantation average around $517,177, while homes in The Retreat at Greenbrier average around $478,290.
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REIN updates its listings on a daily basis. Data last updated: Oct 05, 2026.
This application does not include information on all of the properties available for sale at this time.