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Chesterfield, VA 55+ active adult communities & homes for sale
Living in Chesterfield
Chesterfield is a southern suburb of Richmond in Central Virginia. Known for its history and outdoor recreation, it offers plenty of golf courses, nature walks, and historical…
Chesterfield is a southern suburb of Richmond in Central Virginia. Known for its history and outdoor recreation, it offers plenty of golf courses, nature walks, and historical tours for its residents. Besides this, local amenities like a farmers market, breweries, and a large shopping center make Chesterfield a popular destination for active adults.
Climate & Geography
Located 20 miles from Richmond, Chesterfield experiences a humid subtropical climate. Summers are some of the warmest in the state, and winters are mild to cool. Though freezing temperatures occur several times in the winter, the Blue Ridge Mountains to the west act as a partial barrier to winter storms and extreme temperatures. Residents can expect less than average snowfall, higher than average rainfall, and 206 days of sunshine.
Recreation, Culture & Entertainment
Like much of the state, one of Chesterfield’s biggest draws is its outdoor recreation. Pocahontas State Park, in the middle of the county, has several campsites and hiking trails. Along the eastern border is James River, where residents and fish, kayak, and canoe, and the Dutch Gap Conservation Area, a 796-acre with an abundance of wildlife. Robious Landing Park and Rockwood Park also have trails, nature centers, and picnic shelters.
Chesterfield also embraces its history. Henricus Historical Park along the James River is a large, living history museum with costumed actors and guided trails. The Chesterfield Historical Society of Virginia is located by the Chesterfield Historical Courthouse and has civil war tours and exhibits.
Other amenities include the Chesterfield Towne Center, the largest enclosed shopping center in the Richmond area, the Metro Richmond Zoo, and the Chesterfield County Farmers Market during the summer. Golfers can visit several courses, including First Tee Chesterfield, The Golf Club at the Highlands, and Magnolia Green Golf Club, among others.
With Ashton Creek Vineyards and Steam Bell Beer Works, residents don’t have to travel far for local brews. However, nearby Richmond is a short drive away with even more golfing, breweries, and shopping.
Cost of Living & Taxes
Chesterfield’s cost of living hovers just slightly above the national average, but below the state average. Other indexes like utilities and transportation match the national average, while groceries and health care are below.
Virginia is generally tax friendly to retirees. Social Security is not taxed and other forms of retirement income are partially taxes and eligible for deductions. Both property and sales taxes are low. Groceries are taxed, but at a lower rate of 2.5 percent.
Health Care
The Richmond metro area recently ranked in the top 100 communities according to Gallup’s Well-Being Index. Virginia also ranked within the top 27 states.
There are no nationally ranked hospitals in Chesterfield county. The only two hospitals within county lines are Bon Secours St. Francis Medical Center and Sheltering Arms Hospital South, both located in Midlothian. Nearby Richmond has several high performing hospitals according to U.S. News, including Chippenham Hospital, VCU Medical Center, and Bon Secours St. Mary’s Hospital.
Frequently Asked Questions
In Chesterfield, there are no large communities, no medium communities, and 5 small communities with less than 500 homes.
The smallest 55+ communities in Chesterfield has 62 homes, the largest has 200 homes, and the average communities consists of 118 homes.
Yes, there are new 55+ homes available in Chesterfield. The most recent communities started in Chesterfield include Reserve at Oasis, Lake Margaret at the Highlands, Kenbrook at Harpers Mill. There are also 3 communities in Chesterfield that offer new construction homes, including Lake Margaret at the Highlands, Reserve at Oasis, Kenbrook at Harpers Mill.
No, there are no gated 55+ communities in Chesterfield.
On average, listings in 55+ communities in Chesterfield stay on the market for around 511 days. The average price of homes for sale in these communities is approximately $547,829, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Lake Margaret at the Highlands average around $738,674, while homes in Reserve at Oasis average around $488,037.
21 communities near Chesterfield
45 homes near Chesterfield
Relevance
3 beds
|3 baths
|1,854 sq ft
|Townhouse
3 beds
|3 baths
|2,154 sq ft
|Townhouse
3 beds
|3 baths
|2,387 sq ft
|Townhouse
3 beds
|3 baths
|2,601 sq ft
|Condo
2 beds
|2 baths
|2,152 sq ft
|House
3 beds
|3 baths
|2,996 sq ft
|House
3 beds
|4 baths
|2,123 sq ft
|Townhouse
2 beds
|2 baths
|1,842 sq ft
|House
3 beds
|3 baths
|2,569 sq ft
|Condo
4 beds
|4 baths
|2,063 sq ft
|Townhouse
2 beds
|3 baths
|1,960 sq ft
|Townhouse
3 beds
|3 baths
|2,266 sq ft
|Townhouse
4 beds
|4 baths
|2,131 sq ft
|Townhouse
2 beds
|2 baths
|1,568 sq ft
|Townhouse
2 beds
|4 baths
|2,185 sq ft
|Townhouse
3 beds
|3 baths
|2,266 sq ft
|Townhouse
3 beds
|3 baths
|2,085 sq ft
|Condo
2 beds
|2 baths
|1,967 sq ft
|House
2 beds
|3 baths
|1,980 sq ft
|Townhouse
4 beds
|4 baths
|4,077 sq ft
|House
3 beds
|4 baths
|2,784 sq ft
|Townhouse
3 beds
|4 baths
|3,002 sq ft
|Townhouse
3 beds
|4 baths
|3,002 sq ft
|Townhouse
3 beds
|4 baths
|2,776 sq ft
|Townhouse
3 beds
|3 baths
|2,297 sq ft
|Townhouse
2 beds
|2 baths
|1,162 sq ft
|Condo
3 beds
|3 baths
|2,299 sq ft
|Townhouse
3 beds
|2 baths
|1,524 sq ft
|Condo
2 beds
|3 baths
|2,167 sq ft
|Townhouse
3 beds
|3 baths
|2,441 sq ft
|Townhouse
3 beds
|3 baths
|2,301 sq ft
|Townhouse
2 beds
|3 baths
|2,344 sq ft
|Townhouse
2 beds
|3 baths
|2,517 sq ft
|Townhouse
4 beds
|4 baths
|3,255 sq ft
|House
3 beds
|4 baths
|2,290 sq ft
|Townhouse
3 beds
|4 baths
|2,063 sq ft
|Townhouse
2 beds
|2 baths
|1,524 sq ft
|Condo
3 beds
|3 baths
|2,263 sq ft
|Condo
Frequently Asked Questions
In Chesterfield, there are no large communities, no medium communities, and 5 small communities with less than 500 homes.
The smallest 55+ communities in Chesterfield has 62 homes, the largest has 200 homes, and the average communities consists of 118 homes.
Yes, there are new 55+ homes available in Chesterfield. The most recent communities started in Chesterfield include Reserve at Oasis, Lake Margaret at the Highlands, Kenbrook at Harpers Mill. There are also 3 communities in Chesterfield that offer new construction homes, including Lake Margaret at the Highlands, Reserve at Oasis, Kenbrook at Harpers Mill.
No, there are no gated 55+ communities in Chesterfield.
On average, listings in 55+ communities in Chesterfield stay on the market for around 511 days. The average price of homes for sale in these communities is approximately $547,829, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Lake Margaret at the Highlands average around $738,674, while homes in Reserve at Oasis average around $488,037.
Richmond Area 55+ Housing Market Trends
Number of Listings
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REIN updates its listings on a daily basis. Data last updated: Sep 28, 2026.
This application does not include information on all of the properties available for sale at this time.