70 days on market
$499,000
17314 Jolly Cir
Windsor, Virginia 23487
MLS# 10625596 · ALL OTHERS AREA 65 · Isle of Wight County VA
Updated May 27, 2026 · Source: REIN MLS
Est. payment
$2,922/mo
Edit below
Price / sq ft
$285
1,749 sq ft
Days on market
70
HOA
None
Year built
1949
77 yrs old
Beds
4
Full Baths
3
Half Baths
0
Sq Ft
1,749
Garage
Yes
Schools
- ElementaryWindsor Elementary—
- MiddleGeorgie D. Tyler Middle School—
- HighWindsor—
Info provided by GreatSchools
About this home
Tucked away on 2.57 beautiful acres, this one-of-a-kind property offers the perfect blend of space, charm, and functionality. With over 2,500 square feet of living space, the home features 4 bedrooms and 3 full baths, including a convenient first-floor primary suite. Gorgeous hardwood floors run throughout, and the home is filled with character and unique details you just don't find in newer construction.Outside, the…
Listed by Anna Boyer · Howard Hanna Real Estate Svcs.
VaHome Team property overview
17314 Jolly Circle sits on 2.57 private acres in Windsor, Virginia — a four-bedroom, three-bath home built in 1949 with 1,749 square feet of living space. Wide-open land, a rural pace, and reasonable drives to two military installations make this address genuinely hard to replicate.
Read full property overview ↓Show less ↑
Why this home stands out
More than two and a half acres in Isle of Wight County is the headline here. Most Hampton Roads properties give you a measured yard; 17314 Jolly Circle gives you room to breathe — space for a garden, a workshop, outbuildings, or simply a long view with no neighbor in your sightline. The 1949 construction means solid bones and a footprint that has stood for decades, while three full baths across 1,749 square feet keeps daily logistics comfortable for a household of four.
ALL OTHERS AREA 65 and the Windsor real estate market
Windsor, Virginia sits in the heart of Isle of Wight County — one of the quieter, more rural corners of the Hampton Roads region. The town itself is small by design, and that's exactly the draw. Life here runs at a measured pace: you get genuine acreage, low traffic, and a community where neighbors still wave from driveways. The surrounding countryside is a mix of farmland, wooded lots, and long stretches of two-lane road that make the commute feel like a decompression chamber after a long workday. Windsor homes for sale in this part of Isle of Wight County tend to offer lot sizes that simply don't exist closer to the coast, and 17314 Jolly Circle is a textbook example of that trade. You're far enough from the urban core to feel removed, yet close enough to Smithfield, Suffolk, and the broader Hampton Roads metro that errands and entertainment stay accessible. Isle of Wight County carries a reputation for strong community ties, rural character, and a slower, steadier quality of life that's increasingly rare in the region.
What's nearby
Windsor's small commercial core puts basic conveniences within a short drive — fuel, a post office, and local diners are easy to reach. Smithfield, roughly 20 minutes east, expands your options considerably with grocery stores, pharmacies, hardware stores, and the historic downtown along the Pagan River. Franklin is a comparable distance to the southwest for additional shopping. Outdoor recreation is woven into the landscape here: the Blackwater River and surrounding state forest land offer fishing, kayaking, and hiking within a reasonable drive. Isle of Wight County's parks and the broader rural trail network give active households plenty to work with on weekends.
For different buyers
For military families relocating
Joint Staff J7 Suffolk is about 28 minutes from 17314 Jolly Circle, and Joint Base Langley-Eustis sits roughly 37 minutes away — both manageable for daily commutes. The 2.57-acre lot gives military families the kind of private, low-density space that's hard to find near base gates. A VA loan can make this acreage property more accessible than many buyers expect, and Isle of Wight County's lower cost of living stretches a housing allowance further.
For families upgrading
If your current home feels like the walls are closing in, 17314 Jolly Circle answers that with 2.57 acres and four bedrooms across a solid, well-proportioned floor plan. There's genuine outdoor space here — room for kids to roam, space for a vegetable garden, and enough buffer from neighbors that weekend projects don't require an apology. Three full baths mean morning routines stay civilized even with a full house.
Frequently asked questions
How far is 17314 Jolly Circle from Joint Staff J7 Suffolk?
The drive runs approximately 28 minutes under normal conditions, heading northeast through Isle of Wight County toward Suffolk. It's a straightforward commute on mostly rural two-lane roads with minimal congestion.
How far is 17314 Jolly Circle from Joint Base Langley-Eustis?
Fort Eustis is roughly 37 minutes from this address, making it a workable daily commute for service members stationed there. The route travels through Isle of Wight County and into Newport News.
What is the lot size at 17314 Jolly Circle?
The property sits on 2.57 acres — a notably large parcel for the Hampton Roads region that provides substantial privacy, outdoor utility space, and room for future improvements or outbuildings.
Is 17314 Jolly Circle in a flood zone?
Flood zone status for this address is detailed in the FloodRisk tile on this page, which pulls current FEMA map data. Isle of Wight County's inland, elevated terrain generally carries lower flood risk than coastal Hampton Roads communities, but always verify with current maps.
Does 17314 Jolly Circle have an HOA?
Based on available property data, this address does not appear to be governed by a homeowners association, which is common for rural acreage parcels in Isle of Wight County.
Tom and Dariya Milan at LPT Realty know Isle of Wight County inside and out. Reach out to get your questions answered and schedule a walkthrough of 17314 Jolly Circle.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
4
Full Baths
3
Half Baths
0
Approx Sq Ft
1,749
Stories
2
Fireplaces
0
Flooring
Ceramic, Wood
Heating
Propane Gas
Cooling
Central Air
Laundry
Interior Features
Fireplace Gas-propane, Scuttle Access, Walk-In Attic, Walk-In Closet, Window Treatments
Appliances
Dryer, Microwave, Elec Range, Refrigerator, Washer
Sale & Tax History
List Price
$499,000
Price / Sq Ft
$285
Annual Taxes
$2,244
Monthly Tax
$187
HOA
None
Tax Rate (effective)
0.45%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Mar 18, 2026 | $499,000 | — |
| Currently listed | — | $499,000 | — |
Looking for multi-year tax assessments or prior sales? REIN MLS only ships data for the current listing. For full property history, check the city assessor record:
Tax data above from REIN public-records sync. Sale timeline tracked from this listing's first appearance in our feed forward; prior owner sales are not included.
Comparable Properties
Comps are selected by city, bed count, square footage and price proximity. Composite similarity score weights bed match, sqft variance, price variance, and straight-line distance.
Military Commute
Drive times to nearest basesDrive times via Google Maps with current traffic patterns. Times are typical and may vary by time of day. Use the "Analyze" button up top to see live drive time to your saved base.
Estimate your monthly payment
$2,922/moPrincipal & interest
$2,589
Property tax
$187
Home insurance
$146
PMI
None
HOA
None
Estimate only. Insurance assumed at 0.35% of home value annually. Actual taxes, insurance, and rate will vary by lender, credit, and property. Contact a lender for a personalized quote.
Listed by Howard Hanna Real Estate Svcs. · MLS# 10625596
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$499,000
17314 Jolly CIR, WINDSOR VA 23487
Windsor, Virginia 23487
Request InfoQuick Facts
Schedule a tour
In-person or videoClick a day to pick a time