182 days on market
$525,000
17314 Jolly Cir
Windsor, Virginia 23487
MLS# 10601284 · ALL OTHERS AREA 65 · Isle of Wight County VA
Updated Mar 11, 2026 · Source: REIN MLS
Est. payment
$3,064/mo
Edit below
Price / sq ft
$300
1,749 sq ft
Days on market
182
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—
- MiddleWindsor—
- HighWindsor—
Info provided by GreatSchools
About this home
They don't make them like this anymore! Experience the perfect blend of charm, space, and functionality with this beautifully crafted brick home situated on 2.57 acres. Offering 4 bedrooms and 3 full baths, this home showcases gorgeous hardwood floors, a recently updated kitchen, and a spacious basement that provides excellent potential for additional living, recreation, or entertaining space. The kitchen was thought…
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 ranch built in 1949 that trades subdivision density for genuine breathing room. Isle of Wight County living, roughly half an hour from Suffolk and under 40 minutes from Fort Eustis.
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Why this home stands out
Two and a half acres in Windsor is a different kind of ownership. There's space to park a boat, run a garden, or simply let kids and dogs disappear into the yard without worrying about neighbors ten feet away. The 1949 ranch footprint keeps single-floor living practical across all 1,749 square feet, while three full baths mean nobody's waiting in line on a busy morning. It's the kind of lot that's genuinely hard to find this close to Hampton Roads.
ALL OTHERS AREA 65 and the Windsor real estate market
Windsor is a small town in Isle of Wight County — the kind of place where the pace slows down on purpose. Residents here tend to value land, quiet roads, and a genuine sense of community over walkable retail strips or high-density convenience. The town sits in the western reaches of Hampton Roads, close enough to Suffolk, Chesapeake, and Newport News to reach jobs and amenities without living inside the congestion. If you've been searching for new townhomes for sale and kept feeling like the lots were too small and the neighbors too close, Windsor flips that equation entirely. Properties here typically come with acreage, mature trees, and the kind of outdoor space that changes how you actually use your home. Isle of Wight County is well-regarded for its rural character and lower-density development patterns, and Windsor reflects that identity clearly. It's a genuine small-town address with real regional access — a combination that's increasingly rare in coastal Virginia.
What's nearby
Windsor's everyday conveniences are a short drive away. The town center has local dining and a post office, and Route 460 connects you quickly to Suffolk's fuller retail corridor — groceries, pharmacies, hardware stores, and restaurants are all within a reasonable drive west. Franklin is reachable to the south for additional services. For outdoor recreation, the Blackwater River corridor and surrounding Isle of Wight County parks offer fishing, hiking, and paddling. The region's agricultural roots mean farm stands and open land are genuinely part of the landscape here, not just a marketing talking point.
For different buyers
For military families relocating
Joint Staff J7 Suffolk is about 28 minutes from Jolly Circle, and Joint Base Langley-Eustis (Fort Eustis) sits roughly 37 minutes east — both well within a typical military commute window. A VA loan can make a 2.57-acre property like this more accessible than many buyers expect, and BAH rates for the Suffolk area have historically supported Isle of Wight County price points. Plenty of room for a PCS move with gear, vehicles, and family in tow.
For families upgrading
If you've outgrown a smaller home and want four bedrooms, three full baths, and actual land — not a postage-stamp backyard — 17314 Jolly Circle is worth a serious look. The 2.57-acre lot gives kids genuine outdoor space and gives adults room for gardens, workshops, or just privacy. Ranch-style houses for sale near me is a common search for families who want single-floor convenience without sacrificing square footage, and this one delivers on both counts.
Frequently asked questions
How far is 17314 Jolly Circle from Joint Staff J7 Suffolk?
The drive from Jolly Circle to Joint Staff J7 Suffolk is approximately 28 minutes under normal traffic conditions, heading east on Route 460 toward Suffolk.
How far is 17314 Jolly Circle from Joint Base Langley-Eustis (Fort Eustis)?
Joint Base Langley-Eustis (Fort Eustis) is roughly 37 minutes from this address, accessible via Route 460 east through Suffolk and into Newport News.
What is the lot size at 17314 Jolly Circle?
The property sits on 2.57 acres, which is substantially larger than most residential lots in the broader Hampton Roads region and provides significant privacy and outdoor utility.
Is 17314 Jolly Circle in a flood zone?
Flood zone status for this property is displayed in the FloodRisk tile on this page — check that section for the current FEMA designation specific to this parcel.
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 consistent with the rural, acreage-lot character of this part of Isle of Wight County.
Want to walk the full 2.57 acres and see the floor plan in person? Tom and Dariya Milan at LPT Realty can arrange a showing and answer questions about Isle of Wight County ownership.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
17314 Jolly CIR, Windsor
Map and Street View imagery © Google. Imagery may not be current.
Map data ©Google. Click and drag inside the map to explore the surrounding area.
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, Washer
Sale & Tax History
List Price
$525,000
Price / Sq Ft
$300
Annual Taxes
$2,244
Monthly Tax
$187
HOA
None
Tax Rate (effective)
0.43%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Nov 8, 2025 | $525,000 | — |
| Currently listed | — | $525,000 | — |
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
$3,064/moPrincipal & interest
$2,724
Property tax
$187
Home insurance
$153
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# 10601284
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$525,000
17314 Jolly CIR, WINDSOR VA 23487
Windsor, Virginia 23487
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