19 days on market
$650,000
18517 Shady Pine Ln
Windsor, Virginia 23487
MLS# 10636500 · WINDSOR · Isle of Wight County VA
Updated yesterday · Source: REIN MLS
Est. payment
$3,989/mo
Edit below
Price / sq ft
$168
3,868 sq ft
Days on market
19
HOA
None
Year built
2001
25 yrs old
Beds
5
Full Baths
5
Half Baths
0
Sq Ft
3,868
Garage
Yes
Schools
- ElementaryWindsor Elementary—
- MiddleSmithfield Middle—
- HighWindsor—
Info provided by GreatSchools
About this home
Escape to your own private 14.84-Acre wooded retreat in Windsor! Discover ultimate privacy and timeless charm in this 5-bedroom, 5-bath Cape Cod Farmhouse. Nestled on 14.84 beautifully wooded acres, this estate blends grand architecture with cozy, functional living. The heart of the home features an open living room boasting vaulted ceilings and a dramatic two-story fireplace that flows effortlessly into a classic ki…
Listed by Lori Bauer · Long & Foster Real Estate Inc.
VaHome Team property overview
18517 Shady Pine Lane is a five-bedroom, five-bath home in Windsor, Virginia, offering nearly 3,900 square feet of living space on a quiet lane in Isle of Wight County — a rare combination of size, privacy, and small-town Southern charm.
Read full property overview ↓Show less ↑
Why this home stands out
Square footage this generous is hard to find in Windsor, and five full bathrooms means nobody is waiting in line on a busy morning. Built in 2001, the home sits on Shady Pine Lane — a low-traffic address that feels removed from the rush without actually being far from anything you need. The layout is built for real life: room for a home office, guests, a growing family, or all three at once.
About the Windsor real estate market
Windsor is one of those small Virginia towns that people discover and then quietly tell their closest friends about. Anchored in Isle of Wight County, it sits in the heart of Hampton Roads' western corridor — close enough to Suffolk, Smithfield, and the broader metro area to feel connected, yet far enough removed to breathe easy. The pace here is genuinely slower, the roads are lined with mature trees, and neighbors tend to know each other's names. Shady Pine Lane fits right into that character: a residential street where the houses have space between them and the yards actually feel like yards. Windsor Virginia real estate has been drawing buyers who want more home for their investment without sacrificing access to jobs, bases, and everyday amenities. Isle of Wight County is also known for its strong civic identity — local festivals, a historic courthouse district in nearby Smithfield, and a community that takes pride in staying livable.
What's nearby
Day-to-day errands are straightforward from Shady Pine Lane. Windsor has local dining and convenience options within minutes, and the town of Smithfield — about 15 minutes east — adds a full range of grocery stores, pharmacies, hardware stores, and restaurants along with its famous historic waterfront district. Suffolk is similarly close and brings big-box retail, medical facilities, and additional dining variety. For outdoor time, Isle of Wight County parks and the Blackwater River area offer trails, fishing, and open space. The drive to downtown Suffolk or the Harbour View commercial corridor in northern Suffolk takes roughly 20–25 minutes.
For different buyers
For military families relocating
Joint Staff J7 in Suffolk is about 19 minutes from Shady Pine Lane, and NSA Northwest Annex sits roughly 26 minutes out — both very manageable commutes. Five bedrooms and five baths give military families the flexibility to host visiting family, set up a dedicated workspace for remote duty requirements, or simply spread out after a deployment. A VA loan can make a home at this square footage more accessible than many buyers expect.
For families upgrading
If you've outgrown your current home, 3,868 square feet and five bedrooms give you room to stop compromising. Everyone gets their own space — kids, guests, a home office, a playroom — without the household feeling crowded. Windsor's quieter pace and Isle of Wight County's community feel make it a genuinely comfortable place to put down longer roots, and the lot size means outdoor life is part of the package too.
Frequently asked questions
How far is 18517 Shady Pine Lane from Joint Staff J7 Suffolk?
The drive from Shady Pine Lane to Joint Staff J7 in Suffolk is approximately 19 minutes under normal traffic conditions, making it one of the more convenient base commutes available in the Windsor area.
How far is 18517 Shady Pine Lane from NSA Northwest Annex?
NSA Northwest Annex is roughly 26 minutes from this address, a reasonable commute that keeps you well within range without requiring you to live right on the edge of the base corridor.
What county is 18517 Shady Pine Lane in?
The property is located in Isle of Wight County, Virginia, which governs zoning, property taxes, and local services for this address.
Is 18517 Shady Pine Lane in a flood zone?
Flood zone status for this property is detailed in the FloodRisk tile on this page, which pulls current FEMA map data for the specific parcel.
What is the lot and layout like at 18517 Shady Pine Lane?
The home is a five-bedroom, five-bathroom single-family residence built in 2001 with 3,868 square feet of living space, situated on Shady Pine Lane in Windsor — a low-traffic residential street with the kind of spacing between homes that's increasingly hard to find in Hampton Roads.
Tom and Dariya Milan at LPT Realty know Windsor and Isle of Wight County well — reach out to get your questions answered and schedule a walkthrough of Shady Pine Lane.
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
5
Full Baths
5
Half Baths
0
Approx Sq Ft
3,868
Stories
2
Fireplaces
0
Flooring
Carpet, Laminate/LVP, Vinyl, Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer, Dryer Hookup, Elec Range, Refrigerator, Washer, Washer Hookup
Sale & Tax History
List Price
$650,000
Price / Sq Ft
$168
Annual Taxes
$5,115
Monthly Tax
$426
HOA
None
Tax Rate (effective)
0.79%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | May 30, 2026 | $650,000 | — |
| Currently listed | — | $650,000 | — |
Public-Records Assessment
Source: City Assessor via Hampton Roads Regional Parcels. Fetched Jun 8, 2026.
Total Assessed
$87,100
Land
$87,100
Improvement
N/A
Parcel ID: 50-01-032
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
$3,989/moPrincipal & interest
$3,373
Property tax
$426
Home insurance
$190
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 Long & Foster Real Estate Inc. · MLS# 10636500
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$650,000
18517 Shady Pine LN, WINDSOR VA 23487
Windsor, Virginia 23487
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