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Windsor › ALL OTHERS AREA 65 › 44 N Court St✓ Source: REIN MLS #10642458 · record updated Jul 16, 2026 · synced every 2 min · your inquiry is never resold
44 N Court ST, WINDSOR VA 23487 - Main photo
44 N Court ST, WINDSOR VA 23487 - Photo 2
44 N Court ST, WINDSOR VA 23487 - Photo 3
44 N Court ST, WINDSOR VA 23487 - Photo 4
44 N Court ST, WINDSOR VA 23487 - Photo 5
$296,999
$142 / sqft · est. $1,822/mo →
4beds
2baths
2,086sqft
15days on market

44 N Court St, Windsor, VA 23487

ActiveResidential · built 1960 · ALL OTHERS AREA 65

About this home

The listing, in the seller's words

This 4-bedroom, 2-bath ranch offers comfortable one-level living with a spacious and functional layout.Interior features a blend of laminate and wood flooring throughout the main living areas. Enjoy a largebackyard perfect for relaxing, entertaining, or outdoor activities. Conveniently located near dining,schools, shopping, and major roadways for easy commuting.Property is in good condition and being sold as-is. Lender Approved Short Sale

Listing courtesy of Ronald Sawyer · RE/MAX Prime · REIN MLS #10642458

VaHome team overview

Our read on this home

At a glance

44 N Court Street is a four-bedroom, two-bath home on nearly half an acre in Windsor, Virginia — a quiet Isle of Wight County town with small-town charm, easy access to Suffolk, and more breathing room than you'll find closer to the coast.

Read the full overview ↓

Why this home stands out

Built in 1960, this 2,086-square-foot home sits on a generous 0.43-acre lot on a named street in the heart of Windsor — giving you real yard space, four true bedrooms, and the kind of elbow room that's genuinely hard to find at this size. The lot alone sets it apart from the tighter parcels common in newer subdivisions nearby, and the single-family footprint means no shared walls and no compromises.

ALL OTHERS AREA 65 and the Windsor real estate market

Windsor is a small incorporated town in Isle of Wight County, Virginia — the kind of place where neighbors actually wave and the pace of life feels intentional rather than accidental. Court Street sits right in the town core, which means walkable access to parks, local eateries, and everyday conveniences without sacrificing the quiet that makes small-town living worth it. Windsor homes for sale on named streets like this one tend to draw buyers who want genuine community over suburban anonymity. The town is compact enough that you know your surroundings quickly, yet connected enough — via Route 460 and Route 258 — that Hampton Roads is well within reach. Isle of Wight County as a whole has a reputation for well-maintained public spaces, low-density development, and a strong sense of local identity. If you've been eyeing the region but want something a step removed from the congestion of Virginia Beach or Chesapeake, Windsor offers a compelling alternative with real infrastructure and real community around it.

What's nearby

Daily life is easy from 44 N Court Street. Robinson Park, Garris Event Park, and Centennial Park are all within a short walk, giving you green space in multiple directions. Fizz Fusion coffee shop is just 0.3 miles away — a solid morning routine anchor. For food, Redd's Filling Station, Domino's Pizza, and Burger King are all within a few minutes on foot. Dollar General and a BP station cover quick grocery and errand runs at 0.3 and 0.4 miles respectively. Coastal Point Gymnastics and Sports Centre rounds out the immediate area with active programming close to home.

For different buyers

For military families relocating

Joint Staff J7 in Suffolk is about 21 minutes from 44 N Court Street — a manageable commute that puts you well outside the congestion zone around base. A VA loan can make a property like this especially accessible, and the lot size gives military families the outdoor space that apartment or townhome living rarely delivers. NSA Northwest Annex is roughly 43 minutes out for dual-military households.

For families upgrading

Four bedrooms and 2,086 square feet on nearly half an acre gives a growing family real room to spread out — indoors and out. The 0.43-acre lot is large enough for a genuine backyard, and the proximity to multiple parks means the kids have options beyond the property line too. Windsor's small-town setting adds a layer of community that's hard to manufacture in larger suburban developments.

More buyer questions

How far is 44 N Court Street from Joint Staff J7 Suffolk?

The drive is approximately 21 minutes under normal traffic conditions, heading east via Route 460. It's one of the more comfortable base commutes available in Isle of Wight County.

What is the lot size at 44 N Court Street?

The lot measures 0.43 acres — just under half an acre — which is notably generous for an in-town Windsor address and provides meaningful yard space front and back.

Is 44 N Court Street in a flood zone?

Flood zone status for this address is displayed in the FloodRisk tile on this page, which pulls current FEMA map data for the most accurate and up-to-date designation.

What is Windsor, Virginia like as a place to live?

Windsor is a small incorporated town in Isle of Wight County with a genuine small-town feel, walkable parks, local dining, and easy highway access to the broader Hampton Roads metro — it attracts buyers who want community without the density of larger cities.

Does 44 N Court Street have an HOA?

This property is not part of a platted HOA subdivision, so there are no mandatory homeowner association dues or restrictions tied to the address.

Tom and Dariya Milan at LPT Realty know Windsor and Isle of Wight County well — reach out to get your questions answered and arrange a walkthrough of 44 N Court Street.

Summary generated by AI from public records and publicly available information.

Schools

  • ElementaryWindsor Elementary
    —
  • MiddleGeorgie D. Tyler Middle School
    —
  • HighWindsor
    —

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1960

Price / sqft

$142

HOA

None

Taxes

$2,333/yr

County

Isle of Wight County VA

Waterfront

Yes

MLS #

10642458

Interior

Bedrooms
4
Full baths
2
Approx. sqft
2,086
Stories
1
Flooring
Laminate/LVP, Vinyl, Wood
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
6
Other rooms
1st Floor BR, Breakfast Area
Appliances
Dishwasher, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Equipment
Ceiling Fan

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick,Vinyl
Pool
No Pool
Fencing
Chain Link,Full
Waterfront
Not Waterfront

Utilities & systems

Heating
Electric, Heat Pump
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Lot size
0.2000
Subdivision
ALL OTHERS AREA 65
Zoning
RES
Ownership
Fee Simple
Garage
No
Parking
4 Space
Possession
AT CLOSING
Disclosures
Short/Comp Sale

Sources: REIN MLS record · city assessor · null fields are suppressed, never faked

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 51093C

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Not in a designated hurricane evacuation zone.

Source: Virginia Dept. of Emergency Management — Know Your Zone

Location intelligence

Minutes to real places, not a score

Location & Neighborhood

Places within ~1 mile, ordered by distance from this property. Powered by Google Places.

Military Commute

Drive times to nearest bases

Drive 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.

The numbers

Run the real carrying cost

Estimates only — taxes come from the public record; confirm rates with your lender. VA-eligible buyers: $0-down financing may apply.

Estimate your monthly payment

$1,822/mo

Principal & interest

$1,541

Property tax

$194

Home insurance

$87

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.

Value & history

Judge value on real ground

Asking vs. assessment

100% of $295,700

City assessment record · taxes $2,333/yr

Land share of assessed value

19% — $55,000

Improvements $240,700 · assessor record ✓

Why we show no algorithmic estimate.

National AVMs misprice homes whose value drivers they can't see. Instead: the sourced assessment above, the carrying cost, real price history, and honest comparables below.

Price context — similar nearby homes

$340,000 – $445,000

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

16 Holland DR · 0.6 mi · 2,033 sqft$419,900 sold 2026-04
25 E Griffin ST · 0.6 mi · 2,133 sqft$340,000 sold 2026-05
24 N Court ST · 0.2 mi · 1,785 sqft$370,000 sold 2026-04

Sale & Tax History

List Price

$296,999

Price / Sq Ft

$142

Annual Taxes

$2,333

Monthly Tax

$194

HOA

None

Tax Rate (effective)

0.79%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJul 1, 2026$296,999—
Price reducedJul 16, 2026$296,999−$3,000
Currently listed—$296,999—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

Asking near assessment

Total Assessed

$295,700

Land

$55,000

Improvement

$240,700

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:

Windsor Assessor (Google)

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.

Market tempo

15 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Real questions, answered from the record

Is 44 N Court St in a good school zone?+
The assigned zones on the listing record are Windsor Elementary (GreatSchools 4/10), Georgie D. Tyler Middle School, Windsor (GreatSchools 4/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 44 N Court St in a flood zone?+
FEMA maps this parcel in Zone X, outside the high-risk Special Flood Hazard Area. See the flood section on this page for details and sources.
Is there a gym near 44 N Court St?+
Yes — Coastal Point Gymnastics and Sports Centre is about 0.3 miles away, per the cached nearby-places record for this address.
Are there parks near 44 N Court St?+
Robinson Park is about 0.3 miles away.
Where is the nearest grocery store to 44 N Court St?+
Dollar General is about 0.3 miles away. The closest dining on record is Redd's Filling Station (0.3 mi).
Does 44 N Court St have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 44 N Court St built?+
It was built in 1960, per the listing record.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data — never invented.

The people

You'll talk to a person, not a lead queue

TD

Tom & Dariya Milan

LPT Realty · Hampton Roads · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of Ronald Sawyer · RE/MAX Prime · REIN MLS #10642458

Call or text (757) 777-7577

Ask Dariya — instant answers

Schools, flood, drive times, what it really costs to own — answered from this page's data, by chat or voice.

Schedule a private tour

Free, no obligation — your inquiry goes to Tom & Dariya, never resold.

44 N Court St, Windsor — photo

See it in person — the record only says so much.

Call or text (757) 777-7577

44 N Court St, Windsor, Virginia 23487 · MLS #10642458 · Source: REIN MLS + public record. Information deemed reliable but not guaranteed — verify independently. School zones subject to change; confirm with the local school division. All locations are described by neutral geographic fact. Equal Housing Opportunity.

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