ChesapeakeKEMP WOODS1045 Winchester Way✓ Source: REIN MLS #10642649 · record updated Jul 2, 2026 · synced every 5 min · your inquiry is never resold
1045 Winchester WAY, CHESAPEAKE VA 23320 - Main photo
1045 Winchester WAY, CHESAPEAKE VA 23320 - Photo 2
1045 Winchester WAY, CHESAPEAKE VA 23320 - Photo 3
1045 Winchester WAY, CHESAPEAKE VA 23320 - Photo 4
1045 Winchester WAY, CHESAPEAKE VA 23320 - Photo 5
$590,000
$227 / sqft · est. $3,654/mo →
4beds
2.1baths
2,600sqft
0days on market

1045 Winchester Way, Chesapeake, VA 23320

New ListingResidential · built 1990 · KEMP WOODS

About this home

The listing, in the seller's words

Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier's premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake's most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property's potential. Schedule your showing today to make this house YOUR HOME!

Listing courtesy of Val Milan · Swell Real Estate Co · REIN MLS #10642649

VaHome team overview

Our read on this home

At a glance

1045 Winchester Way is a four-bedroom, two-and-a-half-bath single-family home in Chesapeake, Virginia, offering 2,600 square feet of living space built in 1990. It sits minutes from the USCG Finance Center and a short drive from Norfolk Naval Shipyard.

Read the full overview ↓

Why this home stands out

What sets 1045 Winchester Way apart is the combination of generous square footage and a well-established 1990s neighborhood that has had decades to mature — think tree-lined streets and a settled, community feel that newer developments simply haven't had time to develop. Four true bedrooms and a half-bath on the main level give growing households real room to spread out without compromise.

KEMP WOODS and the Chesapeake real estate market

Winchester Way sits within Chesapeake, one of the largest cities by land area on the East Coast and consistently ranked among Virginia's most livable communities. The surrounding area carries the hallmarks of a mature 1990s residential pocket: established trees, quiet streets, and neighbors who have put down real roots. Chesapeake strikes a balance that's hard to find — suburban calm with genuine urban access. You're close enough to Norfolk and Portsmouth to reach major employment corridors quickly, yet far enough removed to come home to a slower pace. The city's own parks system, waterways, and trail networks give outdoor-minded residents plenty to explore without leaving city limits. Local grocery anchors, dining, and everyday retail are all within a short drive, and the road network fans out in multiple directions, making commutes in almost any direction manageable. For anyone weighing where in Hampton Roads to plant a flag, Chesapeake offers stability, space, and a community identity that holds its character year after year.

What's nearby

Daily life is easy here. Grocery runs, pharmacy stops, and coffee breaks are all within a few minutes of Winchester Way. Greenbrier Mall and the surrounding Greenbrier corridor — one of Chesapeake's primary retail and dining hubs — is close enough to handle most errands in a single trip. City parks and walking trails are accessible without a long drive, and Interstate 64 is nearby for anyone commuting toward Virginia Beach, Norfolk, or beyond. The USCG Finance Center Chesapeake is roughly three minutes away, and Norfolk Naval Shipyard is reachable in about fourteen minutes — a meaningful advantage for service members watching the clock.

For different buyers

For military families relocating

Three minutes to the USCG Finance Center Chesapeake and fourteen minutes to Norfolk Naval Shipyard — that kind of proximity is genuinely rare in one address. A VA loan can make this four-bedroom home even more accessible, and the extra square footage means space for a home office, a guest room for visiting family, or a dedicated study area when the next PCS order arrives.

For families upgrading

If you've outgrown your current space, 2,600 square feet across four bedrooms and two and a half baths gives everyone in the household room to breathe. The mature neighborhood setting means the hard work of establishing a community is already done — sidewalks, established trees, and longtime neighbors come standard. There's real room here to grow into, not just move into.

More buyer questions

How far is 1045 Winchester Way from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is approximately 14 minutes from 1045 Winchester Way under typical traffic conditions, making it one of the more commute-friendly addresses in Chesapeake for Shipyard personnel.

How far is 1045 Winchester Way from the USCG Finance Center Chesapeake?

The USCG Finance Center Chesapeake is roughly 3 minutes away — close enough that a forgotten badge is a minor inconvenience, not a major detour.

What is the property type and size at 1045 Winchester Way?

1045 Winchester Way is a single-family residential home with 2,600 square feet of living space, four bedrooms, and two and a half bathrooms, built in 1990.

Is 1045 Winchester Way in a flood zone?

Flood zone information for 1045 Winchester Way is displayed in the FloodRisk tile on this page, which pulls current FEMA map data for the most accurate and up-to-date designation.

Can a VA loan be used to purchase 1045 Winchester Way?

Yes — as a single-family residential property, 1045 Winchester Way is generally eligible for VA loan financing, which can offer qualified buyers significant advantages including no down payment requirement.

Want to see 1045 Winchester Way in person? Tom and Dariya Milan at LPT Realty know this corner of Chesapeake well — reach out and let's set up a walkthrough.

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

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1990

Price / sqft

$227

HOA

None

Taxes

$5,047/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10642649

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

Flood & environment

The flood answer first — quantified, not buried

FEMA flood zone X · outside the high-risk area · FIRM 510034

Flood Risk

Looking up FEMA flood zone…

Hurricane evacuation zone: not in a designated evacuation zone · VDEM Know Your Zone

Outside all mapped AICUZ jet-noise contours and Accident Potential Zones.

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

$3,654/mo

Principal & interest

$3,061

Property tax

$421

Home insurance

$172

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

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

$610,000$649,900

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.

700 Argyll ST · 1 mi · 2,623 sqft$639,900 sold 2026-05
702 Argyll ST · 1 mi · 2,552 sqft$634,900 sold 2026-05
624 Appalachian CT · 1.3 mi · 2,640 sqft$649,900 sold 2026-04

Sale & Tax History

List Price

$590,000

Price / Sq Ft

$227

Annual Taxes

$5,047

Monthly Tax

$421

HOA

None

Tax Rate (effective)

0.86%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJul 3, 2026$590,000
Currently listed$590,000

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:

Chesapeake Real Estate Assessor

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

0 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 1045 Winchester Way in a good school zone?+
The assigned zones on the listing record are Greenbrier Intermediate (GreatSchools 6/10), Greenbrier Middle (GreatSchools 6/10), Indian River (GreatSchools 3/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1045 Winchester Way 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.
Does 1045 Winchester Way have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 1045 Winchester Way built?+
It was built in 1990, 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 Val Milan · Swell Real Estate Co · REIN MLS #10642649

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.

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

Call or text (757) 777-7577

1045 Winchester Way, Chesapeake, Virginia 23320 · MLS #10642649 · 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.