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Chesapeake › KEMP WOODS › 1045 Winchester Way✓ Source: REIN MLS #10645167 · record updated Sep 1, 2026 · synced every 2 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
$579,000
$223 / sqft · est. $3,594/mo →
4beds
2.1baths
2,600sqft
42days on market

1045 Winchester Way, Chesapeake, VA 23320

Under ContractResidential · built 1990 · KEMP WOODS

Facts & features

Type

Residential

Year built

1990

Price / sqft

$223

HOA

None

Taxes

$5,047/yr

County

Chesapeake VA

MLS #

10645167

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
2,600
Stories
2
Flooring
Carpet, Ceramic, Wood
Ensuite bedrooms
1
Total rooms
12
Other rooms
Attic, Breakfast Area, Fin. Rm Over Gar, Foyer, Loft, PBR with Bath, Office/Study, Pantry, Porch, Utility Closet, Utility Room
Appliances
Dishwasher, Disposal, Dryer Hookup, Gas Range, Washer Hookup
Equipment
Cable Hookup, Ceiling Fan, Gar Door Opener, Jetted Tub
Accessibility
Main Floor Laundry

Construction & exterior

Style
Traditional, Transitional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick,Vinyl
Pool
No Pool
Fencing
Back Fenced,Decorative,Privacy

Utilities & systems

Heating
Forced Hot Air, Nat Gas, Zoned
Cooling
Central Air, Zoned
Water heater
Gas
Water
City/County
Sewer
City/County

Lot, parking & ownership

Lot size
0.4000
Subdivision
KEMP WOODS
Zoning
R15S
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Off Street, Driveway Spc, Street
Possession
CLOSING
Disclosures
Disclosure Statement

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

About this home

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 #10645167

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

Meet 1045 Winchester Way — a four-bedroom, 2.5-bath Chesapeake home built in 1990 with 2,600 square feet of living space, three minutes from the USCG Finance Center and 14 minutes from Norfolk Naval Shipyard, sitting in one of the city's most convenient inland corridors.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23320, homes for sale zoned for Indian River High School, and homes for sale zoned for Greenbrier Primary School. Browse every listing among homes for sale in Chesapeake — updated from the REIN MLS every few minutes. Nearby, look at Plantation Lakes homes for sale, Chesapeake waterfront homes for sale, Chesapeake condos and townhomes for sale, and new construction homes in Chesapeake.

Read the full overview ↓

Why this home stands out

What sets this address apart is the rare combination of square footage, commute math, and everyday convenience. At 2,600 square feet, there's genuine room to spread out — four bedrooms and a half-bath give the layout real flexibility for home offices, guests, or growing households. Add a sub-five-minute drive to the USCG Finance Center Chesapeake and you have a location that simply doesn't come up often among Chesapeake homes for sale at this size.

KEMP WOODS and the Chesapeake real estate market

Winchester Way sits in the heart of Chesapeake's Greenbrier corridor — one of the city's most established and well-connected inland areas. Greenbrier has long been a go-to for families and professionals who want suburban breathing room without sacrificing access to major employers, retail, and interstate ramps. The streets here have a settled, mature feel: established tree canopy, consistent lot sizes, and neighbors who tend to stay put. Chesapeake itself is Virginia's second-largest city by land area, which means the city delivers on space — wide roads, lower density than Norfolk or Virginia Beach, and a reputation for solid infrastructure. Families comparing homes for sale in Chesapeake often land in the Greenbrier area specifically because it threads the needle between city amenities and a quieter pace of daily life. The 23320 zip code covers a broad swath of central Chesapeake, and Winchester Way is positioned near its commercial and residential sweet spot.

What's nearby

Daily life is easy here. Within a mile, you'll find a genuinely diverse dining lineup: PRIME757 Food Truck is just half a mile out for local flavor, while Inaka Sushi and Hibachi Chesapeake and Top Mongolian both sit at 0.8 miles for weeknight variety. Tropical Smoothie Cafe and Ginger Sweets Pastry Cafe handle morning runs and afternoon pick-me-ups at under a mile, with a 7-Eleven at 0.9 miles for quick stops. Wellness options are equally close — TEALL Transformation Yoga and Dawn Pilates Studio are both within a mile, making it realistic to build a routine without a long drive. Greenbrier's broader retail corridor puts grocery stores, pharmacies, and big-box shopping within easy reach as well.

For different buyers

For military families relocating

Three minutes to the USCG Finance Center Chesapeake makes 1045 Winchester Way one of the shortest commutes you'll find in the area. Norfolk Naval Shipyard is 14 minutes out, so dual-military or civilian-spouse households have solid options in both directions. A VA loan pairs naturally with a home this size — four bedrooms and 2,600 square feet give you the space that makes a long-term purchase feel right.

For families upgrading

Families comparing homes for sale zoned for Indian River High School and homes for sale zoned for Greenbrier Primary School will find 1045 Winchester Way worth a close look. Four bedrooms and 2,600 square feet give everyone room to claim their own space, and the Greenbrier corridor's walkable amenities and quick highway access make the upgrade feel like it covers all the bases at once.

More buyer questions

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

The USCG Finance Center Chesapeake is approximately three minutes by car from 1045 Winchester Way, making it one of the closest residential options to that installation in the area.

How far is 1045 Winchester Way from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about 14 minutes from 1045 Winchester Way, a manageable daily commute that keeps Portsmouth and Norfolk employment centers within reach.

What zip code is 1045 Winchester Way in?

The property is in the 23320 zip code, which covers a large portion of central Chesapeake including the Greenbrier corridor — one of the most in-demand areas among homes for sale in 23320.

Is 1045 Winchester Way in a flood zone?

Flood zone status for this address is detailed in the FloodRisk tile on this page, which pulls the current FEMA designation for the parcel.

Does 1045 Winchester Way have a garage?

Garage details for this property are confirmed in the full listing specs — check the features section of this page for the most accurate information on parking and storage.

Want to walk through 1045 Winchester Way or compare it with other Chesapeake homes for sale? Tom and Dariya Milan at LPT Realty are ready to help — reach out to schedule a visit.

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

Homes like this one sell fast — see the next one first

Chesapeake$490K – $670K4+ beds

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Schools

VaHome School Score

Our own 1–10 rating, scored from Virginia Department of Education data.

VaHome School Score — calculated by VaHome.com from Virginia Department of Education assessment, progress, and attendance data. Attendance zones come from the MLS listing record; confirm the current zone with the school division before making an offer.

Flood & environment

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 hurricane evacuation zone.

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

Explore this neighborhood

Plantation Lakes

Plantation Lakes is a lake-oriented residential community in the Greenbrier area of Chesapeake, Virginia, set within the 23320 ZIP code near I-64 and the Greenbrier shopping district.

$390K

Median sale · 12 mo

$235

Sold $/sq ft

7d

Days on market

1

For sale now

$135K

HH income

85.7%

Owner-occupied

REIN MLS closed sales, trailing 12 mo · U.S. Census ACS 2024 5-year

Explore Plantation Lakes →
Map of Plantation Lakes with neighborhood boundaryNeighborhood

Chesapeake real estate →

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

$3,594/mo

Principal & interest

$3,004

Property tax

$421

Home insurance

$169

PMI

None

HOA/Condo (paid separately)

None

Estimate only. Association (HOA/condo) fees are paid separately and are not included in the payment above. 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

116% of $499,700

City assessment record · taxes $5,047/yr

Land share of assessed value

34% — $170,000

Improvements $329,700 · assessor record ✓

Price context — similar nearby homes

$485,000 – $690,000

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.

1208 Cowpens CT · 1.6 mi · 2,520 sqft$620,000 sold 2026-06
1209 Cowpens CT · 1.6 mi · 2,520 sqft$690,000 sold 2026-05
813 Arcadia RD · 1.5 mi · 2,442 sqft$485,000 sold 2026-04

Sale & Tax History

List Price

$579,000

Price / Sq Ft

$223

Annual Taxes

$5,047

Monthly Tax

$421

HOA

None

Tax Rate (effective)

0.87%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJul 21, 2026$579,000—
Price reducedAug 3, 2026$579,000−$6,000
Currently listed—$579,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

16% above assessment

Total Assessed

$499,700

Land

$170,000

Improvement

$329,700

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:

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.

Questions buyers ask

Is 1045 Winchester Way in a good school zone?+
The assigned zones on the listing record are Greenbrier Primary, Greenbrier Middle (VaHome School Score 7.2/10), Indian River (VaHome School Score 4.9/10). 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 #10645167

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.

1045 Winchester Way, Chesapeake — photo

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

Call or text (757) 777-7577

1045 Winchester Way, Chesapeake, Virginia 23320 · MLS #10645167 · 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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