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Chesapeake › KEMP WOODS › 1045 Winchester Way✓ Source: REIN MLS #10645167 · record updated Sep 28, 2026 · synced every 2 min · your inquiry is never resold
1045 Winchester WAY, CHESAPEAKE VA 23320 - Main photo
4beds
2.1baths
2,600sqft
42days on market

1045 Winchester Way, Chesapeake, VA 23320

SoldResidential · built 1990 · KEMP WOODS

Facts & features

Type

Residential

Year built

1990

Price / sqft

$219

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

Tom & Dariya's overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · Brokered by LPT Realty

At a glance

Four-bedroom, 2.1-bath home on Winchester Way in Chesapeake. Built in 1990, this 2,600-square-foot residence sits just minutes from the Coast Guard Finance Center. It's the kind of location that anchors homes for sale in 23320.

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

Winchester Way offers a practical floor plan with four bedrooms spread across 2,600 square feet. The 2.1 baths provide flexibility for different schedules. A single-family layout from 1990 means solid bones and a straightforward design. You get genuine living space without the complexity of newer construction quirks. This is a home built to last, in a location built for access.

KEMP WOODS and the Chesapeake real estate market

Chesapeake is Virginia's largest city by area, blending suburban comfort with working-waterfront character. Winchester Way sits in a residential pocket where daily errands stay close and base commutes stay short. The neighborhood feels established—tree-lined streets, single-family homes, and the kind of stability that comes from decades of families choosing the same blocks. Chesapeake homes for sale span a wide range, but this zip code leans toward practical, no-fuss living. You're minutes from shopping, dining, and the water. The city itself is easy to navigate: major routes like Route 17 and I-64 connect you to Norfolk, Virginia Beach, and the broader region. If you're comparing homes for sale in Chesapeake, note that this location cuts your commute significantly.

What's nearby

Daily life is easy here. PRIME757 FOOD TRUCK sits just half a mile away for quick meals. Inaka Sushi and Hibachi Chesapeake and Top Mongolian are both under a mile, so dinner options are varied. Coffee runs take you to Tropical Smoothie Cafe, 7-Eleven, or Ginger Sweets Pastry Cafe—all within a mile. If fitness matters, TEALL Transformation Yoga and Dawn Pilates Studio are close by.

For different buyers

Base commute and VA loan notes

About three minutes to USCG Finance Center Chesapeake and fourteen minutes to Norfolk Naval Shipyard. VA loan financing is widely available in this zip code, and the straightforward layout means you can move in without major surprises. Four bedrooms give you real flexibility.

Room to grow

Four bedrooms and 2.1 baths spread across 2,600 square feet give you genuine room to grow. The single-family layout from 1990 offers a practical floor plan with solid bones. Storage and living space are built in, not squeezed. You're not paying for trendy finishes—you're buying a home that works.

More buyer questions

How far is 1045 Winchester Way from the Coast Guard Finance Center?

About three minutes by car. It's one of the shortest commutes in the region.

What is the drive time to Norfolk Naval Shipyard?

Roughly fourteen minutes, depending on traffic. The route is straightforward via Route 17.

Are there restaurants and coffee shops nearby?

Yes. PRIME757 FOOD TRUCK is half a mile away, and Inaka Sushi, Top Mongolian, and three coffee shops are all within a mile.

What schools are zoned for this address?

This address is zoned for homes for sale zoned for Indian River High School and homes for sale zoned for Greenbrier Primary School. Check the Schools tile for details.

Is this a single-family home?

Yes. It's a four-bedroom, 2.1-bath single-family residence built in 1990.

Ready to tour 1045 Winchester Way? Contact Tom & Dariya Milan at LPT Realty to schedule your visit today.

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

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

Chesapeake$480K – $655K4+ beds

By subscribing you agree to receive listing emails from Tom & Dariya Milan, Realtors, at most one a day. Unsubscribe anytime · Privacy PolicyBrokered by LPT Realty

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 (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 510034

Low / Moderate Risk

FEMA flood zone

X (low to moderate risk)

Base flood elevation

Not applicable in low-risk zones

Zone X is outside the Special Flood Hazard Area; FEMA doesn\u2019t define a BFE here.

Property elevation

14.7 ft above sea level

USGS 3DEP digital elevation model

Outside the high-risk Special Flood Hazard Area. Federal flood insurance is NOT required, though optional preferred-rate NFIP coverage is still worth considering in coastal Hampton Roads.

Data sources: Flood zone and base flood elevation come from FEMA\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 actual elevations across a single property can vary by several feet higher or lower than the figure shown. Use these numbers as a starting reference and do your own due diligence (a professional survey or elevation certificate) before relying on them for any financial, insurance, or construction decision.

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-focused neighborhood in the Greenbrier area of Chesapeake, Virginia. It sits in 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

$3,539/mo

Principal & interest

$2,952

Property tax

$421

Home insurance

$166

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

114% 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

Own a home nearby? See what it is worth today — What's your Chesapeake home worth?

Sale & Tax History

List Price

$569,000

Price / Sq Ft

$219

Annual Taxes

$5,047

Monthly Tax

$421

HOA

None

Tax Rate (effective)

0.89%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 17, 2026$569,000—
Price reducedSep 28, 2026$569,000−$10,000
SoldSep 24, 2026$569,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

14% 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 7.1/10), Indian River (VaHome School Score 4.3/10). 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

Brokered by 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.

This home has sold

Curious what it means for your own plans? Ask about similar homes nearby, or what your home might sell for in this market.

🏡 Similar homes for saleWhat's my home worth?
1045 Winchester Way, Chesapeake — photo

This one's sold — the next one doesn't have to be.

🏡 Homes for sale in ChesapeakeCall 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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