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ChesapeakeSUNRAY377 Homestead Rd✓ Source: REIN MLS #10644941 · record updated Jul 30, 2026 · synced every 2 min · your inquiry is never resold
377 Homestead RD, CHESAPEAKE VA 23321 - Main photo
377 Homestead RD, CHESAPEAKE VA 23321 - Photo 2
$1,195,000
$271 / sqft · est. $7,311/mo →
4beds
4.1baths
4,416sqft
13days on market

377 Homestead Rd, Chesapeake, VA 23321

Off MarketResidential · built 2008 · SUNRAY

Facts & features

Type

Residential

Year built

2008

Price / sqft

$271

HOA

None

Taxes

$9,147/yr

County

Chesapeake VA

MLS #

10644941

Interior

Bedrooms
4
Full baths
4
Half baths
1
Approx. sqft
4,416
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP, Wood
Ensuite bedrooms
4
First-floor bed & full bath
Yes
Total rooms
9
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, Fin. Rm Over Gar, Foyer, Loft, PBR with Bath, Pantry, Porch, Utility Room, Workshop
Appliances
Dishwasher, Dryer, Microwave, Elec Range, Refrigerator, Washer
Equipment
Cable Hookup, Ceiling Fan, Gar Door Opener, Jetted Tub, Security Sys
Accessibility
Handheld Showerhead, Main Floor Laundry

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick,Vinyl
Pool
In Ground Pool
Fencing
Decorative,Picket,Wood Fence

Utilities & systems

Heating
Heat Pump, Zoned
Cooling
Heat Pump, Zoned
Water heater
Electric
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
8.9300
Subdivision
SUNRAY
Zoning
A1
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 3+ Car, Multi Car, Driveway Spc
Possession
SETTLEMENT
Disclosures
Disclosure Statement, Pet on Premises

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

About this home

Dreaming of a Serene Country Retreat just minutes from the city? YOU FOUND IT! A Rare Jewel! Horse Lover's Dream! Almost 9 ac Family Sanctuary. Elegant Custom Built, 4 Ensuite BRs & 1/2 Bath home w/an amazing 10' x 50' front porch! Lovely entry foyer opens to Great Room w/cathedral ceiling, hand scraped engineered flooring & wood burning fireplace framed w/bookshelf cabinetry. 1st Floor Primary BR boasts expansive Bath w/2 Separate Granite Vanities, jetted tub, separate shower & Grand Walk-In Closet. PBR Plantation Shutters reveal peaceful views of property! 10 ft ceilings down & 9 ft up. Kitchen w/granite counters, 2 large pantries, ample cabinetry & generous eat-in area. Formal Dining Room for festive gatherings. Upstairs reveals open sitting area w/chandelier. Expansive FROG-4th Bedroom. 3 Covered porches. 3 Car Garage, Spacious 2 Stall Stable, Large Storage Barn, approx 30' x 20' IG Pool w/stamped concrete surround. Fruit trees & acreage for hobby farming. Don't miss this one!

Listing courtesy of Genine Cooper · The Real Estate Group · REIN MLS #10644941

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

377 Homestead Road is a substantial 4,416-square-foot, four-bedroom, four-and-a-half-bath home built in 2008 in Chesapeake, Virginia. With generous living space, multiple full baths, and quick access to two major military installations, this property suits a wide range of households.

Read the full overview ↓

Why this home stands out

At over 4,400 square feet with four full baths plus a half bath, 377 Homestead Road offers a scale that's genuinely rare in western Chesapeake. Built in 2008, the home hits a sweet spot — modern construction standards and systems without the premium attached to brand-new builds. Four true bedrooms means everyone gets real space, not a converted flex room.

SUNRAY and the Chesapeake real estate market

Chesapeake is one of the largest cities by land area on the entire East Coast, and the 23321 zip code — covering the Port Norfolk and western Chesapeake corridors — reflects that breathing room. Streets here tend to be quieter than those closer to the Virginia Beach oceanfront or downtown Norfolk, yet Interstate 664 and Route 17 keep you genuinely connected. Homestead Road sits in a residential pocket where lots are generous and neighbors aren't stacked on top of each other. The broader Chesapeake identity is built around space, lower density, and a slower pace that still puts you within a reasonable drive of everything Hampton Roads has to offer — waterfront dining, major retail corridors, and the cultural draw of downtown Norfolk are all within reach. City services are well-established, and the area has attracted steady long-term homeowners who tend to stay put, which keeps the streetscape stable and cared-for.

What's nearby

Day-to-day errands and meals are straightforward from Homestead Road. Frank's Restaurant and Frank's Truck Stop are both about a mile away — a local institution for no-fuss, hearty food that regulars swear by. Beyond that immediate radius, the broader western Chesapeake and Portsmouth corridor fills in quickly with grocery options, pharmacies, and the kind of everyday retail that makes life run smoothly. The Western Branch area and the commercial stretch along Route 17 add additional dining and shopping depth within a short drive.

For different buyers

For military families relocating

Norfolk Naval Shipyard is roughly 15 minutes from 377 Homestead Road, and Naval Medical Center Portsmouth is just a minute farther. That commute math works well for E-6 and above households where BAH supports a larger home. A VA loan is a natural fit here — four bedrooms and four and a half baths give a military family genuine long-term flexibility across multiple duty-station cycles.

For families upgrading

If your current home has you tripping over each other, 4,416 square feet changes the conversation entirely. Four bedrooms means dedicated guest space or a real home office without sacrificing a bedroom. Four full baths eliminates the morning bottleneck. Built in 2008, the systems and finishes are modern enough that you're not inheriting a renovation project on day one.

More buyer questions

How far is 377 Homestead Road from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is approximately 15 minutes from 377 Homestead Road under typical traffic conditions. The route via I-664 South is straightforward and avoids most of the congestion that affects other Hampton Roads commutes.

How far is 377 Homestead Road from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is about 16 minutes away, just slightly farther than Norfolk Naval Shipyard. Both bases are accessible via the same general corridor, making this location practical for households with ties to either installation.

Is 377 Homestead Road in a flood zone?

Flood zone status for this address is displayed in the dedicated FloodRisk tile on this page, which pulls current FEMA map data. It's worth reviewing before making any decisions, as designations can change over time.

What is the lot size at 377 Homestead Road?

Lot size details are included in the full property data panel on this page. Western Chesapeake lots in this area tend to be more generous than those closer to the coast, which is part of the appeal of the 23321 zip code.

Does 377 Homestead Road have an HOA?

HOA status is confirmed in the property details section of this listing page. If an HOA is in place, the details panel will note it — though specific fee amounts are subject to change and best confirmed directly with the association.

Want to walk through 377 Homestead Road or talk through whether it fits your situation? Tom and Dariya Milan at LPT Realty know this part of Chesapeake well — reach out and let's talk.

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

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

Evacuation Zone B

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

Explore this neighborhood

Dock Landing

Dock Landing is a residential community in the Western Branch area of Chesapeake, Virginia, centered along Dock Landing Road in the 23321 ZIP code.

$536K

Median sale · 12 mo

$222

Sold $/sq ft

18d

Days on market

0

For sale now

$169K

HH income

95.3%

Owner-occupied

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

Explore Dock Landing
Map of Dock Landing with neighborhood boundaryNeighborhood

Chesapeake homes for sale

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

Homes at this tier often trade in cash or portfolio financing — the calculator below shows a financed view; taxes are from the public record.

Estimate your monthly payment

$7,311/mo

Principal & interest

$6,201

Property tax

$762

Home insurance

$349

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

Price context — similar nearby homes

$497,000$818,500

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 4 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

433 Truitt RD · 0.8 mi · 4,459 sqft$685,000 sold 2026-07
1507 Burrowin DR · 1.5 mi · 4,193 sqft$818,500 sold 2026-05
1544 Lauren Ashleigh DR · 1.8 mi · 3,991 sqft$720,000 sold 2026-05

Sale & Tax History

List Price

$1,195,000

Price / Sq Ft

$271

Annual Taxes

$9,147

Monthly Tax

$762

HOA

None

Tax Rate (effective)

0.77%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJul 22, 2026$1,195,000
Currently listed$1,195,000

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.

Questions buyers ask

Is 377 Homestead Rd in a good school zone?+
The assigned zones on the listing record are Southwestern Elementary (VaHome School Score 4.8/10), Jolliff Middle (VaHome School Score 8.2/10), Western Branch (VaHome School Score 6.2/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 377 Homestead Rd 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 377 Homestead Rd have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 377 Homestead Rd built?+
It was built in 2008, 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 Genine Cooper · The Real Estate Group · REIN MLS #10644941

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.

377 Homestead Rd, Chesapeake — photo

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

Call or text (757) 777-7577

377 Homestead Rd, Chesapeake, Virginia 23321 · MLS #10644941 · 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.