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ChesapeakeSUNRAY377 Homestead Rd✓ Source: REIN MLS #10644941 · record updated Jul 20, 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
377 Homestead RD, CHESAPEAKE VA 23321 - Photo 3
377 Homestead RD, CHESAPEAKE VA 23321 - Photo 4
377 Homestead RD, CHESAPEAKE VA 23321 - Photo 5
$1,195,000
$271 / sqft · est. $7,311/mo →
4beds
4.1baths
4,416sqft
3days on market

377 Homestead Rd, Chesapeake, VA 23321

New ListingResidential · built 2008 · SUNRAY

About this home

The listing, in the seller's words

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

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

2008

Price / sqft

$271

HOA

None

Taxes

$9,147/yr

County

Chesapeake VA

Waterfront

Yes

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
Waterfront
Not Waterfront

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

Flood & environment

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

Flood Risk

Looking up FEMA flood 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

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

$497,000$818,500

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 3 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

1507 Burrowin DR · 1.5 mi · 4,193 sqft$818,500 sold 2026-05
433 Truitt RD · 0.8 mi · 4,459 sqft$699,000 under contract
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 17, 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.

Market tempo

3 days on market — read it in context

Higher-priced homes market more slowly by nature: the buyer pool is smaller and diligence is heavier. Days-on-market at this tier is a rhythm, not a warning.

Questions buyers ask

Real questions, answered from the record

Is 377 Homestead Rd in a good school zone?+
The assigned zones on the listing record are Southwestern Elementary (GreatSchools 5/10), Jolliff Middle (GreatSchools 7/10), Western Branch. 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.