✓ Source: REIN MLS #10652901 · record updated Oct 2, 2026 · synced every 2 min · your inquiry is never resold

1 / 34

3D aerial flyover

$440,000est. $2,740/mo all-in · adjust →

3beds

3baths

2,020sqft

$218per sqft

22days on market

4057 Woodland Dr, Chesapeake, VA 23321

Under ContractResidential · built 1952 · 0.76 acres · DOCK LANDING · MLS #10652901

Price per sqft$218compare with nearby sales Schools

Western BranchHigh6.3

JolliffMiddle7.6

Edwin W. ChittumElementary7.8

VaHome School Score Flood

Low / moderate riskZone X

flood insurance not required HOANoneno HOA fee on the MLS record Est. payment$2,740/moall-in · 20% down · 6.75% · adjust Price since listing…checking price history Taxes$3,938/yrasking is 113% of assessment Condo feeNAnot a condo

OverviewAbout this home

Welcome home to this stunningly renovated farmhouse, where modern design meets classic charm in the heart of Chesapeake. Completely rebuilt from the studs up, this 3-bedroom, 3-bathroom gem offers 1,963 square feet of thoughtfully designed living space across two stories on 3/4th an acre. Step inside to an open-concept kitchen featuring striking black-and-white countertops, statement lighting, and modern farmhouse accents throughout. The main-level primary suite is a true retreat, boasting two generous closets and a spa-inspired bathroom with a sleek, step-in tiled shower. Sophisticated gray-toned flooring flows seamlessly throughout the home, adding warmth and cohesive style to every room. Outside, a detached garage provides excellent storage or workshop potential. Come make your dreams your reality! This one will not last long!

Listing courtesy of Brian Merritt · Merritt Realty Inc. · REIN MLS #10652901

Facts & features

TypeResidential

Year built1952

Price / sqft$218

HOANone

Taxes$3,938/yr

CountyChesapeake VA

MLS #10652901

Interior

Bedrooms: 3
Full baths: 3
Approx. sqft: 2,020
Stories: 2
Flooring: Laminate/LVP
Ensuite bedrooms: 1
First-floor bed & full bath: Yes
Total rooms: 7
Other rooms: 1st Floor BR, 1st Floor Primary BR, Attic, PBR with Bath, Porch, Utility Room
Appliances: Dishwasher, Disposal, Microwave, Gas Range, Refrigerator, Washer

Construction & exterior

Style: Cottage
Subtype: Detached
Foundation: Crawl
Roof: Asphalt Shingle
Exterior: Vinyl
Pool: No Pool
Fencing: Back Fenced,Chain Link

Utilities & systems

Heating: Forced Hot Air, Programmable Thermostat
Cooling: Central Air, Zoned
Water heater: Gas
Water: City/County
Sewer: City/County

Lot, parking & ownership

Lot size: 0.7580
Subdivision: DOCK LANDING
Zoning: R15S
Ownership: Fee Simple
Garage: Yes
Parking: Garage Det 2 Car, Oversized Gar, 4 Space, Off Street
Possession: SETTLE
Disclosures: Disclosure Statement

Sources: REIN MLS record · city assessor

Tom & Dariya's overview

Our read on this home

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

At a glance

Meet 4057 Woodland Drive in Chesapeake—a three-bedroom, three-bath home built in 1952 with 2,020 square feet of living space. You're about 13 minutes from Naval Medical Center Portsmouth and 14 minutes from Norfolk Naval Shipyard. Chesapeake homes for sale in this location offer solid bones and convenient access to both bases and everyday amenities.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23321, homes for sale zoned for Western Branch High School, and homes for sale zoned for Edwin W. Chittum Elementary School. Nearby, look at Dock Landing 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

This mid-century home sits on a residential block with good bones and straightforward layout. Three bedrooms and three full baths give you flexibility for a home office, guest space, or personal retreat. The 2,020-square-foot floor plan feels open and livable. You'll find grocery stores, restaurants, and the Western Branch Softball fields all within a mile. The location keeps you close to two major military installations without the hustle of a dense urban corridor.

DOCK LANDING and the Chesapeake real estate market

Woodland Drive runs through a quiet Chesapeake neighborhood where tree-lined streets and single-family homes set a relaxed pace. The area has the feel of an established residential community—neighbors know the block, and there's room to breathe. Chesapeake itself is Virginia's largest city by land area, blending suburban calm with urban conveniences. Getting around is straightforward: major roads connect you to shopping, dining, and employment centers across the region. If you're comparing homes for sale in Chesapeake, note that this zip code puts you in a well-served corridor. Naval Medical Center Portsmouth lies about 13 minutes away, and Norfolk Naval Shipyard is roughly 14 minutes out. Daily life here is easy—grocery stores like ALDI and BJ's Wholesale Club are under a mile away, and casual dining options (Zero's Subs, Panda Express, Taco Bell) cluster nearby. Anyone comparing homes for sale zoned for Western Branch High School and homes for sale zoned for Edwin W. Chittum Elementary School will find both serving this neighborhood.

What's nearby

You're minutes from essential errands and recreation. ALDI and BJ's Wholesale Club sit less than a mile away for groceries and bulk shopping. Dining options—Zero's Subs, Panda Express, and Taco Bell—are all within a mile, so weeknight dinner is quick and close. The Western Branch Softball fields offer outdoor recreation and community gathering space just 0.8 miles from your door. Schools, parks, and retail all sit within easy reach, making daily routines efficient and low-stress.

For different buyers

Base commute and VA loan notes

About 13 minutes to Naval Medical Center Portsmouth and 14 minutes to Norfolk Naval Shipyard puts this address in a convenient commute band for active-duty and civilian personnel. VA loan financing is common in this zip code, and the home's three-bedroom layout works well for move-in readiness. Established neighborhood means no waiting for new construction—you can settle in right away.

Room to grow

Three bedrooms give you a master suite plus two additional rooms for a home office, hobby space, or guest quarters. Three full baths mean morning routines run smoothly. The 2,020-square-foot layout spreads across the home without feeling cramped. A fenced yard and mature trees offer outdoor space for play and relaxation. Storage and flexibility are built into this floor plan.

Schools · VaHome School ScoreAssigned schools

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

HighWestern Branch High School

6.3/10

MiddleJolliff Middle School

7.6/10

ElementaryEdwin W. Chittum Elementary School

7.8/10

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.

How Far Is?

Driving distance by road and typical drive time via Google Maps, to the nearest location of each.

Also nearby

Distances are straight-line (as the crow flies) from this property, not driving miles. Places within ~1 mile, nearest first. Powered by Google Places.

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

Chesapeake$370K – $510K3+ 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

Military Commute

Drive times to nearest bases

NMCP

Navy

20min·8.5mi

NNSY

Navy

17min·8.1mi

USCG Portsmouth

Coast Guard

19min·9.3mi

NSA HR

Navy

35min·21.6mi

USCG Finance Ctr

Coast Guard

22min·18mi

Typical drive times from Google Maps, without live traffic. Rush hour and tunnel backups can add time.

Flood & environmentFlood risk (FEMA)

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’t define a BFE here.

Property elevation

15.5 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’s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service — 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

Evacuation Zone C

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

Explore this neighborhoodDock Landing

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

$568KMedian sale · 12 mo

$221Sold $/sq ft

32dDays on market

1For sale now

$169KHH income

95.3%Owner-occupied

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

Explore Dock Landing →

Neighborhood

Chesapeake houses for sale →

CostPayment calculator

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

$2,740/mo

Down payment20% · $88,000

Interest rate6.75%

Loan term30 years

Principal & interest

$2,283

Property tax

$328

Home insurance

$128

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 & historyComparables

Asking vs. assessment113% of $389,900City assessment record · taxes $3,938/yr

Land share of assessed value42% · $165,000Improvements $224,900 · assessor record ✓

Price context: similar nearby homes$346,400 – $478,000The 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.

4227 Meander WAY · 1.1 mi · 2,034 sqft$370,000 sold 2026-02

4106 Riverside DR · 1.1 mi · 1,960 sqft$362,000 sold 2026-06

4122 Riverside DR · 1.1 mi · 1,916 sqft$365,000 sold 2026-10

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

Sale & Tax History

List Price

$440,000

Price / Sq Ft

$218

Annual Taxes

$3,938

Monthly Tax

$328

HOA

None

Tax Rate (effective)

0.90%

Sale Timeline (this listing)

Event	Date	Price	Detail
Listed	Sep 11, 2026	$440,000	—
Currently listed	—	$440,000	—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

13% above assessment

Total Assessed

$389,900

Land

$165,000

Improvement

$224,900

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.

CompareThis home next to what else is for sale nearby

Home	Price	Beds	Baths	Sqft	$ / sqft
4057 Woodland Drthis home	$440,000	3	3	2,020	$218
Loading nearby homes for sale…

Active comparables from the REIN MLS, the same homes shown under Comparable Properties. Context for judging the asking price, not an appraisal.

Questions buyers ask

Is 4057 Woodland Dr in a good school zone?

The assigned zones on the listing record are Edwin W. Chittum Elementary (VaHome School Score 7.8/10), Jolliff Middle (VaHome School Score 7.6/10), Western Branch (VaHome School Score 6.3/10). School attendance zones can change — always confirm enrollment with the local school division.

Is 4057 Woodland Dr 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 4057 Woodland Dr have an HOA?

No — there are no HOA, condo, or association dues on the listing record for this property.

When was 4057 Woodland Dr built?

It was built in 1952, per the listing record.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data. Never invented.

Tom & Dariya Milan | LPT Realty

See it in person with Tom & Dariya

We're local Hampton Roads Realtors. Pick a day and time; one of us confirms by text and meets you there. Prefer to talk first? Call or text (757) 777-7577.

Name

Phone (optional)

Free, no obligation. One of us confirms by text, usually within the hour during the day. Your inquiry goes to Tom & Dariya, never resold. We use your details to arrange this tour and to follow up with you about it.

4057 Woodland Dr, Chesapeake, Virginia 23321 · MLS #10652901 · 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.

✆

4057 Woodland Dr, Chesapeake, VA 23321

OverviewAbout this home

Facts & features

Our read on this home

Why this home stands out

DOCK LANDING and the Chesapeake real estate market

What's nearby

For different buyers

Base commute and VA loan notes

Room to grow

More buyer questions

Schools · VaHome School ScoreAssigned schools

How Far Is?

Also nearby

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

Military Commute

Flood & environmentFlood risk (FEMA)

🌊 Flood Risk (FEMA)

Hurricane Evacuation Zone

Explore this neighborhoodDock Landing

CostPayment calculator

Estimate your monthly payment

Value & historyComparables

Sale & Tax History

Sale Timeline (this listing)

Public-Records Assessment

Comparable Properties

CompareThis home next to what else is for sale nearby

Questions buyers ask

See it in person with Tom & Dariya

Flood Risk (FEMA)