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Portsmouth › MERRIFIELDS › 4029 Wyndybrow Dr✓ Source: REIN MLS #10656373 · record updated Oct 3, 2026 · synced every 2 min · your inquiry is never resold
4029 Wyndybrow DR, PORTSMOUTH VA 23703 - Main photo
4029 Wyndybrow DR, PORTSMOUTH VA 23703 - Photo 2
4029 Wyndybrow DR, PORTSMOUTH VA 23703 - Photo 3
4029 Wyndybrow DR, PORTSMOUTH VA 23703 - Photo 4
4029 Wyndybrow DR, PORTSMOUTH VA 23703 - Photo 5
4beds
3baths
2,704sqft
1days on market

4029 Wyndybrow Dr, Portsmouth, VA 23703

New ListingResidential · built 1965 · MERRIFIELDS

Facts & features

Type

Residential

Year built

1965

Price / sqft

$161

HOA

None

Taxes

$4,250/yr

County

Portsmouth VA

MLS #

10656373

Interior

Bedrooms
4
Full baths
3
Approx. sqft
2,704
Stories
2
Flooring
Carpet, Laminate/LVP
First-floor bed & full bath
Yes
Total rooms
11
Other rooms
1st Floor BR, Attic, PBR with Bath, Office/Study, Pantry
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Equipment
Ceiling Fan

Construction & exterior

Style
Split-Level
Subtype
Detached
Foundation
Crawl, Slab
Roof
Asphalt Shingle
Exterior
Brick,Vinyl
Pool
No Pool
Fencing
Back Fenced,Chain Link

Utilities & systems

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

Lot, parking & ownership

Lot size
0.3300
Subdivision
MERRIFIELDS
Zoning
GR
Ownership
Fee Simple
Garage
No
Parking
Driveway Spc
Possession
SETTLEMENT
Disclosures
Disclosure Statement, Owner Agent

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

About this home

This 4 bed, 3 bath home has been fully renovated and is move in ready! Enter into your new home where the living room flows seamlessly into the kitchen and dining area. The kitchen features brand new cabinetry, granite counter tops, stainless steel appliances, a beautiful farmhouse sink and a large pantry with plenty of storage. Downstairs you will also find brand new LVP flooring throughout, a den with built in shelving, a bedroom with a walk-in closet, a full bathroom and an extra space that could be an office, playroom or easily turned into a 5th bedroom. Upstairs features brand new carpet, a master bedroom with a tiled shower, and a massive walk-in closet, as well as two additional bedrooms. Fresh paint and new fixtures throughout. Brand new HVAC. This home checks all the boxes and is ready for you to call it yours today!

Listing courtesy of Elisa Benjamin · Keller Williams Realty Twn Ctr · REIN MLS #10656373

Tom & Dariya's overview

Our read on this home

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

At a glance

4029 Wyndybrow Drive is a four-bedroom, three-bath home in Portsmouth, Virginia, built in 1965 with 2,704 square feet of living space. The location puts Naval Medical Center Portsmouth about ten minutes away. Churchland Park is just down the street, and everyday errands are close at hand.

Keep searching in Portsmouth

See all Portsmouth homes for sale, including homes for sale in 23703, homes for sale zoned for Churchland High School, and homes for sale zoned for Churchland Elementary School. Browse every listing among homes for sale in Portsmouth — updated from the REIN MLS every few minutes. Nearby, look at Churchland homes for sale, Portsmouth waterfront homes for sale, Portsmouth condos and townhomes for sale, and new construction homes in Portsmouth.

Read the full overview ↓

Why this home stands out

At 2,704 square feet, this home gives you real room to spread out. Four bedrooms and three full baths mean no one is sharing a sink in the morning rush. The 1965 build era means solid construction with proportions you rarely find in newer homes — wider hallways, generous room sizes, and a layout that actually breathes. Wyndybrow Drive sits in a quiet residential pocket of Portsmouth where the streets are lined with mature trees and neighbors tend to stay put.

MERRIFIELDS and the Portsmouth real estate market

Wyndybrow Drive sits in the Churchland area of Portsmouth, one of the city's most established residential corridors. The streets here are wide and tree-lined, and the housing stock runs toward mid-century single-family homes on generous lots. It has the feel of a neighborhood that was built to last. Churchland carries a strong sense of place — longtime residents, well-kept yards, and a pace that feels genuinely unhurried. Portsmouth itself is a city with real character. It borders Norfolk across the Elizabeth River and connects to the broader Hampton Roads region by bridge-tunnel and interstate. Getting around is straightforward: Interstate 664 is nearby, and the rest of the metro opens up quickly. Downtown Portsmouth has a walkable waterfront, independent restaurants, and a growing arts scene. Anyone browsing homes for sale in Portsmouth will notice that Churchland offers some of the best lot sizes and square footage per block in the city. The 23703 zip code covers this part of Portsmouth and includes a mix of established neighborhoods that have held their appeal for decades.

What's nearby

Churchland Park is 0.2 miles away — a quick walk for an afternoon outside. Ebony Heights Park is about a mile out and adds another green space option. Game Face restaurant and China Li Chinese Cuisine are both within 0.2 miles, so dinner is never far. A 7-Eleven sits 0.3 miles away for coffee, snacks, or a last-minute errand stop. The concentration of everyday options this close to a quiet residential street is one of the practical advantages of this location.

For different buyers

Base commute and VA loan notes

Naval Medical Center Portsmouth is about ten minutes by car — one of the shortest base commutes in the city. NSA Hampton Roads is roughly eleven minutes in the other direction. VA loan financing is widely used in this zip code, and the home's size and layout mean you are not compromising on space to stay close to the installation. Four bedrooms and three baths hold up well through multiple duty cycles.

For buyers drawn to character

A 1965 build in this condition and at this size is not easy to find. The floor plan has the proportions that define mid-century residential construction — rooms with actual square footage, not the chopped-up layouts common in newer builds. Mature landscaping, a settled street, and neighbors who have been here for years add up to a home with genuine roots. Anyone comparing homes for sale in 23703 will notice that this address stands apart on square footage and lot character.

More buyer questions

How far is 4029 Wyndybrow Drive from Naval Medical Center Portsmouth?

The drive is about ten minutes under normal traffic conditions. That puts it among the closer residential options to the installation in Portsmouth.

What school zone does 4029 Wyndybrow Drive fall in?

This address is in the Portsmouth Public Schools district. Buyers comparing homes for sale zoned for Churchland High School and homes for sale zoned for Churchland Elementary School will want to confirm current zoning directly with Portsmouth Public Schools, as boundaries can change.

Is 4029 Wyndybrow Drive in a flood zone?

Flood zone status for this address is shown in the FloodRisk tile on this page. You can also verify the current designation through FEMA's flood map service.

What parks are near 4029 Wyndybrow Drive?

Churchland Park is 0.2 miles away, making it an easy walk. Ebony Heights Park is about a mile out for additional green space.

Does the Churchland area of Portsmouth have an HOA?

4029 Wyndybrow Drive does not carry an HOA, so there are no association dues or governing restrictions tied to the property.

Tom and Dariya Milan with LPT Realty know Portsmouth well. Reach out to schedule a walkthrough or to get your questions answered about this address.

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

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

Portsmouth$365K – $505K4+ 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 515529

Flood Risk

Looking up FEMA flood zone…

Explore this neighborhood

Churchland

Churchland is a settled home neighborhood in Portsmouth, Virginia. It is known for tree-lined streets and well-kept homes built across many decades.

$324K

Median sale · 12 mo

$207

Sold $/sq ft

16d

Days on market

3

For sale now

$66K

HH income

46%

Owner-occupied

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

Explore Churchland →
Map of Churchland with neighborhood boundaryNeighborhood

Portsmouth 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

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

$2,738/mo

Principal & interest

$2,257

Property tax

$354

Home insurance

$127

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

$399,000 – $513,000

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.

3812 Pine RD · 0.8 mi · 2,237 sqft$455,000 sold 2026-06
4256 Sedgewyck CIR · 0.9 mi · 2,272 sqft$416,000 sold 2026-09
6002 CAMPBELL ST · 1.2 mi · 2,430 sqft$450,000 sold 2026-02

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

Sale & Tax History

List Price

$435,000

Price / Sq Ft

$161

Annual Taxes

$4,250

Monthly Tax

$354

HOA

None

Tax Rate (effective)

0.98%

Sale Timeline (this listing)

EventDatePriceDetail
ListedOct 2, 2026$435,000—
Currently listed—$435,000—

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:

Portsmouth 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

1 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Is 4029 Wyndybrow Dr in a good school zone?+
The assigned zones on the listing record are Churchland Elementary (VaHome School Score 5/10), Churchland Middle (VaHome School Score 2.7/10), Churchland (VaHome School Score 5.9/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 4029 Wyndybrow 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 4029 Wyndybrow Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 4029 Wyndybrow Dr built?+
It was built in 1965, 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 Elisa Benjamin · Keller Williams Realty Twn Ctr · REIN MLS #10656373

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.

4029 Wyndybrow Dr, Portsmouth — photo

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

Call or text (757) 777-7577

4029 Wyndybrow Dr, Portsmouth, Virginia 23703 · MLS #10656373 · 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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