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ChesapeakeHOMESTEAD ACRES2744 Horseshoe Dr✓ Source: REIN MLS #10636036 · record updated Aug 29, 2026 · synced every 2 min · your inquiry is never resold
2744 Horseshoe DR, CHESAPEAKE VA 23322 - Main photo
2744 Horseshoe DR, CHESAPEAKE VA 23322 - Photo 2
2744 Horseshoe DR, CHESAPEAKE VA 23322 - Photo 3
2744 Horseshoe DR, CHESAPEAKE VA 23322 - Photo 4
2744 Horseshoe DR, CHESAPEAKE VA 23322 - Photo 5
$465,000
$235 / sqft · est. $2,913/mo →
4beds
2baths
1,975sqft
95days on market

2744 Horseshoe Dr, Chesapeake, VA 23322

Under ContractResidential · built 1978 · HOMESTEAD ACRES

Facts & features

Type

Residential

Year built

1978

Price / sqft

$235

HOA

None

Taxes

$4,378/yr

County

Chesapeake VA

MLS #

10636036

Interior

Bedrooms
4
Full baths
2
Approx. sqft
1,975
Stories
1
Flooring
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
6
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, Fin. Rm Over Gar, PBR with Bath, Office/Study, Pantry, Porch, Screened Porch, Sun Room
Appliances
Dishwasher, Dryer, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer, Washer Hookup
Equipment
Ceiling Fan, Gar Door Opener
Accessibility
Main Floor Laundry

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick,Wood
Pool
No Pool
Fencing
Back Fenced,Wood Fence

Utilities & systems

Heating
Electric, Heat Pump
Cooling
Central Air, Heat Pump
Water heater
Electric
Water
Well
Sewer
Septic

Lot, parking & ownership

Subdivision
HOMESTEAD ACRES
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 1 Car, Garage Det 2 Car, Multi Car, Driveway Spc
Possession
SETTLEMENT
Disclosures
Disclosure Statement

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

About this home

Nestled in the sought-after Homestead Acres community of Chesapeake, this beautifully maintained brick ranch offers the perfect blend of comfort, charm, and functionality. Enjoy an inviting open floor plan with spacious living areas, an updated kitchen, bright sunroom, and screened-in porch to enjoy year-round. Step outside to a large backyard retreat complete with a built-in firepit, great for relaxing evenings under the stars. Additional features include reverse osmosis system, water softener maintained by Moody's, and HVAC less than 3 years old with smart system technology. Conveniently located near top-rated schools, shopping, dining, and more. Please ask details from agent on short sale details.

Listing courtesy of Jessica Haynes · Keller Williams Capital Props. · REIN MLS #10636036

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

2744 Horseshoe Drive is a four-bedroom, two-bath single-family home in Chesapeake, Virginia, offering 1,975 square feet of living space on a property built in 1978. It sits in one of Hampton Roads' most consistently sought-after cities for space, value, and quality of life.

Read the full overview ↓

Why this home stands out

What sets 2744 Horseshoe Drive apart is the combination of genuine square footage — nearly 2,000 feet across four bedrooms — and the breathing room that Chesapeake's lower-density neighborhoods tend to deliver. Homes from this era were built with functional floor plans and solid bones, and this one carries that tradition. You get real living space without the cramped feel that newer, smaller builds sometimes bring.

HOMESTEAD ACRES and the Chesapeake real estate market

Chesapeake is one of the largest cities by land area on the entire East Coast, and that scale translates directly into the lifestyle here. Streets are wider, lots are deeper, and the pace feels noticeably calmer than the denser urban cores nearby. The area around Horseshoe Drive sits in the 23322 zip code — one of the more established pockets of Chesapeake — where mature trees line residential streets and neighbors tend to stay put for years. If you've been browsing houses in chesapeake va for sale and wondering which zip code actually delivers on the promise of suburban comfort, 23322 is a strong answer. Chesapeake sits in its own independent city jurisdiction, meaning city services without the congestion of a traditional downtown grid. You're close enough to Virginia Beach, Norfolk, and the broader Hampton Roads metro to access everything the region offers, while still coming home to a quieter, more spacious corner of it.

What's nearby

Daily life is genuinely convenient from Horseshoe Drive. Grocery options, pharmacies, and everyday retail along Battlefield Boulevard are within a short drive, making routine errands quick and painless. Greenbrier Mall and the broader Greenbrier corridor — one of Hampton Roads' busiest commercial zones — is accessible without a long haul. For outdoor time, Northwest River Park offers trails, camping, and open water not far south. The Western Branch and Great Bridge areas are both nearby, giving you access to local dining, coffee shops, and community staples. Interstate 64 and the Virginia Beach Expressway are both reachable, connecting you to the wider metro with ease.

For different buyers

For military families relocating

Chesapeake sits at a practical crossroads for Hampton Roads military families. Naval Station Norfolk, Naval Air Station Oceana, and Joint Expeditionary Base Little Creek are all reachable within a reasonable commute window. Four bedrooms gives a growing family real room to spread out, and Chesapeake's stable neighborhoods tend to hold their value well across PCS cycles — something worth weighing when you're planting roots for two or three years at a time.

For families upgrading

If your current home is starting to feel tight, 1,975 square feet across four bedrooms is a meaningful step up. There's room for a dedicated home office, a guest room that actually functions as one, and common spaces that don't double as everything else. Chesapeake's 23322 zip code has long attracted families making exactly this move — trading up for space and stability in a city that consistently delivers both.

More buyer questions

How far is 2744 Horseshoe Drive from Naval Station Norfolk?

Naval Station Norfolk is roughly 20 to 30 minutes from Horseshoe Drive depending on traffic and the route taken. The drive typically runs north via Interstate 64 or surface roads through the Western Branch corridor.

What is the lot and neighborhood feel like around Horseshoe Drive in Chesapeake?

The 23322 zip code is characterized by established residential streets with mature landscaping, moderate lot sizes, and a lower-density feel compared to more urban parts of Hampton Roads. It's a settled, quiet area that has attracted long-term homeowners for decades.

Is 2744 Horseshoe Drive in a flood zone?

Flood zone status for this address is detailed in the FloodRisk tile on this page, which pulls current FEMA map data. It's worth reviewing before making any decisions, as flood zone designations can affect insurance requirements.

How old is the home at 2744 Horseshoe Drive and what does that mean for buyers?

The home was built in 1978, placing it in a generation of construction known for solid framing, functional layouts, and larger room proportions than many newer builds. Buyers should plan for standard due-diligence checks on systems like HVAC, roofing, and electrical, as is typical for homes of this era.

Does the Chesapeake area around this address have an HOA?

HOA status for 2744 Horseshoe Drive is noted in the listing details on this page. Chesapeake neighborhoods from the late 1970s vary — some have voluntary civic leagues, others have no formal HOA structure at all.

Ready to get a closer look at 2744 Horseshoe Drive? Tom and Dariya Milan know Chesapeake well — reach out and they'll walk you through everything you need to know.

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

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

Chesapeake$395K – $535K4+ 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 510034

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Evacuation Zone D

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

Explore this neighborhood

Hickory

Hickory is a rural-meets-suburban community in the southern reaches of Chesapeake, Virginia, set along the Battlefield Boulevard South corridor as it runs toward the North Carolina line.

$625K

Median sale · 12 mo

$245

Sold $/sq ft

18d

Days on market

43

For sale now

$132K

HH income

82.9%

Owner-occupied

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

Explore Hickory
Map of Hickory with neighborhood boundaryNeighborhood

homes for sale in Chesapeake

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

$2,913/mo

Principal & interest

$2,413

Property tax

$365

Home insurance

$136

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

107% of $433,500

City assessment record · taxes $4,378/yr

Land share of assessed value

38% — $165,000

Improvements $268,500 · assessor record ✓

Price context — similar nearby homes

$450,000$675,000

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.

2736 Horseshoe DR · 0 mi · 1,900 sqft$450,000 sold 2026-04
2805 Bunch Walnuts RD · 0.2 mi · 1,940 sqft$625,000 sold 2026-05
2841 Bunch Walnuts RD · 0.3 mi · 2,016 sqft$585,000 sold 2026-03

Sale & Tax History

List Price

$465,000

Price / Sq Ft

$235

Annual Taxes

$4,378

Monthly Tax

$365

HOA

None

Tax Rate (effective)

0.94%

Sale Timeline (this listing)

EventDatePriceDetail
ListedMay 26, 2026$465,000
Price increasedAug 3, 2026$465,000+$25,000
Currently listed$465,000

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

7% above assessment

Total Assessed

$433,500

Land

$165,000

Improvement

$268,500

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 2744 Horseshoe Dr in a good school zone?+
The assigned zones on the listing record are Hickory Elementary (VaHome School Score 8.2/10), Hickory Middle (VaHome School Score 9.2/10), Grassfield (VaHome School Score 8.8/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 2744 Horseshoe 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 2744 Horseshoe Dr have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 2744 Horseshoe Dr built?+
It was built in 1978, 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 Jessica Haynes · Keller Williams Capital Props. · REIN MLS #10636036

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

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2744 Horseshoe Dr, Chesapeake — photo

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

Call or text (757) 777-7577

2744 Horseshoe Dr, Chesapeake, Virginia 23322 · MLS #10636036 · 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.