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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
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

Tom & Dariya's overview

Our read on this home

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

At a glance

A four-bedroom, two-bath home built in 1978 on Horseshoe Drive in Chesapeake's 23322 zip code — solid square footage, a well-established street, and easy reach of two military installations make this one of the more practical addresses in the area.

Read the full overview ↓

Why this home stands out

At 1,975 square feet, 2744 Horseshoe Drive gives four-bedroom households genuine breathing room without the overhead of a newer, larger build. The 1978 construction era typically means wider lots, more mature tree cover, and a neighborhood rhythm that newer subdivisions are still working to develop. Add a sub-20-minute commute to USCG Finance Center Chesapeake and you have a property that quietly checks a lot of boxes.

HOMESTEAD ACRES and the Chesapeake real estate market

Horseshoe Drive sits in Chesapeake's southwestern corridor — a part of the city where the pace slows down without sacrificing convenience. The 23322 zip code is one of the most sought-after in the region, anchored by established residential streets, generous lot sizes, and a strong sense of community that's built up over decades. Chesapeake itself is Virginia's second-largest city by land area, which means you get suburban breathing room alongside real infrastructure: well-maintained roads, a robust parks system, and city services that punch above their weight. Families comparing homes for sale in 23322 often note how the area balances quiet neighborhoods with quick access to shopping corridors and major commuter routes. If you're weighing Chesapeake homes for sale across different parts of the city, this southwestern pocket consistently earns high marks for livability and long-term stability.

What's nearby

Daily life runs smoothly from this address. Grocery options — including Harris Teeter and Food Lion locations — are within a short drive along the Battlefield Boulevard corridor. Pharmacy, urgent care, and routine retail are all close at hand. Greenbrier Mall and its surrounding shopping district sit roughly 15 minutes north for bigger-ticket errands. Green space is accessible too: Northwest River Park and Chesapeake City Park both offer trails, water access, and open fields within a reasonable drive. Dining along Battlefield Boulevard covers everything from casual weeknight spots to sit-down family meals.

For different buyers

For military families relocating

USCG Finance Center Chesapeake is about 19 minutes away, and Norfolk Naval Shipyard clocks in at roughly 28 — both well within a comfortable daily commute. A VA loan can make the financing side of this purchase straightforward, and the four-bedroom layout handles PCS moves and growing households with ease. Chesapeake's 23322 zip code is a proven landing spot for military families who want stability between assignments.

For families upgrading

Four bedrooms and nearly 2,000 square feet give a growing family real options — dedicated space for a home office, a guest room, or a playroom without anyone feeling crowded. The 1978 build era means a larger lot footprint than most newer construction, and the established neighborhood provides the kind of settled, long-term neighbors that make a street feel like a community. Families comparing homes for sale zoned for Grassfield High School and homes for sale zoned for Hickory Elementary School will find this address worth a close look.

More buyer questions

How far is 2744 Horseshoe Drive from USCG Finance Center Chesapeake?

The drive is approximately 19 minutes under normal traffic conditions, making it one of the closer residential options to that installation in the area.

How far is 2744 Horseshoe Drive from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about 28 minutes away, a manageable commute that keeps this address in range for shipyard personnel living on the Chesapeake side of the water.

Is 2744 Horseshoe Drive in a flood zone?

Flood zone status for this address is detailed in the FloodRisk tile on this page — check there for the most current FEMA designation and what it means for insurance requirements.

What is the square footage and layout of 2744 Horseshoe Drive?

The home offers 1,975 square feet of living space across four bedrooms and two full baths, a layout that works well for families, remote workers needing a dedicated office, or anyone who simply wants room to spread out.

Are there homes for sale in Chesapeake with similar specs in this zip code?

The 23322 corridor does have comparable properties from time to time, but four-bedroom homes on established streets with this square footage tend to move — browsing homes for sale in Chesapeake filtered by zip code is the fastest way to see what's currently available alongside this address.

Tom and Dariya Milan at LPT Realty know this corner of Chesapeake well. Reach out to get honest answers about the neighborhood, the commute, and whether this address fits your plans.

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

Pleasant Grove

Pleasant Grove is one of southeastern Chesapeake's fastest-growing areas, set along the Mount Pleasant Road and Battlefield Boulevard corridor south of the Great Bridge area.

$548K

Median sale · 12 mo

$250

Sold $/sq ft

30d

Days on market

19

For sale now

$138K

HH income

84.7%

Owner-occupied

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

Explore Pleasant Grove
Map of Pleasant Grove 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

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

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

Brokered by 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.