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Chesapeake › HOMESTEAD ACRES › 2744 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

This four-bedroom, two-bath home sits on a quiet street in Chesapeake, about eight minutes from NSA Northwest Annex. Built in 1978 with nearly 2,000 square feet, it offers solid bones and room to settle in. The location puts you close to base commutes while keeping daily life centered in a residential neighborhood.

Read the full overview ↓

Why this home stands out

You'll find 1,975 square feet across four bedrooms and two full baths—genuine space for a household that needs it. The single-story layout makes daily flow straightforward, and the lot gives you room to breathe. If you're comparing homes for sale in 23322, this address delivers practical floor plan and a settled residential feel without the premium price tag of newer construction.

HOMESTEAD ACRES and the Chesapeake real estate market

This corner of Chesapeake has the quiet, tree-lined character of an established residential area. Streets here are lined with single-family homes set back from the road, and neighbors tend to stay put. The neighborhood sits inland from the water, centered on everyday convenience rather than waterfront drama. Chesapeake itself is Virginia's largest city by land area, sprawling across farmland, neighborhoods, and commercial corridors. Getting around means a car—there's no walkable downtown core—but that trade-off buys you space and lower density. The city balances suburban calm with access to Hampton Roads employment centers. Anyone comparing Chesapeake homes for sale will notice the range: waterfront estates, suburban neighborhoods, and rural acreage all coexist here. Daily errands pull you toward the commercial strips that anchor each district, but the residential blocks stay peaceful.

What's nearby

Grocery and pharmacy stops are a short drive away on the main commercial corridors that ring this neighborhood. A few casual dining spots and a coffee shop sit within five minutes by car. The area isn't known for walkable entertainment, but that's part of the trade: quieter streets, less through-traffic, more breathing room. Parks and recreation facilities are scattered throughout Chesapeake; you'll find playgrounds and open space without a long search. The neighborhood itself is residential and settled, so most social life happens at home or in the wider city.

For different buyers

Base commute and VA loan notes

About eight minutes to NSA Northwest Annex and roughly 19 minutes to USCG Finance Center Chesapeake. This address works well for base commuters seeking a straightforward drive and a home ready to occupy. VA loan financing is common in this zip code, and the four-bedroom layout gives you room without requiring years of renovation.

Room to grow

Four bedrooms and two baths give you genuine space to spread out. The single-story floor plan is easy to navigate, and the lot size lets you add a garden, play area, or storage shed without cramping. Anyone comparing homes for sale zoned for Grassfield High School or homes for sale zoned for Hickory Elementary School will find this address offers the room-to-grow layout that makes long-term living comfortable.

More buyer questions

How far is 2744 Horseshoe Drive from NSA Northwest Annex?

About eight minutes by car. The commute is straightforward and doesn't require crossing major traffic corridors.

What is the square footage and bedroom count?

The home is 1,975 square feet with four bedrooms and two full baths. That's solid space for a household that needs room to live.

Is this home in a flood zone?

Check the FloodRisk tile on this listing page for detailed flood zone and flood insurance information specific to this address.

When was this house built?

1978. The home has been standing for over 45 years and reflects the solid construction standards of that era.

What zones apply to this address?

This address falls within the zones for homes for sale zoned for Hickory Elementary School and homes for sale zoned for Grassfield High School. Visit the Schools tile for ratings and details.

Ready to explore 2744 Horseshoe Drive? Reach out to Tom & Dariya Milan to schedule a tour and ask any questions about the home or neighborhood.

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

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

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 (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\u2019t define a BFE here.

Property elevation

17.9 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\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 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 D

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

Explore this neighborhood

Pleasant Grove

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

$550K

Median sale · 12 mo

$253

Sold $/sq ft

28d

Days on market

15

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

$410,000 – $670,000

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

Free, no obligation — your inquiry goes to Tom & Dariya, never resold.

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.

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