Home/Virginia/Chesapeake/HICKORY MANOR/421 Middleton WAY, CHESAPEAKE VA 23322
421 Middleton WAY, CHESAPEAKE VA 23322 - Main photo
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Coming Soon
Active
Under Contract
Sold

90 days on market

$615,000

421 Middleton Way

Chesapeake, Virginia 23322

MLS# 10616469 · HICKORY MANOR · Chesapeake VA

Updated Apr 15, 2026 · Source: REIN MLS

Est. payment

$3,864/mo

Edit below

Price / sq ft

$244

2,518 sq ft

Days on market

90

HOA

None

Year built

2024

2 yrs old

Beds

4

Full Baths

2

Half Baths

1

Sq Ft

2,518

Garage

Yes

ResidentialTraditional2 StoryCondoWaterfront — Not Waterfront

Schools

Info provided by GreatSchools

About this home

Welcome to this exquisitely upgraded Wells floorplan by The Dragas Companies, built in 2024 and located in sought-after Hickory Manor. This 4-bedroom, 2.5-bath home offers over 2,500 sq ft with $29K+ in builder upgrades. The chef's kitchen features Cashew shaker cabinets, a contrasting pewter-green island, Calacatta Idillio quartz countertops, gas range, tile backsplash, large pantry, and new LG stainless refrigerato…

Listed by Joshua Smith · Keller Williams Realty Twn Ctr

VaHome Team property overview

At a glance

Meet 421 Middleton Way — a brand-new 2024 construction in Chesapeake's Hickory Manor community. Four bedrooms, two and a half baths, and 2,518 square feet give you serious room to grow, all in a city that consistently ranks among Virginia's most livable.

Read full property overview ↓

Why this home stands out

Built in 2024, this home skips the renovation math entirely. Every system — roof, HVAC, plumbing, electrical — is factory-fresh, and the builder's structural warranty typically travels with the property. At 2,518 square feet with four bedrooms and a half bath off the main living area, the floor plan is sized for real life: room for a home office, overnight guests, and a household that actually uses its space.

HICKORY MANOR and the Chesapeake real estate market

Hickory Manor sits in the Hickory area of Chesapeake — one of the city's quieter, more residential pockets, far enough from the waterfront bustle to feel genuinely suburban but close enough to major corridors that errands stay quick. The streets here are newer, the lots are well-kept, and the neighbors tend to be long-term — the kind of community where people put down roots. Chesapeake itself is the second-largest city by land area in the continental United States, and that scale translates into variety: you get rural greenways, established retail strips, and tight-knit neighborhoods all within the same city limits. If you've been browsing chesapeake va homes for sale and wondering whether the city lives up to its reputation, Hickory Manor is a strong answer. Chesapeake sits in the heart of Hampton Roads, giving residents easy access to Norfolk, Virginia Beach, and the broader region without sacrificing the lower-density feel that draws so many families here in the first place.

What's nearby

Day-to-day errands are almost embarrassingly convenient from 421 Middleton Way. A Walmart Supercenter is just 0.4 miles out, and a Target Grocery sits another two minutes down the road at 0.6 miles — between the two, a full week's shopping rarely requires a second stop. Quick-service options are clustered nearby as well: Subway, Arby's, and McDonald's are all within half a mile when you need lunch without a detour. Coffee runs are equally painless, with Dunkin' and Panera Bread both at the 0.5-mile mark. On the fitness front, the YMCA at Edinburgh is 0.5 miles away and offers full-facility amenities, while Anytime Fitness at 0.7 miles covers the 24-hour crowd.

For different buyers

For military families relocating

USCG Finance Center Chesapeake is roughly a 15-minute drive from 421 Middleton Way, and Norfolk Naval Shipyard is about 25 minutes out — both well within the range most military households target when using BAH to anchor a housing budget. A VA loan pairs cleanly with new construction like this, and Chesapeake's relatively lower property-tax rate stretches that benefit further.

For families upgrading

Four bedrooms and 2,518 square feet in a 2024-built home means you're not inheriting someone else's deferred maintenance list — you're starting fresh. Hickory Manor's suburban feel, combined with the convenience of Walmart, Target, a YMCA, and multiple dining options all within half a mile, makes the logistics of a busy household significantly easier to manage.

Frequently asked questions

How far is 421 Middleton Way from USCG Finance Center Chesapeake?

The drive is approximately 15 minutes under normal traffic conditions, making it one of the more convenient addresses in the area for Coast Guard personnel assigned to that command.

How far is 421 Middleton Way from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is roughly 25 minutes away, a commute that's very manageable for Shipyard workers living in Chesapeake.

What year was 421 Middleton Way built?

The home was built in 2024, meaning all major systems and structural components are essentially new — a meaningful advantage over older resale inventory in the area.

Is 421 Middleton Way in a flood zone?

Flood zone designation for this address is covered in the FloodRisk tile on this page, which pulls current FEMA map data for the specific parcel.

Does Hickory Manor have an HOA?

Hickory Manor does have a homeowners association; the current governing documents and any community rules can be confirmed during the due-diligence period of a transaction.

Curious whether 421 Middleton Way fits your timeline and goals? Tom and Dariya Milan at LPT Realty know this part of Chesapeake well — reach out and let's talk through the details.

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

Location & Neighborhood

Location & Street View

421 Middleton WAY, Chesapeake

Map and Street View imagery © Google. Imagery may not be current.

Map data ©Google. Click and drag inside the map to explore the surrounding area.

Flood Risk

Looking up FEMA flood zone…

Property Details

Bedrooms

4

Full Baths

2

Half Baths

1

Approx Sq Ft

2,518

Stories

2

Fireplaces

0

Flooring

Carpet, Vinyl

Heating

Nat Gas

Cooling

Central Air

Laundry

Interior Features

Fireplace Gas-natural, Primary Sink-Double, Scuttle Access, Walk-In Closet

Appliances

Dishwasher, Disposal, Dryer, Microwave, Gas Range, Refrigerator, Washer

Sale & Tax History

List Price

$615,000

Price / Sq Ft

$244

Annual Taxes

$5,928

Monthly Tax

$494

HOA

None

Tax Rate (effective)

0.96%

Sale Timeline (this listing)

EventDatePriceDetail
ListedFeb 8, 2026$615,000
Currently listed$615,000

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:

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.

About buying in Chesapeake

Chesapeake is Virginia's second-largest city by area and offers a mix of suburban subdivisions, rural acreage, and waterfront properties along the Intracoastal Waterway. Western Branch, Greenbrier, and Great Bridge are among the most sought-after neighborhoods, with top-rated public schools and easy access to I-64 and the Chesapeake Expressway. The city is known for lower property taxes and larger lot sizes compared to neighboring Virginia Beach and Norfolk, which makes it especially attractive to families looking for more space.

See more Chesapeake homes for sale →

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.

Estimate your monthly payment

$3,864/mo

Principal & interest

$3,191

Property tax

$494

Home insurance

$179

PMI

None

HOA

None

Estimate only. 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.

Listed by Keller Williams Realty Twn Ctr · MLS# 10616469

Data provided by REIN MLS. Information deemed reliable but not guaranteed.

OFF MARKET

$615,000

421 Middleton WAY, CHESAPEAKE VA 23322

Chesapeake, Virginia 23322

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Quick Facts

TypeResidential
Year Built2024
Lot Size
Taxes$5,928/yr
HOANone
HeatingNat Gas
CoolingCentral Air

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