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ChesapeakeHICKORY MANOR355 Middleton Way✓ Source: REIN MLS #10635073 · record updated Sep 18, 2026 · synced every 2 min · your inquiry is never resold
355 Middleton WAY, CHESAPEAKE VA 23322 - Main photo
355 Middleton WAY, CHESAPEAKE VA 23322 - Photo 2
355 Middleton WAY, CHESAPEAKE VA 23322 - Photo 3
355 Middleton WAY, CHESAPEAKE VA 23322 - Photo 4
355 Middleton WAY, CHESAPEAKE VA 23322 - Photo 5
4beds
2.1baths
2,500sqft
126days on market

355 Middleton Way, Chesapeake, VA 23322

Under ContractResidential · built 2021 · HICKORY MANOR

Facts & features

Type

Residential

Year built

2021

Price / sqft

$240

Condo fee

$69/mo

HOA fee

$145/mo

Taxes

$6,082/yr

County

Chesapeake VA

MLS #

10635073

Association amenities

ClubhouseExercise RmGround MaintPlaygroundsPoolTrash Pickup

$69/mo condo fee + $145/mo HOA fee · Westfield at Hickory Manor Condo Association · per the REIN MLS listing record — confirm inclusions with the association.

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
2,500
Stories
2
Flooring
Carpet, Vinyl
Ensuite bedrooms
1
Total rooms
7
Other rooms
Foyer, PBR with Bath, Pantry, Porch
Appliances
Dishwasher, Disposal, Dryer Hookup, Energy Star Appliance(s), Microwave, Range, Refrigerator, Washer Hookup
Equipment
Cable Hookup

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Fencing
Back Fenced,Privacy

Utilities & systems

Heating
Nat Gas
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
HICKORY MANOR
Zoning
PUD
Ownership
Condo
Garage
Yes
Parking
Garage Att 1 Car, Driveway Spc
Possession
SETTLEMENT
Disclosures
Common Interest Community, Disclosure Statement, Resale Certif Req

See more Chesapeake condos & townhomes.

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

About this home

Welcome to resort-style living in highly sought-after Hickory Manor! Beautifully maintained and showing like brand new, this stunning home offers the perfect blend of modern comfort and style. The bright, open-concept living spaces are highlighted by a showstopping kitchen featuring upgraded cabinets, premium countertops, and a custom backsplash added after the original build. Beyond the pristine, move-in-ready interior, you will enjoy a low-maintenance lifestyle with unparalleled HOA amenities that are truly one-of-a-kind in Hickory. Enjoy worry-free living with grounds maintenance and trash pickup included. Spend weekends at the resort-style pool with its outdoor kitchen and cabana, hit the 24/7 fitness center, or host parties in the expansive clubhouse great room. The neighborhood boasts scenic trails, 5 community lakes, a playground, and vibrant monthly community events. Schedule your tour today!

Listing courtesy of E Ashley McDougal · RE/MAX Alliance · REIN MLS #10635073

Tom & Dariya's overview

Our read on this home

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

At a glance

355 Middleton Way is a 2021-built, four-bedroom, two-and-a-half-bath single-family home in Chesapeake, Virginia, offering 2,500 square feet of modern construction in the 23322 zip code — close to daily errands, fitness, and two military installations.

Read the full overview ↓

Why this home stands out

Built in 2021, this home skips the guesswork that comes with older construction — systems, finishes, and structural components are all recent vintage. At 2,500 square feet across four bedrooms, there's genuine room to spread out without the sprawl of a much larger footprint. The half-bath on the main level is a small detail that makes a real difference in daily life, and the Chesapeake location puts two significant bases within a reasonable commute.

HICKORY MANOR and the Chesapeake real estate market

Chesapeake is one of the largest cities by land area in the entire country, and the 23322 corridor captures some of its most livable character — suburban in feel, practical in layout, and genuinely easy to get around. The Hickory area of south Chesapeake draws families who want newer development without sacrificing access to the broader Hampton Roads metro. Streets here tend to be quiet, lots are generous by regional standards, and the overall pace feels intentional rather than rushed. Chesapeake homes for sale in this zip code consistently attract buyers who want proximity to Norfolk and Virginia Beach without paying for a coastal address. The city itself invests heavily in parks, trails, and public infrastructure, and that shows in neighborhoods like this one — well-maintained, owner-occupied, and community-minded. If you're weighing homes for sale in Chesapeake, this part of the city offers a strong combination of modern inventory and everyday convenience.

What's nearby

Daily errands are almost effortless from Middleton Way. A Walmart Supercenter sits just 0.4 miles out, and a Target Grocery is another two minutes down the road at 0.6 miles — between the two, a full weekly shop rarely requires a long drive. Quick-service options are equally close: Subway at 0.4 miles, and Arby's, McDonald's, and Panera Bread all within 0.6 miles for those mornings when Dunkin' is already on the route. Fitness is just as accessible — the YMCA at Edinburgh is 0.6 miles away, and Anytime Fitness adds a 24-hour option at 0.7 miles. The overall walkability score for this block is genuinely high for a Chesapeake address.

For different buyers

For military families relocating

The USCG Finance Center Chesapeake is roughly 15 minutes from Middleton Way, and Norfolk Naval Shipyard adds a second option about 25 minutes out — making this address workable for dual-military households or those weighing a VA loan purchase with commute time in mind. A 2021 build also means fewer surprise maintenance costs in those first years of ownership, which matters when PCS timelines are tight.

For families upgrading

Four bedrooms and 2,500 square feet give a growing family genuine flexibility — a dedicated home office, a guest room, or a playroom are all on the table without anyone feeling crowded. Families comparing homes for sale zoned for Hickory High School and homes for sale zoned for Hickory Elementary School will find that this address puts both within the same district, simplifying school-year logistics considerably.

More buyer questions

How far is 355 Middleton Way from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is approximately 25 minutes from 355 Middleton Way under typical traffic conditions. The route via I-664 or local arterials gives commuters a few options depending on the time of day.

How far is 355 Middleton Way from the USCG Finance Center Chesapeake?

The USCG Finance Center Chesapeake is about 15 minutes away, making it one of the closer base-adjacent addresses available among homes for sale in 23322.

What year was 355 Middleton Way built?

The home was built in 2021, placing it among the newer single-family construction in this part of Chesapeake. That means current building codes, modern mechanical systems, and no deferred maintenance from decades of prior ownership.

Is there a HOA at 355 Middleton Way?

The property is part of a planned community typical of 2021-era Chesapeake development — HOA status should be confirmed through current disclosure documents, but newer subdivisions in this corridor commonly carry an association.

What is the flood zone status for 355 Middleton Way?

Flood zone designation for this address is detailed in the FloodRisk tile on this page. Chesapeake does include flood-prone areas, so reviewing that information alongside any lender requirements is a smart early step.

Tom and Dariya Milan at LPT Realty know this corner of Chesapeake well — reach out to talk through the neighborhood, the commute math, or what a VA loan could look like for this address.

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

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

Chesapeake$505K – $690K4+ 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

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

40

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

houses 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

$3,795/mo

Principal & interest

$3,113

Property tax

$507

Home insurance

$175

PMI

None

HOA/Condo (paid separately)

$214

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

100% of $602,200

City assessment record · taxes $6,082/yr

Land share of assessed value

36% — $215,300

Improvements $386,900 · assessor record ✓

Price context — similar nearby homes

$540,000$695,000

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.

314 Middleton WAY · 0.1 mi · 2,502 sqft$569,900 sold 2026-06
320 Middleton WAY · 0.1 mi · 2,431 sqft$555,000 sold 2026-07
508 Esterview LN · 0.2 mi · 2,431 sqft$540,000 sold 2026-08

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

Sale & Tax History

List Price

$599,900

Price / Sq Ft

$240

Annual Taxes

$6,082

Monthly Tax

$507

HOA + condo fees

$214 / mo

Tax Rate (effective)

1.01%

Sale Timeline (this listing)

EventDatePriceDetail
ListedMay 15, 2026$599,900
Price reducedJul 10, 2026$599,900−$19,100
Currently listed$599,900

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

Asking near assessment

Total Assessed

$602,200

Land

$215,300

Improvement

$386,900

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 355 Middleton Way 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), Hickory (VaHome School Score 8.8/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 355 Middleton Way 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.
Is there a gym near 355 Middleton Way?+
Yes — YMCA at Edinburgh is about 0.4 miles away, per the cached nearby-places record for this address.
Where is the nearest grocery store to 355 Middleton Way?+
Walmart Supercenter is about 0.2 miles away. The closest dining on record is Subway (0.2 mi).
Does 355 Middleton Way have an HOA or condo association?+
Both — this unit carries a condo association fee and a separate HOA (property owners association) fee. Current amounts for each are shown in the facts section on this page. The association of record is Westfield at Hickory Manor Condo Association. Association amenities on record include: Clubhouse, Exercise Rm, Ground Maint, Playgrounds, Pool, Trash Pickup.
When was 355 Middleton Way built?+
It was built in 2021, 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 E Ashley McDougal · RE/MAX Alliance · REIN MLS #10635073

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.

355 Middleton Way, Chesapeake — photo

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

Call or text (757) 777-7577

355 Middleton Way, Chesapeake, Virginia 23322 · MLS #10635073 · 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.