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Chesapeake › BAYBERRY PLACE › 1416 Woodside Ct✓ Source: REIN MLS #10655585 · record updated Oct 5, 2026 · synced every 2 min · your inquiry is never resold
1416 Woodside CT, CHESAPEAKE VA 23320 - Main photo
1416 Woodside CT, CHESAPEAKE VA 23320 - Photo 2
3beds
2baths
1,718sqft
0days on market

1416 Woodside Ct, Chesapeake, VA 23320

Coming SoonResidential · built 1979 · BAYBERRY PLACE

Facts & features

Type

Residential

Year built

1979

Price / sqft

$262

HOA fee

$31/mo

Taxes

$3,968/yr

County

Chesapeake VA

MLS #

10655585

Interior

Bedrooms
3
Full baths
2
Approx. sqft
1,718
Stories
1
Flooring
Ceramic, Laminate/LVP
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
7
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, Foyer, PBR with Bath
Appliances
Dishwasher, Disposal, Dryer, Microwave, Elec Range, Refrigerator, Washer
Equipment
Cable Hookup, Ceiling Fan, Jetted Tub
Accessibility
Main Floor Laundry

Construction & exterior

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

Utilities & systems

Heating
Heat Pump, Programmable Thermostat
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
BAYBERRY PLACE
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Driveway Spc
Possession
CLOSING
Disclosures
Common Interest Community, Disclosure Statement

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

About this home

Welcome to 1416 Woodside Court, a charming Chesapeake ranch offering comfortable one-level living and a floor plan designed for everyday life and entertaining. The spacious eat-in kitchen features granite countertops and a large center island, while the inviting living area is anchored by a wood-burning fireplace. Three bedrooms, two full baths, and a two-car garage provide plenty of flexibility. Major updates include a new 30-year architectural roof and water heater, both replaced in 2025 as well as new flooring in the bedrooms. Outside, enjoy a large backyard with room to relax, play, garden, or entertain. Tucked away on a court yet conveniently located near interstate access, shopping, dining, and everyday amenities, this move-in-ready home combines thoughtful updates and welcoming spaces.

Listing courtesy of Katrina Cantrell · BHHS RW Towne Realty · REIN MLS #10655585

Tom & Dariya's overview

Our read on this home

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

At a glance

1416 Woodside Court is a three-bedroom, two-bath home in Chesapeake, Virginia. Built in 1979, it offers 1,718 square feet on a quiet cul-de-sac street. The USCG Finance Center is about three minutes away. Browsing Chesapeake homes for sale? This address puts you close to everything in the Greenbrier corridor.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23320, homes for sale zoned for Indian River High School, and homes for sale zoned for Greenbrier Intermediate School. Browse every listing among homes for sale in Chesapeake — updated from the REIN MLS every few minutes. Nearby, look at Bayberry homes for sale, Chesapeake waterfront homes for sale, Chesapeake condos and townhomes for sale, and new construction homes in Chesapeake.

Read the full overview ↓

Why this home stands out

Cul-de-sac living is hard to find at this price point in central Chesapeake. Woodside Court sits tucked off the main grid, so through traffic is essentially zero. The 1979 build means solid construction with room dimensions that feel generous by today's standards. Two full baths, three bedrooms, and 1,718 square feet give you real everyday function. Mill Lake Park and Woodgate Commons are both within half a mile.

BAYBERRY PLACE and the Chesapeake real estate market

Woodside Court sits in the Greenbrier area of Chesapeake — one of the city's most established and convenient corridors. Streets here are lined with mature trees and single-family homes from the late 1970s and early 1980s. The lots are comfortable, the pace is calm, and neighbors tend to stay a long time. Greenbrier is not a single subdivision but a broad zone of interconnected communities anchored by retail, parks, and easy highway access. Anyone comparing homes for sale in 23320 will notice how central this zip code really is. Chesapeake itself is Virginia's second-largest city by land area. It stretches from the North Carolina border up through the Great Dismal Swamp and into the dense suburban core near Interstate 64. The Greenbrier section is where most of that suburban energy concentrates. You're close to Greenbrier Mall, the Chesapeake Expressway, and multiple routes into Norfolk and Virginia Beach. Daily errands, commutes, and weekend plans all come together without much effort from this part of the city.

What's nearby

Groceries are easy here. Harris Teeter and Target Grocery are both about 0.9 miles away, and The Vitamin Shoppe is just 0.6 miles out. Ruby Love's and Krispy Krunchy Chicken are a short drive at 0.3 miles for quick meals. Winston's Cafe and Panera Bread are both 0.7 miles away when you want a proper coffee stop. For fitness, D1 Training East Chesapeake is 0.5 miles out, with HOTWORX Chesapeake and Compound CrossFit each at 0.7 miles. Woodgate Commons and Mill Lake Park are both within half a mile for outdoor time close to home.

For different buyers

Base commute and VA loan notes

The USCG Finance Center Chesapeake is about three minutes from Woodside Court — one of the shortest base commutes you'll find in this zip code. Norfolk Naval Shipyard is roughly 11 minutes away. VA loan financing is widely used in this part of Chesapeake, and the 1979 build date means the home has an established condition history. Three bedrooms and two full baths cover the basics without compromise.

For first-time buyers

Three bedrooms, two full baths, and 1,718 square feet give you a real foothold without overextending. The cul-de-sac location keeps the street quiet and low-traffic. Woodgate Commons and Mill Lake Park are both within half a mile for outdoor space you don't have to maintain. Anyone sorting through homes for sale in Chesapeake will find this address checks a lot of practical boxes at a manageable scale.

More buyer questions

How far is 1416 Woodside Court from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about 11 minutes from Woodside Court by car. The route runs west through Chesapeake into Portsmouth with no major bottlenecks outside of peak hours.

What schools serve 1416 Woodside Court?

This address falls within the Chesapeake City Public Schools zone. Buyers comparing homes for sale zoned for Indian River High School or homes for sale zoned for Greenbrier Intermediate School will want to confirm current zoning directly with Chesapeake City Public Schools.

Is 1416 Woodside Court in a flood zone?

Flood zone status for this address is covered in the FloodRisk tile on this page. Always verify with FEMA's current flood map before closing.

What parks are near 1416 Woodside Court?

Woodgate Commons and Mill Lake Park are both within half a mile of the home. Both offer accessible outdoor space without a long drive.

Does the Greenbrier area of Chesapeake have an HOA?

HOA status varies by subdivision within the Greenbrier corridor. Woodside Court itself should be verified through a title search or the Chesapeake city records before purchase.

Want to see 1416 Woodside Court in person? Tom and Dariya Milan are ready to set up a walkthrough and answer every question you have about 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$380K – $520K3+ 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…

Explore this neighborhood

Bayberry

Bayberry is an established community in the Greenbrier area of Chesapeake, Virginia. It lies in the 23320 ZIP code. The area sits off Eden Way North, near Greenbrier Mall and the Greenbrier Parkway/I-64 corridor.

$440K

Median sale · 12 mo

$206

Sold $/sq ft

23d

Days on market

5

For sale now

$87K

HH income

56.4%

Owner-occupied

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

Explore Bayberry →
Map of Bayberry 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

$2,797/mo

Principal & interest

$2,335

Property tax

$331

Home insurance

$131

PMI

None

HOA/Condo (paid separately)

$31

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

Price context — similar nearby homes

$322,000 – $467,843

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.

610 Station Square CT · 2.3 mi · 1,700 sqft$325,000 sold 2026-07
523 Track XING · 2.3 mi · 1,670 sqft$326,625 sold 2026-03
503 Thornloe LN · 2.5 mi · 1,711 sqft$425,000 sold 2026-07

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

Sale & Tax History

List Price

$450,000

Price / Sq Ft

$262

Annual Taxes

$3,968

Monthly Tax

$331

HOA fee

$31 / mo

Tax Rate (effective)

0.88%

Sale Timeline (this listing)

EventDatePriceDetail
ListedOct 5, 2026$450,000—
Currently listed—$450,000—

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.

Questions buyers ask

Is 1416 Woodside Ct in a good school zone?+
The assigned zones on the listing record are Greenbrier Intermediate (VaHome School Score 5.7/10), Greenbrier Middle (VaHome School Score 7.2/10), Indian River (VaHome School Score 4.9/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1416 Woodside Ct 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 1416 Woodside Ct have an HOA?+
Yes — HOA dues are on record for this property (the current amount is shown in the facts section on this page). The association of record is na.
When was 1416 Woodside Ct built?+
It was built in 1979, 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 Katrina Cantrell · BHHS RW Towne Realty · REIN MLS #10655585

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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1416 Woodside Ct, Chesapeake — photo

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

Call or text (757) 777-7577

1416 Woodside Ct, Chesapeake, Virginia 23320 · MLS #10655585 · 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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