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✓ Source: REIN MLS #10651368 · record updated Oct 4, 2026 · synced every 2 min · your inquiry is never resold
1629 Waterside DR, CHESAPEAKE VA 23320 - Main photo
4beds
2.1baths
2,400sqft
36days on market

1629 Waterside Dr, Chesapeake, VA 23320

Off MarketResidential · built 1987 · BAYBERRY PLACE

Chapter · The Water

Life on the water

The waterfront is the reason this home exists. Its water record, straight from the listing: Lake.

Frontage

Lake ✓ VERIFIED

Source: REIN MLS listing record · waterfront features as listed

About this home

This stunning home combines waterfront living, a cul-de-sac location and the convenience of being just minutes from the heart of Greenbrier! Meticulously maintained and extensively refreshed, this 2,400 SF home offers 4 bedrooms, 2.5 baths, a spacious FROG & an expansive backyard overlooking the water. Watch the seasons change from your windows and enjoy the serene setting that water views provide. Major 2025 updates include dual HVAC systems, gas water heater, appliances, engineered hardwood floors, fresh interior paint, blinds, lighting, faucets, switches, receptacles, door hardware & more. The kitchen features new tile, backsplash & lighting, plus a large pantry. Enjoy a primary suite with walk-in closet, spa tub, tiled shower & double vanity. A large deck & pergola overlook the lawn and lake, complemented by mature landscaping, new fencing & a shed. Approx. 5 minutes to Greenbrier shopping, dining & the future Chesapeake Costco!

Listing courtesy of Laura Blackwood · Serhant · REIN MLS #10651368

Facts & features

Type

Residential

Year built

1987

Price / sqft

$223

HOA fee

$31/mo

Taxes

$4,586/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10651368

HOA association includes

Ground MaintTrash Pickup

$31/mo HOA fee · NA · per the REIN MLS listing record — confirm inclusions with the association.

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
2,400
Stories
2
Flooring
Vinyl, Wood
Ensuite bedrooms
1
Total rooms
8
Other rooms
Attic, Breakfast Area, PBR with Bath, Office/Study, Utility Room
Appliances
Dishwasher, Dryer, Microwave, Elec Range, Refrigerator, Washer
Equipment
Ceiling Fan

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick,Vinyl
Pool
No Pool
Fencing
Back Fenced,Other,Privacy
Waterfront
Lake

Utilities & systems

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

Lot, parking & ownership

Lot size
0.4000
Subdivision
BAYBERRY PLACE
Zoning
RES
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, 2 Space, Driveway Spc, Street
Possession
CLOSING
Disclosures
Common Interest Community, Disclosure Statement

See more Chesapeake waterfront homes.

Sources: REIN MLS record · city assessor

Tom & Dariya's overview

Our read on this home

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

At a glance

Meet 1629 Waterside Drive, a four-bedroom, two-bath home in Chesapeake built in 1987. At 2,400 square feet, you'll find room to spread out on a residential lot. It's just minutes from the water and close to everyday conveniences.

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 Great Bridge Primary School. 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

This home sits on a quiet street with direct access to Chesapeake's waterside lifestyle. Four bedrooms and over two full baths give you flexible space for a home office, guest room, or hobby area. The 1987 construction means solid bones and a layout built for real living, not trends. You're walking distance to parks, gyms, and dining spots. Daily life is easy here—groceries, coffee, and fitness are all nearby.

BAYBERRY PLACE and the Chesapeake real estate market

Waterside Drive sits in a residential pocket of Chesapeake where water access and suburban calm coexist. Tree-lined streets and established homes create a settled feel. You're minutes from Woodgate Commons and Mill Lake Park, both perfect for outdoor time. Chesapeake itself is Virginia's largest city by land area, blending rural charm with urban services. Shopping, dining, and recreation are woven throughout the city. Route 17 and Route 168 connect you to Norfolk, Virginia Beach, and beyond. If you're comparing homes for sale in 23320, note that this zip code offers that rare mix of waterside living and easy commuting. Anyone comparing Chesapeake homes for sale will find this location strikes a balance between seclusion and accessibility.

What's nearby

The Vitamin Shoppe, Target Grocery, and Harris Teeter are all under a mile away for your weekly shopping. Coffee lovers can hit 7-Eleven or Panera Bread within walking distance, or try Winston's Cafe nearby. For a quick meal, Ruby Love's, Krispy Krunchy Chicken, and 7-Eleven are steps away. Fitness options include D1 Training East Chesapeake, HOTWORX, and Compound CrossFit—all less than a mile out. Woodgate Commons and Mill Lake Park offer green space and recreation right in your neighborhood.

For different buyers

Base commute and VA loan notes

About four minutes to USCG Finance Center Chesapeake and ten minutes to Norfolk Naval Shipyard. VA loan financing is widely available in this area, and the home's established condition means you can close and move in without major repairs. Waterside Drive puts you close to base commutes while keeping your family in a quiet, residential setting.

Room to grow

Four bedrooms give each person their own space—or claim one as a home office or playroom. Two full baths plus a half bath mean less morning conflict. The 2,400-square-foot layout spreads across a residential lot with room to work with. A home this size lets you grow into the space without outgrowing the address.

More buyer questions

How far is 1629 Waterside Drive from USCG Finance Center Chesapeake?

About four minutes by car. It's one of the closest commutes you'll find in this area.

What is the drive time to Norfolk Naval Shipyard?

Roughly ten minutes from the home. You're well-positioned for a shipyard commute.

Are there parks nearby?

Yes. Woodgate Commons and Mill Lake Park are both within half a mile, perfect for outdoor time and recreation.

Can I find groceries and dining close by?

Absolutely. Harris Teeter, Target Grocery, and The Vitamin Shoppe are under a mile away. Restaurants and coffee shops like Panera Bread and Ruby Love's are even closer.

What schools are in the area for homes for sale zoned for Indian River High School and homes for sale zoned for Great Bridge Primary School?

The area is zoned for these schools, which serve the Waterside Drive neighborhood. Check the Schools tile on this page for full details.

Ready to explore this Chesapeake home? Contact Tom & Dariya Milan at LPT Realty to schedule your tour today.

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

How Far Is?

Driving distance by road and typical drive time via Google Maps, to the nearest location of each. Straight-line distances in “What’s nearby” are shorter.

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

Chesapeake$450K – $620K4+ 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 (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

20.1 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

Not in a designated hurricane evacuation zone.

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

2

For sale now

$87K

HH income

56.4%

Owner-occupied

U.S. Census ACS 2024 5-year

Explore Bayberry →
Map of Bayberry with neighborhood boundaryNeighborhood

Chesapeake real estate →

Location intelligence

What's nearby

Location & Neighborhood

Distances are straight-line (as the crow flies) from this property, not driving miles. Places within ~1 mile, nearest first. Powered by Google Places.

Military Commute

Drive times to nearest bases

USCG Finance Ctr

Coast Guard

7min·2.5mi

NNSY

Navy

18min·11.8mi

USCG Portsmouth

Coast Guard

16min·10.3mi

NMCP

Navy

20min·12.1mi

Little Creek

Navy

22min·13.2mi

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

Payment Calculator

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

$3,314/mo

Principal & interest

$2,775

Property tax

$382

Home insurance

$156

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

Comparables

Asking vs. assessment

118% of $454,100

City assessment record · taxes $4,586/yr

Land share of assessed value

40% — $180,000

Improvements $274,100 · assessor record ✓

Price context — similar nearby homes

$425,000 – $520,000

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.

1127 Norcova CT · 2.2 mi · 2,410 sqft$450,000 sold 2026-05
1028 Austin DR · 2.3 mi · 2,339 sqft$497,000 sold 2026-08
800 Broad Reach RD · 2.4 mi · 2,383 sqft$475,000 sold 2026-09

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

Sale & Tax History

List Price

$534,900

Price / Sq Ft

$223

Annual Taxes

$4,586

Monthly Tax

$382

HOA fee

$31 / mo

Tax Rate (effective)

0.86%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 29, 2026$534,900—
Currently listed—$534,900—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

18% above assessment

Total Assessed

$454,100

Land

$180,000

Improvement

$274,100

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 1629 Waterside Dr in a good school zone?+
The assigned zones on the listing record are Great Bridge Primary, Greenbrier Middle (VaHome School Score 7.1/10), Indian River (VaHome School Score 4.3/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1629 Waterside 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.
Is 1629 Waterside Dr a waterfront property?+
Yes. The listing record shows: Lake.
Does 1629 Waterside Dr 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. Association amenities on record include: Ground Maint, Trash Pickup.
When was 1629 Waterside Dr built?+
It was built in 1987, 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

Listing courtesy of Laura Blackwood · Serhant · REIN MLS #10651368

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.

1629 Waterside Dr, Chesapeake — photo

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

Call or text (757) 777-7577

1629 Waterside Dr, Chesapeake, Virginia 23320 · MLS #10651368 · 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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