1629 Waterside Dr was listed for sale on Aug 29, 2026. The last list price was $534,900. It came off the market on Oct 4, 2026. It is not listed for sale in the REIN MLS.
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
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
Facts & features
TypeResidential
Year built1987
Price / sqft$223
HOA fee$31/mo
Taxes$4,586/yr
CountyChesapeake VA
WaterfrontYes
MLS #10651368
HOA association includes
Ground MaintTrash Pickup
$31/mo HOA fee · 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
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.
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.
Schools · VaHome School ScoreAssigned schools
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.
How Far Is?
Driving distance by road and typical drive time via Google Maps, to the nearest location of each.
Also nearby
Distances are straight-line (as the crow flies) from this property, not driving miles. Places within ~1 mile, nearest first. Powered by Google Places.
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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
Typical drive times from Google Maps, without live traffic. Rush hour and tunnel backups can add time.
Flood & environmentFlood risk (FEMA)
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’t 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’s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service — 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.
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.
Last list price vs. assessment118% of $454,100City assessment record · taxes $4,586/yr
Land share of assessed value40% · $180,000Improvements $274,100 · assessor record ✓
Price context: similar nearby homes$385,000 – $520,000The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for the last list price, not an appraisal or an estimate of this home's value.
1028 Austin DR · 2.3 mi · 2,339 sqft$497,000 sold 2026-08
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:
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.
CompareThis home next to what else is for sale nearby
Home
Price
Beds
Baths
Sqft
$ / sqft
1629 Waterside Drthis home, last list price
$534,900
4
2.1
2,400
$223
Loading nearby homes for sale…
Active comparables from the REIN MLS, the same homes shown under Comparable Properties. Context for judging the asking price, not an appraisal.
Questions about this home
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.
Off the marketSee what this home is worth now
This home is not listed for sale in the REIN MLS. The home value tool estimates a current value from recent nearby sales.
Listing courtesy of Laura Blackwood · Serhant · REIN MLS #10651368
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.
