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ChesapeakeJOLLIFF LANDING AT WESTERN BRANCH5103 Annapolis Dr✓ Source: REIN MLS #10641728 · record updated Jul 5, 2026 · synced every 2 min · your inquiry is never resold
5103 Annapolis DR, CHESAPEAKE VA 23321 - Main photo
5103 Annapolis DR, CHESAPEAKE VA 23321 - Photo 2
5103 Annapolis DR, CHESAPEAKE VA 23321 - Photo 3
5103 Annapolis DR, CHESAPEAKE VA 23321 - Photo 4
5103 Annapolis DR, CHESAPEAKE VA 23321 - Photo 5
$574,900
$229 / sqft · est. $3,682/mo →
4beds
3baths
2,515sqft
8days on market

5103 Annapolis Dr, Chesapeake, VA 23321

ActiveResidential · built 2024 · JOLLIFF LANDING AT WESTERN BRANCH

About this home

The listing, in the seller's words

Welcome to The Dogwood in Jolliff Landing, one of the community's most sought after floor plans offering the perfect blend of luxury, flexibility, and everyday comfort. This beautifully designed ranch features 4 bedrooms, 3 full baths, and 2 true primary suites including a spacious upstairs FROG suite with its own private full bath ideal for multigenerational living, guests, a private retreat, office, or media space.Why wait on new construction when this move in ready home already offers the upgrades, space, and versatility buyers are searching for? The open concept design is perfect for entertaining while the resort style community amenities including a clubhouse, pool, playgrounds, sports field, and scenic sidewalks create a lifestyle buyers fall in love with.In a neighborhood full of inventory, this layout stands apart. Schedule your private tour today before this opportunity is gone.

Listing courtesy of Christina Bryant Pierre · Pierre & Associates Realty · REIN MLS #10641728

VaHome team overview

Our read on this home

At a glance

5103 Annapolis Drive is a 2024-built, four-bedroom, three-bath single-family home in Chesapeake, Virginia, offering 2,515 square feet of modern construction in a city known for its spacious lots, low traffic, and easy access to Hampton Roads military installations.

Read the full overview ↓

Why this home stands out

Built in 2024, this home carries all the advantages of new construction — current building codes, modern mechanical systems, and a layout designed for the way people actually live today. Four bedrooms and three full baths across 2,515 square feet gives every household member genuine breathing room, and Chesapeake's western corridor keeps commute times to multiple bases short without the congestion of the oceanfront.

JOLLIFF LANDING AT WESTERN BRANCH and the Chesapeake real estate market

Annapolis Drive sits in the western reaches of Chesapeake, Virginia — specifically in the 23321 zip code, a pocket of the city that feels deliberately unhurried. Wide streets, newer subdivisions, and a strong sense of residential calm define this part of town. Chesapeake is the second-largest city by land area in the entire United States, which means you get genuine space here: larger lots, lower density, and room to breathe that older, more built-out Hampton Roads cities simply can't match. The city's western side is particularly well-positioned for military families, with Interstate 664 and Route 17 both within easy reach, making it straightforward to reach Naval Station Norfolk, NSA Northwest Annex, or Naval Medical Center Portsmouth without fighting through downtown traffic. Chesapeake consistently ranks among Virginia's safest cities, and its mix of newer development alongside preserved wetlands and green space gives the area a character that's hard to replicate elsewhere in the region.

What's nearby

Day-to-day errands are handled with ease from Annapolis Drive. The Western Branch corridor along Route 17 puts grocery stores, pharmacies, and big-box retail within a short drive. Several local coffee shops and casual dining spots are clustered nearby, and the Chesapeake City Park system offers trails, open fields, and recreational facilities a short distance away. For medical needs, Naval Medical Center Portsmouth is roughly 17 minutes out — a meaningful convenience for active-duty families. Interstate 664 access is close, connecting you quickly to Suffolk, Newport News, and the broader Hampton Roads network.

For different buyers

For military families relocating

NSA Northwest Annex is about 15 minutes away, and Naval Medical Center Portsmouth is roughly 17 — making 5103 Annapolis Drive a practical choice for active-duty households who want a short commute without sacrificing square footage. New construction means no deferred maintenance surprises during a PCS move, and a VA loan pairs naturally with a 2024 build that already meets modern appraisal standards.

For families upgrading

If your current home feels like it shrank overnight, 2,515 square feet with four bedrooms and three full baths gives everyone their own space again. Built in 2024, there's nothing to fix, update, or apologize for — you're starting fresh in a home that matches how families actually use space today, in a part of Chesapeake where the streets are quiet and the lots are generous.

More buyer questions

How far is 5103 Annapolis Drive from NSA Northwest Annex?

NSA Northwest Annex is approximately 15 minutes from 5103 Annapolis Drive under typical traffic conditions. The route primarily follows local roads through western Chesapeake, avoiding most of the congestion that affects other parts of Hampton Roads.

How far is 5103 Annapolis Drive from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is roughly 17 minutes away, accessible via Interstate 664 and the Downtown Tunnel or the Midtown Tunnel depending on your preferred route.

What year was 5103 Annapolis Drive built?

The home was built in 2024, making it a true new-construction property with current-code systems, modern finishes, and no deferred maintenance history.

Is 5103 Annapolis Drive in a flood zone?

Flood zone information for this address is displayed in the dedicated FloodRisk tile on this page, which pulls current FEMA map data for the most accurate and up-to-date designation.

Does 5103 Annapolis Drive have an HOA?

HOA status for this property is confirmed in the listing details section — if an HOA is present, that information will be noted there along with any applicable rules or community amenities.

Tom and Dariya Milan at LPT Realty know western Chesapeake well — reach out to get your questions answered and schedule a walkthrough of 5103 Annapolis Drive.

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

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

2024

Price / sqft

$229

HOA fee

$80/mo

Taxes

$5,421/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10641728

HOA association includes

ClubhousePlaygroundsPoolTrash Pickup

$80/mo HOA fee · N/A · per the REIN MLS listing record — confirm inclusions with the association.

Interior

Bedrooms
4
Full baths
3
Approx. sqft
2,515
Stories
2
Flooring
Carpet, Laminate/LVP
Ensuite bedrooms
2
First-floor bed & full bath
Yes
Total rooms
8
Other rooms
1st Floor BR, Breakfast Area, Fin. Rm Over Gar, Foyer, PBR with Bath, Pantry, Porch, Utility Room
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Equipment
Attic Fan, Cable Hookup, Ceiling Fan, Gar Door Opener

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Waterfront
Not Waterfront

Utilities & systems

Heating
Forced Hot Air
Cooling
Central Air
Water heater
Gas
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
JOLLIFF LANDING AT WESTERN BRANCH
Zoning
RES
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Multi Car, Driveway Spc
Possession
NEGOTIABLE
Disclosures
Disclosure Statement, Resale Certif Req

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

Flood & environment

The flood answer first — quantified, not buried

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

Western Branch

Western Branch is a residential neighborhood in Chesapeake, Virginia, characterized by tree-lined streets and a mix of single-family homes. The area reflects the broader suburban character of Chesapeake while maintaining its own distinct identity.

$400K

Median sale · 12 mo

$204

Sold $/sq ft

33d

Days on market

47

For sale now

$95K

HH income

72%

Owner-occupied

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

Explore Western Branch
Map of Western Branch with neighborhood boundaryNeighborhood

homes 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

$3,682/mo

Principal & interest

$2,983

Property tax

$452

Home insurance

$168

PMI

None

HOA

$80

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.

Value & history

Judge value on real ground

Asking vs. assessment

107% of $536,700

City assessment record · taxes $5,421/yr

Land share of assessed value

29% — $155,000

Improvements $381,700 · assessor record ✓

Why we show no algorithmic estimate.

National AVMs misprice homes whose value drivers they can't see. Instead: the sourced assessment above, the carrying cost, real price history, and honest comparables below.

Price context — similar nearby homes

$436,900$554,900

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.

2200 Captiva LN · 0.3 mi · 2,468 sqft$554,900 sold 2026-05
4827 Condor DR · 1.1 mi · 2,511 sqft$550,000 sold 2026-06
4701 Harlan CT · 1.1 mi · 2,569 sqft$530,000 sold 2026-05

Sale & Tax History

List Price

$574,900

Price / Sq Ft

$229

Annual Taxes

$5,421

Monthly Tax

$452

HOA fee

$80 / mo

Tax Rate (effective)

0.94%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 27, 2026$574,900
Currently listed$574,900

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

7% above assessment

Total Assessed

$536,700

Land

$155,000

Improvement

$381,700

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.

Market tempo

8 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Real questions, answered from the record

Is 5103 Annapolis Dr in a good school zone?+
The assigned zones on the listing record are Western Branch Primary, Western Branch Middle, Western Branch. School attendance zones can change — always confirm enrollment with the local school division.
Is 5103 Annapolis 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 there a gym near 5103 Annapolis Dr?+
Yes — Candlewood Suites Chesapeake/Suffolk by IHG is about 0.6 miles away, per the cached nearby-places record for this address.
Does 5103 Annapolis 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 N/A. Association amenities on record include: Clubhouse, Playgrounds, Pool, Trash Pickup.
When was 5103 Annapolis Dr built?+
It was built in 2024, 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

LPT Realty · Hampton Roads · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of Christina Bryant Pierre · Pierre & Associates Realty · REIN MLS #10641728

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.

5103 Annapolis Dr, Chesapeake — photo

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

Call or text (757) 777-7577

5103 Annapolis Dr, Chesapeake, Virginia 23321 · MLS #10641728 · 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.