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ChesapeakeJOLLIFF LANDING AT WESTERN BRANCH5108 Annapolis Dr✓ Source: REIN MLS #10630795 · record updated Jun 3, 2026 · synced every 2 min · your inquiry is never resold
5108 Annapolis DR, CHESAPEAKE VA 23321 - Main photo
5108 Annapolis DR, CHESAPEAKE VA 23321 - Photo 2
5108 Annapolis DR, CHESAPEAKE VA 23321 - Photo 3
5108 Annapolis DR, CHESAPEAKE VA 23321 - Photo 4
5108 Annapolis DR, CHESAPEAKE VA 23321 - Photo 5
4beds
2baths
2,145sqft
0days on market

5108 Annapolis Dr, Chesapeake, VA 23321

Under ContractResidential · built 2026 · JOLLIFF LANDING AT WESTERN BRANCH

Facts & features

Type

Residential

Year built

2026

Price / sqft

$252

HOA fee

$80/mo

Taxes

$6,204/yr

County

Chesapeake VA

MLS #

10630795

HOA association includes

ClubhouseExercise RmOther

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

Interior

Bedrooms
4
Full baths
2
Approx. sqft
2,145
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
1
First-floor bed & full bath
Yes
Total rooms
11
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, Fin. Rm Over Gar, Foyer, PBR with Bath, Pantry, Porch, Utility Room
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Elec Range, Washer Hookup
Equipment
Ceiling Fan
Accessibility
Level Flooring

Construction & exterior

Style
Ranch
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Fiber Cement
Pool
No Pool

Utilities & systems

Heating
Nat Gas, Programmable Thermostat, Zoned
Cooling
Central Air, Zoned
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, 2 Space, Driveway Spc, Street
Possession
CLOSING
Miscellaneous
Warranty Plan
Disclosures
Common Interest Community, Contract Owner, Exempt from Disclosure/Disclaimer, Occupancy Permit

See more Chesapeake new construction homes.

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

About this home

A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 4 bedrooms including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

Listing courtesy of Christian Ramirez · RHOAD & CO. · REIN MLS #10630795

Tom & Dariya's overview

Our read on this home

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

At a glance

A brand-new 2026-built, four-bedroom, two-bath home in Chesapeake, Virginia — 2,145 square feet of fresh construction sitting minutes from NSA Northwest Annex and Naval Medical Center Portsmouth, with coffee, dining, and fitness options practically at the front door.

Read the full overview ↓

Why this home stands out

New construction in 2026 means everything — the roof, the mechanicals, the finishes — is factory-fresh and covered by builder warranties, so you're not inheriting anyone else's deferred maintenance. Four bedrooms give you real flexibility: a dedicated home office, a guest room, and space to grow. At 2,145 square feet, the layout breathes without feeling oversized, and the Chesapeake address keeps two major military installations within a short, predictable commute.

JOLLIFF LANDING AT WESTERN BRANCH and the Chesapeake real estate market

Chesapeake is one of the largest cities by land area on the East Coast, and the 23321 zip code sits in its northwestern corner — a quieter, more suburban pocket that still connects quickly to the rest of Hampton Roads via Interstate 664 and Route 17. The Western Branch corridor here has a settled, family-oriented feel: wide streets, newer subdivisions mixed with established ones, and a genuine sense of community without the congestion you'd find closer to the oceanfront. Annapolis Drive itself benefits from that character — it's the kind of address that anchors homes for sale in 23321 with long-term livability in mind. Chesapeake as a whole consistently ranks among Virginia's most desirable cities for quality of life, and this corner of it delivers that promise with a little more breathing room and a lot less traffic noise.

What's nearby

Daily life is genuinely easy here. A Starbucks Coffee Company is just 0.2 miles away — close enough to walk on a good morning. Gather Cafe and Fruitsplash Factory are both within half a mile when you want something different. For an evening out, Branches Tasting Room is a 0.5-mile trip. Fitness is equally convenient: Onelife Fitness - Chesapeake Square Gym and the National Personal Training Institute are both under a mile away, with a third option at Candlewood Suites Chesapeake/Suffolk by IHG rounding out the mix. You won't need to drive far to handle the everyday stuff.

For different buyers

For military families relocating

NSA Northwest Annex is roughly 15 minutes away, and Naval Medical Center Portsmouth is about 17 — both well within the range that makes daily commuting manageable across most duty schedules. A VA loan pairs naturally with new construction like this, since there's no seller-deferred maintenance to negotiate around. Four bedrooms handle PCS moves with room to spare, and Chesapeake's western corridor is a proven landing spot for military households.

For families upgrading

Families comparing homes for sale zoned for Western Branch High School and homes for sale zoned for Western Branch Primary School will find 5108 Annapolis DR worth a close look. Four bedrooms, two full baths, and 2,145 square feet of brand-new space give an upgrading family genuine room to settle in — no renovation projects, no aging systems to budget around, just a clean slate in a neighborhood that already has the infrastructure families depend on.

More buyer questions

How far is 5108 Annapolis DR from NSA Northwest Annex?

NSA Northwest Annex is approximately 15 minutes from 5108 Annapolis DR under typical traffic conditions. The route via Route 17 is straightforward and avoids most of the congestion that affects other parts of Hampton Roads.

Is 5108 Annapolis DR in a flood zone?

Flood zone status for this address is detailed in the FloodRisk tile on this page, which pulls the current FEMA designation. Your agent can walk you through what that means for insurance requirements before you make an offer.

What is the HOA situation at 5108 Annapolis DR?

HOA details for this address — including whether an association exists and what it covers — should be confirmed directly with the listing agent or builder, as new construction communities sometimes establish HOAs after initial sales begin.

How far is 5108 Annapolis DR from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is about 17 minutes from this address, making it a realistic daily commute for medical staff or service members assigned there. The drive primarily follows Interstate 664 east.

What are the nearest grocery and dining options to 5108 Annapolis DR?

Starbucks Coffee Company is 0.2 miles away for a quick morning stop, and Branches Tasting Room and Fruitsplash Factory are both within half a mile for dining. Larger grocery stores serving the Western Branch area of Chesapeake are a short drive along the Route 17 corridor.

Tom and Dariya Milan at LPT Realty know this corner of Chesapeake well — reach out to get your questions answered and schedule a walkthrough of 5108 Annapolis DR.

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

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

Chesapeake$455K – $625K4+ 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…

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

$203

Sold $/sq ft

33d

Days on market

49

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

Chesapeake homes for sale

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

$3,476/mo

Principal & interest

$2,801

Property tax

$517

Home insurance

$157

PMI

None

HOA/Condo (paid separately)

$80

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

$419,900$448,900

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.

4960 Apricot WAY · 0.5 mi · 2,044 sqft$436,900 sold 2026-03
4954 Apricot WAY · 0.5 mi · 2,044 sqft$447,900 sold 2026-05
4950 Apricot WAY · 0.5 mi · 2,044 sqft$448,900 sold 2026-04

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

Sale & Tax History

List Price

$539,900

Price / Sq Ft

$252

Annual Taxes

$6,204

Monthly Tax

$517

HOA fee

$80 / mo

Tax Rate (effective)

1.15%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 4, 2026$539,900
Currently listed$539,900

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 5108 Annapolis Dr in a good school zone?+
The assigned zones on the listing record are Western Branch Primary, Western Branch Middle (VaHome School Score 6.7/10), Western Branch (VaHome School Score 6.2/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 5108 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 5108 Annapolis Dr?+
Yes — Candlewood Suites Chesapeake/Suffolk by IHG is about 0.6 miles away, per the cached nearby-places record for this address.
Are there parks near 5108 Annapolis Dr?+
Meadowbrook Memorial & Cremation Gardens is about 1 miles away.
Does 5108 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, Exercise Rm, Other.
When was 5108 Annapolis Dr built?+
It was built in 2026, 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 Christian Ramirez · RHOAD & CO. · REIN MLS #10630795

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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5108 Annapolis Dr, Chesapeake — photo

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

Call or text (757) 777-7577

5108 Annapolis Dr, Chesapeake, Virginia 23321 · MLS #10630795 · 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.