Skip to main content
ChesapeakeJOLLIFF LANDING AT WESTERN BRANCH2239 Captiva Ln✓ Source: REIN MLS #10597348 · record updated Feb 20, 2026 · synced every 2 min · your inquiry is never resold
2239 Captiva LN, CHESAPEAKE VA 23321 - Main photo
2239 Captiva LN, CHESAPEAKE VA 23321 - Photo 2
2239 Captiva LN, CHESAPEAKE VA 23321 - Photo 3
2239 Captiva LN, CHESAPEAKE VA 23321 - Photo 4
2239 Captiva LN, CHESAPEAKE VA 23321 - Photo 5
$542,900
$226 / sqft · est. $3,508/mo →
4beds
2.1baths
2,400sqft
165days on market

2239 Captiva Ln, Chesapeake, VA 23321

Under ContractResidential · built 2026 · JOLLIFF LANDING AT WESTERN BRANCH

About this home

The listing, in the seller's words

PRE-SOLD SYCAMORE

Listing courtesy of Steve Freeman · RHOAD & CO. · REIN MLS #10597348

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

2239 Captiva LN is a brand-new 2026-built, four-bedroom home in Jolliff Landing at Western Branch — one of Chesapeake's freshest addresses. With 2,400 square feet, 2.5 baths, and a location that puts two major military installations within 16 minutes, this is a home built for real life.

Read the full overview ↓

Why this home stands out

New construction in an established western Chesapeake corridor is genuinely rare. At 2239 Captiva LN, you're getting a 2026-built single-family home with four bedrooms and 2,400 square feet of thoughtfully laid-out living space — not a resale with someone else's choices baked in. The half-bath adds everyday practicality, and the Jolliff Landing at Western Branch address puts you inside one of the area's most quietly sought-after pockets, well away from the congestion of the eastern corridors.

JOLLIFF LANDING AT WESTERN BRANCH and the Chesapeake real estate market

Jolliff Landing at Western Branch sits in the northwest quadrant of Chesapeake, Virginia — a city that regularly earns recognition for livability, low crime relative to its size, and a genuinely suburban feel without sacrificing access to the broader Hampton Roads metro. Western Branch is the kind of neighborhood where streets feel intentional: wide, tree-lined, and built around families who actually use their front yards. If you've been searching northwest Chesapeake VA homes for sale and wondering which pocket delivers the best balance of newness and neighborhood maturity, this corridor tends to rise to the top of that conversation. Chesapeake itself spans from the Dismal Swamp to the Elizabeth River, but the western branch area occupies a particularly convenient slice — close enough to Suffolk, Portsmouth, and Norfolk to make commuting manageable, yet far enough removed to feel genuinely residential. For buyers exploring homes for sale chesapeake bay-adjacent, the western branch area offers that same sense of open, water-influenced Virginia landscape without the flood-zone complexity of coastal addresses.

What's nearby

Daily life runs smoothly from Captiva LN. A Starbucks Coffee Company is just 0.2 miles away — close enough to walk on a good-weather morning. Half a mile out, Branches Tasting Room gives you a solid local spot for an evening out, and Fruitsplash Factory and Gather Cafe round out the casual dining and coffee options within the same short radius. Fitness is equally convenient: Onelife Fitness - Chesapeake Square Gym and National Personal Training Institute are both within 0.7 miles, so skipping leg day has no geographic excuse here. The broader Chesapeake Square corridor adds grocery, pharmacy, and retail options that cover most weekly errands without a highway on-ramp.

For different buyers

For military families relocating

NSA Northwest Annex is a 15-minute drive from 2239 Captiva LN, and Naval Medical Center Portsmouth is only a minute farther at 16. For military households weighing a VA loan purchase, this location checks the commute box without compromise. New construction means no deferred maintenance surprises — just move in, set up, and let the assignment unfold on your terms.

For families upgrading

Four bedrooms and 2,400 square feet give a growing family genuine room to breathe — not just technically enough space, but comfortably enough. The half-bath on the main level means morning routines don't create a bottleneck, and a 2026 build date means everything from the roof to the mechanicals is starting fresh. Jolliff Landing at Western Branch is the kind of address that tends to hold its value as the neighborhood continues to mature.

More buyer questions

How far is 2239 Captiva LN from NSA Northwest Annex?

NSA Northwest Annex is approximately 15 minutes from 2239 Captiva LN under typical traffic conditions, making it one of the more commute-friendly locations in western Chesapeake for personnel assigned there.

How far is 2239 Captiva LN from Naval Medical Center Portsmouth?

Naval Medical Center Portsmouth is about 16 minutes away — just one minute more than NSA Northwest Annex — which makes this address practical for households where one or both adults are assigned to either installation.

What is the flood zone status for 2239 Captiva LN?

Flood zone information for this address is displayed in the FloodRisk tile on this page; buyers are encouraged to review that detail and discuss it with their lender or insurance agent as part of due diligence.

Is there an HOA in Jolliff Landing at Western Branch?

Jolliff Landing at Western Branch does have an HOA; prospective buyers should request the current HOA documents to review covenants, rules, and any applicable dues structure before making an offer.

What are the closest grocery and retail options to 2239 Captiva LN?

The Chesapeake Square corridor, within a short drive, provides grocery, pharmacy, and general retail options that cover most weekly errands, and a Starbucks Coffee Company sits just 0.2 miles from the front door.

Tom and Dariya Milan at LPT Realty know this corner of Chesapeake well. Reach out to get the full picture on 2239 Captiva LN — and what it takes to make it yours.

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

2026

Price / sqft

$226

HOA fee

$80/mo

Taxes

$5,429/yr

County

Chesapeake VA

MLS #

10597348

HOA association includes

ClubhouseExercise Rm

$80/mo HOA fee · N/A · 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
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
1
Total rooms
11
Other rooms
Assigned Storage, Attic, Breakfast Area, Foyer, PBR with Bath, Pantry, Porch, Screened Porch, Utility Room
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Elec Range, Washer Hookup
Equipment
Ceiling Fan
Accessibility
Low Pile Carpet

Construction & exterior

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

Utilities & systems

Heating
Forced Hot Air, 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, 4 Space, Driveway Spc, Street
Possession
CLOSING
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

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.

$372K

Median sale · 12 mo

$205

Sold $/sq ft

32d

Days on market

40

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

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

$3,428/mo

Principal & interest

$2,817

Property tax

$452

Home insurance

$158

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

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

$422,900$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.

4946 Apricot WAY · 0.6 mi · 2,044 sqft$422,900 sold 2026-03
4938 Apricot WAY · 0.6 mi · 2,044 sqft$448,900 sold 2026-06
4950 Apricot WAY · 0.6 mi · 2,044 sqft$448,900 sold 2026-04

Sale & Tax History

List Price

$542,900

Price / Sq Ft

$226

Annual Taxes

$5,429

Monthly Tax

$452

HOA fee

$80 / mo

Tax Rate (effective)

1.00%

Sale Timeline (this listing)

EventDatePriceDetail
ListedFeb 20, 2026$542,900
Currently listed$542,900

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

Real questions, answered from the record

Is 2239 Captiva Ln 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 2239 Captiva Ln 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 2239 Captiva Ln?+
Yes — Candlewood Suites Chesapeake/Suffolk by IHG is about 0.5 miles away, per the cached nearby-places record for this address.
Does 2239 Captiva Ln 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.
When was 2239 Captiva Ln 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

LPT Realty · Hampton Roads · answer their own phone

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

Listing courtesy of Steve Freeman · RHOAD & CO. · REIN MLS #10597348

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.

2239 Captiva Ln, Chesapeake — photo

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

Call or text (757) 777-7577

2239 Captiva Ln, Chesapeake, Virginia 23321 · MLS #10597348 · 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.