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ChesapeakeHADLEY PARK AT GREENBRIER1439 Rollesby Way✓ Source: REIN MLS #10647568 · record updated Aug 6, 2026 · synced every 2 min · your inquiry is never resold
1439 Rollesby WAY, CHESAPEAKE VA 23320 - Main photo
1439 Rollesby WAY, CHESAPEAKE VA 23320 - Photo 2
1439 Rollesby WAY, CHESAPEAKE VA 23320 - Photo 3
1439 Rollesby WAY, CHESAPEAKE VA 23320 - Photo 4
1439 Rollesby WAY, CHESAPEAKE VA 23320 - Photo 5
$345,000
$184 / sqft · est. $2,543/mo →
3beds
2.1baths
1,870sqft
0days on market

1439 Rollesby Way, Chesapeake, VA 23320

New ListingResidential · built 2016 · HADLEY PARK AT GREENBRIER

About this home

The listing, in the seller's words

Welcome home to this beautifully maintained 3-bedroom, 2.5-bath condo in the highly desirable Greenbrier area of Chesapeake. This well designed home features two primary suites, each with a private bath, offering exceptional flexibility for guests, roommates, or multigenerational living. The bright open floor plan provides comfortable living and entertaining space, while the 1st floor bedroom can be used as a home office or guest room. Conveniently located near shopping, dining, parks, and major interstates, this low-maintenance home combines comfort, convenience, and an unbeatable location.

Listing courtesy of Susan Deckner · 1st Class Real Estate Flagship · REIN MLS #10647568

VaHome team overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · LPT Realty

At a glance

1439 Rollesby Way is a 2016-built, three-bedroom townhome-style residence in Chesapeake, Virginia, offering 1,870 square feet, 2.5 baths, and a location that puts groceries, parks, and two military installations within a short drive of your front door.

Read the full overview ↓

Why this home stands out

Built in 2016, this home skips the guesswork that comes with older construction — systems, finishes, and structural components are all relatively young. The Greenbrier corridor of Chesapeake is one of the area's most self-contained pockets: coffee, groceries, fitness studios, and green space are all within half a mile, yet the neighborhood itself stays quiet and residential. For households tied to the Coast Guard Finance Center — literally two minutes away — the commute math is hard to beat.

HADLEY PARK AT GREENBRIER and the Chesapeake real estate market

Chesapeake is Virginia's second-largest city by land area, and the Greenbrier section sits near its commercial and geographic heart. The area has a well-established, mature feel — wide roads, retail corridors that actually have what you need, and parks woven throughout the grid. Mill Lake Park is just 0.4 miles away, offering a natural exhale from daily life without requiring a drive. Greenbrier Country Club adds a leisure anchor nearby, and the mix of independent spots and national names along the corridor means you're never far from a good meal or a morning coffee. Chesapeake sits at the crossroads of Hampton Roads, giving you reasonable access to Norfolk, Virginia Beach, and Suffolk without living in the middle of any of them. It's the kind of city that rewards people who want a quieter base of operations without sacrificing convenience.

What's nearby

Daily errands are genuinely easy from 1439 Rollesby Way. Harris Teeter and DG Market are both within 0.6 miles for grocery runs of any size. When you'd rather not cook, America's Greatest Wings & Gyro, Great Wall Chinese Restaurant, and Taco Bell are all within half a mile. Einstein Bros. Bagels, Starbucks, and Sun Flour Cafe round out the morning coffee options at 0.6 miles. For fitness, you have three distinct choices nearby: Greenbrier Country Club at 0.4 miles, Changing Lives Martial Arts Greenbrier at 0.5 miles, and Dawn Pilates Studio at 0.6 miles. Mill Lake Park, Field 4, and City View Park give you outdoor options in multiple directions.

For different buyers

For military families relocating

The USCG Finance Center Chesapeake is about two minutes from the front door — as close as a commute gets without living on base. Norfolk Naval Shipyard is roughly 12 minutes out, making this address workable for dual-military households. A VA loan can make the financing side straightforward, and the 2016 build year means you're not inheriting decades of deferred maintenance.

For first-time buyers

A 2016 build in an established Chesapeake neighborhood is a solid starting point — newer systems, a layout that makes sense, and a location where you can walk to coffee or a park without planning around it. At 1,870 square feet with three bedrooms and 2.5 baths, there's real room to grow here, and the Greenbrier area's infrastructure means you're already surrounded by everything a first home needs nearby.

More buyer questions

How far is 1439 Rollesby Way from the USCG Finance Center Chesapeake?

The USCG Finance Center Chesapeake is approximately two minutes away by car — one of the shortest base commutes you'll find in the area. It's a genuine advantage for Coast Guard personnel assigned there.

How far is 1439 Rollesby Way from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about 12 minutes from this address under typical traffic conditions. That puts it well within a reasonable daily commute for shipyard personnel.

Is 1439 Rollesby Way in a flood zone?

Flood zone information for this address is displayed in the FloodRisk tile on this page, which pulls current FEMA map data. We recommend reviewing that section and discussing it with your agent.

What parks are near 1439 Rollesby Way?

Mill Lake Park is the closest at 0.4 miles, followed by Field 4 at 0.7 miles and City View Park at 0.8 miles. All three are reachable without getting on a major road.

Does 1439 Rollesby Way have an HOA?

HOA status for this property is confirmed in the listing details section of this page. If you have questions about what's included or governed, your agent can pull the full HOA documents for review.

Tom and Dariya Milan at LPT Realty know Chesapeake's Greenbrier corridor well. Reach out to get your questions answered or schedule a walkthrough of 1439 Rollesby Way.

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

2016

Price / sqft

$184

Condo fee

$387/mo

Taxes

$3,186/yr

County

Chesapeake VA

MLS #

10647568

Condo association includes

Ground MaintPoolTrash PickupWater

$387/mo condo fee · Hadley Park Condo · per the REIN MLS listing record — confirm inclusions with the association.

Interior

Bedrooms
3
Full baths
2
Half baths
1
Approx. sqft
1,870
Stories
2
Flooring
Carpet, Laminate/LVP
Ensuite bedrooms
2
Total rooms
5
Other rooms
1st Floor BR, PBR with Bath, Pantry, Porch
Appliances
Dishwasher, Disposal, Dryer, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer, Washer Hookup
Equipment
Ceiling Fan

Construction & exterior

Style
2 Unit Condo
Subtype
Attached
Foundation
Slab
Roof
Composite
Exterior
Vinyl
Pool
No Pool
Fencing
Back Fenced

Utilities & systems

Heating
Nat Gas
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
HADLEY PARK AT GREENBRIER
Unit / floor
1
Ownership
Condo
Garage
No
Parking
1 Space, Assigned/Reserved, Lot, Multi Car
Possession
SETTLEMENT
Miscellaneous
Pet Restrictions
Disclosures
Common Interest Community, Disclosure Statement, Resale Certif Req

See more Chesapeake condos & townhomes.

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…

Explore this neighborhood

Greenbrier

Greenbrier is a residential neighborhood located in Chesapeake, Virginia, offering a suburban setting with tree-lined streets and well-maintained homes.

$332K

Median sale · 12 mo

$229

Sold $/sq ft

13d

Days on market

30

For sale now

$88K

HH income

76.1%

Owner-occupied

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

Explore Greenbrier
Map of Greenbrier with neighborhood boundaryNeighborhood

see more Chesapeake homes

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

$2,156/mo

Principal & interest

$1,790

Property tax

$266

Home insurance

$101

PMI

None

HOA/Condo (paid separately)

$387

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

$365,000$467,843

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.

801 Westbrook LN · 1.7 mi · 1,860 sqft$385,000 sold 2026-05
1022 Bowling Green TRL · 1.8 mi · 1,829 sqft$417,513 sold 2026-06
708 Tiffany Green CT · 1.9 mi · 1,804 sqft$365,000 sold 2026-06

Sale & Tax History

List Price

$345,000

Price / Sq Ft

$184

Annual Taxes

$3,186

Monthly Tax

$266

Condo fee

$387 / mo

Tax Rate (effective)

0.92%

Sale Timeline (this listing)

EventDatePriceDetail
ListedAug 6, 2026$345,000
Currently listed$345,000

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

0 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 1439 Rollesby Way in a good school zone?+
The assigned zones on the listing record are Greenbrier Primary, Greenbrier Middle (GreatSchools 6/10), Indian River (GreatSchools 3/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1439 Rollesby Way 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.
Does 1439 Rollesby Way have a condo association?+
Yes — condo association fees are on record for this unit (the current amount is shown in the facts section on this page). The association of record is Hadley Park Condo. Association amenities on record include: Ground Maint, Pool, Trash Pickup, Water.
When was 1439 Rollesby Way built?+
It was built in 2016, 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 Susan Deckner · 1st Class Real Estate Flagship · REIN MLS #10647568

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.

1439 Rollesby Way, Chesapeake — photo

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

Call or text (757) 777-7577

1439 Rollesby Way, Chesapeake, Virginia 23320 · MLS #10647568 · 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.