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ChesapeakeEMERALD FOREST1301 Simon Dr✓ Source: REIN MLS #10632029 · record updated Sep 15, 2026 · synced every 2 min · your inquiry is never resold
1301 Simon DR, CHESAPEAKE VA 23320 - Main photo
1301 Simon DR, CHESAPEAKE VA 23320 - Photo 2
1301 Simon DR, CHESAPEAKE VA 23320 - Photo 3
1301 Simon DR, CHESAPEAKE VA 23320 - Photo 4
1301 Simon DR, CHESAPEAKE VA 23320 - Photo 5
6beds
4.1baths
4,767sqft
131days on market

1301 Simon Dr, Chesapeake, VA 23320

ActiveResidential · built 2005 · EMERALD FOREST

Facts & features

Type

Residential

Year built

2005

Price / sqft

$226

HOA fee

$45/mo

Taxes

$10,172/yr

County

Chesapeake VA

MLS #

10632029

Interior

Bedrooms
6
Full baths
4
Half baths
1
Approx. sqft
4,767
Stories
3
Flooring
Bamboo, Carpet, Ceramic, Wood
Ensuite bedrooms
3
First-floor bed & full bath
Yes
Total rooms
12
Other rooms
Attic, Breakfast Area, Foyer, PBR with Bath, Office/Study, Pantry
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Gas Range, Refrigerator, Washer Hookup
Equipment
Cable Hookup

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Brick
Pool
In Ground Pool
Fencing
Back Fenced

Utilities & systems

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

Lot, parking & ownership

Lot size
0.4070
Subdivision
EMERALD FOREST
Zoning
R15S
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 3+ Car, 3 Space
Possession
SETTLEMENT
Disclosures
Common Interest Community, Resale Certif Req

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

About this home

Luxury Redefined at 1301 Simon Drive Experience the pinnacle of Chesapeake living in this custom 4,767 sq. ft. brick estate. Nestled on a spacious corner lot in Greenbrier, this 6-bed, 4.5-bath masterpiece blends timeless elegance with modern high-tech luxury. The Interior Experience: Ultimate Comfort: Enjoy radiant heated floors Chef's Dream: Gourmet kitchen with high-end appliances and a sleek wet bar. Grand Design: Cathedral ceilings and a dramatic winding staircase. Your Private Oasis: Step outside to a brand-new, gorgeous pool oasis. Whether you're hosting a summer gala or a quiet evening by the water, this backyard is designed for pure relaxation. The Bells & Whistles: Oversized 3-car garage. Lavish primary suite with a champagne bubble spa-tub. Premium finishes and smart-home integration throughout. 1301 Simon Drive | Luxury is in the details.

Listing courtesy of Eugene Shull · KW Metro Center · REIN MLS #10632029

Tom & Dariya's overview

Our read on this home

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

At a glance

Meet 1301 Simon Drive — a six-bedroom, four-and-a-half-bath home in Chesapeake's Emerald Forest neighborhood, offering 5,612 square feet on nearly half an acre. Built in 2005, this is the kind of large-footprint property that rarely surfaces among Chesapeake homes for sale.

Read the full overview ↓

Why this home stands out

Scale is the headline here. With six bedrooms, four full baths, a half bath, and 5,612 square feet spread across a 0.407-acre lot, 1301 Simon Drive gives growing households genuine room to breathe. Emerald Forest is a well-established community, and homes of this size within it are uncommon. Whether you need dedicated office space, guest suites, or a flex room that can grow with your family, the floor plan has room for every scenario you can imagine.

EMERALD FOREST and the Chesapeake real estate market

Emerald Forest sits in the Greenbrier corridor of Chesapeake — one of the city's most connected and convenient pockets. The neighborhood itself is mature and tree-lined, with generous lot sizes that keep things feeling open rather than cramped. Chesapeake is Virginia's second-largest city by area, and the Greenbrier section gives you the best of that scale: suburban calm with quick access to I-64, Route 168, and the broader Hampton Roads metro. Families comparing homes for sale in Chesapeake often land here because the infrastructure is already in place — parks, grocery stores, fitness studios, and restaurants are all within a short drive or walk. The zip code 23320 covers a broad swath of central Chesapeake, and Emerald Forest is one of its most recognizable addresses. Daily life is easy here, and the commute picture — whether you're heading to Norfolk, Virginia Beach, or the Outer Banks — is genuinely manageable.

What's nearby

Everyday errands are simple from 1301 Simon Drive. DG Market and Harris Teeter are both within 0.6 miles for grocery runs. For a morning coffee, Einstein Bros. Bagels, Starbucks Coffee Company, and Sun Flour Cafe are all within easy reach. Dinner options include America's Greatest Wings & Gyro, Great Wall Chinese Restaurant, and Taco Bell — all within half a mile. Mill Lake Park is just 0.4 miles away for a quick walk or afternoon outside, with Field 4 and City View Park close behind. Greenbrier Country Club, Changing Lives Martial Arts Greenbrier, and Dawn Pilates Studio round out the fitness options nearby.

For different buyers

For military families relocating

The USCG Finance Center Chesapeake is literally three minutes away, which makes 1301 Simon Drive a rare find for Coast Guard personnel. Norfolk Naval Shipyard is a straightforward 12-minute drive as well. A home this size — six bedrooms, nearly 5,600 square feet — handles PCS moves with ease, and a VA loan can make the financing picture even cleaner for eligible buyers.

For families upgrading

If your current home has started to feel like a puzzle you can't solve, 1301 Simon Drive offers a different kind of math. Six bedrooms and 5,612 square feet on nearly half an acre means everyone gets their own space — and there's still room for the spaces that belong to everyone. Families comparing homes for sale zoned for Indian River High School will find this address checks that box while delivering a footprint that's genuinely hard to outgrow.

More buyer questions

How far is 1301 Simon Drive from the USCG Finance Center Chesapeake?

The USCG Finance Center Chesapeake is approximately 3 minutes away by car — one of the closest residential options to the base in the area.

How far is 1301 Simon Drive from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about 12 minutes from 1301 Simon Drive, making it a practical commute for shipyard personnel and contractors.

What is the lot size at 1301 Simon Drive?

The lot measures 0.407 acres — just under half an acre — which is notably generous for the Greenbrier area of Chesapeake and provides real outdoor space front and back.

Is 1301 Simon Drive in a flood zone?

Flood zone status for this address is covered in the FloodRisk tile on this page, which pulls current FEMA map data for the 23320 zip code.

Are there parks within walking distance of 1301 Simon Drive?

Yes — Mill Lake Park is just 0.4 miles away, and both Field 4 and City View Park are under a mile, giving the neighborhood solid access to green space for walks, recreation, and outdoor time.

Tom and Dariya Milan at LPT Realty know Emerald Forest well. Reach out to get the full picture on 1301 Simon Drive and what homes for sale in 23320 are doing right now.

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

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

Chesapeake$910K – $1.2M6+ 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

Not in a designated hurricane evacuation zone.

Source: Virginia Dept. of Emergency Management — Know Your Zone

Explore this neighborhood

Emerald Forest

Emerald Forest is a wooded residential subdivision in the Greenbrier area of Chesapeake, Virginia, set north of Volvo Parkway and centrally located in Hampton Roads near the Virginia Beach line.

1

For sale now

$85K

HH income

61.8%

Owner-occupied

U.S. Census ACS 2024 5-year

Explore Emerald Forest
Map of Emerald Forest 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

Homes at this tier often trade in cash or portfolio financing — the calculator below shows a financed view; taxes are from the public record.

Estimate your monthly payment

$6,739/mo

Principal & interest

$5,578

Property tax

$848

Home insurance

$314

PMI

None

HOA/Condo (paid separately)

$45

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

Asking vs. assessment

107% of $1,007,100

City assessment record · taxes $10,172/yr

Land share of assessed value

22% — $225,000

Improvements $782,100 · assessor record ✓

Price context — similar nearby homes

$674,900$1,169,000

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.

1345 Simon DR · 0.2 mi · 4,751 sqft$899,900 sold 2026-01
1208 Masters ROW · 0.2 mi · 4,518 sqft$880,000 sold 2026-08
1317 Baffy LOOP · 0.2 mi · 5,317 sqft$1,169,000 sold 2026-07

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

Sale & Tax History

List Price

$1,075,000

Price / Sq Ft

$226

Annual Taxes

$10,172

Monthly Tax

$848

HOA fee

$45 / mo

Tax Rate (effective)

0.95%

Sale Timeline (this listing)

EventDatePriceDetail
ListedMay 7, 2026$1,075,000
Price reducedJul 13, 2026$1,075,000−$122,000
Currently listed$1,075,000

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

7% above assessment

Total Assessed

$1,007,100

Land

$225,000

Improvement

$782,100

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:

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

131 days on market — read it in context

Higher-priced homes market more slowly by nature: the buyer pool is smaller and diligence is heavier. Days-on-market at this tier is a rhythm, not a warning.

Questions buyers ask

Is 1301 Simon Dr in a good school zone?+
The assigned zones on the listing record are Indian River (VaHome School Score 4.9/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1301 Simon 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 1301 Simon Dr?+
Yes — Greenbrier Country Club is about 0.6 miles away, per the cached nearby-places record for this address.
Are there parks near 1301 Simon Dr?+
Mill Lake Park is about 0.4 miles away.
Where is the nearest grocery store to 1301 Simon Dr?+
DG Market is about 0.7 miles away. The closest dining on record is Einstein Bros. Bagels (0.6 mi).
Does 1301 Simon 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 Emerald Forest Homeowners Association.
When was 1301 Simon Dr built?+
It was built in 2005, 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 Eugene Shull · KW Metro Center · REIN MLS #10632029

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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1301 Simon Dr, Chesapeake — photo

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

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1301 Simon Dr, Chesapeake, Virginia 23320 · MLS #10632029 · 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.