276 days on market
$724,900
1453 Whittamore Rd
Chesapeake, Virginia 23322
MLS# 10581503 · FENTRESS · Chesapeake VA
Updated Feb 2, 2026 · Source: REIN MLS
Est. payment
$4,096/mo
Edit below
Price / sq ft
$273
2,660 sq ft
Days on market
276
HOA
None
Year built
2025
1 yrs old
Beds
5
Full Baths
3
Half Baths
0
Sq Ft
2,660
Garage
Yes
Schools
- ElementarySouthwestern Elementary School8/10
- MiddleHickory Middle School7/10
- 9/10
Info provided by GreatSchools
About this home
Welcome to this fantastic 5BR 3 Full Bath home currently under construction on a 1+ acre lot feeding Hickory Schools! Boasting 2660SF of modern living space with a 1st floor BR & full bath! This beautifully designed 2-story home features 9' first floor ceilings, LVP flooring throughout. Gourmet kitchen w/granite counters, 42" wall cabinets and Whirlpool appliances. 2-car garage with electric car charger; huge lot and…
Listed by David Drogus · G Daniels & Company
VaHome Team property overview
Meet 1453 Whittamore Road — a brand-new 2026-built, five-bedroom home on a full acre-plus lot in Chesapeake's quiet Fentress area. With three baths, 2,660 square feet, and room to breathe in every direction, this is the kind of space that's genuinely hard to find.
Read full property overview ↓Show less ↑
Why this home stands out
New construction on over an acre is a rare combination in this part of Chesapeake. Most buyers have to choose between a fresh build in a dense subdivision or elbow room on an older property — 1453 Whittamore Road offers both. Five bedrooms give you flexibility for a growing household, a home office, or a dedicated guest suite, and the 1.06-acre lot means your neighbors aren't right on top of you.
FENTRESS and the Chesapeake real estate market
Fentress sits in the southern reaches of Chesapeake, Virginia — a low-density pocket where larger lots and a slower pace define daily life. The area draws people who want genuine space without sacrificing city access, and it delivers on both counts. Chesapeake itself is one of the most geographically expansive cities in the country, and Fentress captures that character well: wide skies, tree-lined roads, and properties that actually have room between them. If you've been searching through houses for sale in Chesapeake and keep landing on tight suburban lots, Fentress tends to stand out immediately. The broader city offers strong infrastructure, a well-regarded park system, and convenient corridors heading north toward Virginia Beach and Norfolk. Locally, the Fentress community has a distinctly residential feel — no busy commercial strips cutting through, just neighborhoods that take their time.
What's nearby
Daily errands are more convenient than the rural setting might suggest. Grocery options and everyday retail are reachable within a short drive along the Battlefield Boulevard corridor. For outdoor time, Northwest River Park is one of the region's standout nature destinations and sits close by — hiking trails, kayak launches, and open space all in one spot. The Chesapeake Expressway puts Virginia Beach within easy reach when you want a change of scenery. A handful of local dining spots and a pharmacy are accessible without a long haul, keeping routine life practical even on a quiet country road.
For different buyers
For military families relocating
USCG Finance Center Chesapeake is just 12 minutes away, and NAS Oceana is a manageable 23-minute drive — making 1453 Whittamore Road a strong fit for military households at either installation. A VA loan can make a new-construction purchase like this more accessible, and the BAH rates for the Chesapeake area tend to align well with properties in this size range. Five bedrooms handles PCS moves with family in tow without anyone feeling squeezed.
For families upgrading
If your current home has started to feel like it's shrinking around you, 1453 Whittamore Road is the kind of upgrade that resets the clock. Five bedrooms, three full baths, 2,660 square feet of brand-new construction, and a 1.06-acre lot give everyone in the household their own space — indoors and out. There's a real backyard here, room for a playset or a garden, and no shared walls to worry about. Chesapeake Glen buyers who've outgrown smaller footprints often find this type of property hits the reset button they were looking for.
Frequently asked questions
How far is 1453 Whittamore Road from USCG Finance Center Chesapeake?
The drive is approximately 12 minutes under normal conditions. It's one of the closer military installations to this address, making it a practical daily commute.
How far is 1453 Whittamore Road from NAS Oceana?
NAS Oceana is roughly 23 minutes away, heading northeast through Chesapeake toward Virginia Beach. The route is straightforward with minimal congestion outside of peak hours.
What is the lot size at 1453 Whittamore Road?
The lot measures 1.06 acres, which is notably generous for a new-construction home in the Chesapeake area and provides substantial outdoor space on all sides.
Is 1453 Whittamore Road 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 assessment.
When was 1453 Whittamore Road built?
The home was built in 2026, making it a brand-new construction with all the systems, materials, and code compliance that come with a modern build.
Want to walk through 1453 Whittamore Road or ask about the build specs? Tom and Dariya Milan at LPT Realty know this part of Chesapeake well — reach out and let's talk.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
1453 Whittamore RD, Chesapeake
Map and Street View imagery © Google. Imagery may not be current.
Map data ©Google. Click and drag inside the map to explore the surrounding area.
Flood Risk
Property Details
Bedrooms
5
Full Baths
3
Half Baths
0
Approx Sq Ft
2,660
Stories
2
Fireplaces
0
Flooring
Carpet, Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Disposal, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$724,900
Price / Sq Ft
$273
Annual Taxes
$1,474
Monthly Tax
$123
HOA
None
Tax Rate (effective)
0.20%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Aug 6, 2025 | $724,900 | — |
| Currently listed | — | $724,900 | — |
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:
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.
About buying in Chesapeake
Chesapeake is Virginia's second-largest city by area and offers a mix of suburban subdivisions, rural acreage, and waterfront properties along the Intracoastal Waterway. Western Branch, Greenbrier, and Great Bridge are among the most sought-after neighborhoods, with top-rated public schools and easy access to I-64 and the Chesapeake Expressway. The city is known for lower property taxes and larger lot sizes compared to neighboring Virginia Beach and Norfolk, which makes it especially attractive to families looking for more space.
Military Commute
Drive times to nearest basesDrive 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.
Estimate your monthly payment
$4,096/moPrincipal & interest
$3,761
Property tax
$123
Home insurance
$211
PMI
None
HOA
None
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.
Listed by G Daniels & Company · MLS# 10581503
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$724,900
1453 Whittamore RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
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