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ChesapeakeHILLCREST785 Caddie St✓ Source: REIN MLS #10644309 · record updated Sep 3, 2026 · synced every 2 min · your inquiry is never resold
785 Caddie ST, CHESAPEAKE VA 23322 - Main photo
785 Caddie ST, CHESAPEAKE VA 23322 - Photo 2
785 Caddie ST, CHESAPEAKE VA 23322 - Photo 3
785 Caddie ST, CHESAPEAKE VA 23322 - Photo 4
785 Caddie ST, CHESAPEAKE VA 23322 - Photo 5
5beds
3baths
2,600sqft
49days on market

785 Caddie St, Chesapeake, VA 23322

Under ContractResidential · built 2026 · HILLCREST

Facts & features

Type

Residential

Year built

2026

Price / sqft

$230

HOA

None

Taxes

$6,352/yr

County

Chesapeake VA

MLS #

10644309

Interior

Bedrooms
5
Full baths
3
Approx. sqft
2,600
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
2
First-floor bed & full bath
Yes
Total rooms
9
Other rooms
1st Floor BR, 1st Floor Primary BR, Attic, Breakfast Area, Fin. Rm Over Gar, In-Law Suite, Porch, Utility Room
Appliances
Dishwasher, Dryer Hookup, Energy Star Appliance(s), Microwave, Elec Range, Refrigerator, Washer Hookup
Equipment
Cable Hookup, Ceiling Fan, Gar Door Opener

Construction & exterior

Style
Transitional
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Brick,Vinyl
Pool
No Pool
Fencing
Back Fenced

Utilities & systems

Heating
Forced Hot Air
Cooling
Central Air, Zoned
Water heater
Electric
Water
Well
Sewer
Septic

Lot, parking & ownership

Lot size
0.5680
Subdivision
HILLCREST
Zoning
R8S
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Multi Car, Off Street, Driveway Spc
Possession
SETTLE
Disclosures
Disclosure Statement, Occupancy Permit

See more Chesapeake new construction homes.

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

About this home

Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

Listing courtesy of Linda Jones · BHHS RW Towne Realty · REIN MLS #10644309

Tom & Dariya's overview

Our read on this home

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

At a glance

785 Caddie Street is a brand-new 2026-built, five-bedroom, three-bath home on a generous quarter-acre lot in Chesapeake's Hillcrest neighborhood — offering fresh construction, room to grow, and straightforward access to both Coast Guard and Navy installations.

Read the full overview ↓

Why this home stands out

New construction in an established neighborhood is a rare combination, and 785 Caddie Street delivers exactly that. At 2,600 square feet across five bedrooms and three full baths, the floor plan gives every household member genuine breathing room. The 0.274-acre lot adds outdoor flexibility that most newer builds simply can't match — space for a future pool, a garden, or just a backyard worth spending time in.

HILLCREST and the Chesapeake real estate market

Hillcrest sits in the southern reaches of Chesapeake, a city that consistently ranks among Virginia's most livable for its blend of low-density neighborhoods, mature tree cover, and easy regional connectivity. The 23322 zip code is one of the city's most sought-after pockets — quiet enough to feel suburban, yet close enough to major corridors that daily errands never feel like an expedition. Streets in Hillcrest tend to be calm and well-kept, with neighbors who take pride in their properties. Chesapeake itself spans from the Elizabeth River waterfront all the way south to the North Carolina line, giving residents access to city-level amenities without city-level density. Families comparing homes for sale in Chesapeake often land in this zip code because the lot sizes are larger, the pace is unhurried, and the commute math works whether you're heading north toward Norfolk or east toward Virginia Beach.

What's nearby

Everyday life runs smoothly from Caddie Street. Grocery runs are quick — Publix and Harris Teeter locations serving the 23322 corridor keep the pantry stocked without a long drive. Greenbrier Mall and the surrounding retail district along Greenbrier Parkway put dining, shopping, and services within a 10-to-15-minute radius. Chesapeake City Park offers trails, athletic fields, and open green space for weekend activity. The Western Branch and Great Bridge areas add additional dining and coffee options close by. Interstate 64 is accessible within minutes, connecting you to Norfolk, Virginia Beach, and the broader Hampton Roads metro whenever the occasion calls for it.

For different buyers

For military families relocating

At 14 minutes from the USCG Finance Center Chesapeake and 24 minutes from Norfolk Naval Shipyard, 785 Caddie Street keeps the commute short and the neighborhood calm. Five bedrooms handle PCS arrivals, visiting family, or a dedicated home office without compromise. A VA loan pairs naturally with new construction here — no deferred maintenance, no seller concessions needed to offset age.

For families upgrading

Five bedrooms and three full baths on a quarter-acre lot give a growing family the square footage and outdoor room they've been waiting for. Families comparing homes for sale zoned for Grassfield High School and homes for sale zoned for Southeastern Elementary School will find 785 Caddie Street lands squarely in that attendance zone — new construction with the school boundaries already solved.

More buyer questions

How far is 785 Caddie Street from USCG Finance Center Chesapeake?

The drive runs approximately 14 minutes under normal traffic conditions, making it one of the more convenient home locations for personnel assigned to that installation.

How far is 785 Caddie Street from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is roughly 24 minutes away via local routes and Interstate 64, a manageable daily commute for Shipyard personnel living in Chesapeake.

Is 785 Caddie Street in a flood zone?

Flood zone status for this address is detailed in the FloodRisk tile on this page, which pulls current FEMA map data for the 23322 area.

What zip code is 785 Caddie Street in, and what does that mean for buyers?

The property falls in the 23322 zip code — one of the more in-demand addresses among homes for sale in 23322 — known for larger lots, newer construction, and proximity to Chesapeake's southern retail and park amenities.

Does 785 Caddie Street have an HOA?

HOA status for the Hillcrest neighborhood should be confirmed through current disclosure documents; your agent can pull that detail during the due-diligence period.

Tom and Dariya Milan at LPT Realty know Chesapeake homes for sale inside and out — reach out today to schedule a walkthrough of 785 Caddie Street and get your questions answered.

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

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

Chesapeake$505K – $690K5+ 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

Hillcrest Farms

Hillcrest Farms is a residential community of detached single-family homes in south-central Virginia Beach, with access via Dam Neck Road.

$650K

Median sale · 12 mo

$206

Sold $/sq ft

20d

Days on market

4

For sale now

$165K

HH income

99.2%

Owner-occupied

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

Explore Hillcrest Farms
Map of Hillcrest Farms 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

$3,812/mo

Principal & interest

$3,108

Property tax

$529

Home insurance

$175

PMI

None

HOA/Condo (paid separately)

None

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

$555,000$660,000

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.

645 Ravenwoods DR · 0.6 mi · 2,467 sqft$600,000 sold 2026-08
523 Middleton WAY · 1.1 mi · 2,456 sqft$615,000 sold 2026-01
511 Cavendish WAY · 1.3 mi · 2,632 sqft$555,000 sold 2026-07

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

Sale & Tax History

List Price

$599,000

Price / Sq Ft

$230

Annual Taxes

$6,352

Monthly Tax

$529

HOA

None

Tax Rate (effective)

1.06%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJul 16, 2026$599,000
Currently listed$599,000

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.

Questions buyers ask

Is 785 Caddie St in a good school zone?+
The assigned zones on the listing record are Southeastern Elementary (VaHome School Score 7.2/10), Hickory Middle (VaHome School Score 9.2/10), Grassfield (VaHome School Score 8.8/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 785 Caddie St 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 785 Caddie St have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 785 Caddie St 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 Linda Jones · BHHS RW Towne Realty · REIN MLS #10644309

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.

785 Caddie St, Chesapeake — photo

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

Call or text (757) 777-7577

785 Caddie St, Chesapeake, Virginia 23322 · MLS #10644309 · 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.