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Chesapeake › HILLCREST › 785 Caddie St✓ Source: REIN MLS #10644309 · record updated Jul 16, 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
$599,000
$230 / sqft · est. $3,812/mo →
5beds
3baths
2,600sqft
0days on market

785 Caddie St, Chesapeake, VA 23322

New ListingResidential · built 2026 · HILLCREST

About this home

The listing, in the seller's words

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

VaHome team overview

Our read on this home

At a glance

Meet 785 Caddie Street — a brand-new 2026-built five-bedroom, three-bath home on a generous quarter-acre lot in Chesapeake's HILLCREST neighborhood. With 2,600 square feet of thoughtfully designed space, this address delivers room to grow in one of Hampton Roads' most accessible cities.

Read the full overview ↓

Why this home stands out

New construction in 2026 means everything here is yours first — fresh systems, modern finishes, and a layout built for how people actually live today. Five bedrooms give you flexibility that older homes in this price range rarely offer: a dedicated home office, a proper guest suite, and still room for the whole family. The 0.274-acre lot adds genuine outdoor space that many newer builds in the area simply can't match.

HILLCREST and the Chesapeake real estate market

HILLCREST sits in the southern reaches of Chesapeake, a city that consistently draws buyers who want suburban breathing room without sacrificing access to the broader Hampton Roads metro. The streets here are quiet and residential, with the kind of established-neighborhood feel that new construction often lacks — mature trees lining the roads, neighbors who wave, and a pace that slows down the moment you turn off the main corridor. If you've been searching chesapeake homes for sale and wondering where the value still lives, this pocket of the city tends to answer that question. Chesapeake itself spans from the North Carolina border up to the Elizabeth River, and that geography means you're genuinely close to everything — Virginia Beach beaches, Norfolk's waterfront, and the Great Dismal Swamp for weekend hiking — while still coming home to a neighborhood that feels removed from all of it. The city's low crime rates and well-maintained infrastructure make HILLCREST a natural landing spot for families and professionals alike.

What's nearby

Daily life runs smoothly from Caddie Street. Grocery runs are easy with Food Lion and Harris Teeter locations within a short drive along Battlefield Boulevard. For coffee before work, Starbucks and local spots near Greenbrier are under ten minutes away. Chesapeake City Park offers trails, athletic fields, and open green space for weekends when you want to stay close to home. The Greenbrier area — one of Hampton Roads' most complete retail corridors — puts dining, pharmacy, and big-box shopping all within a quick drive. Interstate 64 access keeps Norfolk, Virginia Beach, and the rest of the region well within reach.

For different buyers

For military families relocating

USCG Finance Center Chesapeake is just 14 minutes from the front door, and Norfolk Naval Shipyard is roughly 24 minutes out — both well within a practical daily commute. A VA loan can make financing a new-construction home like this more straightforward than many buyers expect, and the five-bedroom layout gives you room for family, guests, or a dedicated workspace when schedules get demanding.

For families upgrading

If your current home has you bumping into walls, 785 Caddie Street offers a genuine reset. Five bedrooms across 2,600 square feet means every family member gets their own space — and you finally get yours. The 2026 build year means no deferred maintenance surprises, and the quarter-acre lot gives kids room to actually play outside. Chesapeake VA homes for sale at this size and quality in a quiet neighborhood like HILLCREST don't come along every season.

More buyer questions

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

The drive is approximately 14 minutes under normal traffic conditions, making it one of the more convenient addresses in the area for personnel stationed there.

How far is 785 Caddie Street from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about 24 minutes away, a manageable commute that keeps this address in range for shipyard personnel and contractors.

What year was 785 Caddie Street built?

The home was built in 2026, making it brand-new construction with all the benefits of modern systems, materials, and warranties that come with a first-owner property.

Is 785 Caddie Street 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 for the most accurate and up-to-date designation.

Does 785 Caddie Street have an HOA?

HOA status for HILLCREST and this specific address should be confirmed during the transaction process, as community governance can vary by platted section within the neighborhood.

Ready to walk through 785 Caddie Street? Tom and Dariya Milan at LPT Realty know HILLCREST and Chesapeake well — reach out and let's set up a visit.

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

$230

HOA

None

Taxes

$6,352/yr

County

Chesapeake VA

Waterfront

Yes

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
Waterfront
Not Waterfront

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

Flood & environment

FEMA flood zone X · outside the high-risk area · FIRM 510034

Flood Risk

Looking up FEMA flood 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.

2

For sale now

$165K

HH income

99.2%

Owner-occupied

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

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.

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

$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.

517 Middleton WAY · 1.1 mi · 2,456 sqft$615,000 sold 2026-05
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

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.

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 785 Caddie St in a good school zone?+
The assigned zones on the listing record are Southeastern Elementary (GreatSchools 6/10), Hickory Middle (GreatSchools 9/10), Grassfield (GreatSchools 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

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.

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