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Portsmouth › BRIGHTON › 1908 Chestnut St✓ Source: REIN MLS #10629415 · record updated Jun 15, 2026 · synced every 5 min · your inquiry is never resold
1908 Chestnut ST, PORTSMOUTH VA 23704 - Main photo
1908 Chestnut ST, PORTSMOUTH VA 23704 - Photo 2
1908 Chestnut ST, PORTSMOUTH VA 23704 - Photo 3
1908 Chestnut ST, PORTSMOUTH VA 23704 - Photo 4
1908 Chestnut ST, PORTSMOUTH VA 23704 - Photo 5
$210,000
$144 / sqft · est. $1,356/mo →
3beds
2baths
1,456sqft
65days on market

1908 Chestnut St, Portsmouth, VA 23704

ActiveResidential · built 1920 · BRIGHTON

About this home

The listing, in the seller's words

Open-layout fixer in Portsmouth, VA! Great starter home or investment with strong potential. Spacious flow, solid bones, and ready for your updates. Build equity and make it your own—don't miss this opportunity!

Listing courtesy of Dean Rolle · Iron Valley Real Estate HR · REIN MLS #10629415

VaHome team overview

Our read on this home

At a glance

A century-old three-bedroom home on Chestnut Street in Portsmouth, Virginia — just two minutes from Norfolk Naval Shipyard and USCG Base Portsmouth. With 1,456 square feet of living space and a 1920 build, this is classic Hampton Roads character in one of the region's most base-accessible locations.

Read the full overview ↓

Why this home stands out

Homes this close to two major installations — Norfolk Naval Shipyard and USCG Base Portsmouth literally two minutes away — are genuinely rare. Add a 1920 build that carries the kind of architectural bones you simply don't find in newer construction: thick plaster walls, period proportions, and a street presence that newer subdivisions can't replicate. For buyers who want proximity and character in the same package, 1908 Chestnut Street is a hard combination to beat.

BRIGHTON and the Portsmouth real estate market

Chestnut Street sits in the heart of Portsmouth, one of Hampton Roads' oldest and most historically layered cities. Portsmouth homes near the shipyard corridor tend to be tight-knit, walkable blocks where neighbors actually know each other — the kind of street culture that takes decades to develop and can't be manufactured. The city itself straddles the Elizabeth River directly across from Norfolk, giving you access to the broader metro without the Norfolk price premium. Downtown Portsmouth is just minutes away, where the waterfront has seen steady reinvestment — think local restaurants, the Children's Museum of Virginia, and the Portside festival grounds. The Olde Towne historic district, one of the largest collections of pre-Civil War architecture on the East Coast, is a short drive or bike ride. Portsmouth's blend of maritime heritage, walkable neighborhoods, and genuine community identity makes it one of the more underappreciated addresses in coastal Virginia.

What's nearby

Day-to-day errands are straightforward from 1908 Chestnut Street. Grocery options and pharmacy stops are reachable within a short drive along the main corridors. The Elizabeth River Trail connects Portsmouth's waterfront to miles of multi-use path — great for morning runs or weekend rides. Portside Marina and the downtown waterfront put coffee shops and casual dining within easy reach. For bigger shopping runs, Military Highway and the broader Chesapeake corridor are accessible via I-264. Norfolk's Ghent neighborhood and MacArthur Center are just across the river via the Downtown Tunnel.

For different buyers

For military families relocating

Two minutes to Norfolk Naval Shipyard and two minutes to USCG Base Portsmouth — the commute math here is almost unfair. For active-duty families, that kind of gate-to-door time means more hours at home and fewer hours in Hampton Roads traffic. A VA loan can make ownership at this location straightforward, and the 1920 build gives you a home with real character rather than cookie-cutter finishes. This address was practically drawn with military households in mind.

For first-time buyers

A three-bedroom, two-bath home built in 1920 with 1,456 square feet in Portsmouth checks a lot of boxes for a first purchase — manageable size, genuine character, and a location that holds long-term appeal thanks to its proximity to two major installations. The bones of a century-old home reward buyers who appreciate craftsmanship over the uniform look of newer builds. If you've been exploring a VA loan, this kind of base-adjacent address is exactly the scenario that benefit was designed for.

More buyer questions

How far is 1908 Chestnut Street from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is approximately two minutes from 1908 Chestnut Street — one of the shortest gate-to-door commutes you'll find in the Portsmouth market. The proximity is a significant draw for active-duty personnel and civilian shipyard employees alike.

How far is 1908 Chestnut Street from USCG Base Portsmouth?

USCG Base Portsmouth is also roughly two minutes away, making 1908 Chestnut Street exceptionally well-positioned for Coast Guard families. Both installations are accessible without getting on a major highway.

What is the property type and size at 1908 Chestnut Street?

1908 Chestnut Street is a residential single-family home with 3 bedrooms, 2 bathrooms, and 1,456 square feet of living space, built in 1920.

Is 1908 Chestnut Street in a flood zone?

Flood zone status 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 flood insurance implications with your agent.

What is the neighborhood like around 1908 Chestnut Street in Portsmouth?

The Chestnut Street area sits in a mature, walkable part of Portsmouth with a mix of early-twentieth-century homes and long-established community character. Downtown Portsmouth's waterfront, the Olde Towne historic district, and the Elizabeth River Trail are all close by.

Want to see 1908 Chestnut Street in person or talk through the numbers? Tom and Dariya Milan at LPT Realty know this Portsmouth corridor well — reach out and let's set something up.

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

1920

Price / sqft

$144

HOA

None

Taxes

$2,458/yr

County

Portsmouth VA

Waterfront

Yes

MLS #

10629415

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

Flood & environment

The flood answer first — quantified, not buried

FEMA flood zone AE · base flood elevation 8 ft · Special Flood Hazard Area (flood insurance typically required) · FIRM 515529

Flood Risk

Looking up FEMA flood zone…

Zone AE typically means lenders require flood insurance — factor it into the monthly numbers below.

Hurricane evacuation zone: Zone A · VDEM Know Your Zone

Outside all mapped AICUZ jet-noise contours and Accident Potential Zones.

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

$1,356/mo

Principal & interest

$1,090

Property tax

$205

Home insurance

$61

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

Asking vs. assessment

106% of $198,280

City assessment record · taxes $2,458/yr

Land share of assessed value

28% — $54,690

Improvements $143,590 · assessor record ✓

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

$85,000 – $287,000

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.

34 Alden AVE · 1.5 mi · 1,504 sqft$260,000 sold 2026-04
31 Decatur ST · 1.6 mi · 1,400 sqft$265,000 sold 2026-03
19 Burtis ST · 1.6 mi · 1,400 sqft$85,000 sold 2026-05

Sale & Tax History

List Price

$210,000

Price / Sq Ft

$144

Annual Taxes

$2,458

Monthly Tax

$205

HOA

None

Tax Rate (effective)

1.17%

Sale Timeline (this listing)

EventDatePriceDetail
ListedApr 11, 2026$210,000—
Currently listed—$210,000—

Public-Records Assessment

Source: City Assessor via Hampton Roads Regional Parcels.

6% above assessment

Total Assessed

$198,280

Land

$54,690

Improvement

$143,590

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:

Portsmouth 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

65 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 1908 Chestnut St in a good school zone?+
The assigned zones on the listing record are Brighton Elementary (GreatSchools 5/10), Cradock Middle, Manor High (GreatSchools 2/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 1908 Chestnut St in a flood zone?+
FEMA maps this parcel in Zone AE with a base flood elevation of 8 ft — a high-risk flood band where lenders typically require flood insurance. See the flood section on this page for the full details and sources, and verify with an elevation certificate.
Is there a gym near 1908 Chestnut St?+
Yes — Brikhouse Boxing and Fitness, LLC is about 0.2 miles away, per the cached nearby-places record for this address.
Are there parks near 1908 Chestnut St?+
Jefferson Park is about 0.3 miles away.
Where is the nearest grocery store to 1908 Chestnut St?+
Dollar General is about 0.2 miles away. The closest dining on record is 7-Eleven (0.1 mi).
Does 1908 Chestnut St have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 1908 Chestnut St built?+
It was built in 1920, 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 Dean Rolle · Iron Valley Real Estate HR · REIN MLS #10629415

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.

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

Call or text (757) 777-7577

1908 Chestnut St, Portsmouth, Virginia 23704 · MLS #10629415 · 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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