Skip to main content
VaHome.com
Portsmouth › PRENTIS PARK › 2104 Chestnut St✓ Source: REIN MLS #10656721 · record updated Oct 6, 2026 · synced every 2 min · your inquiry is never resold
2104 Chestnut ST, PORTSMOUTH VA 23704 - Main photo
2104 Chestnut ST, PORTSMOUTH VA 23704 - Photo 2
2104 Chestnut ST, PORTSMOUTH VA 23704 - Photo 3
2104 Chestnut ST, PORTSMOUTH VA 23704 - Photo 4
2104 Chestnut ST, PORTSMOUTH VA 23704 - Photo 5
3beds
2.1baths
1,592sqft
0days on market

2104 Chestnut St, Portsmouth, VA 23704

New ListingResidential · built 2009 · PRENTIS PARK

Facts & features

Type

Residential

Year built

2009

Price / sqft

$179

HOA

None

Taxes

$3,030/yr

County

Portsmouth VA

MLS #

10656721

Interior

Bedrooms
3
Full baths
2
Half baths
1
Approx. sqft
1,592
Stories
2
Flooring
Laminate/LVP
Ensuite bedrooms
1
Total rooms
6
Other rooms
Attic, PBR with Bath, Porch
Appliances
Dishwasher, Dryer, Microwave, Range, Washer

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Crawl
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool

Utilities & systems

Heating
Heat Pump
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
PRENTIS PARK
Zoning
UR
Ownership
Fee Simple
Garage
No
Parking
Driveway Spc, Street
Possession
SETTLEMENT
Disclosures
Disclosure Statement

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

About this home

Charming 3-bedroom, 2.5-bath home offering 1,592 sq ft in Portsmouth's Prentis Park area. Situated on a corner lot, this two-story property features a welcoming covered front porch, classic exterior details, and established landscaping. The main level offers a functional layout with comfortable living spaces, while the upper level provides three bedrooms and two full baths. Enjoy outdoor living from the spacious rear deck overlooking the yard. Conveniently located in Portsmouth with easy access to nearby shopping, dining, parks, and major roadways. A great opportunity to own a home with character, outdoor space, and a desirable corner-lot setting.

Listing courtesy of Tiffany Gelzinis · Real Broker LLC · REIN MLS #10656721

Tom & Dariya's overview

Our read on this home

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

At a glance

2104 Chestnut Street is a 3-bedroom, 2.1-bath home built in 2009 in Portsmouth, Virginia. At 1,592 square feet, it offers a modern layout in a city packed with history and convenience. Norfolk Naval Shipyard is about two minutes away. Few Portsmouth homes for sale sit this close to the waterfront district and two major installations.

Keep searching in Portsmouth

See all Portsmouth homes for sale, including homes for sale in 23704, homes for sale zoned for Manor High School, and homes for sale zoned for Brighton Elementary School. Browse every listing among homes for sale in Portsmouth — updated from the REIN MLS every few minutes. Nearby, look at Brighton homes for sale, Portsmouth waterfront homes for sale, Portsmouth condos and townhomes for sale, and new construction homes in Portsmouth.

Read the full overview ↓

Why this home stands out

Most homes built in this zip code before 2005 carry decades of deferred maintenance. This one was built in 2009, so the bones are newer — think updated systems, modern framing standards, and a layout designed for the way people actually live. Add a half-bath on the main level, 1,592 square feet of usable space, and a location that puts two federal installations within a two-minute drive, and 2104 Chestnut Street stands apart from older stock nearby.

PRENTIS PARK and the Portsmouth real estate market

Chestnut Street sits in a walkable, close-knit section of Portsmouth near the Elizabeth River waterfront. The streets here mix newer infill construction with established brick homes, giving the block a grounded, lived-in feel. Sidewalks connect you to parks, local eateries, and everyday errands without getting in a car. Portsmouth itself is one of the oldest cities in Virginia, and that history shows in the architecture, the riverfront, and the Olde Towne historic district just to the north. The city is compact and easy to navigate. Interstate 264 and the Downtown Tunnel connect Portsmouth to Norfolk and Virginia Beach in under 20 minutes. The Midtown Tunnel adds another direct route east. Public transit runs through the area, and the Passenger Ferry to Norfolk's waterfront is a short drive away. Anyone comparing homes for sale in Portsmouth will notice how much city you get for the square footage here. The 23704 zip code anchors the southwestern edge of the city, right against the shipyard and the river.

What's nearby

Church Food Mart is just 0.1 miles away for quick grocery runs. Save & Save Supermarket is half a mile out for a fuller shop. Emma's Restaurant and Lil Mammas Soul Kitchen are both 0.2 miles away — two solid options for a weeknight dinner without the drive. Ziggy's Street Eats is another 0.1 mile further. Mariner's Reef Cafe handles your morning coffee at 0.4 miles. Jefferson Park and Lansing Park are both within 0.4 miles for outdoor time. The Effingham Street Family YMCA is 0.8 miles away, and Callaghan Gym and Fitness Center is just 0.4 miles if you prefer a smaller gym.

For different buyers

Base commute and VA loan notes

Norfolk Naval Shipyard is about two minutes from 2104 Chestnut Street — one of the shortest base commutes you will find among homes for sale in 23704. USCG Base Portsmouth is equally close. VA loan financing is common in this zip code, and a 2009 build means the property meets standard VA appraisal conditions without the surprises older homes can bring.

For first-time buyers

A 2009 build means fewer unknowns than the older homes that dominate this part of Portsmouth. Three bedrooms, two full baths, a half-bath downstairs, and 1,592 square feet give you real room without overextending. Groceries, parks, and restaurants are all within half a mile. For anyone comparing homes for sale zoned for Manor High School and homes for sale zoned for Brighton Elementary School, this block checks both boxes.

More buyer questions

How far is 2104 Chestnut Street from Norfolk Naval Shipyard?

Norfolk Naval Shipyard is about two minutes away by car — roughly 0.5 miles southwest of the property. It is one of the closest residential streets to the main gate.

What is the flood zone status for 2104 Chestnut Street?

Flood zone information for this address is covered in the FloodRisk tile on this page. We recommend reviewing it before making any decisions.

Is there a homeowners association at 2104 Chestnut Street?

This property does not carry an HOA, so there are no association dues or use restrictions tied to the address.

What parks are near 2104 Chestnut Street?

Jefferson Park and Lansing Park are both within 0.4 miles. Scotts Creek Park is about 0.6 miles away and offers additional green space along the water.

When was 2104 Chestnut Street built?

The home was built in 2009, making it newer construction relative to most of the surrounding neighborhood stock in the 23704 zip code.

Tom and Dariya Milan know Portsmouth inside and out. Reach out to schedule a walkthrough of 2104 Chestnut Street and get straight answers about the neighborhood, the commute, and the process.

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

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

Portsmouth$240K – $330K3+ beds

By subscribing you agree to receive listing emails from Tom & Dariya Milan, Realtors, at most one a day. Unsubscribe anytime · Privacy PolicyBrokered by LPT Realty

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

Flood Risk (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 515529

High Risk

FEMA flood zone

AE (1% annual chance)

Base flood elevation

8 ft above sea level

Property elevation

6.7 ft above sea level

1.3 ft below BFE

USGS 3DEP digital elevation model

Special Flood Hazard Area — 1% annual chance of flooding. Federal flood insurance is required on most mortgages.

Data sources: Flood zone and base flood elevation come from FEMA\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 actual elevations across a single property can vary by several feet higher or lower than the figure shown. Use these numbers as a starting reference and do your own due diligence (a professional survey or elevation certificate) before relying on them for any financial, insurance, or construction decision.

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

Explore this neighborhood

Brighton

Brighton is a neighborhood in Portsmouth, Virginia. It has tree-lined streets and a mix of home styles. They reflect the area's deep local roots.

$275K

Median sale · 12 mo

$171

Sold $/sq ft

22d

Days on market

18

For sale now

$46K

HH income

55.2%

Owner-occupied

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

Explore Brighton →
Map of Brighton with neighborhood boundaryNeighborhood

Portsmouth houses for sale →

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

$1,814/mo

Principal & interest

$1,479

Property tax

$253

Home insurance

$83

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

$151,000 – $325,000

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.

908 Lincoln ST · 0.1 mi · 1,554 sqft$281,900 sold 2026-06
1807 Chestnut St · 0.1 mi · 1,512 sqft$305,000 sold 2026-06
2803 Elm AVE · 0.4 mi · 1,652 sqft$277,000 sold 2026-08

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

Sale & Tax History

List Price

$285,000

Price / Sq Ft

$179

Annual Taxes

$3,030

Monthly Tax

$253

HOA

None

Tax Rate (effective)

1.06%

Sale Timeline (this listing)

EventDatePriceDetail
ListedOct 6, 2026$285,000—
Currently listed—$285,000—

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:

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

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

Is 2104 Chestnut St in a good school zone?+
The assigned zones on the listing record are Brighton Elementary (VaHome School Score 3/10), Cradock Middle (VaHome School Score 1.4/10), Manor High (VaHome School Score 3.6/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 2104 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.
Does 2104 Chestnut St have an HOA?+
No — there are no HOA, condo, or association dues on the listing record for this property.
When was 2104 Chestnut St built?+
It was built in 2009, 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 Tiffany Gelzinis · Real Broker LLC · REIN MLS #10656721

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.

2104 Chestnut St, Portsmouth — photo

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

Call or text (757) 777-7577

2104 Chestnut St, Portsmouth, Virginia 23704 · MLS #10656721 · 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.

✆