0 days on market
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$375,000
4021 Tanglewood Trl
Chesapeake, Virginia 23325
MLS# 10637502 · TANGLEWOOD · Chesapeake VA
Updated 16 hours ago · Source: REIN MLS
Est. payment
$2,315/mo
Edit below
Price / sq ft
$251
1,494 sq ft
Days on market
0
New listing
HOA
None
Year built
1958
68 yrs old
Beds
3
Full Baths
2
Half Baths
0
Sq Ft
1,494
Garage
No
About this home
Move-in ready today! The big-ticket items are already completed for you at 4021 Tanglewood Trail. This beautiful corner lot in a quiet, established neighborhood has seen all the large items updated recently. Brand new kitchen in 2026; new HVAC and ductwork in 2025; new roof and plumbing (including sewer line to the street) in 2024. Enjoy original hardwood floors and updated bathrooms as well. The converted garage is…
Listed by Jerry Trickie · KW Coastal Virginia Chesapeake
VaHome Team property overview
4021 Tanglewood Trail is a 3-bedroom, 2-bath, 1,494-square-foot home built in 1958 in Chesapeake, Virginia. Sitting close to multiple green spaces and just minutes from two major military installations, it offers a grounded, established neighborhood feel with everyday conveniences close at hand.
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Why this home stands out
What sets Tanglewood Trail apart is the combination of mid-century bones and a location that genuinely delivers on convenience. Three parks are within a mile, a local farm market is under a mile away, and both USCG Base Portsmouth and Norfolk Naval Shipyard are a seven-minute drive. For a 1,494-square-foot home on a quiet residential street, the access-to-footprint ratio is hard to beat in this part of Chesapeake.
TANGLEWOOD and the Chesapeake real estate market
4021 Tanglewood Trail sits in an established residential pocket of Chesapeake, Virginia — a city that consistently ranks among the safest and most livable in the mid-Atlantic. This part of Chesapeake carries the quiet, tree-lined character you'd expect from a neighborhood built out in the late 1950s: mature landscaping, wide lots, and streets where neighbors actually know each other. It's not a flashy new-construction corridor, and that's exactly the point. The homes here have history, and the community around them has settled into something comfortable and real. Chesapeake itself spans from the Dismal Swamp to the Elizabeth River, giving residents access to both natural escapes and urban amenities without the density of neighboring Norfolk or Virginia Beach. The 23325 zip code places you close to the city's northern edge, which means quick access into Portsmouth and Norfolk while still enjoying Chesapeake's comparatively relaxed pace. Daily life here moves at a human speed — walkable green space, local flavor, and a genuine sense of place.
What's nearby
Lecove Park is just 0.7 miles away, and Blue Heron Landing Park is only slightly farther at 0.8 miles — both easy walks or quick bike rides for anyone who likes to start the day outside. Poplar Hall Park rounds out the trio at a flat mile. For groceries and fresh produce, Beasley's Farm is 0.9 miles away — a local option that beats a big-box run on most days. When you're ready to eat out, Levels Lounge and A Taste of the Caribbean are both under a mile, giving you solid variety without a long drive. A 7-Eleven nearby covers quick coffee and convenience stops.
For different buyers
For military families relocating
USCG Base Portsmouth and Norfolk Naval Shipyard are each about seven minutes from the front door — an unusually short commute that makes rotation planning a lot less stressful. A VA loan can make purchasing a home like this straightforward, and the established neighborhood means you're not waiting on new infrastructure to catch up. Short drives, real community, and a home with room to settle in.
For first-time buyers
A 3-bedroom, 2-bath home built in 1958 means you're getting real square footage — 1,494 feet — in a neighborhood that's already proven itself over decades. There's no guesswork about how the street will develop; it's been here. For a first purchase, that kind of stability matters. Add three parks within a mile and local dining close by, and daily life feels comfortable from day one.
Frequently asked questions
How far is 4021 Tanglewood Trail from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is approximately seven minutes from 4021 Tanglewood Trail by car. The route is straightforward and avoids most of the congestion that affects longer cross-city commutes in Hampton Roads.
How far is 4021 Tanglewood Trail from USCG Base Portsmouth?
USCG Base Portsmouth is also about seven minutes away, making this address unusually well-positioned for personnel assigned to either installation. Both bases are accessible without navigating major highway interchanges.
What parks are near 4021 Tanglewood Trail?
Three parks fall within a mile of the address: Lecove Park at 0.7 miles, Blue Heron Landing Park at 0.8 miles, and Poplar Hall Park at 1.0 mile. All three are reachable on foot or by bike from Tanglewood Trail.
Is 4021 Tanglewood Trail 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. It's worth reviewing before making any decisions, as flood zone designations can affect insurance requirements.
What is the neighborhood like around 4021 Tanglewood Trail?
The street sits in an established, mid-century residential neighborhood in northern Chesapeake — quiet, tree-lined, and close to both green space and local dining. It has the feel of a community that's been around long enough to have real character.
Tom and Dariya Milan at LPT Realty know this part of Chesapeake well. Reach out to get honest answers about the home, the neighborhood, and what buying here actually looks like.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
3
Full Baths
2
Half Baths
0
Approx Sq Ft
1,494
Stories
1
Fireplaces
0
Flooring
Carpet, Laminate/LVP, Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer Hookup, Microwave, Elec Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$375,000
Price / Sq Ft
$251
Annual Taxes
$3,121
Monthly Tax
$260
HOA
None
Tax Rate (effective)
0.83%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 4, 2026 | $375,000 | — |
| Currently listed | — | $375,000 | — |
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:
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
Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled hourly from the REIN feed.
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
$2,315/moPrincipal & interest
$1,946
Property tax
$260
Home insurance
$109
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 KW Coastal Virginia Chesapeake · MLS# 10637502
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$375,000
4021 Tanglewood TRL, CHESAPEAKE VA 23325
Chesapeake, Virginia 23325
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