0 days on market
$259,000
2209 Wintergreen Dr
Chesapeake, Virginia 23323
MLS# 10637358 · BRENTWOOD · Chesapeake VA
Updated yesterday · Source: REIN MLS
Est. payment
$1,478/mo
Edit below
Price / sq ft
$262
989 sq ft
Days on market
0
New listing
HOA
None
Year built
1952
74 yrs old
Beds
3
Full Baths
1
Half Baths
0
Sq Ft
989
Garage
Yes
Schools
- ElementaryG.A. Treakle Elementary School8/10
- MiddleDeep Creek Middle School7/10
- 5/10
Info provided by GreatSchools
About this home
This charming home is located in a well-established, tranquil setting filled with longtime residents and a true sense of community. Lovingly maintained by previous owner for 63 years, the property offers character and pride of ownership throughout. Enjoy a large fenced backyard with plenty of space for entertaining, gardening, pets or relaxing outdoors. Conveniently located while still offering a tranquil residential…
Listed by Debbie Crevier-Kent · Cottage Street Realty LLC
VaHome Team property overview
A compact, well-located three-bedroom home in Chesapeake built in 1952, sitting just minutes from Norfolk Naval Shipyard and USCG Base Portsmouth. At 989 square feet on a manageable lot, it offers straightforward living with everyday conveniences practically at your doorstep.
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Why this home stands out
What sets 2209 Wintergreen Drive apart is its rare combination of military-base proximity and walkable daily convenience. Norfolk Naval Shipyard is a six-minute drive, USCG Base Portsmouth is seven minutes away, and groceries, dining, a gym, and two parks are all within a half-mile. For a 1952-era home, that kind of location efficiency is genuinely hard to beat in this price range of Chesapeake.
BRENTWOOD and the Chesapeake real estate market
Wintergreen Drive sits in a quiet, established residential pocket of western Chesapeake — a city that consistently ranks among the most livable in Virginia thanks to its low-density feel, strong infrastructure, and easy access to the broader Hampton Roads region. The streets here have a settled, neighborhood-first character: modest yards, mature trees, and neighbors who tend to stick around. If you've been searching chesapeake homes for sale 23321 and wondering what daily life actually looks like in this zip code, this corner of the city gives you a clear answer — calm and convenient in equal measure. Chesapeake sits in its own independent city jurisdiction, meaning you get city services without the density of Norfolk or Virginia Beach. The western side of Chesapeake in particular has a reputation for accessibility: you're close to the Elizabeth River, close to the shipyard corridor, and still within reasonable reach of downtown Norfolk and the Chesapeake city center.
What's nearby
Day-to-day errands are genuinely easy from Wintergreen Drive. Food Lion is just 0.6 miles away for grocery runs, and Dunkin' is the same distance when you need a morning coffee. Prefer a quick stop? McDonald's and 7-Eleven are both within half a mile. For dining, Hardee's, Fortune China, and Hypnotic's Restaurant and Lounge are all within 0.3 miles — a walkable dinner option on any given evening. Planet Fitness is 0.4 miles away if you keep a regular workout schedule. Families and anyone who enjoys outdoor time will appreciate Brentwood Play Area just 0.2 miles from the front door, with Afton Park offering more green space at 0.7 miles.
For different buyers
For military families relocating
Norfolk Naval Shipyard is six minutes from your front door, and USCG Base Portsmouth is seven. For active-duty households, that kind of commute is a genuine quality-of-life advantage — less time in the car means more time at home. A VA loan can make this three-bedroom a straightforward path to ownership, and the location means your BAH works efficiently in this part of Chesapeake.
For first-time buyers
Three bedrooms, one bath, and under a thousand square feet — 2209 Wintergreen Drive is a practical, manageable starting point for first-time ownership. The 1952 build gives it solid bones, and the surrounding neighborhood is established and stable. With groceries, a gym, parks, and dining all within walking distance, you're stepping into a home that supports real daily life from day one.
Frequently asked questions
How far is 2209 Wintergreen Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is approximately six minutes by car from 2209 Wintergreen Drive, making it one of the closest residential options to the shipyard in the Chesapeake area.
How far is 2209 Wintergreen Drive from USCG Base Portsmouth?
USCG Base Portsmouth is about seven minutes away by car — a short, straightforward commute that makes this address a practical choice for Coast Guard personnel.
What is the flood zone status for 2209 Wintergreen Drive?
Flood zone designation for this property is displayed in the FloodRisk tile on this page; we recommend reviewing it and discussing flood insurance options with your agent before making any decisions.
Is there a park near 2209 Wintergreen Drive?
Yes — Brentwood Play Area is just 0.2 miles away, and Afton Park is 0.7 miles from the address, giving you two accessible outdoor spaces close to home.
Does 2209 Wintergreen Drive have a garage?
Garage details for this property are best confirmed through the current listing data or by scheduling a walkthrough with your agent, as structural features can vary with updates over time.
Curious whether 2209 Wintergreen Drive fits your situation? Tom and Dariya Milan at LPT Realty know this part of Chesapeake well — reach out and let's talk through it.
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
1
Half Baths
0
Approx Sq Ft
989
Stories
1
Fireplaces
0
Flooring
Carpet, Vinyl, Wood
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer Hookup, Range, Elec Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$259,000
Price / Sq Ft
$262
Annual Taxes
$706
Monthly Tax
$59
HOA
None
Tax Rate (effective)
0.27%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 1, 2026 | $259,000 | — |
| Currently listed | — | $259,000 | — |
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
$1,478/moPrincipal & interest
$1,344
Property tax
$59
Home insurance
$76
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 Cottage Street Realty LLC · MLS# 10637358
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$259,000
2209 Wintergreen DR, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
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