301 Windlesham Dr
Chesapeake, VA 23322
Great Bridge East- 4 Beds
- 4 Baths
- 2,590 sqft (on 2.05 acres)
4 Beds
4 Baths
2,590 sqft
(on 2.05 acres)
Local Information
-- mins to
Description
Move-in ready and perfectly positioned in the highly sought-after Great Bridge School District, this rare 2-acre property offers exceptional space, privacy, and versatility. In addition to the attached 2-car garage, the standout feature is the impressive 2700+sqft detached garage — ideal for car enthusiasts, hobbyists, storage, or future expansion possibilities. Thoughtful updates include vinyl siding (2015), vinyl windows (2016), HVAC replacement (2017 & 2021), a 50-gallon water heater and architectural roof (2018), plus a full interior refresh in 2026 with new lighting and plumbing fixtures, fresh paint, new carpet, and updated hardware throughout. Hard-surface flooring flows through all main living areas and a relaxing hot tub conveys. Enjoy outdoor living on the long front porch with swing or the screened back porch overlooking the spacious yard. All kitchen and laundry appliances convey. A truly unique opportunity — come see it today!
301 Windlesham Dr, Chesapeake, VA 23322 is a 4 bedroom, 4 bathroom, 2,590 sqft single-family home in Great Bridge East, built in 1983. It is currently off market. The Trulia Estimate is $653,300, with a rent estimate of $3,860/month.
Home Highlights
Parking
Garage
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
47 days ago
Home Details for 301 Windlesham Dr
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Interior Details Basement: Crawl SpaceNumber of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom, Full Bathroom, Dining Room, Family Room, Great Room, Kitchen, Living Room, Utility Room |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4 |
Dimensions and Layout Living Area: 2590 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Disposal, Dryer, Microwave, Electric Range, Refrigerator, Washer, Electric Water HeaterDishwasherDisposalDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Heat Pump,ZonedHas CoolingAir Conditioning: Heat Pump,ZonedHas HeatingHeating Fuel: Heat Pump |
Fireplace & Spa Number of Fireplaces: 1Fireplace: Wood BurningSpa: Hot TubHas a FireplaceHas a Spa |
Windows, Doors, Floors & Walls Window: Window TreatmentsDoor: Storm Door(s)Flooring: Carpet, Laminate/LVP, VinylCommon Walls: No Common Walls |
Levels, Entrance, & Accessibility Stories: 2Levels: TwoAccessibility: Front-mounted Range Controls, Main Floor LaundryFloors: Carpet, Laminate LVP, Vinyl |
View Has a ViewView: Trees/Woods |
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Exterior Home Features Roof: Asphalt ShinglePatio / Porch: Deck, Porch, Screened PorchFencing: None |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 5No CarportHas a GarageNo Attached GarageNo Open ParkingParking Spaces: 5Parking: Garage Att 2 Car,Garage Det 3+ Car,Oversized,Garage Door Opener |
Pool Pool: None |
Frontage Waterfront: Not WaterfrontNot on Waterfront |
Water & Sewer Sewer: City/County |
Farm & Range Not Allowed to Raise Horses |
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Year Built Year Built: 1983 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Transitional |
Building Construction Materials: Vinyl SidingNot a New ConstructionNot Attached Property |
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Price List Price: $652,500 |
Status Change & Dates Off Market Date: Sat May 23 2026Possession Timing: Settlement |
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MLS Status: Sold |
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Direction & Address City: ChesapeakeCommunity: All Others Area 32 |
School Information Elementary School: Southeastern ElementaryJr High / Middle School: Great Bridge MiddleHigh School: Great Bridge |
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No HOA |
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Lot Area: 2.05 Acres |
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Contingencies: Non Contingent |
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Mls Number: 10635700Attic: Walk-In |
Last check for updates: about 7 hours ago
Listed by Madonna Bossa
World Class Realty, (757) 228-7773
Bought with: Paul Morreira, Iron Valley Real Estate HR, (757) 645-9700
Source: REIN Inc., MLS#10635700

Market trends in Chesapeake
Last updated May 2026
Avg. sale price
$386K
$3.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$213
$3MoM
Available listings
909
54MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $5,318 |
| Assessment | $526,500 |
Home facts updated by county records
Comparable Sales for 301 Windlesham Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.03 | Single-Family Home | $620,000 | 02/04/26 | 4 | 3 | 3,532 | |
0.20 | Single-Family Home | $714,000 | 10/10/25 | 4 | 3 | 2,490 | |
0.34 | Single-Family Home | $1,100,000 | 06/01/26 | 5 | 4.5 | 4,319 | |
0.33 | Single-Family Home | $550,000 | 02/20/26 | 4 | 2.5 | 2,780 | |
0.18 | Single-Family Home | $775,000 | 04/24/26 | 5 | 3 | 3,328 | |
0.17 | Single-Family Home | $808,000 | 06/17/26 | 5 | 3.5 | 3,600 | |
0.45 | Single-Family Home | $500,000 | 10/06/25 | 4 | 3 | 2,322 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 301 Windlesham Dr.
What Locals Say about Great Bridge East
At least 103 Trulia users voted on each feature.
97 % Say yards are well-kept
94 % Say car is needed
93 % Say parking is easy
90 % Say people would walk alone at night
89 % Say it's dog friendly
86 % Say it's quiet
81 % Say kids play outside
80 % Say there's holiday spirit
66 % Say streets are well-lit
62 % Say neighbors are friendly
58 % Say they plan to stay for at least 5 years
50 % Say there are sidewalks
40 % Say there's wildlife
40 % Say there are community events
35 % Say it's walkable to grocery stores
21 % Say it's walkable to restaurants
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near 301 Windlesham Dr
Off Market Homes Near 301 Windlesham Dr

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Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.
This application does not include information on all of the properties available for sale at this time.
Copyright 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW. REIN updates its listings on a daily basis. Data last updated: 2026-07-06 23:22:16 PDT.
Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.
This application does not include information on all of the properties available for sale at this time.