3 Bed / 2 ½ Bath Log Home on 5.37 acres in Isle of Wight County, VA!

$550,000
Windsor, VA
5.4 acres

9161 Whispering Pines Trl
Windsor, VA 23487
United States

New
This listing is provided by Land and Farms Realty.

For immediate assistance with this listing call Caleb Hooker at 757-810-5303 (chooker@mossyoakproperties.com). 

Great rural retreat for your new homestead with this 3 Bed / 2 ½ Bath Stunning Log Home on 5.37 acres near Windsor, Virginia! Call Caleb Hooker at 757-810-5303 to schedule a showing today.

Nestled in the heart of Isle of Wight County, Virginia, this charming rural retreat offers a mix of modern comforts and country appeal. This stunning 2 floor log home sits on 5.37 acres and offers countless opportunity for the homesteader or as a great rural retreat close to the amenities of town! 

• Home: 1,742 sq ft log home with a rustic yet functional layout:  

First Floor:  

â—¦ 13 x12.5 ft Primary bedroom with ensuite 

â—¦ Large open living/dining area (27 x 27 ft) with fireplace and vaulted ceiling, 

â—¦ Galley style kitchen with large pantry, includes electric range, dishwasher, microwave, and double doored refrigerator 

â—¦ 7.5 x 7 ft utility room complete with washer and dryer and a tankless hot water heater. 

â—¦ Half bath and rear deck access off the kitchen.  

Second Floor: 

â—¦ 13 x 12 ft Bedroom 1 

â—¦ 13 x 11.5 ft Bedroom 2 

â—¦ 9 x 10 ft Full bath 

â—¦ 11.5 x 13.5 ft versatile loft space (great for an office, sitting area, or extra guest sleeping). 

• Exterior Features: 

• Secluded setting surrounded by mature timber, with Villines Swamp along the north side, enhancing wildlife habitat. 

• Full-length covered front porch. 

• Walk-out rear deck leading to an 18 ft above-ground pool. 

• Double car metal-roof carport (24 x 22). 

• 40 x 24 metal building with double roll-up doors, insulation, climate control, and loft storage/workspace (ideal for workshop or boat storage). 

• 32 x 10 barn/storage shed with a 32 x 22 pull-through covered storage area, plus chicken/duck pens.

Isle of Wight County School District 

• Elementary – K-5 – Windsor Elementary  

• Middle School – 6-8 – Georgie D. Tyler Middle School 

• High School – 9-12 – Windsor High School  

With all the features, this homestead offers a blend of seclusion, modern amenities, and practical outbuildings, perfect for those seeking a peaceful country lifestyle with space for hobbies or small-scale farming. Located just 15 minutes from both downtown historic Smithfield or Windsor, Virginia, the property offers great access to both US-460 or US-17 and the greater Hampton Roads area.  

Whether you’re looking for a peaceful rural escape or your own small farmette, this property offers the ideal blend of privacy, natural beauty, and accessibility. With so much to offer, it truly is a rare find in the heart of southern Virginia! 

Links of Interest: Isle of Wight County: 

https://www.isleofwight.gov/  

Town of Smithfield: https://www.smithfieldva.gov/  

Historic Fort Boykin: https://www.historicisleofwight.com/fort-boykin.html  

Chippokes State Park: https://www.dcr.virginia.gov/state-parks/chippokes   

I invite you to explore the embedded map in this listing for a birds-eye view of the property and surrounding area 

https://id.land/maps/e8b9f503dcb34b3ce9b9c523b680094d/share/unbranded 

This property is shown by appointment only with proof of funds required. Please contact me to schedule your showing today!

For more information on this and other land for sale in Isle of Wight County, contact Caleb Hooker at 757-810-5303 or by email at chooker@mossyoakproperties.com, or visit landandfarmsrealty.com.

Last updated
October 4, 2025
MLS ID / MOPLS ID
91261
Barn
Bird Watching
Hunting
Recreational
Residential
Small Game Hunting
Turkey Hunting
Upland Game
Whitetail Hunting
Address

9161 Whispering Pines Trl
Windsor, VA 23487

Acreage
5.37
Bedrooms
3
Bathrooms
2
MLS ID / MOPLS ID
91261
Price
$550,000

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