# 8368 Whispering Pines Trail, Windsor, VA 23487

> **TL;DR:** 3bd/2ba single family, $400,000 ($181/sqft), built 1975, 2,208 sqft.
> A/C. Est. $2,140/mo. Listed 94 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $400,000 |
| Price/sqft | $181 |
| Bedrooms | 3 |
| Bathrooms | 2 full |
| Square Feet | 2,208 |
| Year Built | 1975 |
| Lot Size | 194,278 sqft (4.46 acres) |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 94 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $2,023 |
| Estimated Insurance | $117 |
| **Total** | **$2,140** |

## Nearby Schools

- **Elementary:** Windsor Elementary
- **Middle:** Georgie D. Tyler Middle School

## Key Amenities

- A/C

## Property Highlights

- Built in 1975
- 4.46 acre lot

## Description

### Agent Description
Welcome to Whispering Pines Trail, a rare opportunity to own a beautifully updated home on 4.46 private acres in Windsor. This 3-bedroom, 2-bath home offers 2,208 square feet of move-in ready living space with a fully updated kitchen, renovated primary bath, new flooring, paint, and trim throughout. The spacious upstairs family room is wired for surround sound and projector, with the screen conveying. Outdoors, you'll find exceptional workshop and storage space including a 30'x86' main shop, a 26'x37' secondary shop and cinder block pump house with room for additional storage. Enjoy the peace and privacy of country living while having room for hobbies, equipment, recreation, or a home-based business. A truly unique property offering space, versatility, and endless possibilities in desirable Windsor. Owner Financing available.

## Location

- **Address:** 8368 Whispering Pines Trail, Windsor, VA 23487
- **County:** Isle of Wight County VA
- **Neighborhood:** ALL OTHERS AREA 65
- **Coordinates:** 36.908614, -76.776964
- **Google Maps:** https://www.google.com/maps?q=36.908614,-76.776964

## Virtual Tour & Media

- **Video Tour:** https://atlas-reel-estate-co.aryeo.com/sites/eojbvqnz/unbranded

## Listing Agent

- **Name:** Leslie Brennan
- **Brokerage:** Aweigh Real Estate
- **Phone:** (757) 724-8657
- **Broker Phone:** (757) 724-8657
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/8368-Whispering-Pines-Trl_Windsor_VA_23487_M55913-85658?f=listhub&s=REINVA&m=10641278&c=propsimple)

## Photos

![8368 Whispering Pines Trail - Photo 1](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1409804580r.jpg)

![8368 Whispering Pines Trail - Photo 2](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1800931217r.jpg)

![8368 Whispering Pines Trail - Photo 3](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f826718342r.jpg)

![8368 Whispering Pines Trail - Photo 4](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1527206682r.jpg)

![8368 Whispering Pines Trail - Photo 5](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1832256551r.jpg)

![8368 Whispering Pines Trail - Photo 6](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3409466984r.jpg)

![8368 Whispering Pines Trail - Photo 7](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f4189658750r.jpg)

![8368 Whispering Pines Trail - Photo 8](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3108917850r.jpg)

![8368 Whispering Pines Trail - Photo 9](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3725195785r.jpg)

![8368 Whispering Pines Trail - Photo 10](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2463754350r.jpg)

![8368 Whispering Pines Trail - Photo 11](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2656580730r.jpg)

![8368 Whispering Pines Trail - Photo 12](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1823970357r.jpg)

![8368 Whispering Pines Trail - Photo 13](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2712521295r.jpg)

![8368 Whispering Pines Trail - Photo 14](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3572328279r.jpg)

![8368 Whispering Pines Trail - Photo 15](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1430272518r.jpg)

![8368 Whispering Pines Trail - Photo 16](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2513151883r.jpg)

![8368 Whispering Pines Trail - Photo 17](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3057205488r.jpg)

![8368 Whispering Pines Trail - Photo 18](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1746782250r.jpg)

![8368 Whispering Pines Trail - Photo 19](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2790060877r.jpg)

![8368 Whispering Pines Trail - Photo 20](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2337602800r.jpg)

![8368 Whispering Pines Trail - Photo 21](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f40229885r.jpg)

![8368 Whispering Pines Trail - Photo 22](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3802774121r.jpg)

![8368 Whispering Pines Trail - Photo 23](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1842096721r.jpg)

![8368 Whispering Pines Trail - Photo 24](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2836987017r.jpg)

![8368 Whispering Pines Trail - Photo 25](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3915739307r.jpg)

![8368 Whispering Pines Trail - Photo 26](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2557573516r.jpg)

![8368 Whispering Pines Trail - Photo 27](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1599936299r.jpg)

![8368 Whispering Pines Trail - Photo 28](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3901727278r.jpg)

![8368 Whispering Pines Trail - Photo 29](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3571461726r.jpg)

![8368 Whispering Pines Trail - Photo 30](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1309465488r.jpg)

![8368 Whispering Pines Trail - Photo 31](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f334812859r.jpg)

![8368 Whispering Pines Trail - Photo 32](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1893086459r.jpg)

![8368 Whispering Pines Trail - Photo 33](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f979700825r.jpg)

![8368 Whispering Pines Trail - Photo 34](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3094489938r.jpg)

![8368 Whispering Pines Trail - Photo 35](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f897039630r.jpg)

![8368 Whispering Pines Trail - Photo 36](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2364065466r.jpg)

![8368 Whispering Pines Trail - Photo 37](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2862428543r.jpg)

![8368 Whispering Pines Trail - Photo 38](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3324562513r.jpg)

![8368 Whispering Pines Trail - Photo 39](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2861381103r.jpg)

![8368 Whispering Pines Trail - Photo 40](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f2016445842r.jpg)

![8368 Whispering Pines Trail - Photo 41](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f175307737r.jpg)

![8368 Whispering Pines Trail - Photo 42](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3179501547r.jpg)

![8368 Whispering Pines Trail - Photo 43](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f230266682r.jpg)

![8368 Whispering Pines Trail - Photo 44](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3424134609r.jpg)

![8368 Whispering Pines Trail - Photo 45](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3956965802r.jpg)

![8368 Whispering Pines Trail - Photo 46](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f3556773104r.jpg)

![8368 Whispering Pines Trail - Photo 47](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f304021809r.jpg)

![8368 Whispering Pines Trail - Photo 48](http://lh.rdcpix.com/b96fd90715b02b03ee6d8eca1754c9ael-f1390666083r.jpg)

---

**MLS#:** 10641278 | **Updated:** 2026-09-24
**Source:** listhub

*Copyright © 2026 Real Estate Information Network, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/8368-whispering-pines-trail-windsor-va-23487-10641278)

---

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