image

Pleasant Oak: A Timeless Virginia Historic Home Beautiful Historic Home

3665 Old River Trail, Powhatan MLS# 9
21 April 2025

Historic Charm, Enduring Craftsmanship, and Rural Beauty in Powhatan County


Original 18th-Century Architecture Preserved with Care

Story & Photos

DOWNLOAD DETAILED BROCHURE
Aerial view of Pleasant Oak’s 26.18-acre retreat—a hidden gem nestled within a wooded canopy along one of Powhatan’s most scenic byway at 3665 Old River Trail in Powatan.
Aerial View of Pleasant Oak

Aerial view of 3665 Old River Trail in Powhatan, VA—a 26.18-acre historic retreat surrounded by mature woods, open lawns, and curated gardens. A winding drive leads to the main house and barn, offering exceptional privacy and space for gardening, recreation, or future use.

Entry hall at 3665 Old River Trail, Powhatan, VA—a gracious introduction to this historic home, featuring original wide-plank pine floors, hand-planed woodwork, and a classic side-passage staircase.
The Foyer

Entry hall at 3665 Old River Trail, Powhatan, VA—a gracious introduction to this historic home, featuring original wide-plank pine floors, hand-planed woodwork, and a classic side-passage staircase. Sunlight filters through tall six-over-nine windows, highlighting the craftsmanship and colonial character that define Pleasant Oak.

Elegant parlor at 3665 Old River Trail in Powhatan, VA—featuring original heart pine floors, deep-set six-over-nine windows, and a striking colonial fireplace with built-in bookcases.
The Parlor

Elegant parlor at 3665 Old River Trail in Powhatan, VA—featuring original heart pine floors, deep-set six-over-nine windows, and a striking colonial fireplace with built-in bookcases. A beautifully preserved space that reflects the home's 18th-century craftsmanship and timeless character.

Interior view of 3665 Old River Trail in Powhatan, Virginia, featuring original heart pine floors, wide board paneling, and a tiled fireplace.
The Sitting Room

Interior view of 3665 Old River Trail in Powhatan, Virginia, featuring original heart pine floors, wide board paneling, and a tiled fireplace. This warm, historic room reflects the timeless charm and craftsmanship of Pleasant Oak, a beautifully preserved historic property.

Bright passageway at 3665 Old River Trail in Powhatan, Virginia, connecting the original home to the 2001 renovation. Lined with windows overlooking the wooded grounds, this inviting space blends old and new, offering natural light, warm wood floors, and a seamless transition into the modern kitchen and family room at Pleasant Oak.
A Seamless Connection

This light-filled passage at 3665 Old River Trail connects the historic heart of the home to the 2001 addition. Framed by woodland and garden views, it offers a quiet spot to read or write, while creating an easy flow into the updated kitchen and family room. A graceful blend of past and present at Pleasant Oak.

Kitchen and family room at 3665 Old River Trail in Powhatan, Virginia, featuring custom cabinetry, stainless steel appliances, and an open layout. Part of the 2001 addition at Pleasant Oak, this bright space blends modern comfort with historic charm and opens to a screened porch overlooking the gardens.
Kitchen

The spacious kitchen and family room at 3665 Old River Trail were added in 2001, offering modern functionality while preserving the home’s timeless character. With custom cabinetry, stainless appliances, and an open layout perfect for gatherings.

BFamily room at 3665 Old River Trail in Powhatan, Virginia, featuring large windows, a gas fireplace, and traditional furnishings. This inviting space is part of the 2001 addition to Pleasant Oak, offering comfort, natural light, and views of the surrounding gardens.
Light-Filled Gathering Space

he family room at 3665 Old River Trail offers a bright and welcoming retreat with large windows, garden views, and access to the screened porch. Part of the 2001 addition, it features a gas fireplace and classic millwork, creating a cozy atmosphere that complements the home’s historic elegance.

Screened porch at 3665 Old River Trail in Powhatan, Virginia, featuring wooded views, outdoor seating, and space for dining. This tranquil retreat connects to the family room at Pleasant Oak and overlooks the private backyard.
Screened Porch Among the Trees

Step from the family room onto this spacious screened porch at 3665 Old River Trail, designed for year-round enjoyment. Surrounded by mature trees and views of the private backyard, it’s the perfect setting for dining, relaxing, or savoring the peaceful beauty of Pleasant Oak.

Primary bedroom at 3665 Old River Trail in Powhatan, Virginia, featuring heart pine floors, large windows, and a seating area. This spacious suite at Pleasant Oak includes an en suite bath and opens to a private garden patio.
Spacious Primary Suite

The primary bedroom at 3665 Old River Trail offers generous space, abundant natural light, and serene views of the gardens. With original heart pine floors and a cozy seating area, this peaceful retreat includes an en suite bath and direct access to a private patio just outside.

Main-level en-suite guest bedroom at 3665 Old River Trail in Powhatan, Virginia, featuring twin beds, hardwood floors, large windows, and a private bathroom. This comfortable space is ideal for guests or extended family living at Pleasant Oak.
Main Level Second En-Suite Bedroom

There is a second spacious en-suite bedroom on the main floor. This bright and welcoming space features large windows, hardwood floors, and a private bath—perfectly blending function and charm at Pleasant Oak.

View through original doorway at 3665 Old River Trail in Powhatan, Virginia, leading to upstairs rooms in the 18th-century portion of Pleasant Oak, featuring wide-plank floors, period millwork, and early American design.
Original Stair to Upper Chambers

This narrow doorway at 3665 Old River Trail opens to the upstairs rooms of the original 1700s structure. With its hand-hewn trim, wide-plank floors, and steep threshold, it reflects the charm and scale of early American architecture preserved at Pleasant Oak.

iew through original doorway at 3665 Old River Trail in Powhatan, Virginia, leading to upstairs rooms in the 18th-century portion of Pleasant Oak, featuring wide-plank floors, period millwork, and early American design.
Upstairs Bedroom in the 18th-Century Wing

One of three upper-level rooms in the original 1700s section of 3665 Old River Trail, this bedroom features dormered ceilings, mellow wood floors, and a charming fireplace. With period windows framing views of the grounds, it’s a quiet space steeped in early American character.

Second upstairs room at 3665 Old River Trail in Powhatan, Virginia, located in the 18th-century portion of Pleasant Oak. Features include original wood floors, dormer windows, and a view into the adjacent historic bedroom.
Second Upstairs Room in the Original Wing

Across of the other bedroom, this second upstairs room at 3665 Old River Trail features original wood floors, distinctive dormers, and charming views over the rooftops and gardens. A flexible space perfect for a sitting room, office, or guest nook—full of historic character at Pleasant Oak.

Small upstairs room at 3665 Old River Trail in Powhatan, Virginia, with original wide-plank floors, angled ceiling, and a vintage window overlooking the grounds. A quaint historic space in the original section of Pleasant Oak.
Tucked-Away Upper Room

his charming upstairs room at 3665 Old River Trail features original wide-plank floors, sloped ceilings, and a single-paned window framed in period trim. A cozy and quiet space perfect for storage, reading, or as a nostalgic reminder of Pleasant Oak’s 18th-century origins.

Historic smokehouse at 3665 Old River Trail in Powhatan, Virginia, with wood siding, tin roof, and fenced backdrop. A contributing structure to the 18th-century character of Pleasant Oak, reflecting early American homestead life.
The Historic Smokehouse

Completing the historic footprint of Pleasant Oak, this original smokehouse at 3665 Old River Trail stands beneath a canopy of trees. With its weathered wood siding and tin roof, it speaks to the self-sufficient lifestyle of early Virginia homesteads and adds to the authentic charm of this remarkable property.

Pleasant Oak Video

An Enduring Example of 18th-Century Virginia Architecture

A Home with History, Heart, and Soul

c.1760 - 1803

Location

3665 Old River Trail, Powhatan, VA

Nestled along one of Powhatan’s most scenic byways, 3665 Old River Trail offers a rare combination of rural beauty and convenient access. Surrounded by rolling countryside and mature forests, this private and peaceful setting is just 30 minutes from the cultural and culinary scene of Richmond and 10 minutes from the town of Goochland, an hour from Charlottesville and within easy reach of Williamburg and the coast.

Local favorites like Fairfield Coffee & Eatery, The Café at Maidens, and the four-generation County Seat Restaurant provide cozy spots to dine, while 1933 Public House and nearby Mexican, Chinese, and sushi options offer variety. Maxey’s Store and historic taverns round out the area’s unique charm and convenience.

The nearby James River and expansive Powhatan Wildlife Management Area invite outdoor recreation, while surrounding farms, vineyards, and equestrian estates add to the area’s appeal.



By Appointment Only

Do Not Enter Driveway Without Appointment

Listing Agents
Bridget 434-981-4149 & Pam 434-960-0161

Disclaimer
All information is deemed reliable but not guaranteed and is subject to errors, omissions, price changes, prior sale, or withdrawal without notice.

Expanding Our Digital Reach for Sellers

In the competitive world of real estate, standing out to potential buyers and sellers is crucial for success. For sellers, finding the right real estate agent is about more than just a name – it’s about trust, expertise, and confidence that their property will receive the attention it deserves. Additional websites dedicated to specific types of properties or local markets offer sellers distinct advantages. These specialized sites provide a focused platform where sellers and buyers can see how their unique needs are met. By showcasing tailored marketing strategies, local expertise, and property-specific resources, additional websites offer sellers a clearer picture of how their property will be uniquely promoted. This personalized approach not only enhances trust but also demonstrates a deep understanding of the seller's particular market, increasing the likelihood of a successful sale at the best possible price. With more dedicated space to highlight your property’s unique qualities and reach target buyers, these websites give sellers the confidence that their property will stand out in a crowded market. CharlottesvilleEquestrianProperties.com , VirginiaHistoricEstates.com, CharlottesvilleCountryEstates.com, FindaHomeinCharlottesville.com. HistoricHomesinVirginia.com, JumpintoGreenerPastures.com.

In today's digital marketplace, your home's story needs to be told far and wide. By leveraging the power of multiple agent websites, you're not just casting a wider net; you're ensuring your property resonates with a diverse audience, each potentially holding the key to your perfect buyer. This strategic approach elevates your listing beyond a simple address, transforming it into a compelling narrative that reaches the right eyes, at the right time, ultimately maximizing your home's potential and securing a successful sale.

The Power of Specialization
Our Websites Dominate The Market

Equestrian woman in a white shirt and khaki pants walking a chestnut horse with a white blaze, set against the backdrop of a red stable on a sunny day.

Horse Farms

CharlottesvileEquestrianProperties.com is your dedicated resource for horse farms and equestrian properties in Charlottesville and Central Virginia. We're passionate about connecting riders and equine enthusiasts with their dream properties, featuring an exclusive selection of homes, farms, and estates tailored for the equestrian lifestyle, complete with barns, riding arenas, and more.

Aerial view of a charming historic home with a green metal roof, landscaped gardens, mature trees, and a detached round-roofed structure. The fenced pasture suggests a perfect country or equestrian setting.

Virginia Historic Homes

VirginiaHistoricEstates.com is your gateway to historic homes and estates in Charlottesville and Central Virginia. Our expertise lies in connecting discerning buyers with properties built prior to 1940, as well as unique artist retreats that capture the region's artistic spirit. Delve into our detailed listings and immerse yourself in the rich history of Central Virginia.

A stunning brick estate surrounded by lush greenery and blossoming trees, featuring a manicured lawn, a black wooden fence, and a backdrop of rolling hills under a vibrant blue sky with scattered clouds.

Farms & Country Homes

CharlottesvilleCountryEstates.com is your dedicated gateway to the area's finest farms and estates. As the region's original niche property website, we bring unparalleled expertise to showcasing unique rural estates, private retreats, and productive farmland. Trust the proven leader in connecting you with exceptional country properties.