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Ad #7133245
MLS #VAFQ2023262
Listing photo

Rare Opportunity on the DC Side of Warrenton! Welcome to this

5290 HILLSIDE Dr, Warrenton, VA 20187
$925,000
5Beds
5Baths
4,228Sqft
1.6Acres

About this property

Rare Opportunity on the DC Side of Warrenton! Welcome to this truly one-of-a-kind property offering the perfect blend of flexibility, privacy, and modern updates on 1.5 acres with a flat, usable backyard. With no HOA, you'll have the freedom to bring your chickens, start a garden, park your RV or boat, or simply enjoy the space without restrictive covenants. Whether you're looking for multigenerational living, an income-producing opportunity, or simply extra space for guests, this turnkey home delivers. The standout feature is the approximately 1,600-square-foot private apartment addition, fully remodeled in July 2026, offering an incredible opportunity for multigenerational living, rental income, or a private guest retreat. With its own main-level entrance and welcoming front porch, this thoughtfully designed space features freshly refinished hardwood floors, soaring vaulted ceilings, fresh paint, a spacious bedroom overlooking the private backyard, and a beautifully renovated handicap-accessible bathroom. The updated kitchen (July 2026) includes a gas range, dishwasher, and modern finishes. The apartment also includes its own private basement with laundry, a remodeled full bathroom, and a separate exterior entrance. Previously configured with a kitchenette, the existing hookups make it easy to convert the space back into a kitchenette, creating an ideal studio apartment or potential sixth bedroom with its own private living area. A brand-new HVAC system and water heater provide added peace of mind. For maximum flexibility, the apartment also connects to the main home through secure double doors, allowing complete privacy for rental use while maintaining the option to seamlessly incorporate it into the main residence. The main home was extensively remodeled in 2016 and features an impressive gourmet kitchen with a gas cooktop, stainless steel appliances, upgraded cabinetry, and two beautiful 1800s English yellow pine antiques that were thoughtfully repurposed into a stunning 6-foot kitchen island and an undermount double-sink cabinet, all topped with durable, heat-resistant quartz countertops. Rich walnut hardwood flooring flows throughout the main level, where you'll also find a cozy gas fireplace, three spacious bedrooms, and two beautifully updated full bathrooms. The walkout lower level offers even more living space with a large recreation room, a fourth bedroom, and a remodeled full bathroom. Fresh paint and new carpet throughout the home make it completely move-in ready. Major system updates include the roof, windows, HVAC systems, hot water heaters, and deck-all replaced within the past 10 years, making this home as practical as it is beautiful. Step outside to enjoy the oversized deck overlooking a completely private, flat backyard-perfect for entertaining, gardening, or simply relaxing in your own peaceful retreat. Ideally located on the highly desirable DC side of Warrenton, just 1/2 mile from Route 29, this home offers exceptional convenience for commuters, with I-66 and the Gainesville commuter lot just 10 minutes away. Enjoy quick access to shopping and dining at Virginia Gateway, including Wegmans, Target, movie theatre, restaurants, breweries, wineries, golf courses, parks, and the charm of Historic Old Town Warrenton-all while coming home to the peace and privacy of country living.

Property Features

5 Beds
5 Baths
4,228 Sqft
Built in 1979
1.6 Acres
1 Story
Driveway
Siding: Brick
Has Fireplace
Heat Pump (Heating)
$5,502 / yr property tax
Fauquier County
BALDWIN RIDGE Community

Contact Information

Vanessa Ann Gregg

Pearson Smith Realty, LLC

804-873-9453

Location

Map
Listing Agent: Vanessa Ann Gregg (License #: 0225242420) 804-873-9453
Broker: Pearson Smith Realty, LLC 571-386-1080 Listing Site
Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BarrierFreeHome.com
Printed Aug 7, 2026

Photo Gallery

Rare Opportunity on the DC Side of Warrenton! Welcome to this - photo 1

$925,000

5
Beds
5
Baths
4,228
Sqft

5290 HILLSIDE Dr, Warrenton, VA 20187

By contacting this agent you agree to these Terms and Conditions.
Home Virginia Warrenton
Rare Opportunity on the DC Side of Warrenton! Welcome to this - photo 1
MLS# VAFQ2023262
Home For Sale

Rare Opportunity on the DC Side of Warrenton! Welcome to this

Open House: Sun Aug 9, 12-3pm
$925,000

5290 HILLSIDE Dr, Warrenton, VA 20187

5
Beds
5
Baths
4,228
Sqft
1.6
Acres
$925,000
5290 HILLSIDE Dr, Warrenton, VA 20187
5 Beds
5 Baths
4,228 Sqft
1.6 Acres
Rare Opportunity on the DC Side of Warrenton! Welcome to this truly one-of-a-kind property offering the perfect blend of flexibility, privacy, and modern updates on 1.5 acres with a flat, usable backyard. With no HOA, you'll have the freedom to bring your chickens, start a garden, park your RV or boat, or simply enjoy the space without restrictive covenants. Whether you're looking for multigenerational living, an income-producing opportunity, or simply extra space for guests, this turnkey home delivers. The standout feature is the approximately 1,600-square-foot private apartment addition, fully remodeled in July 2026, offering an incredible opportunity for multigenerational living, rental income, or a private guest retreat. With its own main-level entrance and welcoming front porch, this thoughtfully designed space features freshly refinished hardwood floors, soaring vaulted ceilings, fresh paint, a spacious bedroom overlooking the private backyard, and a beautifully renovated handicap-accessible bathroom. The updated kitchen (July 2026) includes a gas range, dishwasher, and modern finishes. The apartment also includes its own private basement with laundry, a remodeled full bathroom, and a separate exterior entrance. Previously configured with a kitchenette, the existing hookups make it easy to convert the space back into a kitchenette, creating an ideal studio apartment or potential sixth bedroom with its own private living area. A brand-new HVAC system and water heater provide added peace of mind. For maximum flexibility, the apartment also connects to the main home through secure double doors, allowing complete privacy for rental use while maintaining the option to seamlessly incorporate it into the main residence. The main home was extensively remodeled in 2016 and features an impressive gourmet kitchen with a gas cooktop, stainless steel appliances, upgraded cabinetry, and two beautiful 1800s English yellow pine antiques that were thoughtfully repurposed into a stunning 6-foot kitchen island and an undermount double-sink cabinet, all topped with durable, heat-resistant quartz countertops. Rich walnut hardwood flooring flows throughout the main level, where you'll also find a cozy gas fireplace, three spacious bedrooms, and two beautifully updated full bathrooms. The walkout lower level offers even more living space with a large recreation room, a fourth bedroom, and a remodeled full bathroom. Fresh paint and new carpet throughout the home make it completely move-in ready. Major system updates include the roof, windows, HVAC systems, hot water heaters, and deck-all replaced within the past 10 years, making this home as practical as it is beautiful. Step outside to enjoy the oversized deck overlooking a completely private, flat backyard-perfect for entertaining, gardening, or simply relaxing in your own peaceful retreat. Ideally located on the highly desirable DC side of Warrenton, just 1/2 mile from Route 29, this home offers exceptional convenience for commuters, with I-66 and the Gainesville commuter lot just 10 minutes away. Enjoy quick access to shopping and dining at Virginia Gateway, including Wegmans, Target, movie theatre, restaurants, breweries, wineries, golf courses, parks, and the charm of Historic Old Town Warrenton-all while coming home to the peace and privacy of country living.
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Property Details

HOME DETAILS

5 Beds
5 Baths
4,228 Sqft
Built in 1979
1.6 Acres
1 Story

EXTERIOR

Driveway
Siding: Brick

INTERIOR

Has Fireplace
Heat Pump (Heating)

FINANCIAL & COMMUNITY

$5,502 / yr property tax
Fauquier County
BALDWIN RIDGE Community
See More Details

Location

Map
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Ad Statistics

Ad Number
7133245
Viewed
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Listing Status
Active
Added
Aug 07, 2026
Last Refreshed
Aug 07, 2026 01:16:08 AM

Listing Information

Data Source
Bright MLS
Source Property ID
VAFQ2023262
Listing Agent: Vanessa Ann Gregg (License #: 0225242420) 804-873-9453
Broker: Pearson Smith Realty, LLC 571-386-1080 Listing Site
Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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Alabama Alaska Arizona Arkansas California Colorado Connecticut Delaware Florida Georgia Hawaii Idaho Illinois Indiana Iowa Kansas Kentucky Louisiana Maine Maryland Massachusetts Michigan Minnesota Mississippi Missouri Montana Nebraska Nevada New Hampshire New Jersey New Mexico New York North Carolina North Dakota Ohio Oklahoma Oregon Pennsylvania Rhode Island South Carolina South Dakota Tennessee Texas Utah Vermont Virginia Washington West Virginia Wisconsin Wyoming
SERVICES
Buy Buy Advertise
COMPANY
Testimonials About Us Office Locations
SUPPORT
Help Contact Us
ADDITIONAL MARKETS
LakeHouse.com MountainHomes.com BeachHouse.com GolfHomes.com
SUBSCRIBE
Receive notifications for new listings
Subscribe
Facebook YouTube

Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 Wheelchair-accessible Housing & Universal Design Homes at Barrier Free Home
Part of Dream Home Network, Inc.
Last updated on 2026.08.07
Terms & Policy