15

5-Bedroom Homes for Sale in Upperville, VA

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  • /66

    $775,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 4,278 Sq Ft

    221 Cannon Way, Warrenton, VA 20186

    Spacious & Stylish 5-Bedroom Colonial with Rare In-Law/Au Pair Suite!Welcome to this beautifully maintained 5-bedroom, 3.5-bath Colonial offering comfort, flexibility, and modern updates across three finished levels. The main floor features an inviting open-concept layout with a cozy gas fireplace, perfect for relaxing or entertaining. The kitchen shines with granite countertops,

    Agent Photo

    Tonya Cuffee

    Samson Properties

    (540) 384-4124

    221 Cannon Way, Warrenton, VA 20186
  • /30

    $1,088,990 New Construction

    • 5 Beds
    • 5.5 Baths
    • 4,377 Sq Ft

    9000 Lee Hwy, Warrenton, VA 20186

    Experience the ultimate in luxurious living with this remarkable home, ready for move-in! Nestled on 6 stunning acres just off Lee Highway and mere minutes from the vibrant heart of downtown Warrenton, this property is a perfect blend of elegance and convenience.Step inside to discover an expansive two-story design featuring a spacious 3-car garage, 5 beautifully appointed bedrooms, 5.5

    Dick Bryan New Home Star Virginia, LLC

    9000 Lee Hwy, Warrenton, VA 20186
  • /77

    $1,200,000

    • 5 Beds
    • 4 Baths
    • 4,298 Sq Ft

    8501 Country Club Ln, Warrenton, VA 20186

    A true country charmer with OVER $100K IN UPGRADES made to this beautiful home! Nestled on just under 2.5 private acres in the heart of Fauquier County, this extraordinary 5-bedroom, 4-bath craftsman home offers a rare blend of timeless character and modern comfort. From the moment you arrive, you’ll be captivated by the expansive wraparound Trex deck, peaceful natural surroundings, and views of

    Keysha Washington Samson Properties

    8501 Country Club Ln, Warrenton, VA 20186
  • /47

    $975,000

    • 5 Beds
    • 3.5 Baths
    • 4,341 Sq Ft

    7736 Warrenton Chase Dr, Warrenton, VA 20187

    **Open House, Saturday, July 26, Noon-3** Welcome to 7736 Warrenton Chase Drive—an exceptional 5-bedroom, 3.5-bath Landon model offering over 4,300 square feet of beautifully finished living space on a 0.61-acre lot backing to mature trees.Step inside to find rich hardwood floors flowing throughout the main level. Just off the entry is a formal dining room, ideal for hosting gatherings and

    Julie Boes Knisely Century 21 Redwood Realty

    7736 Warrenton Chase Dr, Warrenton, VA 20187
  • /30

    $1,150,000

    • 7 Beds
    • 8 Baths
    • 4,666 Sq Ft

    8019 Shipmadilly Ln, Warrenton, VA 20186

    Beautiful Custom built retreat with expansive front porch. The residence features 7 Spacious Bedrooms, 6 Full Bathrooms and two half baths. Primary bedroom with huge walk-in closet is on the main level. Spacious kitchen with all stainless-steel appliances. A smart refrigerator with wifi connection. All hardwood floors on the main level. Upper level provides 4 Spacious bedrooms and 3 Full

    Mandy Cole Samson Properties

    8019 Shipmadilly Ln, Warrenton, VA 20186
  • /2

    $1,350,000 Coming Soon

    • 5 Beds
    • 4.5 Baths
    • 4,226 Sq Ft

    7563 Foxview Dr, Warrenton, VA 20186

    Tucked away at the end of a quiet cul-de-sac, this expansive 5-bedroom, 4.5-bath custom home sits on just shy of 4 beautiful acres in the heart of Warrenton, right outside town limits, so you can enjoy no double tax and no HOA restrictions!Inside, you'll find a rare main-level in-law suite just off the living room, perfect for multigenerational living or guests. The upper level features

    Kaylynn Semple Pearson Smith Realty LLC

    7563 Foxview Dr, Warrenton, VA 20186
  • /17

    $795,000

    • 5 Beds
    • 5.5 Baths
    • 3,422 Sq Ft

    7296 Burke Ln, Warrenton, VA 20186

    Bring your vision to life with this partially finished 5,000 SF Ranch style home nestled on a private and picturesque 10-acre oasis. Offering the perfect canvas for customization. The existing structure offers a solid foundation with much of the heavy lifting already complete, including framing and major systems underway. Offering 5 generously sized bedroom suites, each with a private

    Virginia Smith Arlington Realty, Inc.

    7296 Burke Ln, Warrenton, VA 20186
  • /43

    $687,000

    • 5 Beds
    • 3 Baths
    • 2,092 Sq Ft

    6444 Duhollow Rd, Warrenton, VA 20187

    *** Open House Saturday 7/12 1-3PM *** Private Retreat Just Minutes from Old Town Warrenton! Welcome to your own peaceful escape—nestled on a secluded 1-acre lot yet just minutes from the charm and convenience of historic Old Town Warrenton. This stunning 5BR/3BA home offers 2,100 sq ft of beautifully updated living space, a 2-car garage, and effortless access to major commuter routes connecting

    Paulina Stowell CENTURY 21 New Millennium

    6444 Duhollow Rd, Warrenton, VA 20187
  • /38

    $625,000

    • 5 Beds
    • 3 Baths
    • 2,512 Sq Ft

    7277 Mosby Dr, Warrenton, VA 20187

    Open Sunday July 20, 2025 from 2:00 to 4:00 PM. Welcome to Warrenton Lakes - this beautifully renovated 5 bedroom, 3 bath home is located on almost an acre of park like yard & conveniently located just minutes from Route 29 for easy access to points North or South*Enter into the foyer with formal living and dining rooms*Fabulous eat-in kitchen with painted cabinets & stainless steel appliances

    Becky Miller Piedmont Fine Properties

    7277 Mosby Dr, Warrenton, VA 20187
  • /82

    $940,000

    • 5 Beds
    • 4.5 Baths
    • 5,242 Sq Ft

    9010 Stone Crest Dr, Warrenton, VA 20186

    Open Saturday 7/19 2:00 to 4:00 PMHigh-End, Oasis with over $200k++ in Upgrades, Pet Perks & Premier Yard. This beautifully crafted home combines sophisticated, nature-inspired finishes with thoughtful features. Boasting over $200,000 in professional upgrades, every element has been carefully curated to reflect exceptional quality, comfort and style. Perfectly situated just one block

    Becky Miller Piedmont Fine Properties

    9010 Stone Crest Dr, Warrenton, VA 20186
  • /102

    $1,599,000

    • 5 Beds
    • 5 Baths
    • 5,708 Sq Ft

    8300 Falcon Glen Rd, Warrenton, VA 20186

    Welcome to 8300 Falcon Glen Rd, a timeless and elegant estate nestled in the rolling hills of Warrenton, Virginia. This exceptional 5-bedroom, 3-full bathroom, 2-half bathroom residence is more than just a home—it’s a retreat, a sanctuary, and a place where rural charm meets understated luxury. Positioned within the prestigious Bellevue Farms community, the property offers commanding views of the

    Scott Buzzelli Corcoran McEnearney

    8300 Falcon Glen Rd, Warrenton, VA 20186
  • /10

    $2,830,000

    • 8 Beds
    • 5 Baths
    • 9,000 Sq Ft

    0 Winchester St, Warrenton, VA 20186

    This extraordinary offering includes two historic homes, together with a contiguous .64 acre parcel. For detailed information on each of the properties, please see MLS Listing # VAFQ2016280 for 507 Winchester Street (6000 SF)and Listing #VAFQ2016282 for the adjacent 535 Winchester Street (3000 SF). With a total 5.6 acres in three separate parcels, the properties are perfect as a family complex

    Carole Taylor TTR Sothebys International Realty

    0 Winchester St, Warrenton, VA 20186
  • /49

    $1,575,000

    • 5 Beds
    • 4.5 Baths
    • 5,986 Sq Ft

    507 Winchester St, Warrenton, VA 20186

    Welcome to Historic Boxwood, a stately 1910 stone manor, sited on 2.7 acres of lawns, mature trees and gardens. Located at the edge of Warrenton, Virginia's Historic District, this serene property includes three expansive levels totaling nearly 6000 square feet, and offers timeless craftsmanship, rich architectural detail, and unmatched presence. detailsThe home’s stone façade and classic lines

    Carole Taylor TTR Sothebys International Realty

    507 Winchester St, Warrenton, VA 20186
  • /64

    $849,900

    • 5 Beds
    • 4.5 Baths
    • 4,313 Sq Ft

    7400 Poplar Point Ln, Warrenton, VA 20186

    Back on market at no fault to seller, motivated seller relocating- bring offer, seller offering 1 year home warranty plus Starlink equipment* conveys offering exceptional high-speed WiFi! Secluded 5 bedroom, 4.5 bath Colonial on 10+ Acres w/ Bonus Suite & Creek Access! Create your Mini-Farmette! Beautifully updated 4,313 sq. ft. home at the end of a private lane, set on a wooded 10.5+ acre lot

    Jennifer Young Keller Williams Realty

    7400 Poplar Point Ln, Warrenton, VA 20186
  • /2

    $775,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,343 Sq Ft

    615 Galina Way, Warrenton, VA 20186

    This gorgeous 5 bedroom, 3.5 bath home is located on a lovely cul-de-sac lot backing to a beautiful common area in the heart of Warrenton and is loaded with upgrades and updated including a new roof, newer huge Trex deck, newer HVAC and more! A bright open floor plan infused with architectural details, custom moldings, fresh designer paint, hardwood floors and carpeting, high ceilings, 2

    Jennifer Young Keller Williams Realty

    615 Galina Way, Warrenton, VA 20186
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