16

Leon, VA Houses for Sale

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  • /37

    $415,000

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,744 Sq Ft

    319 N Main St, Madison, VA 22727

    Circa 1840 | A Timeless Madison Treasure Step back in time and own a remarkable piece of Madisons history. Constructed around 1840 by John Richard Gooding and proudly featured in The Historic Homes of Madison, this well-maintained Colonial residence pre-dates the Civil War and is rich with architectural character and enduring charm. From the moment you arrive, the classic columned front porch and

    Kelly Duckett-Corbin RE/MAX Gateway

    319 N Main St, Madison, VA 22727
  • /2

    $1,500,000

    • 4 Beds
    • 2 Baths
    • 1,500 Sq Ft

    4408 N Seminole Trail, Brightwood, VA 22715

    Mike Jamil Smart Realty, LLC

    4408 N Seminole Trail, Brightwood, VA 22715
  • /46

    $674,900

    • 4 Beds
    • 4 Baths
    • 2,991 Sq Ft

    1515 Desert Rd, Madison, VA 22727

    Whole House Generator!Welcome home to your own private retreat in the heart of Reva. Set on 3 peaceful acres surrounded by mature trees and picturesque countryside, this property offers the perfect balance of privacy, comfort, and outdoor living.From the moment you arrive, you'll appreciate the inviting covered front porch that wraps around to an expansive covered deck, creating

    Kerry Shannon Pearson Smith Realty, LLC

    1515 Desert Rd, Madison, VA 22727
  • /71

    $200,000

    • 4 Beds
    • 2.5 Baths
    • 2,932 Sq Ft

    150 N Main St, Madison, VA 22727

    List price is starting bid only. Home will be sold at auction 9/14/2026 @12pm. Contact us or your favorite real estate professional to view this home! Buying at auction is easy and transparent you can get financing!! Historic 4 BR/2.5 BA multi-tenant home on 1.619 +/- acres (circa 1820) -- Detached 30'x36' shop/garage/storage building -- Currently used as a duplex, but easily converted to a

    John Nicholls Nicholls Auction Marketing Group

    150 N Main St, Madison, VA 22727
  • /69

    $475,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,144 Sq Ft

    2303 W Hoover Rd, Haywood, VA 22722

    Recently renovated with the intention of being a forever home, this charming 1940s farmhouse was lovingly transformed while preserving the character, warmth, and timeless appeal that make it so special. Each project was completed with quality, durability, and longevity in mind.With 1,144 square feet, the home offers just enough space to get away to the extraordinarily scenic countryside

    Robin Garbe Century 21 Redwood Realty

    2303 W Hoover Rd, Haywood, VA 22722
  • /136

    $5,850,000

    • 3 Beds
    • 2 Baths
    • 3,023 Sq Ft

    1830 Thrift Rd, Madison, VA 22727

    Woodbourne Estate, circa 1810, is a National and Virginia registered historic landmark set on 53 acres in Madison County, less than 90 miles from Washington, D.C. Nestled in the foothills of the Blue Ridge Mountains, the property combines two extraordinary elements: the award-winning Bald Top Brewing Company and the beautifully restored Woodbourne Manor. Together they create a rare chance to

    Daniel Langberg Virginia Estates, Inc.

    1830 Thrift Rd, Madison, VA 22727
  • /57

    $600,000

    • 3 Beds
    • 3 Baths
    • 2,621 Sq Ft

    398 Ruth Hollow Fire Trail, Madison, VA 22727

    Set on 10.88 wooded acres just 7 miles from the Town of Madison, this move-in-ready 3BD/3BA home sits on an elevated, private lot and has been fully renovated. The main level offers approx. 1,700 finished sq ft, a 1,100+ sq ft finished walkout basement and a covered porch with wooded views. The ideal blend of privacy and convenience. Inside, the open layout includes a fully updated kitchen, new

    JENNIFER KIRBY MONTAGUE, MILLER & CO. - WESTFIELD

    398 Ruth Hollow Fire Trail, Madison, VA 22727
  • /13

    $259,500

    • 2 Beds
    • 1 Bath
    • 1,500 Sq Ft

    1518 Novum Rd, Reva, VA 22735

    Newly listed, two bedroom, one full bath. Structure 5originally built in 1966, as a workshop. Remodeled with County approval dated September 9, 1997, 1,500+- square foot living space, converted to a two bedroom residence. Kitchen, dining area and family room combo. The house is situated on a surveyed 4.728+- acres, within minutes to Culpeper and the Town of Madison. Beautiful views overlooking

    Bill Gentry JEFFERSON LAND & REALTY

    1518 Novum Rd, Reva, VA 22735
  • /50

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 1,881 Sq Ft

    472 Arrington Mountain Rd, Haywood, VA 22722

    Charming 3-bedroom Cape Cod offering true main-level living, upstairs you will find two large bedrooms with new carpet and a full bath. Perfectly situated on over three private, mostly wooded acres surrounded by mature trees and natural beauty. This inviting home features an open and airy floor plan with abundant natural light, creating a warm and welcoming atmosphere ideal for both everyday

    Nicole Bolton Long & Foster Real Estate, Inc.

    472 Arrington Mountain Rd, Haywood, VA 22722
  • /70

    $524,900

    • 4 Beds
    • 2 Baths
    • 1,812 Sq Ft

    359 Malvern Dr, Madison, VA 22727

    Quintessential Malvern! Do not miss this gorgeous light-filled gem in sought after Malvern. Situated on over 7 acres, this architecturally interesting home is truly one of a kind! Nestled amongst the mature trees and landscaping, the property offers abundant privacy, yet this community is conveniently located a short distance from major commuter routes. Offering a traditional, though functional,

    Philip Thornton Long & Foster Real Estate, Inc.

    359 Malvern Dr, Madison, VA 22727
  • /50

    $4,450,000

    • 5 Beds
    • 6 Baths
    • 5,153 Sq Ft

    4578 Ruth Rd, Madison, VA 22727

    Set amidst 17 beautifully landscaped acres, Monte Ventoso is an extraordinary Italian-inspired villa offering the ambiance of a private Mediterranean retreat in the foothills of the Blue Ridge Mountains. Ideally positioned between Washington, D.C. and Charlottesville, VA, the estate combines exceptional privacy with convenient accessibility. A handcrafted fountain imported from Italy creates a

    COURT NEXSEN MCLEAN FAULCONER INC., REALTOR

    4578 Ruth Rd, Madison, VA 22727
  • /67

    $450,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    803 Weaver Hollow Rd, Banco, VA 22711

    Charming Country Retreat on Nearly 8 Acres — Peaceful Setting with Endless Potential! Nestled in the heart of the countryside yet conveniently located just a short drive to Madison, Culpeper, Graves Mountain Lodge, White Oak Canyon, Shenandoah National Park, the Rapidan River, and countless outdoor adventures, this solidly built one-level home offers the perfect blend of privacy, comfort, and

    Kelly Duckett-Corbin RE/MAX Gateway

    803 Weaver Hollow Rd, Banco, VA 22711
  • /132

    $875,000

    • 4 Beds
    • 3.5 Baths
    • 4,497 Sq Ft

    202 Innovation Ln, Madison, VA 22727

    Welcome home to this stunning brick, stone, and vinyl sided Colonial nestled on 3.86 picturesque acres in the heart of Madison County. Offering over-sized living spaces, timeless curb appeal, and endless possibilities, this exceptional property is the perfect blend of elegance, comfort, and country living.Inside, you'll find four spacious bedrooms and three full baths, with generous room

    Brenda Payne Long & Foster Real Estate, Inc.

    202 Innovation Ln, Madison, VA 22727
  • /2

    $585,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,739 Sq Ft

    1267 Oneals Rd, Madison, VA 22727

    A comfortable, sun-lit home with easy flow from formal living spaces to its open, airy new kitchen, great room and casual dining area, to an elevated screened deck. True one-level living is assured with proximity of the primary suite, laundry, powder room, and garage access. There's ample room for a big family in the three upper level bedrooms, and potential for more living space including a full

    JULIA PARKER LYMAN LORING WOODRIFF REAL ESTATE ASSOCIATES

    1267 Oneals Rd, Madison, VA 22727
  • /93

    $749,900

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    1765 Oneals Rd, Madison, VA 22727

    Amazing Views-Amazing Home! Thoughtfully crafted, meticulously renovated and expanded in 2025/26, this amazing 3-bedroom, 2-bath ranch-style home blends modern luxury with timeless country charm across 1,872 square feet of custom-designed main floor living space, offering a harmonious blend of luxury and comfort in a serene rural setting. The front concrete walkway and curved steps welcome you to

    Mr. Mike Butters EXP Realty, LLC

    1765 Oneals Rd, Madison, VA 22727
  • /2

    $299,999

    • 3 Beds
    • 1 Bath
    • 930 Sq Ft

    193 Gate Rd, Madison, VA 22727

    Welcome to Gate Rd! This Cozy 3-bedroom, 1-bath home on a quiet country road in Madison County is waiting for you. With 930 sq ft it offers a functional layout with comfortable living spaces and good natural light. The home sits in a peaceful rural setting with room to enjoy the outdoors. Ideal for buyers seeking simplicity, affordability, or a manageable property in a convenient location.

    Japreshia Terrell Wolford And Associates Realty LLC

    193 Gate Rd, Madison, VA 22727
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