29

Leon, VA Homes for Sale

Section Image
  • /65

    $1,625,000

    • 3 Beds
    • 3 Baths
    • 3,802 Sq Ft

    3638 Oak Park Rd, Madison, VA 22727

    Enjoy your morning coffee from the expansive deck while watching your horses or livestock graze in the beautifully maintained pastures secured by three-board fencing, with the tops of the Blue Ridge Mountains in the distance. Set on 44± acres & bordered on 3 sides by meandering streams, the property offers exceptional privacy & is a nature lover's sanctuary, where you can watch the purple martins

    Gayle Harvey GAYLE HARVEY REAL ESTATE, INC

    3638 Oak Park Rd, Madison, VA 22727
  • /68

    $415,000

    $34K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,744 Sq Ft

    319 N Main St, Madison, VA 22727

    Circa 1840 | A Timeless Madison TreasureStep back in time and own a remarkable piece of Madison’s 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

    Kelly Duckett-Corbin RE/MAX Gateway

    319 N Main St, Madison, VA 22727
  • /18

    $1,200,000

    • Land
    • 114.9 Acres
    • $10,444 per Acre

    00 TBD W Hoover Rd, Madison, VA 22727

    This property has a new entrance. There is so much to offer here. Come to Madison County, start your Organic Farm. Make this your own sanctuary, your own peace and quiet. This property has been untouched for many years. It is in a very sought out area of Madison County, with great access for commute to Northern Virginia, Charlottesville and the Shenandoah Valley. It boasts beautiful views and

    sharon rock CENTURY 21 New Millennium

    00 TBD W Hoover Rd, Madison, VA 22727
  • /8

    $89,900

    $5K PRICE DROP
    • Land
    • 1 Acre
    • $89,900 per Acre

    0 Main St, Madison, VA 22727

    In-town lot, Gravity flow septic system approved, wooded, shared driveway with 1 other lot.

    Bonnie Coffey Samson Properties

    0 Main St, Madison, VA 22727
  • /18

    $299,000

    • Land
    • 10 Acres
    • $29,900 per Acre

    LOT 2 S F T Valley Rd, Madison, VA 22727

    Amazing Opportunity to own 10 acres on Scenic Byway 231!! Perc approved for a 4 bedroom conventional septic. Level building spot about half way up the mountain. Beautiful views from this parcel. Seasonal creek. Lots of wildlife.

    Dana Williams EXP Realty, LLC

    LOT 2 S F T Valley Rd, Madison, VA 22727
  • /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
  • /67

    $430,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3 Baths
    • 1,317 Sq Ft

    452 Rocky Hill Ln, Reva, VA 22735

    Welcome to 452 Rocky Hill Ln in Reva, VA, where peaceful country living, privacy, and room to breathe come together on 7.22 acres! Tucked away in a quiet setting, this charming 3-bedroom home offers 1,317 square feet of comfortable living space on the main level, plus a partially finished basement that provides even more possibilities.Step inside and you’ll find the warmth and character

    Kaley Martin CENTURY 21 New Millennium

    452 Rocky Hill Ln, Reva, VA 22735
  • /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
  • /18

    $309,000

    • Land
    • 10.34 Acres
    • $29,884 per Acre

    LOT 1 S F T Valley Rd, Madison, VA 22727

    Absolutely breathtaking lot on Scenic Highway 231!!!!!! Entrance is in place and approved by VDOT. 4 bedroom perc site approximately half way up the mountain on a lovely flat knoll. Almost 180 degrees of Mountain Views from the building spot. Wildlife trails everywhere! This is a rare opportunity!!!

    Dana Williams EXP Realty, LLC

    LOT 1 S F T Valley Rd, Madison, VA 22727
  • /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
  • /22

    $229,000

    • 4 Beds
    • 1.5 Baths
    • 3,152 Sq Ft

    273 Ridgeview Rd, Brightwood, VA 22715

    Step back in time with this distinctive circa late-1800's home, offering just over 3,000 square feet of conditioned living space and an abundance of original character. Situated on 4.277 acres, this property presents a unique opportunity for those looking to restore a piece of history while creating a home tailored to your vision. The home features 4 generous sized bedrooms with 1full and 1 half

    Cindy Weakley Montague, Miller & Company

    273 Ridgeview Rd, Brightwood, VA 22715
  • /4

    $99,900

    • Land
    • 3.07 Acres
    • $32,541 per Acre

    0 Malvern Dr Unit VAMA2002938, Madison, VA 22727

    Gorgeous 3+ Acre Building Lot in Sought After Malvern. Lot offers a ton of wide open space to build your forever home! Parcel can also be purchased with neighboring property - 359 Malvern Drive.

    Philip Thornton Long & Foster Real Estate, Inc.

    0 Malvern Dr Unit VAMA2002938, Madison, VA 22727
  • /18

    $2,472,000

    • Land
    • 23.09 Acres
    • $107,059 per Acre

    0 Main St N Unit VAMA2002616, Madison, VA 22719

    Discover an exceptional opportunity to acquire three contiguous land parcels totaling 23.103 acres in a highly desirable location between N. Main Street and Business Route 29 in Madison VA. Offering a rare combination of Business (B1) and Residential (R1) zoning, this property provides outstanding flexibility for commercial development, residential housing, or a mixed‑use project.Parcel 1 –

    Kim Gallihugh CENTURY 21 New Millennium

    0 Main St N Unit VAMA2002616, Madison, VA 22719
  • /3

    $312,000

    $40K PRICE INCREASE
    • Land
    • 2.83 Acres
    • $110,247 per Acre

    0 Seminole Trail Unit VAMA108074, Madison, VA 22727

    Commercial Opportunity adjoining Madison Plaza Food Lion Center. Exceptionally well located land parcels with public utilities available. Development plan has all the approvals for a business park with future uses including restaurants, office, retail and service businesses. The property is located at a traffic light across US 29 from the Madison County High School and the southern crossover.

    Bill Gentry Jefferson Land & Realty, Inc.

    0 Seminole Trail Unit VAMA108074, 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
  • /12

    $715,000

    • Land
    • 42 Acres
    • $17,024 per Acre

    TM 39-31&33b Thrift Rd, Madison, VA 22727

    "White Oak Run" - this is one of the most stunning land parcels in Central Virginia. Long State road frontage, with elevated building site, looking at the Blue Ridge and Old Rag Mountain. 42+ Acres that are in land use taxation. Soil evaluation for a four bedroom septic. Land is in predominantly mature hardwoods, and approximately eleven acres open. Several springs feed White Oak Run. New access

    Bill Gentry JEFFERSON LAND & REALTY

    TM 39-31&33b Thrift Rd, Madison, VA 22727
  • /57

    $424,900

    • 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 almost 4 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

    Philip Thornton Long & Foster Real Estate, Inc.

    359 Malvern Dr, Madison, VA 22727
  • /28

    $367,000

    • 3 Beds
    • 2 Baths
    • 2,028 Sq Ft

    301 Dulaney Mountain Rd, Etlan, VA 22719

    Situated near the town of Etlan, this split-level 3-br, 2-bath house sits on almost 10 acres with open and wooded space. Leathers Run traverses through a lower part of the parcel. Come turn this into a property that you will never want to leave!

    Kevin McHaney RE/MAX NEW HORIZONS

    301 Dulaney Mountain Rd, Etlan, VA 22719
  • /36

    $699,000

    • Land
    • 29.52 Acres
    • $23,679 per Acre

    0 Hurt Hollow Rd, Banco, VA 22711

    Amazing opportunity to own 29.5 Acres in Madison County near the Shenandoah National Park! This property offers multiple elevated building sites with potential views of Double Top Mountain! There is a creek meandering along the bottom of the property. Trails are already in place to take a walk and enjoy everything nature has to offer! Plenty of wildlife!

    Dana Williams EXP Realty, LLC

    0 Hurt Hollow Rd, Banco, VA 22711
  • /3

    $411,500

    • Land
    • 3.74 Acres
    • $110,027 per Acre

    0 Seminole Trail Unit VAMA108070, Madison, VA 22727

    Commercial Opportunity adjoining Madison Plaza Food Lion Center. Exceptionally well located land parcels with public utilities available. Development plan has all the approvals for a business park with future uses including restaurants, office, retail and service businesses. The property is located at a traffic light across US 29 from the Madison County High School and the southern crossover.

    Bill Gentry Jefferson Land & Realty, Inc.

    0 Seminole Trail Unit VAMA108070, Madison, VA 22727
  • /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
  • /9

    $379,500

    $79K PRICE DROP
    • Land
    • 10.56 Acres
    • $35,938 per Acre

    48-13o,13v&13u Courthouse Mountain Rd, Madison, VA 22727

    Three exceptionally well located land parcels along Courthouse Mountain Road; adjacent to the Town of Madison. The wooded parcels have soil evaluations for (3) bedroom septic systems. REC electric service available. All parcels are in hardwood timber and accessible from a private road (Toscana Lane). It is uncommon to have parcels with the feeling of privacy and yet within a two minute drive to

    Bill Gentry JEFFERSON LAND & REALTY

    48-13o,13v&13u Courthouse Mountain Rd, Madison, VA 22727
  • /36

    $2,100,000

    • 3 Beds
    • 3 Baths
    • 1,616 Sq Ft

    551 Old Homeplace Ln, Reva, VA 22735

    Situated west of Route 29 in northern Madison County, with 73 acres of pasture and woods, is part of the Old Home Place Farm tract, having a modern 3BR ranch home and a 4,000 sq.ft. multi-purpose building that could be converted to another residence. There are spectacular Blue Ridge Mountain views from the home, and another potential building site. The open land is mostly fenced, primarily gently

    Jim Faulconer MCLEAN FAULCONER INC., REALTOR

    551 Old Homeplace Ln, Reva, VA 22735
  • /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
  • /81

    $1,995,000

    • 3 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    1688 Desert Rd, Reva, VA 22735

    Set against sweeping Blue Ridge Mountain views, Rag View Farm pairs a meticulously cared-for home with productive, versatile land. Six fenced parcels of open pasture make this an ideal turnkey setup for cattle, horses, or a private country estate. The home offers a main-level primary suite, a wrap-around porch for taking in the scenery, and an attached garage with a finished office above —

    Carrie Brown Montague, Miller & Company

    1688 Desert Rd, Reva, VA 22735
  • /6

    $299,999

    • 3 Beds
    • 2 Baths
    • 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

Frequently Asked Questions

What are the most popular zip codes in Leon, VA?
The most popular zip codes in Leon, VA include 22727, 22722, 22719, 22715 and 22735.
What are the most popular neighborhoods near Leon, VA?
The most popular neighborhoods near Leon, VA are Twin Lakes, Earlysville, Northeast Charlottesville and Piney Mountain.
How to Buy a Home How to Finance a Home How to Sell a Home