29

Madison, VA Homes for Sale with Acreage

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  • /14

    $695,000

    $74K PRICE DROP
    • Land
    • 6.3 Acres
    • $110,317 per Acre

    0 Main St N Unit VAMA2002288, Madison, VA 22719

    6.3 Acres of Prime B1 Commercial Land in the Town of Madison Incredible opportunity to own 6.3 acres of commercially zoned land in the heart of Madison County, offered in two parcels—5.8 acres and 0.5 acres. With direct frontage on Main Street and additional secondary access between the Rescue Squad and Madison Plumbing & Electric, this property offers excellent visibility and accessibility for a

    Agent Photo

    Julie Garrett

    Rappahannock Real Estate, LLC.

    0 Main St N Unit VAMA2002288, Madison, VA 22719
  • /22

    $285,000

    $14K PRICE DROP
    • Land
    • 10 Acres
    • $28,500 per Acre

    0 Goods Ln, Madison, VA 22727

    Located in beautiful Madison County — an incredible opportunity to own approximately 10 acres of beautifully maintained open pasture, wooded border, meandering streams and endless potential on a private road. Recently perked for conventional septic. Currently awaiting final division approval, this picturesque property offers a gorgeous homesite setting with the perfect blend of open space and

    Agent Photo

    Julie Garrett

    Rappahannock Real Estate, LLC.

    0 Goods Ln, Madison, VA 22727
  • /73

    $535,000

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

    104 Half Penny Ln, Madison, VA 22727

    Welcome to this beautifully maintained home in the desirable Malvern of Madison community, where comfort, privacy, and flexible living come together on over 3 scenic acres with a wide relaxing creek. Easy commuting to Charlottesville while living the rural lifestyle. Offering more than 3,500 square feet of finished living space, this exceptionally clean home features 3 spacious bedrooms and 3

    Agent Photo

    Julie Garrett

    Rappahannock Real Estate, LLC.

    104 Half Penny Ln, Madison, VA 22727
  • /17

    $1,100,000

    $100K PRICE DROP
    • Land
    • 7.8 Acres
    • $141,026 per Acre

    TBD Seminole Trail, Madison, VA 22727

    Prime 7.8-Acre Development Opportunity in the Heart of Madison County Exceptional location fronting busy Route 29 with additional right-of-way access off Main Street. This 7.8-acre parcel is zoned R1 (Low Density Residential) and offers an outstanding opportunity for residential development or potential civic use. The land is undeveloped and features a mostly level topography—ideal for building.

    Agent Photo

    Julie Garrett

    Rappahannock Real Estate, LLC.

    TBD Seminole Trail, Madison, VA 22727
  • /6

    $1,450,000

    • Land
    • 244 Acres
    • $5,943 per Acre

    0 Mount Zion Church Rd Unit 27296213, Madison, VA 22727

    244.34 acres located in Madison County, VA . Beautiful rolling farm land surronded by multiple streams with abudant wildlife. Mix of wooded (mature hardwoods and planted pines) and open pasture. Currently used for cattle. Great location for homesite, farm, or recreational land. - Fully fenced - 200 Amp electrical service on site- Multiple home sites with interior roadsystem in

    Peter Vick

    0 Mount Zion Church Rd Unit 27296213, Madison, VA 22727
  • /16

    $539,000

    Coming Soon
    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    60 Bee Gum Way, Madison, VA 22727

    Location Location! Private Subdivision on 3,03 acres on a corner lot beautifully lanscaped for privacy. Paved driveway leads you to Split level 3 Bedrooms 31/2 Bath Home with two Master Bedrooms. Fantastic Community amenities Club House, Pool, family visiting accomidations. As you enter Open to kitchen and dining off the right living room area. Opposite end you have 2 bedrooms and a office or

    Heather Parker Fairfax Realty 50/66 LLC

    60 Bee Gum Way, 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
  • /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
  • /9

    $149,000

    • Land
    • 5.5 Acres
    • $27,091 per Acre

    0 Jacks Shop Unit VAMA2002528, Madison, VA 22727

    Ready to Build Your Dream Home in Breathtaking Madison County? Here you can have a gorgeous, all-wooded 5.5 acre lot offering privacy yet convenience, over 300 feet of frontage on a paved, state-maintained road, winter mountain views from your elevated home-site (potential all year round with selective clearing), and just a short distance to the beautiful Rapidan River! Property was previously

    Carl Broyles Montague, Miller & Company

    0 Jacks Shop Unit VAMA2002528, Madison, VA 22727
  • /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
  • /45

    $3,400,000

    • 5 Beds
    • 3 Baths
    • 2,760 Sq Ft

    3111 S Seminole Trail, Madison, VA 22727

    Beautiful 115± acre countryside property in Madison County offering open fields, established fencing and a peaceful rural setting ideal for horses, farming or a private country estate. The land features multiple paddocks, run-in sheds, and a charming brick manager’s residence, providing immediate usability while allowing flexibility for future improvements. The gently rolling acreage offers

    Sharon Merrick HOWARD HANNA ROY WHEELER REALTY CO.- CHARLOTTESVILLE

    3111 S Seminole Trail, 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
  • /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
  • /6

    $1,450,000

    $400K PRICE DROP
    • Land
    • 244.34 Acres
    • $5,934 per Acre

    0 Mount Zion Church Rd Unit 2604632, Madison, VA 22727

    244.34 acres located in Madison County, VA• 200 Amp electrical service on site• Multiple home sites• Interior road system in place• Property subject to nutrient credit and streamrestoration easements• 91.4 acres in the nutrient credit easement- plantedin loblolly pines in 2023• Great recreation land with abundant wildlife Includes 4 tax

    Peter Vick Commonwealth Residential Rlty

    0 Mount Zion Church Rd Unit 2604632, Madison, VA 22727
  • /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
  • /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
  • /41

    $400,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    898 Seville Rd, Madison, VA 22727

    PRICE IMPROVEMENT!! MOVE-IN READY & CONVENIENTLY LOCATED! Built in 2022 and lovingly maintained by the original owner, this nearly new home sits on 3 acres just off Route 29, ideally positioned between Culpeper and Charlottesville and mere minutes from the Greene County line. Enjoy the benefits of living so close to some of Virginia's most beloved small towns and all they have to offer!Step

    Brittany Smyth Piedmont Fine Properties

    898 Seville Rd, Madison, VA 22727
  • /3

    $125,000

    $10K PRICE DROP
    • Land
    • 3 Acres
    • $41,667 per Acre

    0 Tatum School Rd Unit VAMA2002608, Madison, VA 22727

    3-acre wooded lot located in close proximity to Route 15 and Route 29. Bring your builder and build your dream home tucked back on Tatums School Road in Madison. Enjoy pastoral views on the way to the property and a private setting. No covenants and restrictions. TM 65-26A.

    Carrie Brown Montague, Miller & Company

    0 Tatum School Rd Unit VAMA2002608, Madison, VA 22727
  • /69

    $690,000

    • 3 Beds
    • 3.5 Baths
    • 4,544 Sq Ft

    66 Wrights Ln, Madison, VA 22727

    Escape to the peaceful beauty of Madison County with this beautifully maintained 3 bedroom, 3.5 bathroom ranch home nestled on nearly 5 private acres. Offering the convenience of one-level living plus a fully finished basement, this spacious home provides plenty of room for everyday living, entertaining, and relaxing. The thoughtfully designed floor plan features a welcoming living area with a

    Cindy Reed EXP Realty, LLC

    66 Wrights Ln, Madison, VA 22727
  • /129

    $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 sizes

    Brenda Payne Long & Foster Real Estate, Inc.

    202 Innovation Ln, Madison, VA 22727
  • /4

    $125,000

    • Land
    • 1.7 Acres
    • $73,529 per Acre

    0 64 56a S Blueridge Turnpike Unit VAMA2002870, Madison, VA 22727

    Beautiful 1.702-acre building lot in the heart of Madison County! This picturesque property offers the perfect setting for your custom home, featuring gently rolling terrain and a peaceful country atmosphere. Soil work has been completed for a proposed 4-bedroom conventional septic system. Enjoy the convenience of state-maintained road frontage, electric available at the road, and no HOA. Located

    Vicki Jenkins CENTURY 21 New Millennium

    0 64 56a S Blueridge Turnpike Unit VAMA2002870, 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
  • /10

    $50,000

    • Land
    • 1.07 Acres
    • $46,729 per Acre

    0 Washington St, Madison, VA 22727

    List price is starting bid only. Land will be sold 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!! 1.073 +/- acre multi-use vacant land parcel -- The parcel fronts Washington St. and has 140' +/- of road frontage -- Excellent opportunity for potential residential, commercial or investment

    John Nicholls Nicholls Auction Marketing Group

    0 Washington St, Madison, VA 22727
  • /93

    $749,900

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

    1765 Oneals Rd, Madison, VA 22727

    Just listed in Madison County. Thoughtfully crafted, meticulously renovated and expanded in 2025, 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
  • /22

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    1893 Shelby Rd, Madison, VA 22727

    Welcome home to this beautifully updated 3-bedroom, 2-bath home, where modern updates meet peaceful country living! Thoughtfully renovated in 2023, this home offers move-in-ready appeal with updated finishes throughout. Situated on approximately 3 private acres, the property features a newly landscaped yard, a large open lawn, and partially wooded areas that provide both space and privacy.

    Melinda Craig RE/MAX ADVANTAGE-WAYNESBORO

    1893 Shelby Rd, Madison, VA 22727
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