23

Madison, VA Homes for Sale with Acreage

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  • /40

    $629,000

    • 3 Beds
    • 3 Baths
    • 2,713 Sq Ft

    107 Sylvan Ln, Madison, VA 22727

    Nestled in the serene community of Malvern of Madison, this charming ranch-style home offers a perfect blend of comfort and elegance. Built in 1984, this meticulously maintained residence showcases exceptional craftsmanship and thoughtful design throughout its spacious layout. As you step inside, you are greeted by a warm and inviting atmosphere, highlighted by beautiful hardwood floors that flow

    Agent Photo

    Donna Waugh-Robinson

    Corcoran Wiley

    (540) 417-9634

    107 Sylvan Ln, Madison, VA 22727
  • /24

    $4,300,000

    • Land
    • 91.89 Acres
    • $46,795 per Acre

    92 acres Seminole Trail, Madison, VA 22727

    Prime 91.9-Acre Development Opportunity in Madison CountyExceptional offering of nearly 92 acres of prime land fronting Route 29 in the heart of Madison County. Located near the bustling commercial hub and directly neighboring the well-known Yoder’s Country Market, this property offers unmatched visibility and access.The front 12 acres are zoned Commercial (B1), featuring multiple

    Agent Photo

    Julie Garrett

    Rappahannock Real Estate, LLC.

    (540) 701-7352

    92 acres Seminole Trail, Madison, VA 22727
  • /14

    $749,000

    • Land
    • 6.3 Acres
    • $118,889 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.

    (540) 202-2159

    0 Main St N Unit VAMA2002288, Madison, VA 22719
  • /75

    $439,000

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

    150 N Main St, Madison, VA 22727

    Charming 1800’s Colonial in the Heart of Madison – 4BR/2.5BA on 1.61 Acres Step into history with this timeless 1800’s Colonial, perfectly situated on Main Street in downtown Madison. This unique property blends historic character with modern versatility, offering 4 bedrooms, 2.5 baths, and endless possibilities. Currently configured as a duplex with separate entrances and meters, this home can

    Kelly Duckett-Corbin RE/MAX Gateway

    150 N Main St, Madison, VA 22727
  • /24

    $392,000

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft

    33 E Circle Rd, Madison, VA 22727

    Available in May 2025 a modern two BR, two bath, central heat and A/C house situated on a 1.04 acre lot in a small community of widely separated houses adjacent to the Conway (Middle) River. There are no other houses within immediate sight of the house. Two hours from DC, the house is easily accessed on relatively flat terrain and is wooded on two sides with an open stocked pond a couple hundred

    Lawrence Lessin Homes By Owner, Inc.

    33 E Circle Rd, 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

    • 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
  • /56

    $599,000

    • 4 Beds
    • 3.5 Baths
    • 2,290 Sq Ft

    256 N Blue Ridge Turnpike, Madison, VA 22727

    Just a short drive from the Center of the town of Madison. Come home to this spacious one-of-a-kind brick split level home on 4.5 acres is filled with lots character and charm. Enter through gorgeous Brazilian Mahogany double doors framed with custom stained glass into a beautiful large ceramic tiled foyer. The main level includes spacious rooms with multiple skylights filling them with natural

    sharon rock CENTURY 21 New Millennium

    256 N Blue Ridge Turnpike, 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
  • /8

    $165,000

    • Land
    • 5.1 Acres
    • $32,353 per Acre

    TBD Duet Rd, Madison, VA 22727

    Welcome to Life out here in a very popular area in Madison County! Where the solitude is so loud, you hear the birds sing, watch the wildlife roam on your very own private wooded lot. This lot is full of Mature Trees that boasts a nice year-round flowing stream. This all-road frontage lot is a completed buildable lot. Recently perc approved and just awaiting your dream home.

    sharon rock CENTURY 21 New Millennium

    TBD Duet 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

    $420,000

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft

    984 Oak Park Rd, Madison, VA 22727

    Welcome to this beautifully renovated home nestled on 1.6 private acres in Madison, VA. Move-in ready with every major system updated — new HVAC, new roof, and new water heater Inside, you'll find fresh new flooring, recessed lighting throughout, and a clean, contemporary feel from top to bottom. The fully finished basement is a standout feature, offering two versatile bonus rooms perfect for a

    Wendy Chavez Spring Hill Real Estate, LLC.

    984 Oak Park Rd, Madison, VA 22727
  • /20

    $145,000

    • Land
    • 6.01 Acres
    • $24,126 per Acre

    00 Mount Zion Church Rd, Madison, VA 22727

    Escape to Madison County with a property that offers more than just acreage—it offers a future. Located on Mt. Zion Rd, these two surveyed and engineered lots provide the rare flexibility to create a custom living experience. The Main Estate (5.005 Acres): The larger parcel provides ample space for a sprawling homestead. It already includes a 14'x28' shed, giving you a head start for storage

    Derek Greene The Greene Realty Group

    00 Mount Zion Church Rd, 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

    • 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
  • /6

    $1,850,000

    • Land
    • 244.34 Acres
    • $7,571 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
  • /25

    $300,000

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

    211 Lonnie Burke Rd, Madison, VA 22727

    List price is starting bid only. Home will be sold at auction 4/21/2026 @3:30pm. Contact us or your favorite real estate professional to view this home! Buying at auction is easy and transparent you can get financing!! Custom built 4 BR/3 BA Home (Greystone Homes) -- Partially finished basement w/bedroom & bathroom -- Attached garage -- Large rear deck & screened porch -- Located only .7 off of

    John Nicholls Nicholls Auction Marketing Group

    211 Lonnie Burke Rd, 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
  • /58

    $529,000 New Construction

    • 4 Beds
    • 3 Baths

    183 Sleigh Bell Ln, Madison, VA 22727

    Brand-New 4BR/3BA Country Retreat on 3+ Private Acres Welcome home to this stunning brand-new raised rambler, perfectly tucked away on a peaceful cul-de-sac in the desirable Malvern community. Set on over 3 acres with a wooded perimeter for privacy, this property offers the perfect blend of comfort, nature, and modern living. Step onto the charming front porch and take in the sights and sounds of

    Kelly Duckett-Corbin RE/MAX Gateway

    183 Sleigh Bell Ln, Madison, VA 22727
  • /3

    $135,000

    • Land
    • 3 Acres
    • $45,000 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
  • /5

    $75,000

    • Land
    • 1.76 Acres
    • $42,614 per Acre

    0 Poor House Rd Unit VAMA2002480, Madison, VA 22727

    1.759 Acres in Beautiful Madison County! Has been perc tested for a 3 bedroom conventional and brand new survey! Great Lot near Syria and Shenandoah National Park, near Graves Mtn Lodge and several breweries/wineries.

    Dana Williams EXP Realty, LLC

    0 Poor House Rd Unit VAMA2002480, Madison, VA 22727
  • /60

    $255,000

    • 3 Beds
    • 1 Bath
    • 1,293 Sq Ft

    1380 S F T Valley Rd, Madison, VA 22727

    An affordable brick home with great potential—perfect for investors or buyers ready to add their personal touch. Being sold as-is, this property offers solid bones and several key updates already completed, including a water heater, central A/C, pumped septic within the last 5 years. Seller had main floor beam replaced. The home does need some updating, painting and wood and brick work, making it

    Sandy Morris KELLER WILLIAMS ALLIANCE - CHARLOTTESVILLE

    1380 S F T Valley Rd, Madison, VA 22727
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