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Madison, VA Homes for Sale with Acreage

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  • /44

    $545,000

    • 3 Beds
    • 2.5 Baths
    • 2,186 Sq Ft

    628 River Rd, Madison, VA 22727

    This home has an assumable loan option with an interest rate of 2.75%! Reach out today to see if you qualify!Discover this private single-story home set on 7.69 wooded acres with abundant wildlife and a river easement in highly desirable Madison County. This 3-bedroom, 2.5-bath residence offers the perfect blend of comfort and nature.Step inside to an open floor plan featuring beautiful

    Agent Photo

    Melissa Martin

    CENTURY 21 New Millennium

    (540) 730-2187

    628 River Rd, 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
  • /17

    $895,000

    • Land
    • 7.8 Acres
    • $114,744 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.

    (540) 779-1502

    TBD Seminole Trail, Madison, VA 22727
  • /40

    $649,000

    • 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
  • /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
  • /20

    $249,999

    • Land
    • 3.68 Acres
    • $67,935 per Acre

    N White Oak Lake Lakeview Dr, Madison, VA 22727

    3.68 Acres Total | 4 Adjacent Lots (2 Waterfront + 2 Waterview)White Oak Lake – Madison County, VAA once-in-a-lifetime opportunity to own expansive private lakefront property in one of Virginia’s most peaceful, unspoiled counties. These 4 adjacent lots sit on White Oak Lake, a ~52-acre, electric-only lake tucked into the Blue Ridge Mountain foothills, with no public access and no

    Nick Bullard

    N White Oak Lake Lakeview Dr, Madison, VA 22727
  • /24

    $406,000

    • 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

    sharon rock CENTURY 21 New Millennium

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

    $95,000

    • Land
    • 1 Acre
    • $95,000 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
  • /42

    $635,000

    • 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
  • /75

    $885,000

    • 3 Beds
    • 4.5 Baths
    • 4,993 Sq Ft

    298 Courthouse Mountain Ln, Madison, VA 22727

    Welcome to Woodhaven: an architectural sanctuary on 6.47 private acres in the Blue Ridge foothills. A rare find offering seamless silence just 5 minutes from Route 29 and 30 minutes from Charlottesville. This atypical, seven-sided Mid-Century Modern masterpiece unfolds around dramatic two- story soaring wood ceilings. A custom oversized fireplace and brick chimney anchor the living spaces, while

    Julie Holbrook NEST REALTY GROUP

    298 Courthouse Mountain Ln, 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
  • /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
  • /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
  • /18

    $25,000

    • Land
    • 2 Acres
    • $12,500 per Acre

    0 Horn Hollow Ln Unit 11640972, Madison, VA 22727

    List price is starting bid only. Home will be sold at auction 3/3/2026 @10AM. Contact us or your favorite real estate professional to view this home! Buying at auction is easy and transparent you can get financing!! 2.019 +/- acre building lot -- Approved septic & well permits -- Newly installed driveway; access onto 2 state maintained roads -- Located 6 miles from from Rt. 29/Downtown Madison,

    John Nicholls Nicholls Auction Marketing Group

    0 Horn Hollow Ln Unit 11640972, 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
  • /52

    $539,000 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
  • /84

    $560,000

    • 3 Beds
    • 2.5 Baths
    • 2,292 Sq Ft

    1167 Covered Bridge Dr, Madison, VA 22727

    An exceptionally maintained and truly loved home is ready to welcome its next family. This classic brick Cape Cod offers 3 bedrooms plus a bonus room, 3 full baths, and the convenience of a main‐level primary suite. The main floor features a formal dining room, an eat‐in kitchen that opens to the family room, and plenty of natural light throughout. Primary suite on main level make this a dream!

    Mandy Brown CENTURY 21 New Millennium

    1167 Covered Bridge Dr, 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
  • /7

    $290,000

    • 3 Beds
    • 4 Baths
    • 1,906 Sq Ft

    732 Courthouse Mountain Rd, Madison, VA 22727

    Brick rambler located within minutes to the Town of Madison. Brick home features formal dining room, living room with fireplace, kitchen with breakfast area, and family room. Full walk-out basement with recreation room with bar, half bath, and storage area. The original water source was a spring and reservoir; however, Madison County Health Department records do not confirm a well has been

    Norma Gibbs Long & Foster Real Estate, Inc.

    732 Courthouse Mountain Rd, Madison, VA 22727
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