27

Madison, VA Homes for Sale with Acreage

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  • /5

    $315,000 Coming Soon

    • Land
    • 12.5 Acres
    • $25,200 per Acre

    0 John Tucker Unit VAMA2002750, Madison, VA 22727

    Coming Soon in beautiful Madison County — an incredible opportunity to own approximately 12.5 acres or 10 acres of beautifully maintained open pasture with stunning distant mountain views and endless potential. Currently awaiting final division approval, this picturesque property offers a gorgeous homesite setting with the perfect blend of open space and scenic countryside charm. 10 acre lot

    Agent Photo

    Julie Garrett

    Rappahannock Real Estate, LLC.

    (540) 835-5547

    0 John Tucker Unit VAMA2002750, 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
  • /66

    $439,000

    • 4 Beds
    • 2.5 Baths
    • 2,990 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
  • /60

    $599,000

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

    256 N Blue Ridge Turnpike, Madison, VA 22727

    Public Open House Sunday May 3, 2026. There will be refreshments and Drawings for some prizes. Ple Zone Multi-Family. 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

    sharon rock CENTURY 21 New Millennium

    256 N Blue Ridge Turnpike, Madison, VA 22727
  • /47

    $650,000

    • 4 Beds
    • 3 Baths
    • 3,080 Sq Ft

    205 N Main St, Madison, VA 22727

    Welcome to this rare 1836 Federal-style home set in Virginia’s scenic countryside, with sweeping Blue Ridge Mountain views.Listed on the Virginia Landmarks Register and located in a National Register Historic District, this beautifully restored 4BR/3BA home blends historic character with modern updates. Original details like wide-plank hardwood floors, high ceilings, and four fireplaces (two

    Harry Hasbun Keller Williams Realty/Lee Beaver & Assoc.

    205 N Main St, Madison, VA 22727
  • /52

    $540,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    2123 Oak Park Rd, Madison, VA 22727

    Escape the hustle and discover this rare, secluded gem nestled on over 10 private acres in Madison County. This charming 3-bedroom, 2-bath log cabin blends rustic character with modern comfort, offering endless possibilities for your lifestyle.Step onto the spacious covered front and back porches—perfect for relaxing and soaking in the surrounding natural beauty. Inside, you’ll find warm

    Amanda Mitchell Samson Properties

    2123 Oak Park Rd, 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
  • /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
  • /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
  • /20

    $420,000

    • 3 Beds
    • 2 Baths
    • 1,942 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
  • /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
  • /12

    $120,000

    • Land
    • 3.07 Acres
    • $39,088 per Acre

    0 Malvern Dr Unit VAMA2002738, Madison, VA 22727

    Large, open and buildable lot in Malvern of Madison awaits your builder--or we will introduce you to one. This 3.07-acre lot lies right on Malvern Drive just past the entry to Malvern of Madison community. The well-established and friendly community boasts a clubhouse, recreational lake, outdoor pool and play area for children. The lot has been perc'd and the septic designer is ready to submit a

    Timothy Murphy RE/MAX Distinctive Real Estate, Inc.

    0 Malvern Dr Unit VAMA2002738, 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
  • /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
  • /44

    $390,000

    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    1173 Aylor Rd, Madison, VA 22727

    Charming single-family home situated on 2.09 scenic acres in beautiful Madison County. This spacious residence offers 4 bedrooms and 3 full baths, featuring both a comfortable living room and a separate family room—perfect for everyday living and entertaining. The owner’s suite includes a private sitting area, creating a relaxing retreat within the home. Recent updates include a new kitchen floor

    Audrey Badgett ASSIST2SELL - FIRST RATE REALTY, INC.

    1173 Aylor Rd, 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
  • /75

    $900,000

    • 5 Beds
    • 4 Baths
    • 3,168 Sq Ft

    324 N Blue Ridge Turnpike, Madison, VA 22727

    ***OFFERS DUE TUESDAY, 12 MAY, 12 NOON*** Set on 10 private acres in Madison County, this 1930s farmstead approaches its hundredth year with the kind of character that cannot be newly built. Move through the repeated archways, and you will find versatile rooms that adapt to how you actually live — a main-level primary suite with views that make you stay in bed a little longer, flexible upstairs

    Edward Slavis LPT Realty, LLC

    324 N Blue Ridge Turnpike, Madison, VA 22727
  • /2

    $355,000 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,605 Sq Ft

    679 Resettlement Rd, Madison, VA 22727

    Professional photos coming. Welcome to this move-in ready 3 bedroom, 1.5 bath rambler nestled on 2.59 acres of serene land with NO HOA! This property offers the perfect blend of comfort, space, and flexibility, ideal for those seeking a peaceful setting without sacrificing convenience. Enjoy privacy, wide-open spaces, and the freedom to make it your own. Inside, you’ll find a remodeled kitchen

    Christie Shaw Samson Properties

    679 Resettlement Rd, Madison, VA 22727
  • /2

    $335,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,652 Sq Ft

    2747 Twymans Mill Rd, Madison, VA 22727

    Coming Soon in Madison County! Acreage, privacy, and major updates come together at 2747 Twymans Mill Rd in Madison, VA. Set on 3.75 acres, this ranch-style home offers the country setting buyers are searching for, with space for outdoor living, gardening, animals, equipment, hobbies, and room to make it your own. Inside, the main level features an open floor plan where the kitchen, dining area,

    Dianna Banks RE/MAX Gateway

    2747 Twymans Mill Rd, Madison, VA 22727
  • /50

    $465,000

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

    359 Malvern Dr, Madison, VA 22727

    Welcome home to 359 Malvern Drive. This lovely home in the Malvern of Madison community offers the serenity of a four-acre, mostly wooded, private lot, yet in a vibrant community with many amenities. Very accessible to Madison and US Highway 29, the house boasts valuable main floor living with primary bed and bathroom on the main level. A spacious galley kitchen, traditional living and dining

    Janis Murphy RE/MAX Distinctive Real Estate, Inc.

    359 Malvern 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
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