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Madison, VA Homes for Sale

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  • /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
  • /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
  • /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
  • /52

    $475,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 2,376 Sq Ft

    65 Chestnut Rail Ln, Madison, VA 22727

    Exceptional lakefront living on 3 private acres in Madison County, offering breathtaking water views and effortless one-level living. This beautifully updated 3-bedroom, 2-bath home showcases a light-filled open floor plan with vaulted ceilings, gleaming hardwood floors, and expansive windows designed to frame the lake from nearly every room. The upgraded kitchen features quartz countertops,

    Dianna Banks RE/MAX Gateway

    65 Chestnut Rail Ln, 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
  • /44

    $395,000

    • 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
  • /69

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 2,744 Sq Ft

    319 N Main St, Madison, VA 22727

    Circa 1840 | A Timeless Madison Treasure Step 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 front porch

    Kelly Duckett-Corbin RE/MAX Gateway

    319 N Main St, Madison, VA 22727
  • /2

    $409,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 1,692 Sq Ft

    115 Washington St, Madison, VA 22727

    Carrie Brown Montague, Miller & Company

    115 Washington 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

    • 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
  • /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
  • /45

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,502 Sq Ft

    399 Shelby Rd, Madison, VA 22727

    This newly renovated 3-bed, 2-bath home in Madison County makes it easy to picture your life here, waking up to panoramic mountain views, sipping coffee on your deck, and coming back to a space that feels warm and effortless. Inside, the granite countertops and luxury vinyl plank flooring throughout add a clean, modern feel that’s both beautiful and practical for everyday living. The open layout

    Ryan Dickerson Samson Properties

    399 Shelby 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
  • /41

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    453 Lost Valley Rd, Madison, VA 22727

    Mountain views, fresh air, and space to make it your own!Perched on a mountaintop in a private community with very few neighbors, this 3-bedroom, 2-bath home offers the kind of peace and scenery that is hard to find. Surrounded by trees and natural beauty, the setting invites hiking, wildlife watching, and quiet mornings with coffee on the deck.Inside, the home features soaring ceilings,

    Chris Craddock EXP Realty, LLC

    453 Lost Valley Rd, 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
  • /86

    $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
  • /24

    $374,900

    • 3 Beds
    • 2 Baths
    • 1,708 Sq Ft

    2004 Twymans Mill Rd, Madison, VA 22727

    Charming one-level home in Madison County with a perfect blend of country charm, yet just 8 miles to the town of Madison or Orange and 12 miles to Culpeper. With 3 bedrooms and 2 baths it is ideal for easy living. It has central air and heat via a heat pump and also has a chimney for a woodstove if so desired. It has a covered front porch and a deck in the rear. The spacious yard offers room for

    Pamela Debnam Houwzer, LLC

    2004 Twymans Mill 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
  • /65

    $535,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 2,302 Sq Ft

    462 Fox Hunters Ln, Madison, VA 22727

    Tucked away on over 6.5 wooded acres, this 4-bedroom, 3-bath Cape Cod offers the perfect blend of space, privacy, and everyday functionality. The setting is peaceful and natural, with mature trees, a gently flowing creek, and plenty of room to spread out. Inside, the home offers a flexible layout with a main-level primary suite, hardwood flooring, and fresh interior paint throughout. The kitchen

    Lisa Lyons LORING WOODRIFF REAL ESTATE ASSOCIATES

    462 Fox Hunters 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
  • /6

    $290,000

    • 3 Beds
    • 1 Bath
    • 1,280 Sq Ft

    111 Resettlement Rd, Madison, VA 22727

    Welcome to this inviting 3-bedroom, 1-bath home that blends comfort, character, and recent updates. Whether youre a first-time buyer, downsizing, or looking for a solid investment, this property offers great value and everyday livability. The property has new flooring throughout and a kitchen with modern upgrades. It also boasts a large covered front porch perfect for relaxing, morning coffee, or

    Norman Domingo XRealty.NET LLC

    111 Resettlement Rd, Madison, VA 22727
  • /16

    $299,900

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft

    114 Marshall Rd, Madison, VA 22727

    Ranch style home in Madison County VA. This home features 3 bedrooms, 1 bath, an eat-in kitchen, laundry closet, a storage building and a portable carport. The nearly level .65 acre lot makes for a great yard.

    Gary Mitchell Massanutten Realty

    114 Marshall Rd, Madison, VA 22727
  • /19

    $349,900

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    85 Elementary Acres, Madison, VA 22727

    Freshly painted interior, New Carpet just installed. New Roof 5 years ago. Updated windows, HVAC system, Vinyl, New Bath Cabinet & Sink. Full unfinished basement to finish how you like with a bath rough-in. The laundry is in the basement, Hardi Plank Siding. Just outside the town limits and minutes to shopping, schools, dining etc. Back Yard has a privacy fenced area. A creek flows through the

    Bonnie Coffey Samson Properties

    85 Elementary Acres, 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

Frequently Asked Questions

What are the most popular zip codes in Madison, VA?
The most popular zip codes in Madison, VA include 22727, 22715, 22731, 22738 and 22709.
What are the most popular neighborhoods near Madison, VA?
The most popular neighborhoods near Madison, VA are Ruckersville, Twin Lakes, Earlysville, Northeast Charlottesville and Piney Mountain.
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