Madison, VA Homes

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  /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
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  /33

  $535,000 Sold Jul 18, 2025

  1215 Kinderhook Rd, Madison, VA 22727

  • 3 Beds
  • 2.5 Baths
  • 2,237 Sq Ft
  • Built 2000

  Last Sold Summary

  • $239/SF
  • 3 Days On Market

  Current Estimated Value $548,264

  Last Listing Agent Adam Beroza Cheri Woodard Realty

  1215 Kinderhook Rd, Madison, VA 22727
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  /49

  Est $476,999 Not Listed For Sale

  518 Laurel Dr, Madison, VA 22727

  • 3 Beds
  • 3 Baths
  • 1,913 Sq Ft
  • Built 1988

  518 Laurel Dr, Madison, VA 22727

  Last Sold Summary

  • 8% Above List Price
  • $231/SF
  • 2 Days On Market

  Last Sold Price $441,000

  Last Listing Agent Debra Cash REAL ESTATE III, INC.
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  /2

  $885,000

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

  298 Courthouse Mountain Ln, Madison, VA 22727

  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 a

  Julie Holbrook NEST REALTY GROUP

  298 Courthouse Mountain Ln, Madison, VA 22727
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  /38

  $350,000 Sold Oct 14, 2025

  5577 Ruth Rd, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 2,268 Sq Ft
  • Built 1970

  Last Sold Summary

  • $154/SF
  • 13 Days On Market

  Current Estimated Value $353,501

  Last Listing Agent Sharon Cave CENTURY 21 New Millennium

  5577 Ruth Rd, Madison, VA 22727
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  /2

  Est $303,333 Not Listed For Sale

  108 Resettlement Ct, Madison, VA 22727

  • 4 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1972

  108 Resettlement Ct, Madison, VA 22727

  Last Sold Summary

  • 5% Below List Price
  • $302/SF

  Last Sold Price $289,500

  Last Listing Agent Brandon Carroll Samson Properties
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  /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
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  /58

  $410,000 Sold Aug 18, 2025

  573 Liberty Ln, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1995

  Last Sold Summary

  • $188/SF
  • 22 Days On Market

  Last Listing Agent Patti Lillard Montague, Miller & Company

  573 Liberty Ln, Madison, VA 22727
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  /28

  Est $472,596 Not Listed For Sale

  1972 Twymans Mill Rd, Madison, VA 22727

  • 5 Beds
  • 2.5 Baths
  • 2,197 Sq Ft
  • Built 1962

  1972 Twymans Mill Rd, Madison, VA 22727

  Last Sold Summary

  • 11% Above List Price
  • $193/SF
  • 113 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Garlene Daniel Montague, Miller & Company
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  /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
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  /10

  $409,000 Sold Jul 25, 2025

  601 Gibbs Rd, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2025

  Last Sold Summary

  • $304/SF
  • 85 Days On Market

  Last Listing Agent Cinthia Thornhill CENTURY 21 New Millennium

  601 Gibbs Rd, Madison, VA 22727
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  /8

  Est $146,677 Not Listed For Sale

  248 Carpenters Mill Rd, Madison, VA 22727

  • 3 Beds
  • 1 Bath
  • 939 Sq Ft
  • Built 1950

  248 Carpenters Mill Rd, Madison, VA 22727

  Last Sold Summary

  • 40% Above List Price
  • $112/SF
  • 31 Days On Market

  Last Sold Price $105,000

  Last Listing Agent Chauntey Fields BHG Base Camp
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  /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
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  /14

  $39,000 Sold May 12, 2025

  0 Revenooer Rd Unit VAMA2001656, Madison, VA 22727

  • Land
  • 2.46 Acres
  • $15,854 per Acre

  Last Sold Summary

  • 347 Days On Market

  Last Listing Agent NOLAN RIGG EXP Realty, LLC

  0 Revenooer Rd Unit VAMA2001656, Madison, VA 22727
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  /2

  Est $807,254 Not Listed For Sale

  4024 Oak Park Rd, Madison, VA 22727

  • 4 Beds
  • 3 Baths
  • 2,852 Sq Ft
  • Built 1895

  4024 Oak Park Rd, Madison, VA 22727

  Last Sold Summary

  • 8% Below List Price
  • $263/SF

  Last Sold Price $749,000

  Last Listing Agent Cathy Marco Cowan Realty, Inc.
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  /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
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  /84

  $640,000 Sold Aug 20, 2025

  161 Half Penny Ln, Madison, VA 22727

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft
  • Built 2025

  Last Sold Summary

  • $213/SF
  • 136 Days On Market

  Current Estimated Value $622,244

  Last Listing Agent Patti Lillard Montague, Miller & Company

  161 Half Penny Ln, Madison, VA 22727
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  /31

  Est $492,387 Not Listed For Sale

  29 Oaks Ln, Madison, VA 22727

  • 4 Beds
  • 2.5 Baths
  • 2,384 Sq Ft
  • Built 2000

  29 Oaks Ln, Madison, VA 22727

  Last Sold Summary

  • 20% Above List Price
  • $173/SF
  • 24 Days On Market

  Last Sold Price $412,000

  Last Listing Agent NIKI GRIMSLEY AVENUE REALTY, LLC
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  /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
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  /57

  $445,000 Sold Jun 17, 2025

  3947 Hebron Valley Rd, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 1,984 Sq Ft
  • Built 1891

  Last Sold Summary

  • $224/SF
  • 8 Days On Market

  Current Estimated Value $431,828

  Last Listing Agent Karen Crowe Coldwell Banker Realty

  3947 Hebron Valley Rd, Madison, VA 22727
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  /2

  Est $471,141 Not Listed For Sale

  3854 Oak Park Rd, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • Built 1920

  3854 Oak Park Rd, Madison, VA 22727

  Last Sold Summary

  • 11% Below List Price
  • $190/SF

  Last Sold Price $425,000

  Last Listing Agent Terry Cheatle Century 21 New Millennium
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  /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 RE/MAX Gateway

  399 Shelby Rd, Madison, VA 22727
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  /73

  $470,000 Sold Oct 31, 2025

  899 Lindsay Ln, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 2,318 Sq Ft
  • Built 1961

  Last Sold Summary

  • $203/SF
  • 51 Days On Market

  Current Estimated Value $473,701

  Last Listing Agent Brett Sowder RE/MAX Roots

  899 Lindsay Ln, Madison, VA 22727
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  /2

  Not Listed For Sale

  150 Mount Zion Church Rd, Madison, VA 22727

  • 4 Beds
  • 3 Baths
  • 2,052 Sq Ft
  • Built 2004

  150 Mount Zion Church Rd, Madison, VA 22727

  Last Sold Summary

  • $117/SF

  Last Sold Price $239,900

  Last Listing Agent Melda Bates River Fox Realty, LLC
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  /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
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  /8

  $65,000 Sold Jan 02, 2026

  0 Revenooer Rd Unit VAMA2002086, Madison, VA 22727

  • Land
  • 3.06 Acres
  • $21,242 per Acre

  Last Sold Summary

  • 276 Days On Market

  Last Listing Agent Julie Wilcox Julie Wilcox Real Estate, LLC

  0 Revenooer Rd Unit VAMA2002086, Madison, VA 22727
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  Not Listed For Sale

  601 Old Forge Way, Madison, VA 22727

  • 4 Beds
  • 3 Baths
  • 4,022 Sq Ft
  • Built 2002

  601 Old Forge Way, Madison, VA 22727

  Last Sold Summary

  • 33% Below List Price
  • $168/SF
  • 29 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Kim Gallihugh Century 21 New Millennium
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  /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
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  /22

  $250,000 Sold Oct 23, 2025

  273 & 299 Ridgeview, Madison, VA 22727

  • 4 Beds
  • 1.5 Baths
  • 3,152 Sq Ft
  • Built 1891

  Last Sold Summary

  • $79/SF
  • 411 Days On Market

  Last Listing Agent Staci Fox Montague, Miller & Company

  273 & 299 Ridgeview, Madison, VA 22727
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  /2

  Est $504,440 Not Listed For Sale

  94 Anvil Ct, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 2,832 Sq Ft
  • Built 2005

  94 Anvil Ct, Madison, VA 22727

  Last Sold Summary

  • 10% Below List Price
  • $162/SF

  Last Sold Price $460,000

  Last Listing Agent Carrie Brown Montague, Miller & Company
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  /33

  $25,000 Pending

  • 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
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  /29

  $2,050,000 Sold Mar 14, 2025

  15-27,28,31&35 S F T Valley Rd Unit 27,28,31&35, Madison, VA 22719

  • Land
  • 265 Acres
  • $7,736 per Acre

  Last Sold Summary

  • 306 Days On Market

  Last Listing Agent WILLIAM GENTRY JEFFERSON LAND & REALTY

  15-27,28,31&35 S F T Valley Rd Unit 27,28,31&35, Madison, VA 22719
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  /29

  Not Listed For Sale

  104 Half Penny Ln, Madison, VA 22727

  • 3 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 2005

  104 Half Penny Ln, Madison, VA 22727

  Last Sold Summary

  • 20% Above List Price
  • $235/SF
  • 28 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Guillermo Salmon Samson Properties
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  /41

  $399,998

  • 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
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  /29

  $2,050,000 Sold Mar 14, 2025

  15-27,28,31&35 S F T Valley Rd, Madison, VA 22719

  • Land
  • 265 Acres
  • $7,736 per Acre

  Last Sold Summary

  • 9% Below List Price
  • 307 Days On Market

  Last Listing Agent Bill Gentry JEFFERSON LAND & REALTY

  15-27,28,31&35 S F T Valley Rd, Madison, VA 22719
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  /27

  Est $458,654 Not Listed For Sale

  206 Covered Bridge Dr, Madison, VA 22727

  • 3 Beds
  • 2.5 Baths
  • 1,551 Sq Ft
  • Built 1986

  206 Covered Bridge Dr, Madison, VA 22727

  Last Sold Summary

  • 118% Above List Price
  • $135/SF
  • 351 Days On Market

  Last Sold Price $210,075

  Last Listing Agent Bonnie Coffey Samson Properties
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  /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
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  /71

  $780,000 Sold Sep 09, 2025

  643 Lost Valley Rd, Madison, VA 22727

  • 3 Beds
  • 3 Baths
  • 2,596 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 128 Days On Market

  Current Estimated Value $798,624

  Last Listing Agent Michael Gaffney COMPASS-CHARLOTTESVILLE

  643 Lost Valley Rd, Madison, VA 22727
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  /2

  Est $630,210 Not Listed For Sale

  858 Ashlawn Dr, Madison, VA 22727

  • 3 Beds
  • 3 Baths
  • 3,240 Sq Ft
  • Built 1970

  858 Ashlawn Dr, Madison, VA 22727

  Last Sold Summary

  • 5% Below List Price
  • $185/SF

  Last Sold Price $600,000

  Last Listing Agent Kelly Thornton Long & Foster Real Estate, Inc.
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  /26

  $379,900

  • 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

Showing Results 41 - 80, Page 2 of 18