Homes for Sale in 22727

• 

  

  

  /41

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  247 Rapidan Church Ln, Wolftown, VA 22748

  Set atop 17 breathtaking acres in southern Madison County, Azalea Hill offers sweeping eastward views across rolling farmland and an unmatched sense of privacy and tranquility—just five minutes from Route 29. This solidly built, one-level brick home features three bedrooms, hardwood floors, a cozy fireplace, and abundant natural light throughout. Recent updates include a newer HVAC system (2019),

  Carter Montague MONTAGUE, MILLER & CO. - WESTFIELD

  247 Rapidan Church Ln, Wolftown, VA 22748
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /34

  $330,000

  • Land
  • 10 Acres
  • $33,000 per Acre

  0 Elly Rd Unit 674426, Aroda, VA 22709

  Private 10-acre wooded parcel in the quiet Aroda area of Madison County. Gently rolling terrain with mature woods and a small stream along one boundary. Survey completed with proposed septic drainfield location identified, and property corners and drainfield area are clearly marked. Access via a shared private driveway serving several nearby properties, with a power line along one side of the

  Tom Woolfolk KELLER WILLIAMS ALLIANCE - CHARLOTTESVILLE

  0 Elly Rd Unit 674426, Aroda, VA 22709
• 

  

  /34

  $330,000

  • Land
  • 10 Acres
  • $33,000 per Acre

  0 Elly Rd Unit 50 81, Aroda, VA 22709

  Private 10-acre wooded parcel in the quiet Aroda area of Madison County. Gently rolling terrain with mature woods and a small stream along one boundary. Survey completed with proposed septic drainfield location identified, and property corners and drainfield area are clearly marked. Access via a shared private driveway serving several nearby properties, with a power line along one side of the

  Tom Woolfolk KELLER WILLIAMS ALLIANCE - CHARLOTTESVILLE

  0 Elly Rd Unit 50 81, Aroda, VA 22709
• 

  

  /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
• 

  

  /28

  $550,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  1823 Desert Rd, Reva, VA 22735

  Welcome to your mountain retreat on Desert Road. Built in 2024, this thoughtfully designed home was intentionally positioned to capture breathtaking mountain views on clear days while offering the privacy and peace that make it the perfect escape from busy life. Whether you are looking for a full-time residence, weekend getaway, or an investment opportunity, this property offers incredible

  Japreshia Terrell Wolford And Associates Realty LLC

  1823 Desert Rd, Reva, VA 22735
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /16

  $319,900

  • 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
• 

  

  /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
• 

  

  /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

  $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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /11

  $175,000

  • Land
  • 2.13 Acres
  • $82,160 per Acre

  55-38B Seminole Trail, Shelby, VA 22727

  2.1 acre lot located on the route 29 corridor in the Shelby area of Madison County. This wooded lot is zoned B1(Business). The lot features 300 feet of road frontage. No well or septic has been installed on this property. Ideal for retail or service use!

  Carrie Brown Montague, Miller & Company

  55-38B Seminole Trail, Shelby, VA 22727
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /14

  $99,999

  • Land
  • 4.15 Acres
  • $24,096 per Acre

  0 LOT A Main Uno Baptist Church Ln, Rochelle, VA 22727

  Build Your Dream Home on 4.154 Acres in Beautiful Madison County – Priced at $99,999Discover the opportunity to own 4.154 acres of buildable land in Madison County, VA featuring approximately 500 feet of road frontage and multiple potential home sites. The gently landscape offers a scenic setting with open views, privacy, and flexibility to create the property you’ve always envisioned—whether

  Dianna Banks RE/MAX Gateway

  0 LOT A Main Uno Baptist Church Ln, Rochelle, 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
• 

  

  /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
• 

  

  /33

  $289,900

  • Land
  • 11.05 Acres
  • $26,235 per Acre

  0 Orange Rd Unit VAMA2002476, Pratts, VA 22731

  This is the lot you have been waiting for! Very convenient to town, BUT feels like you are in the middle of the country! These 11+ acres are zoned R1, so they can be divided into as many as 6 lots! With Comcast available and a nice stream at the back of the property, the limitation is only your imagination.

  Kevin McHaney RE/MAX New Horizons

  0 Orange Rd Unit VAMA2002476, Pratts, VA 22731
• 

  

  /40

  $599,000

  • 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

  

  Donna Waugh-Robinson

  Corcoran Wiley

  (540) 417-9634

  107 Sylvan Ln, Madison, VA 22727
• 

  

  /36

  $699,000

  • Land
  • 29.52 Acres
  • $23,679 per Acre

  0 Hurt Hollow Rd, Banco, VA 22711

  Amazing opportunity to own 29.5 Acres in Madison County near the Shenandoah National Park! This property offers multiple elevated building sites with potential views of Double Top Mountain! There is a creek meandering along the bottom of the property. Trails are already in place to take a walk and enjoy everything nature has to offer! Plenty of wildlife!

  Dana Williams EXP Realty, LLC

  0 Hurt Hollow Rd, Banco, VA 22711
• 

  

  /32

  $289,900

  • Land
  • 11.04 Acres
  • $26,259 per Acre

  0 Orange Rd Unit 669727, Pratts, VA 22731

  This is the lot you have been waiting for! Very convenient to town, BUT feels like you are in the middle of the country! These 11+ acres are zoned R1, so they can be divided into as many as 6 lots! With Comcast available and a nice stream at the back of the property, the limitation is only your imagination.

  Kevin McHaney RE/MAX NEW HORIZONS

  0 Orange Rd Unit 669727, Pratts, VA 22731
• 

  

  /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
• 

  

  /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
• 

  

  /18

  $430,000

  • Land
  • 39.18 Acres
  • $10,975 per Acre

  TM 23-5A Mitchell Mountain Rd Unit 5A, Haywood, VA 22722

  This is a newly surveyed 39+ acre parcel, located within a short drive to the Towns of Madison and Culpeper; but still in a area surrounded by other large farms and land tracts. The subject property has long State road frontage, and is in Forestal Land Use Taxation. The land is wholly wooded, in a balanced mix of assorted hardwood timber and mountain laurel. There are two spring fed creeks

  WILLIAM GENTRY JEFFERSON LAND & REALTY

  TM 23-5A Mitchell Mountain Rd Unit 5A, Haywood, VA 22722
• 

  

  /18

  $430,000

  • Land
  • 39.18 Acres
  • $10,975 per Acre

  TM 23-5A Mitchell Mountain Rd, Haywood, VA 22722

  This is a newly surveyed 39+ acre parcel, located within a short drive to the Towns of Madison and Culpeper; but still in a area surrounded by other large farms and land tracts. The subject property has long State road frontage, and is in Forestal Land Use Taxation. The land is wholly wooded, in a balanced mix of assorted hardwood timber and mountain laurel. There are two spring fed creeks

  Bill Gentry JEFFERSON LAND & REALTY

  TM 23-5A Mitchell Mountain Rd, Haywood, VA 22722
• 

  

  /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
• 

  

  /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

  

  Julie Garrett

  Rappahannock Real Estate, LLC.

  (540) 202-2159

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

  

  /58

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 3,968 Sq Ft

  1130 Race Ground Rd, Rochelle, VA 22738

  Back on the market by no fault of the seller and NEW PRICE!! Discover serene living in this splendid 4-bedroom, 3.5-bathroom home nestled in the heart of Madison. Step inside and find an abundance of interior space, each room offering comfort and versatility to accommodate your lifestyle. Your primary suite ensures a private sanctuary with ample space and an en-suite bathroom. The living areas

  ERICA GENTILE-HUSSAR AVENUE REALTY, LLC

  1130 Race Ground Rd, Rochelle, VA 22738
• 

  

  /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
• 

  

  /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
• 

  

  /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

  

  Julie Garrett

  Rappahannock Real Estate, LLC.

  (540) 701-7352

  92 acres Seminole Trail, Madison, VA 22727

Showing Results 1 - 40, Page 1 of 2