Homes for Sale in 22727

• 

  

  

  /17

  $1,179,000

  $21K PRICE DROP

  • Land
  • 7.8 Acres
  • $151,154 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.

  

  Julie Garrett

  Rappahannock Real Estate, LLC.

  (540) 870-5863

  TBD Seminole Trail, Madison, VA 22727
• 

  

  

  /14

  $719,000

  $50K PRICE DROP

  • Land
  • 6.3 Acres
  • $114,127 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
• 

  

  

  /22

  $299,000

  • Land
  • 10 Acres
  • $29,900 per Acre

  0 Goods Ln, Madison, VA 22727

  Coming Soon in beautiful Madison County — an incredible opportunity to own approximately 10 acres of beautifully maintained open pasture and endless potential on a private road. Recently perked for conventional septic. Currently awaiting final division approval, this picturesque property offers a gorgeous homesite setting with the perfect blend of open space and scenic countryside charm. Another

  

  Julie Garrett

  Rappahannock Real Estate, LLC.

  (540) 502-4724

  0 Goods Ln, Madison, VA 22727
• 

  

  

  /60

  $415,000

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,756 Sq Ft

  40 John Tucker Rd, Madison, VA 22727

  ***Note: this home is only for sale, any rent ads you see are a scam. *** Why settle for a home that needs work when you can have one that's already been renovated from top to bottom? Situated on a beautiful 2-acre lot in Madison County, this move-in ready home offers the perfect blend of modern updates, privacy, and outdoor space. Enjoy peaceful wooded views, room for pets and gardening, and the

  

  Heather Skowronsky

  Samson Properties

  (540) 518-0210

  40 John Tucker Rd, Madison, VA 22727
• 

  

  

  /19

  $315,000

  • 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 of beautifully maintained open pasture and endless potential. Recently perked for conventional septic. Currently awaiting final division approval, this picturesque property offers a gorgeous homesite setting with the perfect blend of open space and scenic countryside charm. Another 10 acre lot

  

  Julie Garrett

  Rappahannock Real Estate, LLC.

  (540) 495-1565

  0 John Tucker Unit VAMA2002750, Madison, VA 22727
• 

  

  /68

  $435,000

  $14K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /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

  $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
• 

  

  /28

  $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 through the lot. 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
• 

  

  /8

  $89,900

  $5K PRICE DROP

  • 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
• 

  

  /28

  $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 through the lot. 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
• 

  

  /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

  $24K PRICE DROP

  • 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
• 

  

  /16

  $264,900

  $20K PRICE DROP

  • 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.

  Cindy Whitelock Massanutten Realty

  114 Marshall Rd, 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
• 

  

  /18

  $374,900

  $10K PRICE DROP

  • 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
• 

  

  /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

  $40K PRICE INCREASE

  • 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
• 

  

  /41

  $375,000

  $25K PRICE DROP

  • 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
• 

  

  /28

  $499,000

  $51K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /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

  $384,000

  $11K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /50

  $4,450,000

  • 5 Beds
  • 6 Baths
  • 5,153 Sq Ft

  4578 Ruth Rd, Madison, VA 22727

  Set amidst 17 beautifully landscaped acres, Monte Ventoso is an extraordinary Italian-inspired villa offering the ambiance of a private Mediterranean retreat in the foothills of the Blue Ridge Mountains. Ideally positioned between Washington, D.C. and Charlottesville, VA, the estate combines exceptional privacy with convenient accessibility. A handcrafted fountain imported from Italy creates a

  COURT NEXSEN MCLEAN FAULCONER INC., REALTOR

  4578 Ruth Rd, Madison, VA 22727
• 

  

  /40

  $415,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  898 Seville Rd, Madison, VA 22727

  Welcome home to 898 Seville- the modern homestead starter kit for someone ready to put down roots in Madison County! Built in 2022 and lovingly maintained by its original owner, this nearly new home sits on 3 acres just off Route 29, ideally positioned between Culpeper and Charlottesville and only minutes from the Greene County line.Step inside to discover an inviting open-concept floor plan

  Brittany Smyth Piedmont Fine Properties

  898 Seville 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
• 

  /2

  $499,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,404 Sq Ft

  14 Surrey Ct, Madison, VA 22727

  Kathy Campbell Kathy Jean Campbell

  14 Surrey Ct, Madison, VA 22727
• 

  

  /20

  $375,000

  $12K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 897 Sq Ft

  850 Oak Park Rd, Madison, VA 22727

  Enjoy your coffee with the sunrise on the back deck. Then take an afternoon break on the covered front porch to take in the peacefulness Madison county has to offer. Charming and cozy 2 bed 1.5 bath cottage in the foothills of Madison county. Conveniently located to Rt. 29. Everything in this house is brand new, Major rehab completed in 2026. All systems, alliances, electrical, plumbing, HVAC,

  Christopher Pierce MarketPlace REALTY

  850 Oak Park Rd, Madison, VA 22727
• 

  

  /67

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  803 Weaver Hollow Rd, Banco, VA 22711

  Charming Country Retreat on Nearly 8 Acres — Peaceful Setting with Endless Potential! Nestled in the heart of the countryside yet conveniently located just a short drive to Madison, Culpeper, Graves Mountain Lodge, White Oak Canyon, Shenandoah National Park, the Rapidan River, and countless outdoor adventures, this solidly built one-level home offers the perfect blend of privacy, comfort, and

  Kelly Duckett-Corbin RE/MAX Gateway

  803 Weaver Hollow Rd, Banco, VA 22711
• 

  

  /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
• 

  

  /65

  $499,000

  Open Sun 1:30PM - 3:30PM

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft

  1388 Novum Church Rd, Reva, VA 22735

  *Get up to $2,500 with use of preferred lender for closing cost assistance or use funds for a rate buy-down (restrictions apply and not all will qualify, contact listing agent for details)Turn-Key Rambler on 3 Private Acres with Stunning Upgrades! Welcome home to this beautifully maintained 2006-built rambler offering approximately 2,912 sq ft of comfortable living space on a spacious

  Jake McNemar RE/MAX Gateway

  1388 Novum Church Rd, Reva, VA 22735
• 

  

  /34

  $795,000

  Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 2,816 Sq Ft

  99 Bluff Mountain Rd, Madison, VA 22727

  Available for showings starting July 23rd! Tucked away in the beautiful Graves Mill Valley of Madison County, this private 7.5-acre retreat offers breathtaking views of rolling farmland and the Blue Ridge Mountains. A short distance to Shenandoah National Park and the Rapidan Wildlife Management Area, the property is perfectly positioned for outdoor enthusiasts who enjoy hiking, wildlife, fly

  Gayle Harvey Gayle Harvey Real Estate Inc

  99 Bluff Mountain 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

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