Homes for Sale in 22727

/49
$450,000
- 4 Beds
- 2.5 Baths
- 1,856 Sq Ft
319 Fox Hunters Ln, Madison, VA 22727

Charming Colonial on 3.74 Acres in Quiet Fox Ridge Neighborhood Tucked away in the peaceful Fox Ridge community of Madison County, this classic Colonial-style home offers a perfect blend of country charm and family-friendly features. With 4 bedrooms and 2.5 baths, including a convenient main-level bedroom, the layout is ideal for flexible living. The inviting open-concept living and dining area

Julie Garrett

Rappahannock Real Estate, LLC.

(540) 306-5632

319 Fox Hunters Ln, 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
/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
/40
$629,000
- 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
/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
/56
$635,000
- 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
/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
/39
$449,000 Coming Soon
- 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
/84
$560,000
- 3 Beds
- 2.5 Baths
- 2,292 Sq Ft
1167 Covered Bridge Dr, Madison, VA 22727

An exceptionally maintained and truly loved home is ready to welcome its next family. This classic brick Cape Cod offers 3 bedrooms plus a bonus room, 2.5 baths, and the convenience of a main‐level primary suite. The main floor features a formal dining room, an eat‐in kitchen that opens to the family room, and plenty of natural light throughout. Primary suite on main level make this a dream! Two

Mandy Brown CENTURY 21 New Millennium

1167 Covered Bridge Dr, 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
/32
$299,000
- Land
- 11.04 Acres
- $27,083 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
/15
$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
/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 RE/MAX Gateway

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
$399,996
- 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
/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
/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
/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
/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
/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
/5
$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
/33
$299,000
- Land
- 11.05 Acres
- $27,059 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
/7
$299,250
- 3 Beds
- 4 Baths
- 1,906 Sq Ft
732 Courthouse Mountain Rd, Madison, VA 22727

Brick rambler located within minutes to the Town of Madison. Brick home features formal dining room, living room with fireplace, kitchen with breakfast area, and family room. Full walk-out basement with recreation room with bar, half bath, and storage area. The original water source was a spring and reservoir; however, Madison County Health Department records do not confirm a well has been

Norma Gibbs Long & Foster Real Estate, Inc.

732 Courthouse Mountain Rd, Madison, VA 22727
/13
$100,000
- Land
- 4.15 Acres
- $24,096 per Acre
0 LOT A Main Uno Baptist Church Ln, Rochelle, VA 22727

Build your dream home on this 4.154-acre buildable lot in Madison County with 500 ft of road frontage and multiple home sites. Enjoy privacy, open views, and easy access to Madison, Orange & Ruckersville. Discover the perfect opportunity to own over 4 acres of buildable land in Madison County, Virginia, offering approximately 500 feet of road frontage and a gently rolling landscape ideal for

Dianna Banks RE/MAX Gateway

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

Virginia Madison County Madison 22727

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