Madison, VA Homes for Sale under $500,000

Circa 1840 | A Timeless Madison Treasure Step back in time and own a remarkable piece of Madisons 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 and

Kelly Duckett-Corbin RE/MAX Gateway

List price is starting bid only. Home will be sold at auction 9/14/2026 @12pm. Contact us or your favorite real estate professional to view this home! Buying at auction is easy and transparent you can get financing!! Historic 4 BR/2.5 BA multi-tenant home on 1.619 +/- acres (circa 1820) -- Detached 30'x36' shop/garage/storage building -- Currently used as a duplex, but easily converted to a

John Nicholls Nicholls Auction Marketing Group

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

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

PRICE IMPROVEMENT!! MOVE-IN READY & CONVENIENTLY LOCATED! Built in 2022 and lovingly maintained by the original owner, this nearly new home sits on 3 acres just off Route 29, ideally positioned between Culpeper and Charlottesville and mere minutes from the Greene County line. Enjoy the benefits of living so close to some of Virginia's most beloved small towns and all they have to offer!Step

Brittany Smyth Piedmont Fine Properties

7 bedroom 3.5 bath duplex fronting on the Robinson River in scenic Criglersville, Va in Madison County. The home boasts 4500 square feet and is divided into two units one being 3 bedrooms 1.5 baths and the other 4 bedrooms 2 baths. Both units have heat pumps for efficient heating and cooling, 200 amp electrical panels, and their own laundry room. Firefly high speed internet is installed and

Norman Domingo XRealty.NET LLC

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, including a community pool and lake access. Very accessible to Madison and US Highway 29, the house boasts valuable main floor living with primary bed and bathroom on the entry level. A spacious

Janis Murphy RE/MAX Distinctive Real Estate, Inc.