Middletown, VA Homes for Sale under $500,000

"Beautiful On Birmingham" This 4-bedroom, 2 1/2 bath colonial style home is ready for you to move right in! As you enter, you'll be welcomed by the open floor plan! With a large island and plenty of cabinet space the kitchen was built for everyday life and entertainment. Spacious family room, eating area and first floor flex room perfect for a home office! Upstairs you'll find a large primary

Matt Kilmer Samson Properties

This charming ranch-style home, beautifully renovated in 2018, offers a perfect blend of comfort and modern living. Nestled on a serene half-acre lot, the property features a welcoming interior with four spacious bedrooms and a thoughtfully designed layout. Enjoy the warmth of hardwood floors throughout, complemented by upgraded countertops in the eat-in kitchen, which seamlessly connects to the

Lilly Triplett Colony Realty

An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for

Sharon Daniels Coldwell Banker Premier

NEW ROOF INSTALLED AUGUST 2026! Set along Historic Route 11 between Middletown and Stephens City, this single-level 4-bedroom, 3-bathroom home sits on a 0.43-acre lot and has received steady updates over the past four years. Inside, two bedrooms plus the living and dining rooms feature updated flooring, and one bathroom has been fully remodeled. New carpet was recently added in the mudroom and

Jonathan Minerick Homecoin.com

Welcome to this move-in ready Cedar model in the Villages at Middletown—where modern design meets everyday convenience. Offering 4 bedrooms, 2.5 bathrooms, and approximately 1,900 square feet, this home delivers stylish living with an open-concept layout ideal for today’s lifestyle.The main level impresses with a sleek kitchen featuring upgraded mocha cabinetry, stainless steel appliances,

Atul Sharma Long & Foster Real Estate, Inc.

Adorable 5-year-young rancher backing to common area in quaint Middletown! This beautifully maintained home feels practically brand new with luxury vinyl plank flooring throughout the main living areas, brand-new carpet in the bedrooms, and fresh paint throughout. Enjoy easy one-level living with a desirable split-bedroom floor plan. The spacious kitchen opens to the dining and living areas and

Lisa Cox Colony Realty

ROOMY RANCHER ON MORE THAN HALF AN ACRE! IN MIDDLETOWN, COMMUTER CONVENIENT TO I-81, I-66, Winchester, Stephens City, Strasburg and Front Royal. Near historic Belle Grove Plantation and Cedar Creek Battlefield, Laurel Ridge Community College, the Blue Ridge Mountains and the Shenandoah River. Don't let this one get away! So much bigger than it looks! This 3-bedroom rancher at the end of a

Teresa Strohmeyer ERA Oakcrest Realty, Inc.

Welcome to 114 Curtain Fall Drive, an exceptional, practically brand-new ranch home where modern design meets total convenience! Perfectly situated in a vibrant Middletown community with quick access to major commuter routes, local dining, shopping, parks, and schools, this move-in-ready gem delivers effortless one-level living at its absolute finest. From the moment you step inside, sleek LVP

Dan Whitacre Colony Realty