Middleton Crossing Homes for Sale

Middleton Crossing Homes for Sale

Welcome to Middleton Crossing, a delightful subdivision nestled in the heart of Ashland, Missouri, within Boone County. This charming community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, professionals, and retirees alike.

Middleton Crossing is characterized by its picturesque streets lined with beautiful homes, each showcasing unique architectural styles and well-manicured lawns. The neighborhood is designed for comfort and community, featuring spacious properties that provide ample room for outdoor activities and gatherings. With a variety of homes for sale, potential buyers can find options that cater to their specific needs and preferences, whether it’s a cozy starter home or a more expansive residence for a growing family.

Residents of Middleton Crossing enjoy a wealth of amenities and easy access to the vibrant city of Ashland. The area is known for its friendly atmosphere, excellent schools, and a range of recreational opportunities, including parks, walking trails, and community events. The close-knit community fosters a sense of belonging, where neighbors become friends and families thrive.

Additionally, Middleton Crossing is conveniently located just a short drive from Columbia, offering residents access to a wider array of shopping, dining, and entertainment options. With its prime location and inviting atmosphere, Middleton Crossing is more than just a place to live; it’s a place to call home. Explore the homes for sale in this charming subdivision and discover the lifestyle that awaits you in Middleton Crossing!

Newest Middleton Crossing Homes for Sale

$515,000
5 Beds ⋅ 3 Baths ⋅ 436565 MLS
Enjoy the best of Ashland living with a peaceful backyard view, generous living space, and a layout built for everyday ease. This well-cared-for ranch walkout offers space to spread out, gather, and stay organized. Nearly 2,000 square feet are located on the main level, with a split-bedroom design and an easy flow between the main living areas. The kitchen is well equipped with plenty of cabinetry and counter space, and it connects seamlessly to both formal and informal dining, making it ideal for weeknights or hosting. You'll also appreciate the great trim package with arched doorway openings, raised ceilings, and abundant natural light. A large drop zone off the 2-car garage and a conveniently placed laundry room add to the home's everyday function. Two bedrooms are located on the main level, including the primary suite featuring a bay window and an ensuite bathroom with a tiled shower, jetted tub, and a large closet. The finished lower level provides additional living space with a family/rec room with an attached wet bar area, plus walkout access to the phenomenal backyard and large deck, perfect for relaxing or entertaining. Three additional bedrooms are located on this level and share a full hall bathroom (one bedroom is non-conforming). Additional features include unfinished storage space plus a John Deere room with double-door exterior access. Buyer to verify all information including but not limited to schools, taxes, sq. footage, lot size, room sizes, restrictions, easements, HOA fees, etc.

508 MIDDLETON DR, Ashland

Courtesy of Bev & Co. Realty, LLC 573-864-5054

$405,000
4 Beds ⋅ 3 Baths ⋅ 10073823 MLS
Welcome to your ideal move-up home on a sprawling 0.53-acre lot in Ashland's sought-after Middleton Crossing! Offering 4 bedrooms, 2.5 updated bathrooms, and 2,572 sq. ft. of versatile living space, this home gives you the room you need to grow inside and out. The main level features a light-filled living area with a cozy gas fireplace, formal dining, a practical kitchen with breakfast nook, and a private primary suite. Upstairs hosts three additional spacious bedrooms and a full bath--perfect for family, guests, or a home office. Complete with a 3-car garage, covered front porch, back patio, and a massive yard, you'll love the unbeatable proximity to top-rated Southern Boone schools, the YMCA, daycare, parks, and quick US-63 access. Bonus: Sellers are willing to address roof replacement/credit with an acceptable offer!

506 Terra Linda Lane, Ashland

Courtesy of South County Realty

$405,000
4 Beds ⋅ 3 Baths ⋅ 436534 MLS
Welcome to your ideal move-up home on a sprawling 0.53-acre lot in Ashland's sought-after Middleton Crossing! Offering 4 bedrooms, 2.5 updated bathrooms, and 2,572 sq. ft. of versatile living space, this home gives you the room you need to grow inside and out. The main level features a light-filled living area with a cozy gas fireplace, formal dining, a practical kitchen with breakfast nook, and a private primary suite. Upstairs hosts three additional spacious bedrooms and a full bath--perfect for family, guests, or a home office. Complete with a 3-car garage, covered front porch, back patio, and a massive yard, you'll love the unbeatable proximity to top-rated Southern Boone schools, the YMCA, daycare, parks, and quick US-63 access. Bonus: Sellers are willing to address roof replacement/credit with an acceptable offer!

506 TERRA LINDA LN, Ashland

Courtesy of South County Realty

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Listing information is provided courtesy of the Broker Reciprocity/IDX of Bagnell Dam Association of REALTORS® and Lake of the Ozarks Board of REALTORS®, Inc. Multiple Listing Services. Copyright 2026 Multiple Listing Service, Inc. of Bagnell Dam Association of REALTORS® MLS, Inc. and Lake of the Ozarks Board of REALTORS® MLS, Inc. Information is being provided for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information herein is believed to be accurate and timely, but no warranty as such is expressed or implied. 2026 Timberline Real Estate, Real Broker LLC