Middlebury Homes with Wooded Lot features

Welcome to Middlebury, Indiana, a charming town nestled in the heart of Elkhart County. Known for its picturesque landscapes and vibrant community spirit, Middlebury offers a unique blend of small-town charm and modern convenience. With its rich Amish heritage, residents enjoy a tranquil lifestyle surrounded by scenic farmland, beautiful parks, and serene waterways. The town is also home to a variety of local shops, delightful eateries, and engaging community events that foster a strong sense of belonging.

For those seeking a home that harmonizes with nature, Middlebury's real estate market boasts a selection of stunning properties featuring wooded lots. Imagine waking up to the gentle rustle of leaves and the soothing sounds of nature just outside your window. These homes, set amidst lush greenery, provide a perfect retreat for families and nature enthusiasts alike. With ample space for outdoor activities, gardening, or simply enjoying the serene environment, a wooded lot home in Middlebury is a sanctuary for relaxation and exploration.

Additionally, the proximity to local schools, recreational facilities, and major highways makes Middlebury an ideal location for families and commuters. Whether you’re looking for a cozy cottage or a spacious family home, the wooded lots in this enchanting town offer a unique opportunity to embrace a lifestyle that blends comfort with the beauty of nature. Discover your dream home in Middlebury, where every day feels like a peaceful retreat. Come experience the warmth of this community and the allure of its natural surroundings!

Newest Middlebury Homes with Wooded Lot features

$699,000

5 Beds ⋅ 4 Baths ⋅ 202636797 MLS ⋅ 3,582 SqFt. ⋅ Kylee Sulkowski

Welcome home to 217 Greenfield Dr — in Middlebury's Northridge school district, set on a wooded, professionally landscaped lot, this is a home that needs neither updating nor more space, which isn't something you find often at this price. From the moment you step inside, vaulted ceilings in the living and dining rooms set the tone: open and bright, with light pouring through room after room and pooling across the oak flooring. The kitchen has been outfitted with all-new appliances, including a professional-series stove, complete with a pot filler at the range, built-in reverse osmosis filtration, and a double pull-out trash system —the kind of conveniences you'll appreciate every single day. All new energy efficient windows, doors, and garage door in 2026, plus a brand new 2025 composite deck, mean the big-ticket updates are already done — this is a home to move into, not renovate. Then there's the layout most houses simply don't offer: a main-level primary suite for single-story ease, three additional bedrooms upstairs sharing a full bath and arranged around a large loft landing that overlooks the living room below, and a finished walk-out basement with its own second living suite and private office — space for guests, extended family, or a work-from-home setup that doesn't feel like an afterthought. A double-sided fireplace warms both the basement living area and the office, while a second fireplace anchors the formal living room upstairs. Step outside from the lower level and you'll find a second patio — a shaded, private spot to sit out and enjoy even the hottest afternoons. Storage is never an issue, with two oversized storage rooms in the basement and closets throughout, and the 2-car garage adds an epoxy floor and extra workspace for projects or hobbies. Outside, mature woods and a live walnut tree give the backyard a quiet, established feel, along with an irrigation system, and a landscaped dog area tucked behind the shrubbery means even your pets have their own space. The sale includes the adjacent lot, adding extra privacy and breathing room around the home. 217 Greenfield Dr offers a rare combination: real space, real updates, and a layout built for how families actually live, in one of the area's most desired school districts. Schedule your private showing — homes like this don't stay quiet for long.

217 Greenfield Dr, Middlebury

Listing courtesy of Kylee Sulkowski from White Hat Realty Group, LLC.

$4,999,900

6 Beds ⋅ 7 Baths ⋅ 202614607 MLS ⋅ 12,367 SqFt. ⋅ Stephen Smith

Set on over 38 private acres in Middleburry, this remarkable 2018 Fireside Homes estate offers more than 12,000 sq ft of thoughtfully designed living space, combining luxury, privacy, and exceptional craftsmanship. A gated entrance opens to a long drive filled with natural beauty and wildlife. Inside, the home showcases extensive custom hardwoods and cabinetry, along with a fully integrated smart home system that seamlessly manages lighting, security, and entertainment. At the heart of the home, the commercial-grade chef's kitchen stands out with its custom Italian design, premium Gaggenau appliances, multiple ovens, dual dishwashers, built-in espresso system, and an oversized hidden pantry for added function and storage. The main level study offers a refined workspace with rich cherry paneling, herringbone flooring, and a private reading loft accessed by a hidden spiral staircase, exclusively reachable from the study or the primary suite. The main floor primary suite is designed as a true retreat, featuring vaulted ceilings, a two-sided fireplace, private sitting area with deck, and a spa-like bath with heated flooring, walk-in shower, and a walk-in closet with ample storage. The lower level is built for entertaining, with a custom bar, temperature-controlled wine cellar and tasting room, and a spacious gathering area designed for watching sporting events or hosting guests. A dedicated movie theater with professional-grade acoustics, luxury seating, and high-end projection creates an immersive experience. Outdoor living is equally impressive, with multiple covered decks/patios and a fully equipped grilling area. A private spa retreat set within the woods features a sauna, cold plunge, and a wood-fired hot tub, creating a resort-like experience just steps from home. This is only a glimpse into the level of detail and design that truly defines this extraordinary estate. Schedule your private showing to fully experience everything this remarkable property has to offer!

54420 County Road 33rd Rd, Middlebury

Listing courtesy of Stephen Smith from Irish Realty. steve.smith@irishrealty.net

Start Your Search

Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.