Middletown Springs Vermont Real Estate

Calling All Homesteaders! This 13 acre hillside homestead is a rare opportunity to get in on the ground level. The property is a house, not a seasonal camp, with a one room bedroom/kitchen/living area and a private bath. The year-round space is attached to an unfinished gambrel-roof structure with a wood stove and loft. The house features a pumped spring water system, has a design and permit in place to expand the current septic system for a 3 bedroom home, and is equipped with several coops, lofts, and shelters for raising poultry. At the higher elevation the land levels out into a beautiful hardwood forest with abundant wildlife. So roll up your sleeves and get going on this “As Is” opportunity with fiber optic internet and school choice for grades 7-12. No drive-bys please.

Circa 1850 farmhouse with detached 2-car garage on 9.9 acre lot on scenic country road. Offering a large mud room before entering the spacious kitchen and walk-in pantry. The well proportioned dining room, living room and porch complete the 1st level of this home. Upstairs you will find three bedrooms and a bath. Upgrades include windows, insulation and heating system. Less than a 30 minute drive to Manchester and most of Rutland county this is the perfect centralized location. Make an appointment today to see this lovely property.

Step into history and comfort with this 3+ bedroom, 2.5-bath Colonial nestled in the heart of Middletown Springs. This beautiful home boasts timeless character with original moldings, natural pine floors, and a durable slate roof that speaks to its enduring quality. Two inviting brick fireplaces add warmth and charm to the spacious living areas, making this home as cozy as it is elegant. The property’s outdoor spaces are equally impressive. Surround yourself with extensive perennial gardens, raised vegetable beds, and established blueberry and raspberry bushes—perfect for the gardening enthusiast, just needing a little TLC. A garden shed/wood shed provides additional convenience, while the attached garage offers functionality and storage. Modern updates complement the home’s historic character, including fiber optic internet for seamless connectivity. Outdoor lovers will enjoy easy access to skiing at Okemo, Pico, and Killington, swimming and boating on nearby Lake St. Catherine and Lake Bomoseen, and just minutes from the extensive biking network of Slate Valley Trails. This is more than just a home—it’s a lifestyle, offering a rare blend of history, beauty, and modern amenities in a picturesque Vermont setting. School choice for grades 7–12.

Completely rebuilt and thoughtfully upgraded from top to bottom, this beautifully renovated 3-bedroom, 2-bath home in Middletown Springs offers the perfect blend of modern comfort and small-town Vermont charm. Taken down to the studs during an extensive 2020–2021 renovation, nearly every aspect of the home was replaced or improved, creating a truly move-in ready property with quality craftsmanship throughout. Inside, an inviting open-concept layout features gorgeous tongue-and-groove pickle pine ceilings, abundant natural light, and maple flooring throughout the kitchen, living, and dining areas. The beautifully updated kitchen includes granite countertops, custom cabinetry, and newer appliances, flowing seamlessly into the main living space centered around a custom oak gas fireplace surround with granite top. Both bathrooms were fully renovated with stylish tile work and updated fixtures. Major improvements include new plumbing, electrical service and wiring, insulation, drywall, windows, doors, siding, roofing, propane furnace, hot water heater, ducted heat pump with central A/C, water softener, and mineral remover. Outside, the property has been equally transformed with a widened and regraded driveway, expanded yard space, updated porches, underground dog fence, winterized dog kennel, and site preparation for a potential two-car garage. Recent 2025 improvements include spray foam insulation in the basement and crawl space, along with finished basement stairway walls, adding even more efficiency and functionality to this extensively improved home. A must see. Open House this Saturday May 16th from 10:30 to Noon

Breathtaking mountain views greet you at this classic Gambrel-style home. Whether you’re seeking a solo escape or bringing along family and friends, you’ll have plenty of room in the spacious 2,700-square-foot interior or out on the beautifully landscaped 1.5-acre property surrounded by meadows and forest. Inside, you’ll find three generously sized bedrooms plus a bonus room that can serve as a first-floor bedroom, den, or office. The large eat-in kitchen offers ample space for hosting while cooking up your favorite holiday dishes, and flows into the open dining and living areas, anchored by a cozy gas stove. A screened porch and open deck invite you to relax outdoors, while the partially finished basement is perfect for movie nights or games. The walk-out basement, with its utility sink and gardening table, is ideal for green thumbs, and the attached two-car garage makes winter a bit more comfortable.

Nestled alongside a quiet town gravel road on almost 7 acres, this newly built two plus (loft/bedroom and permitted as a 4 bedroom) bedroom, one bath timber frame home is perfect to hang your hat and enjoy nature, peace and quiet. Ideally designed with a full length back porch looking west over the meadow and beautiful wetland area set down below the meadow - Could be perfect for some critters or a horse. The house offers a large entry mudroom, spacious open kitchen living area with cathedral ceilings and a stone countertop, a 20 x 20 loft space, two ground floor bedrooms and a large bath with a nicely tiled shower. Amenities include a large oversized attached garage, a full basement (offering great expansion space) with laundry, a whole house standby propane generator and central AC. A special piece of Vermont nestled in the mountains with easy proximity to the Middletown Springs and Pawlet areas and within 30 to 45 minutes to the larger towns of Rutland and Manchester, and Killington, Bromley, Pico and Okemo Ski mountains as well. School choice 7-12 and state of the art VTEL fiber optic high speed internet.

Do you love old houses but really crave 21st century efficiency? Look no further! This charming 1810 post and beam Cape was stripped down to the studs - from the outside - with new wiring, rock wool insulation, then rigid foam insulation, new clapboards, doors and windows, and recreated classic trim. Whether you are entertaining in the large open kitchen, unwinding on the three season porch, or snuggled down in front of the pellet stove, this house provides for you. Two original bedrooms and an added bath upstairs highlight the old timber frame and original wood floors. The primary bedroom over the kitchen adds skylights to update the classic look. In the back the original barn is now a 2 car garage with another fully insulated 2 car garage/workshop behind that. The beautiful landscaping is highlighted with owner-built stone walls, raised planting beds, walkways, and patios. All of this plus the latest fiber optic internet and school choice for grades 7-12.