Middletown Springs Real Estate

Welcome to Middletown Springs, a picturesque town nestled in the heart of Rutland County, Vermont. Known for its serene landscapes and tight-knit community, Middletown Springs offers a peaceful retreat from the hustle and bustle of city life.

With a rich history dating back to the 18th century, Middletown Springs boasts charming historic architecture and a sense of old-world charm. Residents and visitors alike can explore the town's historic buildings, quaint shops, and scenic parks, providing a glimpse into the town's storied past.

Nature enthusiasts will appreciate the abundance of outdoor recreational opportunities in Middletown Springs. From hiking and biking along scenic trails to fishing and boating in the nearby lakes, there is no shortage of ways to enjoy the great outdoors in this idyllic town.

For those seeking a close-knit community with a strong sense of camaraderie, Middletown Springs is the perfect place to call home. Residents take pride in their town and come together for various community events and celebrations throughout the year.

Whether you're looking to settle down in a peaceful rural setting or simply escape for a weekend getaway, Middletown Springs offers a warm welcome to all who visit. Come discover the beauty and charm of this hidden gem in Rutland County, Vermont.

Newest Listings in Middletown Springs

$70,000

5109096 MLS

Opportunity awaits on 16.40 acres of raw land along Coy Hill Road in Middletown Springs. This primarily wooded parcel offers approximately 300 feet of road frontage and plenty of room to enjoy the privacy and natural beauty of the Vermont countryside. The property extends well back from the road, creating a wonderful sense of seclusion and space. A small stream crosses the property, adding to its natural character, while the wooded acreage offers opportunities for recreation, hiking, hunting, or simply enjoying your own private Vermont retreat. The sloping terrain and mature tree cover create an attractive rural setting, and selective clearing may offer opportunities to open up portions of the property while maintaining privacy. Electricity is available along the road. Whether you are searching for recreational acreage, a long-term land investment, or a property to investigate for future development, this sizeable 16.40-acre parcel offers plenty of possibilities. Property is being offered as undeveloped land. Buyers and buyers agents are encouraged to perform their own due diligence regarding access, boundaries, septic, utilities, permits, easements, restrictions, and any intended use or development of the property. Contact us today to explore the property in person, ask questions, or submit an offer on this unique piece of Vermont land.

00 Coy Hill Rd, Middletown Springs

$495,000

3 Beds ⋅ 2 Baths ⋅ 5107922 MLS

This beautiful 1810, meticulously maintained, village home and 4 car barn have been lovingly restored from top to bottom and inside to out by the current talented owners. And yes, the heat pump is considered a heating system and has heated this home year-round. Air conditioning in the summer and heat source in the winter with the Harmon pellet stove for additional heat. The open kitchen overlooks the spacious dining area and sun filled entrance. A very welcoming room for family and friends to gather during each season of the year. The rooms flow from the kitchen/dining area to the living room with the pellet stove, to the den and then the fully insulated sunroom. The first floor 3/4 bathroom has a step in shower and laundry area. The two interior stairways lead to three bedrooms upstairs and another 3/4 bathroom that overlooks the gardens and beautiful stonewalls (hand built by the seller) that are throughout the property. Beautiful perennial gardens accent the yard. The front, two car garage (16x24) has a stairway up to a full storage or game room area and a car port for additional exterior storage. The back two car garage (20x22) has been fully insulated for a year-round workshop! This beautiful home had the siding removed, insulation added and all new exterior composit LP Smart Siding with a 50 yr. warranty. Basement and sunroom fully insulated also. The home has been thoughtfully plumbed for a conventional furnace if desired. A tranquil setting and a tastefully renovated home that has all the expensive, hard work completed for you. Located in this picturesque town of Middletown Springs with a village green and nearby lakes, rivers, and mountains for outside recreation in any seasons.

59 East St, Middletown Springs

$689,000

3 Beds ⋅ 4 Baths ⋅ 5107736 MLS

Set at the highest point of the property, Higher Ground looks south across open fields and a gently rolling valley toward distant Vermont mountains. Originally constructed as a barn in the 1840s, the post-and-beam structure was moved from the lowest point of the property to its highest and reimagined by the current owners. Original timber framing and authentic barn elements remain integral to the architecture, complemented by modern systems. The main level includes a primary bedroom and adjoining bath, open living and dining areas oriented toward the view. A staircase and bridge lead to two additional bedrooms, each with its own bath. Mature forests, open fields and stone walls give the property a distinctive Vermont character. A 150-foot elevated and enclosed outdoor run or small pets connects directly to the house. The lower level provides 10-foot clear height, workshop, storage, one-car garage and additional bathroom. Historic Middletown Springs is a village of approximately 650 with a general store, post office, library, town hall, and K-6 school, with school choice for grades 7-12. Dorset and Manchester are about 30 minutes through the scenic Mettowee Valley; Rutland is under 40 minutes away, and five premier Vermont ski areas are within about an hour. Boston and New York City are all within roughly four hours, with rail and air connections from Rutland and Albany. For those seeking climate-resilient real estate in Vermont, Higher Ground offers an unusual combination of elevation, open land and water resources. A deep drilled well and access to a natural spring provide multiple water sources and valuable resource independence. Middletown Springs has no local zoning ordinance, offering flexibility for future improvements, additions or an accessory dwelling, subject to Vermont state wastewater and potable-water requirements. Offered turnkey and fully furnished, Higher Ground combines architectural character, privacy, water security and long-term potential.

43 North St, Middletown Springs

$215,000

2 Beds ⋅ 2 Baths ⋅ 5096788 MLS

This newly renovated home in the charming village of Middletown Springs is just a short walk to the town green and country store. Cook up a storm in the modern eat-in kitchen with plenty of cabinet space, then unwind in the spacious living room with its cozy brick fireplace. The first floor features a primary bedroom, a freshly updated 3/4 bath, and a laundry room. Upstairs offers another nicely sized bedroom with its own bathroom, a bonus room, and an attic perfect for storing collectibles, decorations, and more. The property boasts ample space for gardening and yard games, and it’s conveniently close to hiking and biking trails, the VAST system, Lake St. Catherine, and more. (New electrical panel, new oil tank, new insulation in attic)

40 East St, Middletown Springs

$485,000

3 Beds ⋅ 4 Baths ⋅ 5091332 MLS

Riverside Retreat Tucked beside the gentle current of the Poultney River, this property offers the rare combination of natural beauty, functional space, and total flexibility. Three levels of thoughtfully designed living space invite you to spread out, settle in, and make it entirely your own. Step outside onto the expansive back deck - your front-row seat to the river's ever-changing scenery perfect for morning coffee, evening gatherings, or simply soaking in the tranquility that surrounds you. The animal barn and open pastures speak to a life lived closer to the land. Dream of horses, goats, or a hobby farm? The infrastructure is already in place. Prefer lush gardens, native meadows, or private green space? The land is yours to reimagine. Inside and out, this property rewards the visionary. Whether you're drawn to the riverfront setting, the multi-level floor plan, the agricultural possibilities, or simply the sheer breathing room, options abound at every turn. Room to live, grow, and dream - right on the Poultney River

416 East St, Middletown Springs

$499,000

2 Beds ⋅ 1 Baths ⋅ 5087124 MLS

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.

42 Mountain Rd, Middletown Springs

$299,000

4 Beds ⋅ 2 Baths ⋅ 5081575 MLS

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. Motivated Sellers - Bring your offer!!

180 North St, Middletown Springs

$40,000

5070754 MLS

Discover an outstanding opportunity in the heart of the vibrant and picturesque community of Middletown Springs. This versatile 0.30-acre commercial lot offers incredible potential for a variety of uses—whether you’re looking to establish a business, create a mixed-use space, or develop your own vision from the ground up. Conveniently located with electricity at the street, this property also features an existing well and septic system, Buyers and buyers’ agents to perform their own due diligence regarding permitted uses and infrastructure. With its flexible layout and small-town charm, this parcel serves as the perfect blank canvas for your entrepreneurial or investment goals. Don’t miss this opportunity to bring your ideas to life in beautiful Middletown Springs!

73 South St, Middletown Springs

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