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Middletown Springs VT Real Estate

Carved into the ridges of the nearby mountains, Middletown Springs is a town in Rutland County, Vermont well known for its strong community. Over the years, the population has dwindled to about 750 people though the town boasts a rich history as a resort destination with nearby lakes, rivers, and mountains for outdoor activities. Within Middletown Springs are an elementary school, a general store, a public library, and a local restaurant all of which give the town its distinct character. 

Search the latest real estate in Middletown, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ​Register to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

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656 South Street Middletown Springs VT 05757

Middletown Springs, VT656 South Street

Price$599,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 4982313

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3

Come check out Vermont's Breathtaking Landscape...Indulge in the epitome of country living with this extraordinary home set on over 100 acres of picturesque Vermont terrain. Embraced by the natural beauty of rolling hills, expansive meadows, and woodlands, this spacious and open country estate offers a rare opportunity to experience tranquility on a grand scale. All of this surrounding an open and functional Cape style home. This home's architecture combines country elegance and functionality, featuring large windows that invite natural light, high ceilings, and an open floor plan that enhances the feeling of space. The full walkout basement offers a second living space making it great for long term and short term guests alike. Outside you will find a large heated wood shop, a chicken coop, a fire pit, a wonderful stream and private walking trails for miles. So come and see the breathtaking panoramic views from every room, which showcasing the beauty of Vermont's changing seasons. You too can have a front-row seat to nature's ever-evolving spectacle.Welcome Home!

Listed by Joshua Lemieux of Remax Summit

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

20 Buxton Avenue Middletown Springs VT 05757

Middletown Springs, VT20 Buxton Avenue

Price$549,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4993546

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Located at the edge of a small Vermont village on a lovely quiet street, this grand 1900 antique home is quite perfect for gatherings of friends and family. Spacious in size, the home has been lovingly maintained by its current owners and has remarkable period detailing throughout. The property is open, nicely landscaped, and surrounded by farmland. There are beautiful mountain views from the front wrap around porch, as well as from the back deck and patio area. All of the rooms are plentiful is size, and the home has great ceiling height, fireplaces, incredible inlaid floors and staircase, custom woodwork and several pocket doors. The back staircase leads you to the perfect 2nd floor guest area. The large detached barn has plenty of room for car storage and yard equipment.

Listed by Sara Buckley of Josiah Allen Real Estate,Inc.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

27 Lookout Lane Middletown Springs VT 05757

Middletown Springs, VT27 Lookout Lane

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4998381

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

This unique custom built cape cod style home is a must see. It sits on 11 acres with privacy and gorgeous long-range mountain views. The home features 3 bedrooms and 2 bathrooms. The primary bedroom has a large walk-in closet, a beautiful ensuite bathroom featuring a custom tiled shower, and deep jacuzzi tub and it's very own deck to enjoy the beautiful views. The formal living room has beautiful oak wood floors accented with a black walnut and maple band and black walnut plugs. There's also an adorable reading nook, and a magnificent custom built granite fireplace. The unique features of this custom home continue to abound with the black walnut chair rail and oak trim throughout. To round out this one of a kind property, there's a large heated garage to accommodate all kinds of projects both large and small. Located in a school choice town for grades 7-12 and within 30 minutes to Lake St. Catherine and Lake Bomoseen and under 45 minutes to Killington and Pico. And for any outdoor enthusiasts, this property is only about 2 miles from the Fairgrounds trailhead, which is part of miles of trails within the Slate Valley Trail system. These trails are great for walking, jogging, hiking, and biking. Don't miss your chance to own this beautiful Vermont property.

Listed by Sarah Haley of NY and VT Real Estate Company

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

20 Marcy Lane Middletown Springs VT 05757

Middletown Springs, VT20 Marcy Lane

Price$424,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5013934

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Privacy!! Located at the end of private road, this meticulous 3 bedroom, 2 bath one-level home has quality hardwood flooring and updated baths. The large living room offers a brick fireplace with gas insert, fully equipped kitchen with pantry that connects to a spacious dining area. The 17x19 light-filled family room is the perfect gathering space. With all mechanicals updated, this home is in "move-in" condition including new paint both inside and out! Middletown Springs is a wonderful small town that is close to Rutland, Poultney, Castleton and Manchester with everything living in Vermont for all 4 seasons brings! School choice for students grade 7-12 is a plus!

Listed by Nancy Liberatore of Realty One Group Lakes & Homes

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1 North Street Middletown Springs VT 05757

Middletown Springs, VT1 North Street

Price$420,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5003308

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

Known as the Jonas Clark House, this 1814 Brick Georgian style home sits proudly across from the Middletown Springs Village Green. This four bedroom, two bath home features many period details including a formal entry, spacious high ceiling rooms and original woodwork throughout. Other amenities include a modern kitchen, formal dining room, living room and den. Also, there is a basement oven that was used to smoke hams! Outside, relax on the rear porch overlooking the fenced in landscaped grounds. Many possibilities and uses exist for the large attached post and beam barn. This historic property is located minutes from Slate Valley Trails (biking & hiking), Lake St. Catherine Park & Country Club, Dorset Playhouse and Manchester area.

Listed by Alan Gombosi of Northland Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

9 Marcy Lane Middletown Springs VT 05757

Middletown Springs, VT9 Marcy Lane

Price$419,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5010770

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Welcome home! This turn-key, move-in-ready property in the charming town of Middletown Springs has it all. Situated on a spacious .80-acre level lot near the end of a privately maintained dead-end road, this home offers the perfect blend of privacy and convenience-just a short walk from Middletown Springs Elementary School. In the winter, you'll love cozying up by the pellet stove in the large family room, creating a warm and inviting space for relaxing. Come summer, cool off in your very own above-ground swimming pool, or enjoy outdoor activities on the expansive lawn. The large 2-car garage, with storage above and an additional outbuilding, provides ample room for all your outdoor toys and storage needs. Inside, gather for family dinners in the generous dining room, and welcome guests in the front entryway, featuring a beautiful Vermont slate floor. The primary bedroom offers a private 3/4 bath and a mini-split system. With two additional bedrooms on the main floor and unfinished space in the walkout basement, there's plenty of potential for expansion to suit your needs. With no zoning restrictions and school choice for middle school and beyond, this home offers flexibility and opportunity. Enjoy the outdoors with easy access to one of the main trailheads for the Slate Valley biking trails and proximity to Lake St. Catherine, just 20 minutes away. Plus, multiple ski areas are within an hour's drive, making this the perfect location for year-round recreation. A true VT gem!

Listed by Heather Martelle of Realty One Group Lakes & Homes

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

7 Garron Road Middletown Springs VT 05757

Middletown Springs, VT7 Garron Road

Price$349,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5008704

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Nestled on a serene 10.30-acre lot, this contemporary post and beam home is a true retreat for those seeking tranquility and modern comfort. Located just 20 to 25 minutes from Rutland and a short 40 to 45-minute drive to the renowned ski resorts of Killington, Pico, and Okemo, this property offers the perfect balance of seclusion and convenience. As you step inside, you're greeted by an open-concept living space, where soaring ceilings and exposed beams create an airy, inviting atmosphere. The spacious living area seamlessly flows into the dining and kitchen spaces, making it ideal for both intimate family dinners and larger gatherings with friends. Large windows flood the interior with natural light, while providing views of the majestic mountains that surround the property. This home boasts three bedrooms, each designed with comfort and relaxation in mind. The primary bedroom is a true sanctuary ensuring a peaceful retreat at the end of the day. The additional two bedrooms are perfect for family, guests, or even a home office, offering flexibility to suit your needs. Step outside onto the expansive deck, where you can savor your morning coffee or unwind in the evening while soaking in the panoramic views of the surrounding landscape. The outdoor space is perfect for entertaining, gardening, or simply enjoying the natural beauty that this unique property provides. Additional features include two well-appointed bathrooms, ample storage throughout, and a two-car garage.

Listed by Darcy Handy of RE/MAX North Professionals

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

70 West Street Middletown Springs VT 05757

Middletown Springs, VT70 West Street

Price$250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5008608

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1

Welcome to this charming three-bedroom, one-bathroom bungalow, just a short walk from the picturesque town of Middletown Springs. Known as the "Parker House", this 3 X 3 bay house with an overhanging hip roof with exposed rafter tails was built in 1915 by Mr. Towne of Poultney. The slate roof, glowing pine floors, and other preserved historic details inside maintain the home's timeless appeal. You're sure to appreciate the spacious mudroom which offers practical entry space. Through the kitchen you see the charming dining nook with wrap-around windows and a wood ceiling, providing a cozy spot for meals. There is uninterrupted flow between the dining nook and living room. A large walk-up attic presents a fantastic opportunity for expansion. This home is perched on a hill within the scenic Taconic Mountains and boasts a lovely stone patio perfect for outdoor relaxation. The property is surrounded by beautiful lilacs, creating a serene and fragrant environment. Don't miss the chance to make this delightful bungalow your own!

Listed by David Stanley of Ridgeline Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

641 South Street Middletown Springs VT 05757

Middletown Springs, VT641 South Street

Price$249,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5001538

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

This pond-side gem is a fabulous opportunity for the right buyer. As a work in progress you can add our own design elements to the architect guided renovation of this 1820s timber frame. With a large back deck overlooking the pond and the woods beyond this property offers both privacy and gorgeous palette for the changing seasons. Across the road an antique barn and large garden complete the layout. The barn needs either extensive repair or to be removed. Inside the house sunny rooms, two working fireplaces, custom black slate counters and farmhouse sink, a large pantry, and exposed timbers offer a solid start on unleashing the true potential of this lovely home. This property is being sold “as is”. Proximity to ski areas and the lakes, modern fiber optic internet, and school choice 7-12 are just a few of the additional attractions. Showing begin June 24th.

Listed by Robin Chesnut-Tangerman and Scott Mcchesney of McChesney RE,Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.2% last updated on 2024-09-12

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is 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. Data last updated September 19, 2024 2:16 PM EDT

 

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