Vintage homes for sale & real estate in Rupert, VT

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ABOUT THIS HOME
Vintage Home for sale in Rupert, VT:
Luxury home, move-in ready, on 5+ peaceful acres with protected panoramic mountain views and stream frontage, this fully renovated 1909 Federal offers timeless character with a like-new feel—just 2.5 miles from the Dorset Green and dining but away from the bustle. Every inch of the main home has been meticulously updated with premium materials and workmanship. A custom walnut kitchen with high-end built in appliances with island bar seating opens to a warm dining area both ideal for entertaining. New hickory floors run throughout, complemented by handcrafted walnut railings. The first floor features a sunlit living room with a fireplace, half bath, mudroom/laundry, and a primary bedro

$1,795,000

5 beds4.5 baths3,218 sq ft

5491 VT Route 315, Rupert, VT 05776

Fully renovated • Island bar seating • Stream frontage

ABOUT THIS HOME
Vintage Home for sale in Rupert, VT:
This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a 200-amp panel, and a standby propane generator—move-in ready with nothing left to do. The home features 2 bedrooms, a spacious full bath, an open living and dining room flowing seamlessly into the kitchen, a separate laundry room, and a convenient mudroom entry. Two inviting screened porches

$274,500

2 beds1 bath1,400 sq ft

3264 Route 153, West Rupert, VT 05776

Metal roof • Fiber optic internet • Vinyl siding

ABOUT THIS HOME
Vintage Home for sale in Rupert, VT:
Classic late 1800's Colonial home located in the center of the Village of Pawlet. This home offers four bedrooms, one bath in 1500 square feet. All on a 0.16 lot with a detached one car garage. Lot is level and open. Although she'll need some love -- she'll shine again!!

$79,900

4 beds1 bath1,500 sq ft

2984 VT Route 153, Pawlet, VT 05761

6,969 sq ft lot • Garage • Built 1890

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ABOUT THIS HOME
Vintage Home for sale in Rupert, VT:
Storybook Cape full of comfort and charm in a private location surrounded by gardens, specimen maples and an unusual acre of pachysandra ground cover. The home's living room centers around a traditional fireplace and French doors leading to a slate terrace overlooking established gardens. The sun filled dining room features built in cabinets and leads to a custom designed kitchen. A sunroom and powder room complete the first floor. Two spacious bedrooms and adjoining baths with attic storage are on the second floor. Outside, a detached party barn/guest house with exposed beams, stone fireplace, all new Marvin windows, plumbed in bath and kitchen are ready to be completed by a new owner. Ow

$1,350,000

2 beds2.5 baths1,900 sq ft

81 Fern Hl, Dorset, VT 05251

7 acre lot • Garage • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Rupert, VT:
Nestled in the heart of the iconic Dorset village, just steps from the Dorset Field Club and the beloved local theater, this enchanting historic home has been meticulously renovated, rejuvenated, and reimagined with no expense spared. From the moment you arrive, the home's timeless charm and thoughtful updates are evident. A complete reengineering of the roof and replacement of all major systems including a new, energy-efficient heating system ensure peace of mind for years to come. Every room is outfitted with ultra-quiet mini-split units, offering customized comfort year-round. Inside, the interiors have been fully redecorated to blend historic character with modern luxury. A new first-fl

$3,600,000

4 beds3.5 baths2,338 sq ft

198 Church St, Shaftsbury, VT 05251

0.76 acre lot • Garage • Car-dependent

ABOUT THIS HOME
Vintage Home for sale in Rupert, VT:
Prime Buildable Lot in Dorset! Embrace the Best of All Worlds! Discover a rare opportunity to own a ready-to-build lot in the heart of Dorset, perfectly positioned to offer unparalleled access to the town's finest attractions. Just moments from scenic hiking trails, the picturesque Dorset Green, and the esteemed Dorset Field Club, this property is your gateway to a lifestyle of outdoor adventure and community charm. With multiple building sites available, you can design your dream home to maximize the stunning natural beauty and captivating views of this desirable location. Whether you envision a cozy retreat or a grand residence, this lot provides the flexibility to create a space that's

$399,500

— beds— baths— sq ft

2937 Dorset West Rd, Dorset, VT 05251

2.7 acre lot • Car-dependent

Vintage Homes for Sale in Rupert

There are currently 3 vintage homes for sale in Rupert at a median listing price of $475K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Rupert stay on the market for 42 days. This map is refreshed with the newest listings in Rupert every 15 minutes.

In the past month, 2 homes have been sold in Rupert. Find your dream home in Rupert using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Rupert are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Rupert. If you're looking to sell your home in the Rupert area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Rupert with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Wed Oct 08 2025 on the search page

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