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Rupert Vermont Real Estate

Bennington County
Chartered: August 20, 1761
Area: 28,659 Acres = 44.78 Square Miles
Population (US Census, 2000): 704
Population Density (persons per square mile): 15.7

Rupert Vermont is on the western side of Vermont, next to the New York border. It is just northwest of Manchester, Vermont, west of Dorset, Vermont, and south of Pawlet, Vermont. This small, quiet Vermont town features real estate of all types, including primary residences, vacation homes, and retirement homes. Just a short drive away one can be shopping in Manchester’s famous designer outlets or enjoying a play at the Dorset Playhouse. Rupert Vermont real estate is under an hour away from some of Vermont’s most popular ski resorts, including Stratton Mountain Ski Resort, Magic Mountain Ski Resort, and Bromley Mountain Ski Resort.


1127 Route 153 Rupert    [ Photos: 1 ]
Listing Price: $139,000

Charming older home in the center of West Rupert. Has had recent updates in bathrrom and painting upstairs. Wide board floors throughtout most of the house, wood furnace for alternate heating. Attached shed - entry could be added to kitchen or made in to garage.

MLS #: 2608234 [View Property] + Add To Favorites


Tobin Road Rupert    [ Photos: 12 ]
Listing Price: $195,000

Wonderful hill top site. House site and broad views cleared,leaving speciman mature trees for park-like setting. Good pond sites, easy access. Totally private. Easy travel to Pawlet, Rupert and neighboring towns. This property provides the privacy, views and ready access for a spectacular seasonal or year round home. Fantastic value. Adjacent house on 8 acres available for 195,000. See MLS # 2800242.

MLS #: 2708974 [View Property] + Add To Favorites


00 Sykes Hollow Road Rupert    [ Photos: 3 ]
Listing Price: $195,000

High ground over the Sykes Hollow--offering fabulous views of pastures and mountains-- rolling hill.

MLS #: 2808681 [View Property] + Add To Favorites


00 Pawlet Mountain Road Rupert    [ Photos: 4 ]
Listing Price: $225,000

Exceptional gentle rise to tree lined/stone wall pasture / rolling field.Fabulous views to south and west--long range and taconic mountaoin views while Anton peaks nearby. Merck Forrest Foundation of 3000 acres of incredible trails within reach.Soils test from the past lends property to great possibility.Surely the BEST RUPERT HAS TO OFFER! Mettowee School-outstanding. Nearby Dorset/Manchester.

MLS #: 2806844 [View Property] + Add To Favorites


2360 Pawlet Mountain Road Rupert    [ Photos: 11 ]
Listing Price: $295,000

Accessible rural setting with privacy and views, pond, woods and meadow. P&B, super-insulated house on heavy 10 inch poured concrete, drive-in foundation. Adjacent outbuilding with power for studio/office, etc. Rock solid. Currently off-grid, solar generator power and propane heat. Access to utilities on property. Someone's paradise. Yours? (Town says 8+ acres, recent survey measures 11 +/-). Siding is channel rustic vertical wood.

MLS #: 2800242 [View Property] + Add To Favorites


4907 Route 315 Rupert    [ Photos: 10 ]
Listing Price: $398,000

Unique and inviting. Cross your own stone bridge to Green Cottage beside a rushing brook. Cozy and quiet, yet truly livable with open areas and private bedrooms. Surprise private deck off master bath. Screened porch, open deck, woodstoves and fireplace. All taking advantage of private, romantic setting. Story book playhouse. Good two-bay barn, sugar shack. Woods and meadow.

MLS #: 2804411 [View Property] + Add To Favorites


4958 Rte. 315 Rupert    [ Photos: 5 ]
Listing Price: $419,000

Country Charmer just a short drive from the Dorset Village Green. This cape has been lovingly renovated to fit the needs of today's family. Open living/dining/kitchen with wide plank pine floors, beams and fieldstone fireplace. New master suite, 1/2 bath with laundry & large mud room finish the first floor. Two large upstairs bedrooms with new carpet and a full bath. 40' covered front porch & attached two car garage with a bonus room above ready to be finished to suit your needs.

MLS #: 2803340 [View Property] + Add To Favorites


211 Dorset West Road Rupert    [ Photos: 8 ]
Listing Price: $419,000

Lovely old Victorian farmhouse presently two separate units. Easily converted back to one. Second floor has room for expansion. Large workshop on first floor. Barn garage and two other out buildings in great shape. Close proximity to Dorset and Manchester. Excellant investment property with huge potential.

MLS #: 2808730 [View Property] + Add To Favorites


1271 Kent Hollow Rupert    [ Photos: 11 ]
Listing Price: $419,000

Furnishings negotiable.Complete 2x6 walls throughout with full insul.Oil heat 550 gal/yr-well McLain energy star gold series furnace.Orig Anderson thermal pane windows.Doors/sliders are Anderson or Pella.3-Zone Heating.UV Water system added.Under kitchen cabinet lighting.2 Monte Carlo lighting fixtures in great room.Painted int & ext.New flooring throughtout.Fireplace is woodburning with removable gas insert.Creek across st.VAST trails.Balcony off master. Beautiful gardens!Pioneer Surround Sound

MLS #: 2809370 [View Property] + Add To Favorites


211 Dorset West Road Rupert    [ Photos: 9 ]
Listing Price: $419,000

Lovely old victorian farmhouse with barn and 2 other outbuildings in good shape. Presently set up as two seperate rental units - upstairs and down. Could easily be converted back to single family residence. Large workshop on first floor room for expansion on second floor. Covered porch, big mountain views, and decks. Close proximity to Dorset and Manchester.

MLS #: 2808647 [View Property] + Add To Favorites

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