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Land for sale in Rupert Vermont

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$499,000 60 acres 3 Beds | 4 Baths | 1 ½ Bath | 3033 sqft
251 Youlin Rd, Rupert, VT 05776 - Bennington County

60 acres Rupert, VT

Set privately back on /-60 acres of wooded land and gorgeous rolling meadowland is this 3 bedroom, 3 bath , beautifully built and maintained (1998) home. The setting is incredible with /-25 acres of open meadowland great for horses, etc., and the balance in woodland with a brook and pond. The home takes full advantage of the setting with beautiful distant views overlooking the property. Great living space with open kitchen and dining area with french doors to the deck with awning that overlooks the pond. The living room has lots of glass, soaring cathedral ceiling and massive stone fireplace impressive. Other amenities include 1st floor master suite, 28x28 attached heated garage, laundry/mud room with tile floor, skylights and det
Scott Mcchesney Lee D. McChesney Real Estate
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$335,000 9.86 acres 3 Beds | 2 Baths | 2595 sqft
1566 Route 315, Rupert, VT 05768 - Bennington County

9.86 acres Rupert, VT

Classic Farmstead. Over 10,000sf of outbuilding/barn space offering myriad possibilities! Owners had Icelandic horses & have run a successful antiques business (The Country Gallery Antiques) for 25 years! Elegant Victorian home with Rumford FP, crown molding, built-ins, wide plank floors, 9' ceilings; Nice meadowland and pasture land, year round brook & 2 ponds. Main antiques barn was the old W. Rupert Dance Hall - great historic property! *additional /-14A (permitted building lot) available for $74,500.
Scott Mcchesney Lee D. McChesney Real Estate
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$229,900 6.88 acres 3 Beds | 2 Baths | 2500 sqft
6885 Route 153, Rupert, VT 05768 - Bennington County

6.88 acres Rupert, VT

Set along a winding county road on nicely varied land with a pond. Beautiful valley views, stone walls, woods, open hillside pasture, pretty yard with gardens and apple trees and the Indian River right across the road. Spacious house with large LR with brick FP, kitchen with island, formal DR with sliders to screened porch and patio. 3 BR and huge 18x30 studio space (or MA BR) over the attached 2 car garage. Other amenities include separate garden shed with electricity, propane generator automatic back-up system and covered slate walkway/breezeway. Newer furnace, new tile bath, interior paint and more- shows well! Great location. Mettawee school district.
Scott Mcchesney Lee D. McChesney Real Estate
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$147,500 4 acres 1 Bed | 1 Bath | 1000 sqft
617 Ebenville Rd, Rupert, VT 05768 - Bennington County

4 acres Rupert, VT

Large open, bright living room with lots of windows and pine plank floors. Nice privacy set along dead-end town gravel road with great access to hiking and snowmobile trails (Merck Forest & Bear Mountain). Recently updated with new heating system, hot water heater, drilled well and Anderson windows. Beautiful quiet spot - great starter home or retreat at only $147,500 *Inclusive of newly installed state-approved septic system.
Scott Mcchesney Lee D. McChesney Real Estate
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$74,500 14 acres
0 Clark Road, Rupert, VT 05768 - Bennington County

14 acres Rupert, VT

Build and boil in Rupert, VT. A special parcel with great access off town gravel road (asphalt rd only 1/4 mile away), state approved and permitted for 5 bedroom home as well as town subdivision approved with sunset views overlooking spring-fed pond and pasture land and the balance of /- 10 acres of maple trees/sugar bush with a babbling stream. Potential for /-500 tap maple syrup operation. Utility pole right near site. Great proximity to Merck forest - almost touching it's boundary! Also a spring complete with an old spring house - ready to be fixed up for watering the horses or other livestock. All less than 10 minutes to Dorset!
Scott Mcchesney Lee D. McChesney Real Estate
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$49,900 10 acres
761 Ebenville Rd North Side, Rupert, VT 05768 - Bennington County

10 acres Rupert, VT

/-10 A wooded parcel with stream, views set off dead-end town gravel road. Great privacy with access to incredible snowmobiling, hiking, etc...- Merck Forest and Bear Mountain- with trails to Manchester! Complete with one car garage for ATV/snowmobile/mountain bike! State permitted for 3 bedroom home.
Scott Mcchesney Lee D. McChesney Real Estate
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$2,250,000 284 acres 4 Beds | 5 Baths | 3775 sqft
792 Route 153, Rupert, VT 05768 - Bennington County

284 acres Rupert, VT

Stunning Vermont Vernacular on 284 acres! Incredible views, newly constructed(2010)legacy estate built with attention to detail and the highest quality materials. Long private drive to the top of the world! Recreation opportunity abounds! Hunt, fish White Creek or the Battenkill, ATV or snowmobile. Or relax by the 50 ft in ground resort quality pool and take in the view. Great equestrian potential. Four en-suite bedrooms, two fireplaces, gourmet kitchen with Viking range and Liebherr fridge, covered porch, two fireplaces. Finished basement with game room. Beautiful 33 x 28 ft storage barn and lovely grounds. Timber producing property in Current Use Program. Kohler Generator. 30 minutes to Saratoga and 15 minutes to Dorset. Incredible place.
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$1,595,000 175.04 acres 3 Beds | 3 Baths | 3300 sqft
334 Dole Road, Rupert, VT 05776 - Bennington County

175.04 acres Rupert, VT

Mountain View Farm is a horseman's paradise. Panoramic far reaching views. Center chimney reproduction saltbox home with tunnels to the four plus garage garage barn and greenhouse. Brand new five stall horse barn with tack room that could easily be expanded to ten stalls. Two ten acre corrals with heated water troughs overlooks swimmimg pond. Restored cape cod caretaker's or guest home with 5 fireplaces, second pond, mature fruit trees all bordering lands of Merck Forest. Fantastic breathtaking property, a must see!
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$619,000 40 acres 5 Beds | 2 Baths | 3800 sqft
484 Herrick Brook Road, Rupert, VT 05768 - Bennington County

40 acres Rupert, VT

Incredible Mettowee Valley views from a special setting perched up on a hillside. Spacious Colonial Cape Offers Fine Country Living Just 5 miles To Dorset Green.Land Offered W/40 Acres (add. 21 avail w/2nd pond/stream) Fantastic private location yet close to both Manchester and Dorset. Rare find.
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$449,000 7.05 acres 4 Beds | 4 Baths | 2708 sqft
16 Clark Road, Rupert, VT 05768 - Bennington County

7.05 acres Rupert, VT

Well proportioned, handsome colonial farmhouse sits on a very private 7 acre parcel with beautiful mountain views and a pond. The house has 4 bedrooms and 4 baths plus a finished bonus room over the garage with a bthrm, which is presently being used as an office/guest room. Recent improvements include a new roof, updated master bath and new kitchen-both kitchen and mudroom floor are heated. Sit back and enjoy the serene surroundings on the striking new stone patio. An elegant offering not far from Dorset and Manchester.
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$400,000 52 acres 3 Beds | 3 Baths | 1700 sqft
925 Sandgate Road, Rupert, VT 05776 - Bennington County

52 acres Rupert, VT

Magnificent Vermont Get Away or Primary Residence. Truly a slice of Vermont Heaven. 52 Acres of scenic pasture, woods and medows. Main house offers 3 bedrooms, 2 full baths, rustic stone fireplace, large screened in porch and decks. 2 car garage/barn with 2nd level studio apartment features kitchenette, bath, game room and utility room. Views from every direction. Snowshoe, ski, snowmobile right from your back door. Completely move in ready. Short drive from Dorset, Manchester, Arlington and Saratoga. Priced well under assessment value. Don't let this one get away!
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$315,000 35 acres 3 Beds | 3 Baths | 1 ½ Bath | 2346 sqft
4451 Route 315, Rupert, VT 05768 - Bennington County

35 acres Rupert, VT

Spacious 3 bedroom, 2.5 bath colonial on 35 private acres of meadows and woods is only 3.5 miles to the Dorset Village Green. Lovely hardwood floors throughout the home, combined living/dining room opens into inviting sunroom with fireplace, which opens further onto sunny deck with meadow views. Master bedroom suite plus two more bedrooms and additional full bath upstairs. 2 car attached garage is currently in use as a studio but can easily be converted back to garage. House includes generator and ProTran hook-up.
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$315,000 3.79 acres 5 Beds | 2 Baths | 4147 sqft
89 Main Street VT Route 315, Rupert, VT 05768 - Bennington County

3.79 acres Rupert, VT

Historic 1850 Colonial Estate features Four Barns, open meadows and a spring fed pond on 3.75 acres. Screened in porch, hardwood floors, 5 bedrooms, family room, large formal living room all grace this amazing estate. Horse barn features five stalls all with water, full second floor hayloft, large heated garage. Another barn conveniently located on the other side of property and a second large garage for your truck or farm equipment. This estate is zoned village commercial so a bed and breakfast or working horse farm is just the start of endless possibilities. Formerly owned by the famous Spencer Fossel. Come and see this Historic Vermont Estate.
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$219,000 5.9 acres 2 Beds | 2 Baths | 1580 sqft
15 Derby Hill Road, Rupert, VT 05768 - Bennington County

5.9 acres Rupert, VT

TPW Real Estate offers this unique Rupert, Vermont house with barn and garage on 5.9 acres. Call 802-366-1430 to see this today, or visit
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$125,000 2 acres 3 Beds | 2 Baths | 1512 sqft
1683 Kent Hollow Rd., Rupert, VT 05776 - Bennington County

2 acres Rupert, VT

New Price!!! Two acre parcel perfect for pasture and horses. Beautifully maintained Double Wide with Large wrap around deck is amazingly spacious. Glass pained kitchen cabinets, Large eat-in kitchen, walk-in pantry, and three walk-in closets are just a few special features this home has to offer. Set on a convenient, but private setting you will have the best of both worlds.