Upper Valley Homes with a Guest House

MLS Number 4971283

• Residential Single Family
• Bathroom 3
• Construction Existing
• Bedrooms 4
• Square Feet 3,098

Idyllic Alpine Farm in Southern Vermont with easterly views of Mt. Ascutney & the White Mountains. This conserved farm is situated on 63 acres at 1800' elevation, and is your quintessential Vermont hill farm, with rolling meadows, ancient stone walls, & sugar maples lining the roads and filling its woods. Located in South Reading in close proximity to cultural attractions in Woodstock, Brownsville, and the Upper Valley, with skiing just up the road at Okemo and Killington. It also features a classic 3,000 sq. ft. 4BR, 3 BA remodeled colonial farmhouse originally built circa. 1796. Enjoy the views from the farmer's porch, let your horses or cattle graze the lush pastures, enjoy the cozy library around the woodstove, gather in the renovated kitchen and dining room around the farm table, host guests in the spacious bedrooms with bathrooms on all levels. This private location is just 1/4 mile from the paved road and rest secure when you are away with the whole house backup generator and new boiler. Enjoy passive income from the Cottage on Airbnb and VRBO as the current owners have done for the past 3 years or simply use it for private quarters for guests. The property enjoys a substantial year round brook, spring-fed trout-stocked pond, a mix of fenced pasture and timber stands. The farm features 2 historic hand hewn post and beam barns with stalls, tack room, hay/equipment storage, permanent frost free water and a grain bin. Delayed showings start on October 1st (not before).

Listed by John Bassette and Geoff Eckler of Bassette Real Estate Group

MLS Number 4969591

• Residential Single Family
• Square Feet 3,408
• Construction Existing
• Bedrooms 3
• Bathroom 4

Rare Opportunity to Own This Custom Built Quality 3,408 Sq Ft 3 Bedroom 3 1/2 Bath Cape with Attached 2 Car Garage and Separate Detached Barn with Beautiful 2 Bedroom Apartment($1,700/mo. or More Income Potential). The Apartment Needs 2 Egress Windows and Some Other Work Before Being Rentable. 3 More Garage Bays and It's Own Half Bath are in this Terrific Barn. Home Has Southern Pine Floors, Replacement Windows, Buderus Boiler, Cathedral Ceiling 1st Floor Family Room Plus an Unbelievable Lower Level Family Room with Pool Table and Awesome Stone Bar. Hot Tub, Whole House Fan, 2 Generator Hook Ups, Fireplaced Living Room, Recent Roofing, and a Separate Office Are a Few More Details of this Wonderful Property on 1.51 Mostly Open Acres For Space For Your Toys, Equipment, or Just Outside Enjoyment.

Listed by Brian Whipple of Coldwell Banker Homes Unlimited

MLS Number 4968498

• Residential Single Family
• Construction Existing
• Bedrooms 1
• Bathroom 1
• Square Feet 1,658

Located along the rolling hills of Vermont's picturesque countryside sits the Taplin Hill Farm. This unique property offers over 177 acres of open and wooded pastures, manicured lawns, an old sugar bush, a Christmas tree plot and breathtaking long range views. Drive to the Cottage built in 2022 overlooking the swimming pond. This is a Contemporary open concept living with one bedroom and one bath. As you travel up the scenic gravel drive you come to the overlook landing. Here you can sit by the wood burning fire pit, watch the Highlander cows graze and listen to the horses gallop by. Continue to the off-grid barn/home built in 2018. The barn's second floor features cathedral ceilings, a brightly lit kitchen, dining and living area with a wood burning stove. Also, on the second level is a beautiful bedroom with ensuite bath and office all with large windows to maximize the views. The lower level offers a second office space, laundry/utility room and an unfinished storage area. Outside, there are two outbuildings, a chicken coop and acres of fenced in pastures. Up the road another quarter mile sits a private one room off-grid cabin with a kitchenette, and three quarter bath, built in 2016. Here you can sit on the front deck, relax, listen to nature and on a clear day see the top of Mount Washington. The property has high speed internet, is located less than three hours from Boston, and only 15 minutes to I-91. This remarkable property must be seen to be truly appreciated.

Listed by Annette Hartley-White and Laurie Kirkpatrick of Four Seasons Sotheby's Int'l Realty

MLS Number 4968402

• Residential Single Family
• Village Woodstock
• Construction Existing
• Bedrooms 6
• Bathroom 4

Amazing opportunity to own a very special property on the market for the first time in over 50 years. Built in 1880, "Rose Hill" was one of the premier homes in the Woodstock Village area. The 6 bedroom 4 bath house sits on just under 4 private acres and is conveniently located less than a mile from the Village Green and the Woodstock Inn and only 1/4 of a mile from the Rec Center. Stone walkways, mature trees and old gardens dot the landscape. The over sized covered brick porch is waiting to reclaim the lovely views to the South. Inside, you are greeted by a large foyer that leads to the grand living room with a magnificent fireplace centering the room. To the left is the dining room which leads to the kitchen, and a window filled den is off to the right. There is a dutch door out to the porch and an eye catching staircase with a wood banister and ornate spindles that takes you upstairs. The 2nd floor is home to 6 bedrooms including a Primary with ensuite bath and a quaint sitting room. In addition to the main house, there is a detached garage with an apartment above and a 1 bedroom cottage set back on the premises. In need of updates and some renovations, this property is looking for the next steward to return the house to its former glory. Ideal as a primary residence, 2nd home getaway, or redevelopment investment. Short drive to the Woodstock CC and Saskadena 6, while Killington and Dartmouth are less than 30 minutes away.

Listed by Dan Noble of Snyder Donegan Real Estate Group

MLS Number 4968227

• Residential Single Family
• Construction Existing
• Bedrooms 5
• Bathroom 7
• Square Feet 4,510

For nearly two centuries the iconic Kedron Valley Farm has served as the gateway to the village of South Woodstock. Prominently sited on a knoll with lovely valley views in every direction, this warm and inviting post and beam home has been fully rejuvenated, honoring the classic period detail. The main house is ideal for entertaining with bright, generous rooms, and cozy spaces. The living room runs front to back, centered by a fireplace with pine surround and exposed beams. The kitchen is well suited with Thermador appliances, quartz counters and custom mahogany cabinetry. The spacious private primary suite features exposed beams, cathedral ceiling, new tandem bathrooms connected by a walk thru shower, plenty of closet space, laundry and AC. There are four additional guest suites, a TV and reading room w fireplace and built-ins, and clever loft spaces with offices. The charming, separate three-bedroom carriage house is perfect for guests, family or as an income producing rental unit. The property is anchored by a spectacular 4-story bank barn with six horse stalls, fenced paddocks and a run-in shed complete with power and water. The grounds are gorgeous with a beautiful brick terrace, level verdant lawns, grand, 175 year old maple trees, established perennial beds, a private swimming pond, apple orchard, and a fenced har-tru surfaced tennis court sited discreetly at the rear of the property. Seven minutes to Woodstock Village Green. Broker interest.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

MLS Number 4965445

• Residential Single Family
• Square Feet 7,465
• Bathroom 8
• Bedrooms 8
• Construction Existing

Set on over 100 acres of protective field and forest land is one of New Hampshire's most elegant and historic estates remodeled in the late 1800's by Austin Corbin, a dynamic self-made millionaire who was known as the "Father of the Banking Industry" and founder of the nearby 25,000 acre Corbin Park hunting preserve and Blue Mountain Forest. Offering views of Mt. Sunapee and distant hills, flanked by the Sugar River and accessed by a covered bridge, the hilltop residence offers exquisite living space including a 51 foot great room gallery with gilded ceiling, exotic walnut and mahogany detailing and massive fireplace hearth, ornate mahogany bar with curved gilded paper ceiling, elegant paneled reception hall with fireplace and sitting room, modern kitchen with wet-bar pantry, large master suite with delightful sleeping porch, recently installed elevator, central air conditioning and three-car attached garage. Property also includes four bedroom guest house, to be sold subject to life tenancy agreement to caretaker. Several additional outbuildings include gentlemen's library, heated workshop and a wonderful 40 x 45 barn/guest house with vehicle storage. Showings by appointment only-Proof of funds required. A magnificent personal domain!

Listed by Andrew Peterson and George Quackenbos of Four Seasons Sotheby's International Realty

MLS Number 4960337

• Residential Single Family
• Square Feet 5,048
• Construction Existing
• Bathroom 5
• Bedrooms 5

If beauty and convenience are what you seek, look no further than this vibrant home. With rolling green lawns, lush gardens, and outdoor living spaces cascading from the center of this house, this is the ideal spot for unwinding or entertaining in nature's embrace. The stone walls and patios are custom built, creating flow and accentuating the home from every angle like a piece of art. Every upstairs room, the sun porch, and a deck flow into the kitchen. The large windows, vaulted ceilings, wet bar, and TV den with sit up bar are ideal for entertaining crowds or relaxing. One can easily unwind and retreat downstairs to the recently-renovated lower level, where every bedroom is clean, bright, and airy and offers a door to the outside - a true harmony with all the outdoor spaces this home features. The primary bedroom is a retreat unto itself, with steam shower, large walk-in closets, mini fridge and private patio. The guest barn with porch views and lofty living space is sure to delight your overnight guests. Each room in this cottage provides a balance of tranquility and comfort. Every aspect of this home, barn, and cultivated landscape offers a sense of retreat, tucked away on a hill in a quiet neighborhood. Yet, there is so much close by to delight everyone. A quick trip to town for groceries, a walk on trails in the woods, a Mac's Maple famous creamee, a day spent picking strawberries at Edgewater Farm - it's all here!

Listed by Evan Pierce and Leah McLaughry of Four Seasons Sotheby's Int'l Realty

MLS Number 4952773

• Residential Single Family
• Construction Existing
• Bedrooms 5
• Bathroom 6
• Square Feet 6,018

A Vermont Country Estate historic and inspiring and placed upon a hill overlooking the Connecticut River. A large main house, a quaint guest home, a unique treehouse, a clay tennis court, an outdoor living room, and a sprawling barn set the landscape for this quintessential estate. With expansive rooms and gathering spaces, a traditional & contemporary melded design, and opulent lighting are present throughout this Vermont home. An acorn treehouse situated and perched between an oak and a maple tree adorns the center of the property while overlooking the pastures and southern views of the Connecticut River. This Vermont riverfront retreat prominently displays outdoor gathering spaces, opulent views, and resides in an idyllic setting within the surrounding landscape. Within 20 minutes of Dartmouth College and an easy destination spot from Boston and New York, this property is primed for its successors coming from near or far.

Listed by Lochrane Gary and Lori Shipulski of BHHS Verani Upper Valley

MLS Number 4944611

• Residential Single Family
• Construction Existing
• Bedrooms 2
• Square Feet 1,392
• Bathroom 1

A "woods' house" high in the hills of Lyme, surrounded by trees and meadow, in the area known as "Hardscrabble", this custom-built post and beam structure (Outback Post and Beam) would be a great home for a small family, artist, writer, or anyone seeking a beautiful, peaceful spot surrounded by nature. Trout Brook runs across the land, and there are views East and West of surrounding hills. The interior is open, with a tall window-wall facing the woods, much custom carpentry, and offers a relaxed lifestyle. Some finish work remains to be done. Property also includes a detached studio/guest cabin, small 1-car garage/barn, work shed, concrete slab intended for a shop-barn which was never built (24'x50' + 20'x20'), porch, patio and deck. A 3rd floor loft area could be used for sleeping quarters or quiet spot. Water currently supplied by long-serving dug well, but a drilled well is available. This property is a gem, and, needs to be seen to be appreciated. NOTES: 1. This property has been enrolled in Current Use, but the recently completed survey shows less acreage than necessary to be eligible for CU, so that status will need to be addressed. 2. The property is accessed by an "old road", which also provides a non-exclusive ROW access (the only) to the property behind. It is not clear from deeds seen what the ownership of the "old road" is--further research would be needed.

Listed by William Johnson of Big Green Real Estate

MLS Number 4934539

• Residential Single Family
• Bathroom 10
• Square Feet 11,470
• Construction Existing
• Bedrooms 7

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

Listed by Christopher Lang of LandVest,Inc/Woodstock

MLS Number 4923048

• Residential Single Family
• Construction Existing
• Bedrooms 5
• Bathroom 6
• Square Feet 6,799

Old Fitch Farm is one of New England's most extraordinary estates. This remarkable residence is sited graciously on a plateau with 1200' of frontage on the Ottauquechee River, and views to Mt Tom and Woodstock Village. The impeccably restored five-bedroom, six BA main residence, four-bedroom, 2 BA guest cottage and impressive three-story horse barn reflect Federal and Greek revival influences of architect Asher Benjamin. The stately foyer in the main residence is centered by a splendid 3-story mahogany staircase, a true testament to the tradition of quality and fine craftsmanship of the era. The formal common rooms on the main level are spacious, elegant and impeccably appointed. The kitchen is spectacular with Italian tumbled marble floors, custom Dutchmade cabinetry, exceptional appliances, and Butler's pantry with custom quartersawn-oak cabinetry. The Grand Primary Suite commands the second floor with a newly added, discreet elevator, his and hers dressing rooms, impeccably appointed bathrooms, and an office. The second level is further completed by two luxurious guest suites. The third level offers two additional guest rooms with a shared bathroom. Central AC, attached, heated three car garage. There is a spectacular hilltop riding ring with bridle paths lacing through the property. A short stroll to the shops, restaurants and galleries of Woodstock Village. Fifteen minutes to skiing. Two hours, fifteen minutes to Boston. Four and a half hours to NYC.

Listed by Danny Kogut and Laird Bradley of Williamson Group Sothebys Intl. Realty