Upper Valley Homes with a Guest House

Upper Valley Home with a Guest HouseBrowse homes for sale with a guest house in the Upper Valley area. Contact LindeMac Real Estate at 603-643-4900 if you have questions or would like to schedule a tour. 

Houses for Sale with Guest House in NH & VT

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1101 Tattle Street Reading VT 05062

Reading, VT1101 Tattle Street

Price$495,950

Est. Mortgage: $/month

MLS Number 4945249

  • Residential Single Family
  • Bedrooms 5
  • Construction Existing
  • Bathroom 3
  • Square Feet 4,044

True horse property and ready for you to bring it back to what it once was!!!! 39.22 acres hosts an original 1795 farmhouse with so much character!!! 5 bedrooms, fireplaced living room, lovely sun-mudroom and so much more!!! 110x60 indoor arena and stable with 10 stalls and tack/viewing area. Additional shop/barn with 5 additional stall, carriage house and shed for storage. This property is a real gem!!!

Listed by Dick Thackston of R.H. Thackston & Company

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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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36 Pony Hill Lane Lyme NH 03768-3706

Lyme, NH36 Pony Hill Lane

Price$625,000

Est. Mortgage: $/month

MLS Number 4944611

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

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

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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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707 Bowman Road Barnard VT 05031
Active With Contract

MLS Number 4944494

  • Residential Single Family
  • Square Feet 3,584
  • Bathroom 4
  • Bedrooms 3
  • Construction Existing

A beautiful Barnard property with features almost too numerous to list. Designed and built in 2005 by contractor/craftsmen owners known for their exceptional quality, craftsmanship and creativity. The property is unusually friendly and functional for the area with 25.9 private acres of level to rolling lawn, pasture and woods. Close to Silver Lake, the Barnard General Store, the Barnard Inn and a short drive to Woodstock and all the amenities of Teago. Numerous outbuildings on the property include a three stall horse barn with water and power and a large workshop/studio building also with water and power. A jewel of the property, along with the primary residence, is a private very large, deep, spring fed swimming/fishing/skating pond with a guest cottage at the waters edge. Features of the house include three bedrooms, an office, three and one half bathrooms, with a fourth bathroom ready to be completed to the buyers preferences. Fiber optic high speed broad band. Exquisite wood and stone work throughout. There is a light filled family room on the ground level with a wood stove, walk out access and a bank of windows overlooking the lawn and beyond. An exceptional property that can truly only be appreciated by an onsite tour.

Listed by Stan Butler of Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3 Greengate Road Barnard VT 05091

Barnard, VT3 Greengate Road

Price$2,300,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4943214

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,965

Double Dog Farm is a c.1757 cape on 60 acres alongside of Atwood Creek, 15 minutes outside of Woodstock. Sited high on a dead-end road, it was likely built by Dutch immigrants who moved into this mountain valley to fell timber. Later it became a farm where Merino sheep dotted the landscape and stone walls still stand. The site has particular magic: the light on the property is very special, indeed attracting the attention of renowned artists. Artist and illustrator, Rockwell Kent, bought the farm for his wife, who later sold it to portraitist and instrument maker Irwin Hoffman. Hoffman handmade violins and other instruments on the property and co-founded the Vermont Symphony Orchestra, which practiced and performed in the barn. In 2010, the home was renovated including a large addition with a wrap-around porch, a spacious chef's kitchen, dining room, living room and primary bedroom suite. The English barn was built in 1837. There is a two-bedroom cabin completely renovated in 2022, a wind turbine that aerates the swimming pond, small greenhouse, edible landscape of apples, pears, grapes, and berries and an extensive trail network including a lean-to for picnics and camp-outs. Hiking is wonderful out the back door on the property with the dogs off leash and to the Appalachian Trail. Lucy's lookout is a short hike away. Rolling pastures are suitable for livestock. The property abuts conserved land. Fiber optic high speed internet. 5 bay garage. Showings begin 2-24-23.

Listed by T Story Jenks and Dia Jenks of LandVest,Inc/Woodstock

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$
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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18/20 Gould Road Tunbridge VT 05077

Tunbridge, VT18/20 Gould Road

Price$245,000

Est. Mortgage: $/month

Pending

MLS Number 4941613

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,560

2 properties for the price of one with 3.7 acres of land on a dead end road with no zoning!!!!! Double wide has large primary bedroom with spacious bath, a cozy gas fireplace in living room for those chilly nights, lots of natural light, a den/office area with EC fiber at the property already and lots of storage throughout with spacious rooms. The accessory/in-law 990 sq ft dwelling has a new Furnace installed in 10/22, a new hot water heater installed in 2021, 2 bedrooms with an open living/dining area with a cozy-cabin like kitchen, a laundry area along with some additional storage space. This dwelling also has a separate heated area where the hot water heat is which could be used as a workshop or a place for gym equipment. The large barn has water and electricity, a stall area, a chicken coop with ample storage for hay, equipment, tools and various other items. Make your appointment to see this property soon!!!!!

Listed by Gail Wheatley of Vermont Heritage Real Estate

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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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55 Cherry Hill Springfield VT 05156

Springfield, VT55 Cherry Hill

Price$629,000

Est. Mortgage: $/month

MLS Number 4941079

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 8,656

Stately mansion on Cherry Hill formerly known as 11 Summer Hill. During the height of the Industrial Revolution, factories in the center of Springfield lined the shores of the Black River. Many of the machine tool industrialists and entrepreneurs built mansions in the area of Summer Hill, this Georgian colonial is among those stately residences. Arriving guests park under the porte cochere and enter into a handsome entrance hall with coat closet, half bath and sweeping staircase. To the right is an expansive living room with fireplace, bookcase surrounds and French doors that lead to a sunroom with fountain. The elegant dining room is spacious with beautiful crown molding, classic wainscotting and French doors to a sun filled breakfast room. The kitchen is large with three zones, eat-in, prep and cook areas, a laundry room is off of the kitchen and a hallway leads to the large drawing room. The second floor is beautiful and the master and adjoining bedroom both have ensuite baths. The third bedroom with fireplace enjoys jack and jill bath with bedroom four. The remaining two bedrooms were designated for domestic help and share a bath, walk-in linen closet, back staircase and access to an elevator. All baths in the home were redecorated during the art deco era. A 3 bay detached garage has 3 apartments, an additional garage and greenhouse are also on the lovely grounds.

Listed by Susan LeCours and Chelsea Cary of Barrett & Valley Assoc. Inc

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$
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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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353 Greene Road Woodstock VT 05071

Woodstock, VT353 Greene Road

Price$18,000,000

Est. Mortgage: $/month

MLS Number 4934539

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

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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433 Cowdrey Path Woodstock VT 05071

Woodstock, VT433 Cowdrey Path

Price$995,000

Est. Mortgage: $/month

MLS Number 4932619

  • Residential Single Family
  • Bathroom 4
  • Bedrooms 4
  • Construction Existing
  • Square Feet 3,507

Splendid contemporary cape and separate barn guest apartment idyllically nestled on an open and sunny hillside in the heart of South Woodstock horse country. The light and airy interior boasts an open concept gourmet kitchen with dining/living area that opens to both a wonderful screened porch and deck. In addition, there is a warm and spacious family room to gather for games or a movie. The primary bedroom ensuite is detailed with a stunning vaulted ceiling with exposed beams, a newly updated bath, and a lovely balcony overlooking a quintessential Vermont landscape. The additional two bedrooms share a full bath. An upstairs laundry room is an added convenience. As a bonus there is a wonderful barn with a separate guest apartment complete with kitchen and bath! The lower level of the barn has parking for one car as well as ample storage area which could easily be converted back to the original horse stall. New buderus boiler and standing seam roof are at the top of an extensive list of substantial upgrades and improvements to this property. Enjoy the convenience of being just around the corner from the South Woodstock Country Store, the Kedron Valley Inn, Green Mountain Horse Association (GMHA) and just a short ride to the village of Woodstock. A truly special and versatile property!

Listed by Mary Mayhew of Snyder Donegan Real Estate Group

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$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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486 Benedict Road Woodstock VT 05071

Woodstock, VT486 Benedict Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4925674

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 6,040

"BENEDICT HILL" - sited on 38 acres on a quiet gravel road in a premier location in South Woodstock is this truly classic Vermont estate property. The land component is comprised of split-rail fence lined pastures, meadows, woodlands, giant maple trees, ancient stone walls and gardens. The main “Stone House” c. 1820 - with period details and 10' ceilings has 4 bedrooms, 3 full and 2 half-baths, gourmet kitchen, a library-den, a wonderful living room and 3 fireplaces on the main level. A stone patio/covered porch spans the rear of the house, and a 2-car attached garage. The original barn was renovated into a fully finished barn/guest house comprised of a fabulous great room with 30-foot ceilings and stone fireplace, kitchen and dining areas. Open stairs lead up to a loft primary-bedroom and bath. Downstairs is a rec/family room, 2 bedrooms and full bath. The present owners have just completed many renovations. This is a rare opportunity to acquire one of the most special, pastoral Vermont properties to come on the market in years - yet is just 5 mins to the hamlet of South Woodstock, 12 mins to the Woodstock village green, and 20-30 mins to I-89, Hanover/Dartmouth and points beyond. See property specific website.

Listed by John Snyder of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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587 Old River Road Woodstock VT 05091

Woodstock, VT587 Old River Road

Price$8,750,000

Est. Mortgage: $/month

MLS Number 4923048

  • Residential Single Family
  • Bathroom 6
  • Bedrooms 5
  • Construction Existing
  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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67 Hayden Drive Haverhill NH 03785

Haverhill, NH67 Hayden Drive

Price$239,000

Est. Mortgage: $/month

Pending

MLS Number 4921305

  • Residential Single Family
  • Village Woodsville
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1

Comfortable cape privately located on a dead end road just far enough out of town. Short walk to shopping, restaurants and schools. Easy commute to I-91 and I-93 and the Hanover/Lebanon area. The property features a detached two car heated garage with in-law/rental apartment above (with long term tenant). The property is also next to a main snowmobile trail and Swiftwater Road is approved for ATVs for access to the railway network.. Sit on the front deck and watch the sunsets on this one of a kind property. Sale contingent on lot line adjustment. Note: Taxes are for complete property before lot line adjustment.

Listed by Paul Kidder of Lyman Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5518 Vermont Route 12 Barnard VT 05031

Barnard, VT5518 Vermont Route 12

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4882340

  • Residential Single Family
  • Construction Existing
  • Square Feet 7,619
  • Bedrooms 6
  • Bathroom 6

Weddings, events, retreats; this property can be reimagined as a boutique hotel, retreat center, or stately residence! Located minutes from Woodstock, in quintessential Barnard, the attractive and welcoming “Barnard Inn” has been a fine residence since 1796 and in recent decades a destination restaurant. Currently it is well known for catering many distinguished destination Vermont wedding events! Being commercially sound with all permitting and infrastructure in place, many turnkey opportunities exist! Nestled on 10 acres are manicured perennial gardens, lush meadows and working gardens. Walking paths lead to a secluded romantic wedding site at a pond! Owners have created an extensive and appealing private residence within the main brick building. Enter up stairs to a deck, and you'll walk into a sprawling designer kitchen. Continue on to a large living room, 5 bedrooms, family rooms and private spaces. The main building front entrance leads to 3 historic elegant formal dining rooms and an updated state of the art restaurant kitchen. Down the hall is a tavern, with 2 dining areas and a classic tavern bar. Large windows overlook the garden and fire pit area. A detached barn presents a dramatic turnkey event venue! Newly renovated studio apartment below the event barn is perfect for guests who value private space. It is currently used as a highly popular short-term Fine dining and event hosting is established! Transformation into a private estate residence is a potential use!

Listed by John Wetmore of William Raveis Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 6.6% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Broker Reciprocity 

Copyright 2023 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real 2estate displayed on this display comes in part from the IDX Program of New England Real Estate Network. The information being provided is for consumers’ personal, non- 3commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last 4updated March 20, 2023 5:10 PM EDT