Upper Valley Homes with a Guest House

Browse homes for sale with a guest house in the Upper Valley area.

Houses for Sale with Guest House in NH & VT

Contact LindeMac Real Estate at 603-643-4900 if you have questions or would like to schedule a tour. 

111 Garnet Hill Road Sunapee NH 03782

Sunapee, NH111 Garnet Hill Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4815187

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 11
  • Square Feet 4,930

A rare opportunity! This breathtaking family compound boasts 14 acres of private grounds with lake and mountain views! The main house features 11 bedrooms on three floors, an ahead-of-its-time open concept living/dining room, and an expansive wrap around porch. The property includes an additional 2-bedroom ranch style carriage house (circa 1970), ideal for caretakers, extended family members or annual/seasonal renters. The surrounding landscape is appointed with stone walls and terraces originally crafted by Italian stone masons which encompasses two garages and a woodshed. The lush tree covered acreage includes a parcel at the very TOP of Garnet Hill with the potential for 180-degree views of Lake Sunapee and the surrounding mountains. Walk down to your own boathouse, the only one with 4 slips on Lake Sunapee, and enjoy spectacular views of Mt. Sunapee and Loon Island Lighthouse from the expansive 20' x 30' dock. The dock's unique deep-water location originally served as a stop for early steamships delivering mail to local residents. A private short path from the property winds its way down through the woods to the Lake Sunapee Yacht Club to enjoy friends, swimming, boating, and tennis.

Listed by Jessica Dolan and Andy Ivey of Dolan Real Estate

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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88 Dusty Way Fairlee VT 05045

Fairlee, VT88 Dusty Way

Price$2,200,000

Est. Mortgage: $/month

MLS Number 4813770

  • Residential Single Family
  • Construction Existing
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 5,432

Fabulous opportunity on Lake Fairlee! Welcome to the ultimate waterfront property that will ensure your life has plenty of space for gathering. Cozy guest cabin with fireplace and efficiency kitchen and bath offers the space to host family and friend could also be an office or studio. The quality materials and finishings found throughout this five en-suite bedroom masterpiece is elegant yet inviting and comfortable. Enjoy leisure times on the lush green lawn that gently slopes down to 291 feet of sparkling water frontage on picturesque Lake Fairlee. If water activities from the boathouse dock and quiet nights relaxing on the deck or inside the screened porch sound like the slice of heaven you have been longing for? Call now to schedule a tour of this very special waterfront home.

Listed by Penny Loschiavo of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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145 Pellerin Hill Road Springfield NH 03284

Springfield, NH145 Pellerin Hill Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4813152

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 4,200

Privacy and versatility await. This stunning property in the Lake Sunapee area of New Hampshire offers magnificent views of Croydon Mountain and Mount Sunapee. Set on 17.5 acres, this unique property has two single family homes and five outbuildings that include a workshop, an artist's studio, a gorgeous two bedroom apartment, a hot room gym, a sugar house and ample storage areas. The open concept main house, with four bedrooms and 4.5 baths, is westerly facing and light filled; it is the perfect setting for gatherings and entertaining. Complete with an apartment over the garage for an au pair, extension or additional rental income, the home can easily accommodate a variety of needs. At the base of Pellerin Hill is an additional three bedroom and three bathroom home for caretaker, family members or rental income. Make Pellerin Hill your country estate, compound or beautiful home with rental outbuildings.

Listed by Jason Saphire of www.EntryOnly.com

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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75 Charlestown Road Claremont NH 03743

Claremont, NH75 Charlestown Road

Price$435,000

Est. Mortgage: $/month

MLS Number 4811992

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 3,304

Claremont Estate. Tastefully restored treasure, a beautiful 11 room 4 bedroom 2.5 bath 1900's era home! Property includes, a 2 bedroom ranch w/garage for rental or used as a guest house and a magnificent 3 level garage with special lighted show room, elevator/lift from basement to 3rd floor, an applianced party room, exercise room and heated basement workshop. Property is on a total of a 3.97 beautifully landscaped lot and butts the golf course on 2 sides. This property has too many features to mention them all. A must see for the discerning buyer!

Listed by Ann Jacques of Century 21 Highview Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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346 Goodrich Four Corners Road Norwich VT 05055
Active With Contract

MLS Number 4811919

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 1
  • Square Feet 1,024

This enchanting property is comprised of 2 buildings - the main house, and a studio/workspace across the courtyard. Both were designed by well-known local architects, EH and MH Hunter, and demonstrate the economy of space and attention to detail that are their trademarks. The contemporary style is appropriate to the wooded, private setting with large windows in every room inviting nature into the living spaces. A wrap-around deck is the choice for outdoor living in the summertime. The separate studio building is completely self contained and is currently rented on a month to month basis. Located just 3 miles from Norwich Village and also close to Hanover across the River, this property is an outstanding example of Mid Century Modern architecture.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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Jobs Creek Road Sunapee NH 03782

Sunapee, NHJobs Creek Road

Price$7,995,000

Est. Mortgage: $/month

MLS Number 4810818

  • Residential Single Family
  • Construction Existing
  • Bathroom 11
  • Bedrooms 7
  • Square Feet 13,382

Fool on the Hill Farm sits on 200+/- acres overlooking Lake Sunapee and the Mt. Sunapee range. Built with every modern amenity, the home was designed to look and feel as though it has been nestled on the hilltop for more than a century. Adventure & fun are as close as your backyard featuring a private beach, lakefront cabin and deep water boatslip on Lake Sunapee. A gated 3/4 mile drive passes a caretakers house and winds through woodlands arriving at an open, rolling meadow and your home on the hill. Designed to evoke a traditional New England farmhouse a stone facade with white clapboard extensions connect with an inviting porch full of rocking chairs. Interior rooms were designed to transition seamlessly from warm and spacious entertaining spaces to a cozy intimate family living room adjacent to a gourmet country kitchen. Fireplaces crackle throughout. The recreation room is a family favorite offering a fireplace and a rustic-style pub bar. Seven en-suite bedrooms feature spectacular views, full sun and luxurious baths. The master suite features his and her baths & a spiral stair to private offices. Terraced gardens lead to a heated pool & stone cabana with kitchen. Enjoy tennis and basketball day or night on lit courts. Hiking trails throughout the property beckon on crisp fall days. Vegetable , perennial gardens and an apple orchard provide a steady harvest. Two barns are ready for your collections. Privacy, serenity and peace of mind await you at Lake Sunapee!

Listed by Pamela Perkins of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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37 Brothers Road Hartland VT 05048

Hartland, VT37 Brothers Road

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4810260

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 2,800

Hartland Highlands is a Vermont refuge like no other. The land, professionally managed over the span of two decades under the meticulous stewardship of the areas most professional forestry management and land enhancement company, offers over 277 acres of high, rolling meadows, mixed northern hardwoods forests, four ponds, three brooks, miles of interior roads and trails and multiple developable future house sites. This true private kingdom offers a myriad of possibilities for a multi-generational legacy estate, a rural place of refuge or retreat or other more creative possibilities. Enjoying a location that is close to Dartmouth College, Woodstock, Vermont and the crossroads of New England where Interstates 89 and 91 meet, Hartland Highlands offers one of the largest, professionally managed and strategically improved parcels of land currently available anywhere in the Upper Connecticut River Valley. Close to the cultural attractions found only in a town with an Ivy League College and minutes from the picturesque and historic village of Woodstock, Vermont, famous for being one of the prettiest small towns in New England, the kingdom size property offers room to roam without ever leaving the land that you own while still being conveniently located to the country cosmopolitan and lifestyle conveniences of cultured civilization. The historic, expanded Cape on the western side of Brothers Road is surrounded by copious perennial gardens, antique stonewalls and grandfather maples

Listed by Richard Higgerson of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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123 Jenney Road Plainfield NH 03781

Plainfield, NH123 Jenney Road

Price$825,000

Est. Mortgage: $/month

MLS Number 4806088

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 3,500

Flag Farm, located in Meriden NH, is the answer to all your prayers! Stunning 1866 Farmhouse that has been thoughtfully renovated yet the exquisite charm remains. Features include a gourmet kitchen with cathedral ceiling and a cozy wood stove, first floor bedroom option, formal dining room with fireplace, screened in porch, back patio area with water feature, amazing office/study on 3rd floor, and GREAT internet connection. Newly constructed in-law dwelling located in one of the barns. NOT to mention, who doesn't love a barn painted with an American Flag? Come see what the fuss is all about!

Listed by Amy Redpath of Coldwell Banker LIFESTYLES - Hanover

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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58 Freeman Road Plainfield NH 03770

Plainfield, NH58 Freeman Road

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4804473

  • Residential Single Family
  • Construction Existing
  • Bathroom 14
  • Bedrooms 16
  • Square Feet 15,534

THE OAKS- On the market in its entirety for the first time in over 30 years, this elegant historic property was the family estate of artist Maxfield Parrish from 1898 to 1966. It is made up of a main house, the renovated studio building, and a guest house. The Oaks sits on a lovely 45+ acres near Plainfield Village and the Cornish, NH town line. True to its name, the property's winding drive is dotted with magnificent oak trees punctuating the landscape. It culminates with a grand majestic oak that may be one of the oldest in the state and forms a large courtyard on which all three buildings front. There are numerous features still intact on the property that were the direct inspiration for many of Parrish's paintings including archways, reflecting pools, mature landscaping, and the dramatic view of Mount Ascutney to the south. There is an inspiring magic to the property both inside and out. The studio was renovated & restored by the owner architect keeping many of Parrish's original features such as the coffered ceiling, archways, and abundant light. The Oaks would be perfect continuing as a family compound, or reimagined as it once was as a famous country inn, or utilized as an event/ creative/ educational/ artistic space.

Listed by David Donegan of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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22 Woodland Road Sunapee NH 03782

Sunapee, NH22 Woodland Road

Price$1,695,000

Est. Mortgage: $/month

MLS Number 4803526

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 4,229

Room for the entire extended family in this exceptionally well built, energy efficient Lake Sunapee home! Enjoy waterfront vistas from a large deck, master bedroom balcony , the front lawn or permanent wharf. The main house offers a great room with Scandinavian style fireplace, offering radiant heat all day with minimal effort. The Woodmode kitchen features ample storage and workspace. Upstairs find 4 spacious bedrooms including a master suite with bath overlooking the lake. The top level offers a 26x35 rec. room with space for pool, pingpong, kids, crafts or an exercise room. The lowest level is set up for an in law with a kitchenette, great room, bedroom and even a sauna. A two bedroom year round guest house sits in a private location offering opportunity for company or even rental income. Located on a quiet cul de sac street, ideal for walking with kids, dogs, bikes and more. Wake up to the loons calling, this is a perfect location for kayaking and paddleboarding. Lake Sunapee is awaits, are you ready!

Listed by Pamela Perkins of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 Emerson Road Topsham VT 05076

Topsham, VT55 Emerson Road

Price$269,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4800648

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,141

Views from Moosilauke to the Kinsman Twin Peaks, the Franconia Range and of Mount Washington! This unique property offers an endless list of possibilities and enjoyment, peace and quiet and at the end of a town-maintained road. The main house has plenty of room with four bedrooms and flowing floor plan, most of which takes in the views! A huge deck overlooks two ponds that are situated on the lower meadow right down front, one is quite large. An additional guest cottage is 100 yards away offering one bath, one bedroom and space in the main room for gathering, also with a nice deck. Open trails will lead you to the height of the land with additional local views to the west and a lean-to for picnics, etc. A detached two-car garage plus shop area and a great pole shed offer the extra space for your imagination to fill up 40 plus acres of peace and quiet, privacy ponds, meadows, and the list goes on!

Listed by Chuck Clifford of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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3114 Church Hill Road Woodstock VT 05091

Woodstock, VT3114 Church Hill Road

Price$2,740,000

Est. Mortgage: $/month

MLS Number 4800371

  • Residential Single Family
  • Construction New Construction
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 9,320

Between the storied Village of Woodstock, Vermont and the country cosmopolitan hamlet of equestrian-oriented South Woodstock a remarkable retreat can be found. The spectacular post and beam residence and barn/guest house are the result of a collaboration between two partners uniquely qualified and united in the passion to create something extraordinary. The architect designed main house is sited to take maximum advantage of the homes south elevation and provides a view of the barn, fenced pasture and paddock area. Employing old world craftsmanship, C.G. Nichols Builders brought over 35 years of custom residential construction experience to create a dramatic statement in wood, glass and stone. The connected open flow of the first floor plan is centered around the kitchen and its remarkable four season solar surround. The home features the finest quality materials and highest quality and most current construction standards. With approximately 6800 square feet, the 9-room main house offers four bedrooms, four and a half baths, open-concept kitchen, living and dining area, mudroom, entry and expansive first floor master bedroom suite and the main house is surrounded by bluestone terraces, dry laid stone walls, lush lawns and gardens. The detached barn and guest house provide everything one needs for the equestrian lifestyle and the nearby Green Mountain Horse Association is a short 2.5 mile hack away. Delayed showings until 4/15/20.

Listed by Richard Higgerson of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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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Copyright 2020 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated July 13, 2020.