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.

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. 

1726 Skitchewaug Trail Springfield VT 05156

Springfield, VT1726 Skitchewaug Trail

Price$2,300,000

Est. Mortgage: $/month

MLS Number 4918549

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,238

A circa 1734 Cape, displaying authentic detailing of museum quality, in a setting worthy of a Vermont Life Magazine cover! From a New Hampshire location this Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The interior reconstructed with attention to original design will please the most discriminating early New England architecture connoisseur! Authentic post and beam construction, gunstock corner posts, exposed beams, wooden ceilings, extraordinary wide board floors, 4 brick fireplaces, wide board sheathing and hand planed surfaces are revealed throughout! The advantage of contemporary mechanical systems, with full size cement basement and whole house back up generator are unobtrusive nods to present day conveniences! While this classic Cape features traditional format of family oriented rooms and kitchen on the ground floor, with bedrooms above, the owners have tastefully created a privately sited ground level primary bedroom suite to accommodate often sought practicality of a large ground level bedroom, through constructing a 30'x20' wing onto the residence. With vaulted ceiling and dramatic windows framing views of the pond and distant hills, this bedroom easily becomes a favorite room! Completing the expansive 154 acre estate is a private guest cottage with 4 bay garage below, a large swimming pond, equipment storage barn and extensive trails. An authentic Cape without antique home worries!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

159 Howard Road New London NH 03257

New London, NH159 Howard Road

Price$7,500,000

Est. Mortgage: $/month

MLS Number 4917001

  • Residential Single Family
  • Bedrooms 9
  • Square Feet 5,716
  • Construction Existing
  • Bathroom 4

Sought after, very special Lake Sunapee property, set on 8.9 +/- private acres with 412.5 feet of west facing shoreline. Enjoy your summer days on one of the finest sandy beaches, with sandy bottom swimming for all ages. Boaters in the family will love the expansive dock that has room for multiple boats. Take in the panoramic views, including both Herrick Cove lighthouse and Loon Island lighthouse. Property includes a beach house with changing rooms and ample space for equipment and beach toys. The stately 8- bedroom main house is set up off the water, overlooking the lake and beach. It features beautiful hardwood floors, 4 wood burning fireplaces, spacious walk-in pantry, a game room with views from your windows seats and so much more. Spend Summer evenings dining on the large screened porch as you watch the magnificent sunset, then proceed back down to the water for a swim and campfire on the beach. Plenty of room for guests including a quaint guest house just steps away boasts its own screen porch. The carriage house offers parking for cars and a golf cart, a shop, and game-room and office space upstairs. The playhouse offers an additional retreat. Don't miss out on this rare opportunity on beautiful Lake Sunapee!

Listed by Jessica Dolan and Anthony Dolan of Dolan Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

353 Crystal Lake Road Enfield NH 03748

Enfield, NH353 Crystal Lake Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 4915572

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Square Feet 3,524
  • Bedrooms 3

Don't let this truly impressive 1.65 acre Crystal Lake family compound with space for everyone get away! The first floor of the main house has 3 bedrooms, two full bathrooms and an open concept living space with custom cabinetry and an immense island with room for everyone that spills out to an expansive deck with a hot tub and the most captivating lake views and sunrises. Downstairs there is plenty of storage, a one car garage and a permitted one bedroom apartment with a large three season room perfect for relaxing with a book and enjoying the amazing views. Adjacent to the impressive main house, there is also a 632 sq ft guest space/home office with a bathroom and kitchenette. Possibilities abound in the massive space above the recently constructed 4 bay garage with its own electrical service and generator: gameroom, bunkroom, guest house- let your imagination run wild! If you are in the trades or would like to homestead, there are ample outbuildings perfect for woodworking, gardening tools, or keeping animals. All of this with 75 feet of frontage on pristine Crystal Lake with powered storage shed, two 24 foot docks and a boat launch. You will not find another property like this anywhere! It's perfect for your extended family and friends to gather or would also make a fantastic investment property. Conveniently located minutes to Rt 89, Hanover and Lebanon. Showings begin 6/18.

Listed by Heather Cunningham of McIntyre and Company

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1716 Page Hill Road Corinth VT 05040

Corinth, VT1716 Page Hill Road

Price$1,875,000

Est. Mortgage: $/month

MLS Number 4915839

  • Residential Single Family
  • Bathroom 6
  • Construction Existing
  • Bedrooms 6
  • Square Feet 3,992

Page Hill Farm consisting of 114.40 acres of rolling pastures and woodlands, was built in 1816 by Colonel Reuben Page. In 1957 the property was named Pine Plantation and was advertised as a "Halfway House" for male guests needing rest and rehabilitation. The main brick house consists of 3 bedrooms, a living room, dining room, kitchen, and original 3 Rumsford fireplaces. In 2001 a modern extension was added, an ell constructed off the original summer kitchen, consisting of a full bath, two additional bedrooms, an office, and an extensive, cathedral-ceilinged library. The character of the original house was dully preserved. There is a three-bedroom guest house (sold partially furnished), barn with 20 acres of fenced pastures, detached oversized garage (with storage above), and garden shed. The views and grounds are spectacular complete with a swimming pond and miles of trails. End-of-town maintained road offers privacy-thirty minutes to Hanover, NH, and the Upper Valley.

Listed by Daphne Lowe and Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

405 Cross Road Bradford VT 05033

Bradford, VT405 Cross Road

Price$295,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4908448

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

Style and light. Wonderfullly intimate home sweet home with a completely finished, detached barn apartment just 25 minutes to Dartmouth College and Hanover. Rent out the barn apt with a 2nd kitchen, living/dining, full bathroom and a studio/sleeping room upstairs. Set on both sides of Cross Road, enjoy the bright, chic spaces with a wall of south facing glass living room, durable hardwood maple kitchen floor, skylit den currently used as a bedroom and a large bathroom and laundry room on main. Upstairs two six foot or so ceiling bedrooms with a sprawling master; potential to blow open the 2nd floor ceilings for added ceiling height. The barn studio, rented consistently to traveling nurses, Dartmouth employees and students currently for $1,500 a month has a high vaulted 2nd floor bedroom stuccoed ceiling. House features a spacious mudroom and a new presssure treated front steps deck over perennial garden, a 2nd garden in the back yard and a couple of sheds. A narrow meadow across the street is yours too for micro farming, goat, pigs or sheep with such personality goats next door. Throw in uber fast fiber optic nternet so you can telecommute. With almost nothing on the market under the $400k mark, here are a house and accessory income producting stand alone apartment to offset your carrying costs for under $300k. A must see for intimate charm and solid intrinsics.

Listed by Clayton-Paul Cormier Jr of Maple Sweet Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

9 Bridge Street Windsor VT 05089

Windsor, VT9 Bridge Street

Price$219,000

Est. Mortgage: $/month

MLS Number 4907749

  • Residential Single Family
  • Bathroom 2
  • Square Feet 1,538
  • Bedrooms 3
  • Construction Existing

Wow, what an opportunity this is! Two charming homes. The Big house, has a one car garage, covered entryway that has been modified for easy access. The three season front porch is just asking for you to sit and watch the traffic. Hardwood floors and built-ins, spacious kitchen and first floor laundry make for a great place to start a new chapter. A separate driveway provides access to the guest house. Enter through a sun filled three season porch and mudroom which leads into the kitchen. This home also has three bedrooms, a full bath, dining area, and living room! The lot is level with great opportunities for flower gardens, produce beds, or fencing off for the safety and security of your loved ones as they play.

Listed by Chelsea Bevis of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

154 Garnet Hill Road Sunapee NH 03782

Sunapee, NH154 Garnet Hill Road

Price$5,995,000

Est. Mortgage: $/month

Pending

MLS Number 4904906

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 4,873

Garnet Hill is one of the most sought after locations on Lake Sunapee. This waterfront compound is located on 2.1 acres with 220' prime shoreline featuring a level point of land. The 4873 sq.ft. 4+ bedroom main house offers a great room, chef's kitchen and family living spaces that transition to a wide open deck and lush sweeping lawn at the waterfront. All ages will love the sandy beach and sandy bottom swimming. The boaters will appreciate two deep water docks flanking either side of the property. In addition to the spacious gathering rooms, the main house offers 3 separate dens ideal for accommodating "work from home" options for various family members. A top floor family room with a private roof deck provides an ideal retreat. The adjacent 1361 sq.ft. guest house includes an upscale kitchen and spacious living options. There are 2 bedrooms up and a spectacular bunk room down ready to pile in the kids, their cousins and friends for any given weekend. Across the courtyard a large heated barn/garage provides spaces for 4+ vehicles down and family recreation and exercise space up. Wake up to the loons call and mist rising. Plan an early walk around the 1.5 mile Garnet Hill loop. Mirror glass water calls to water skiers and rowers alike. Explore the 11 islands on the Lake - perhaps Bubbas for lunch -it's 7 miles by water. The bustle of Sunapee Harbor is a quick bike ride, walk, paddle board or ride from Garnet Hill. Available for Summer 2022 Occupancy!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

541 & 523 Ely Road Thetford VT 05045

Thetford, VT541 & 523 Ely Road

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4900904

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 7,280

Welcome to Camp Ely, an expansive and whimsical estate perched atop a bluff with views of the wide, meandering Connecticut River. From the original bricks of a cape built in 1818 to an exquisitely designed treehouse nestled among an oak tree with its own acorn nook, this estate has been created with purpose, integrity, and charm. Every design element inspires feelings of comfort and belonging while linking to traditional uses of the land. Take part in a farming past and graze animals in the pasture. Have tea with a friend in the perennial gardens. Invite family into your guest house and make dinner from your vegetable garden. Let the bright and spacious studio space inspire your creative juices to flow steady and constant like the river below. This estate is so much more than a collection of buildings. This estate is an idea. It's an idea of what it means to be at home, to feel like you live in a place that represents you. Let this spacious Vermont Country estate - with all its fundamental elements - be the kernel from which your personal story can grow.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

11 Summer Hill Street Springfield VT 05156

MLS Number 4899122

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

Restore this mansion! 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. The home will need renovating to revive it to grandeur yet appears to be in good condition.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

249 Bragg Hill Norwich VT 05055

Norwich, VT249 Bragg Hill

Price$8,000,000

Est. Mortgage: $/month

MLS Number 4883128

  • Residential Single Family
  • Bathroom 9
  • Square Feet 9,621
  • Construction Existing
  • Bedrooms 6

Huge views, big land, near everything: Hard to imagine that a nearly 200 acre hilltop estate is within walking distance of the village of Norwich. With the scale, sweeping views to the White Mountains, complete privacy and presence of one of the great Vermont country properties, Highlander is just over a mile to Dan & Whit's and the green. The home and barns are built on the site of an old hilltop farm with massive sugar maples, stone walls, hayfields, managed woodlands, and ponds for swimming and wildlife. The home is elegant and comfortable with an indoor/outdoor flow. Relax and take in the views on the patios and porches or supper in the summer room, which opens out to the pool. At the heart of the house is the capacious, recently renovated, kitchen. Extensive perennial gardens unfold throughout the summer, & an edible landscape yields apples, pears, peaches & berries. An active, outdoorsy family shaped the character of Highlander. Many sets were played on the tennis court and active equestrians grew from ponies to top-flight competitors in the roomy 6 stall stable and on the trails. Kids learned hard work bringing in the hay. The swimming pond converts to pond hockey in the winter, & the other 3 ponds host diverse wildlife all year round. The family hosted an annual cider pressing, skied on the trails & raced on sleds down the long meadows. 2 bedroom apartment over 4 bay equipment barn. Easy access to AT trail.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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
  • Bathroom 6
  • Square Feet 7,619
  • Construction Existing
  • Bedrooms 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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

295 Route 106 Reading VT 05062

Reading, VT295 Route 106

Price$599,000

Est. Mortgage: $/month

MLS Number 4857620

  • Residential Single Family
  • Construction Existing
  • Bedrooms 8
  • Square Feet 2,690
  • Bathroom 6

A classic Vermont style home, with a detached fully heated 3 level, 3 bedroom barn! The well conceived multi-bedroom floor plan comfortably accommodates numerous visiting friends and family members or alternatively can provide an easily managed living space for a small family of several people! The principal rooms are gracious in size and beautifully detailed. The 13.49 acres of useful land present opportunities for recreation, keeping animals or growing crops. A wide and beautiful section of the North Branch of the Black River borders an edge of the property! For many years, the current owners ran the highly visible property as a bed and breakfast. On the ground floor of the residence is a sun room with vaulted ceiling, a large living room with propane fired cast iron stove, a bright kitchen with great appliances, a formal dining room, a primary bedroom with ensuite bath, and a large family room with dramatic windows and a wood burning stove. On the second floor are 4 generously sized bedrooms and 2 baths! The detached fully heated and insulated 40' by 24' barn is a wonderful compliment to the residence! On the ground floor, 3 garage doors open to provide parking or extraordinary workshop space. On the second floor are 3 bedrooms with each having its own bath! On the 3rd floor is a 23' long office/studio with endless possibilities! A property well located for skiing, access to equestrian South Woodstock, or the well known shopping and dining amenities of Woodstock Village!

Listed by John Wetmore of William Raveis Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity

Copyright 2022 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 1, 2022.