27 Homes For Sale in Whitingham, VT

Sort by:
$249,000Est. Payment
4 Beds | 4 Baths | 2,350 Sqft

290 Vt Rte 112, Whitingham, VT 05342

House For Sale

4+ bed/4 bath Jacksonville Village Farmhouse on 9 acres! Built in 1840 this home has history and character. For almost 20 years until the late 90's the attached barn was home to The Jacksonville Tavern the first (and only!) bar in town. Many of the original fixtures, including the bar are still in place. The upstairs of the Tavern, originally restaurant seating is a great place to hold a function or could make the ultimate rec room above the bar. The home is in the typical style of the period, a center staircase from the front entry, living room to the right and formal dining room with fireplace to the left. There is a full bath with claw foot tub and main floor bedroom. Upstairs there are 3 additional bedrooms, bath, tons of storage and the center hall is plenty large enough to be an office or den. High speed internet in place here. Located on scenic Rt 112 only 20 minutes north of Greenfield MA the drive from the south takes you through large farms and apple orchards and past road side stands with fresh farm produce. 15-20 minutes north are the shops and restaurants of Wilmington, lakes and Mount Snow skiing. Jacksonville Village is a quint and picturesque has it's own general store, wine and cheese shop, artists studios and Honora Winery. The land has open field, stone walls, wooded areas and is bordered on one side by a year round brook. The house is ready for some TLC but the floor plan, acreage, Tavern, fireplaces and wood floors are certainly worth the sweat equity.

$689,000Est. Payment
12 Beds | 5 Baths | 7,400 Sqft

267 Academy Road, Whitingham, VT 05342

House For Sale

Multi-Generation, Multi-Family or Retreat Center on 33+/- acres. 12 bedrooms. 5 Bathrooms, various sitting areas, lofts, meditation room. The whole building can be nicely divided into 3 different living areas if desired. Christmas Tree lot, chicken coop and woodshed. nice porches, 2 car garage, pond. Close to the VAST Trail and the village center. This would make a wonderful full time or vacation home or Yoga, Meditation or Family retreat center. Must be seen to be believed located at the end of a dead end road create your own run-a-way!!!

$349,000Est. Payment
3 Beds | 2 Baths | 1,800 Sqft

155 Houghton Road, Whitingham, VT 05361

House For Sale

Welcome to Hemlock Grove! A wonderful haven for animal and human alike. This Log Home is a comfortable spot on a knoll. It's to be enjoyed all year round. The inviting sounds of the birds fluttering and chirping will invite you to the generous covered porch and deck. The sunshine pours into the home from all directions. The sunlit open spaces inside invite one to gaze out almost any window to take in the flowers, trees and changing seasons. Low maintenance with perennial gardens, there is virtually no lawn to worry about. Come winter, break your snow mobiles out of your attached shed and hit the VAST trails right from your home. This mostly wooded property is waiting for a family tree house, sledding, snow shoeing and back country skiing! The wood stove will warm you up upon your return. Step inside this Log Home and you will not want to leave the peace and tranquility!

$225,000Est. Payment
3 Beds | 2 Baths | 1,716 Sqft

5825 Vt Rt 100, Whitingham, VT 05361

House For Sale

This easy keeper is low maintenance and convenient with a great floor plan! Situated on 2.2 acres ( off of scenic Route 100) set back from the road there is plenty of open sunny yard for gardens or play and a still enough wooded space to feel tucked away. The full walk out basement is finished with 2 bonus rooms, radiant heat, wood stove, high ceilings and mudroom with built-ins. A 3rd bathroom space is available on this level for future expansion and there is plenty of clean, dry storage. The main floor consists of 3 bedrooms, 2 baths including the primary en suite. Open kitchen, dining, living with large windows and lots of light. Additional storage shed and a workshop with electricity on the property for projects, storage, pets or hobbies. Perfect starter, retirement or an affordable country retreat. Just minutes to Southern Vermont lakes, snowmobile trails, National Forrest and 25 minutes to ski areas. ***Everyone accessing the property must comply with Covid -19 Vermont State mandates for travel, quarantine and health requirements. This is strictly enforced.

$125,000Est. Payment
1 Bed | 1 Bath | 768 Sqft

20 Gates Pond Road, Whitingham, VT 05342

House For Sale

This cozy 1 bedroom home sits in the village of Jacksonville within walking distance to the Jacksonville General Store, Post Office, Winery & Restaurant, the local hairstylist or the park in town. Totally renovated in 2007 including new wiring with 200 AMP service, all new pex plumbing, windows and the list goes on and on. Custom kitchen with maple butcher block countertops, lots of natural woodwork and yellow pine flooring throughout. New high efficiency hot water heater. Great internet service. Municipal sewer, etc. Sit outside in the nice yard area overlooking the river and listen to the soothing sounds of the water. Just a short drive to Mount Snow ski area, Wilmington village, & I-91 in Greenfield.

$169,900Est. Payment
3 Beds | 2 Baths | 1,122 Sqft

7073 Vt Rt 100 Road, Whitingham, VT 05361

House For Sale

Lovingly restored 3 bedroom, 1 1/2 bath home. Large master on the first floor. New kitchen with all new stainless steel appliances, beautiful upscale cabinets, and counter tops with lots of storage. Beautiful decorative window in LR with matching front door. Huge new deck off of the LR and kitchen. New bathrooms are the envy of any DIY'er. Tastefully furnished and decorated. Lake Whitingham is just down the road for summer enjoyment. Ski at Mt Snow Ski Resort, and golf at both Haystack and Mt Snow Golf Courses not to mention enjoy fun times at local breweries, great restaurants all while taking in the clean Vermont air! Enjoy this get away from the hustle and bustle of the big cities.

$450,000Est. Payment
3 Beds | 3 Baths | 1,600 Sqft

134 Sadawga Lake Road, Whitingham, VT 05361

House For Sale

600 feet of owned waterfront with this beautiful new construction home on Sadawga Lake just a short drive from country villages, other lakes, and the Mount Snow ski resort. This amazing four season property has 180 degree views out over the water and green mountains beyond. Enjoy tremendous fishing or boating with a privately owned boat dock, or ice fishing and direct VAST snowmobile access in the wintertime. The spacious home has great features including 3 full suites with tiled baths, custom natural woodwork, open concept kitchen and living areas, breakfast bar and custom cabinets, stone hearth with wood burning fireplace, large mudroom entry, electronic whole home control for lighting and fans, and breathtaking views from every room. There is tremendous additional potential in the large walkout basement which could accommodate an additional suite and living space and is already plumbed for a bath. A true opportunity to have a special spot in Vermont with the best combination of year round use you can find.

$309,000Est. Payment
4 Beds | 2 Baths | 2,412 Sqft

123 Sadawga Lake Road, Whitingham, VT 05361

House For Sale

Excellent LOCATION for so many reasons! Work from home in your office above the garage with dedicated phone and internet. Launch your kayaks in the back yard stream and float on into Lake Sadawga! Beautiful views of local mountains and Lake Sadawga! Trout pond! Fruit trees! Lovely Farmhouse with Large mudroom entry into the Large Kitchen with dining. A great family gathering place! Front porch and bedrooms with views to the Lake. This home is in great shape and ready for the next family to enjoy. The HUGE heated garage with heated space above adds to the Enjoy Your Property with room for ALL the toys! Boats, RV space (in and outside), bikes, personal crafts, snowmobiles etc. Direct VAST access!!!! More garage space around back under the home AND shed space! With water to the shed, bring your horses and other animals! Partially finished attic ALSO! Bring the huge family and all of your friends to your ski and lake home in Vermont!

$229,000Est. Payment
3 Beds | 1 Bath | 1,360 Sqft

664 Wilmington Cross Road, Whitingham, VT 05361

House For Sale

Enjoy country living in this bright move in condition home sited on nearly 2 acres of land and set off the road for privacy. This home features an open living/dining with a pellet stove perfect for entertaining, 3 bedrooms, a whole house generator, barn, and direct VAST snowmobile trail access. The outside of the home was just painted, and new quartz kitchen counter-tops just installed, so all the work has been done! This location is the perfect Vermont getaway or full-time residence only 10 minutes to Wilmington and close to all the summer/winter recreation the valley has to offer.

$99,000Est. Payment
87.52 Acres

0 Lone Pine Road, Whitingham, VT 05361

Lots Land For Sale

End of the road upland forestland abutting 100's of acres of Power Company land that goes all the way to the reservoir. Telephone electric is there for this large parcel on both sides of the road. Great views possible with some clearing. Current Use for lower annual property taxes. South side of Whitingham near the Mass border. All kinds of recreation and good Vermont stuff is a short drive away!

$525,000Est. Payment
4 Beds | 2 Baths | 2,160 Sqft

193 Tyanoga Road, Whitingham, VT 05361

House For Sale

Lake front property on a quiet 5 acres in Southern VT. Wow! Homes like this come on the market so rarely; don't miss your opportunity! This is a beautiful family retreat with original owners. Grassy yard frontage all along the water front, lends itself to outdoor play all day long. Pull the boat out of the basement double doors and enjoy a day on the water. The home has an over-sized 2 car garage, 4 bedrooms and 2 full baths. A full-length deck with 3 sliding doors allows for indoor/outdoor entertaining and watching the sunrise over the lake. ROW length, road frontage and lake frontage are all approximate.

$115,000Est. Payment
1 Bed | 1 Bath | 1,100 Sqft

7888 Vt Route 100, Whitingham, VT 05361

House For Sale

Watch the seasons change around your own cozy cabin! Perfectly sized one bedroom, one bath home in charming Whitingham is ready for your enjoyment. Located on a quiet country road, this house is perfect as a starter home, vacation home, or investment property. House does need some minor repairs and has been winterized so water and electricity are not currently on. Please do not enter property without permission.

$237,500Est. Payment
111.6 Acres

00 Auger Hole Road, Newfane, VT 05361

Lots Land For Sale

PRIVACY PLUS - 111 acres of total privacy, located in Historic Newfane - 15 mins to Mt Snow Ski and Recreation areas and near the cultural attractions in Brattleboro. Bring your home designs and let this piece of Vermont speak to you. Slight slopes, areas of level land, hilly and steep terrain - good habitat for a variety of wild life. Aged stone walls, meandering brooks, Ancient roads and logging trails for hiking. Listen to nothing but the sound of birds and bees and trickling water from the brook. Convenient Country Living - This Piece of land has a Right of Way, electric, phone and cable lines at the paved road. 20 mins to I-91.

$479,000Est. Payment
5 Beds | 4 Baths | 5,794 Sqft

428 Town Hill Road, Whitingham, VT 05361

House For Sale

Extremely charming large spacious country colonial nestled in the Mountains of Southern Vermont. Just a short 1.5 hour drive to Hartford, Ct. This 5 bedroom colonial has been sitting pretty overlooking Sadagawa Lake for approximately 170 years. This property has worn many hats during its existence in Whitingham Vt. Here is your chance to be a homesteader and get back to the basics. Almost 9 acres with mostly open fields. Great sunlight exposure. Large home suited for lots of family or guests. Beautiful hard wood floors. wonderful fireplaces and stunning views from many of the rooms. Stone patio facing westerly to enjoy those striking sunsets. The barn will come in handy to store the recreational toys. This property is a short distance to Harriman Reservoir. This home will come fully furnished with a few exceptions. Sale will include 2 kayaks and a 16 foot canoe. Owner has done very well with rentals. Over 1000 feet of road frontage. Easy drive to Mount Snow as well. Excellent rental opportunity.

$33,500Est. Payment
10.01 Acres

0 Maple Hill Lane 9938, Whitingham, VT 05361

Lots Land For Sale

Pleasant country location, this 10 acre parcel is a great spot for your new home. Soils test from 2006 is available for you to review that identified potential building sites. This surveyed lot is well worth checking out.

$348,995Est. Payment
3 Beds | 4 Baths | 2,200 Sqft

1084 Cyrus Road, Whitingham, VT 05361

House For Sale

Looking for peacefulness, serenity and the perfect idyllic home in Vermont? Come take a look at this upscale constructed log home with plenty of space to kick back, relax or bring the good times here. Sprawling open concept with a mudroom entry leading into a large kitchen. Excellent design for cooking and entertaining. Keg cooler and an over-sized refrigerator/freezer. Extra large island with seating. Spacious living room with a wood panel cathedral ceiling and lots of skylights. First floor master ensuite. Radiant heat on the first floor and the basement. Upstairs there are two bedrooms, a full bath with radiant heat and a loft. Walk out basement with buderus furnace plus a water softener system. Generator included. An efficient outdoor wood pellet furnace for heating options. Covered full front porch overlooking the mountains. Very well maintained home. This home is a 5 star energy rated. A must see!

$565,000Est. Payment
5 Beds | 5 Baths | 4,000 Sqft

2579 Collins Road, Whitingham, VT 05342

House For Sale

Relax with all your family and friends, maybe even all at once. Spread out or get together, there are 5 lovely bedrooms, including a main bedroom with fireplace wing/suite, 5 bathrooms, several sitting areas useful as additional living, reading, or resting, & a 17x19 recreation/game room. Soothing peaceful inviting colors are used throughout. The open concept kitchen with island & double ovens is light & bright, and relatively connected to the breakfast area, living room, and dining room. The terrific view of the fields and mountains just streams in across the large deck into those areas. If your relaxing includes animals &/or hobbies, there are 3 garages and a huge historic post & beam barn. All sorts of Vermont seasonal recreation is only a few minutes away. Great price on a super family place that could satisfy all the generations in your circle. Entire contents and equipment included.

version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >