Previous Previous ImageNext Next Image
Slideshow Divider

Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

Whitingham VT Real Estate

Whitingham is a town located in the Windham County of southern Vermont. Though small, Whtingham has a vibrant community that embraces the town's heritage and charm. Whitingham’s village center is registered as Whitingham Village of Historic District and is listed on the National Register of Historic Places. Many come to Whitingham throughout all 4 seasons to enjoy the beautiful, scenic views including those found on Lake Whitingham. 

Search the latest real estate in Whitingham, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ‚ÄčRegister to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

For more information, any questions you may have & to schedule a show, please feel free to give us a call or contact us online.

267 Academy Road Whitingham VT 05342

Whitingham, VT267 Academy Road

Price$699,999The price has recently decreased

Est. Mortgage: $/month

MLS Number 4970085

  • Residential Single Family
  • Village Jacksonville Village
  • Construction Existing
  • Bedrooms 12
  • Bathroom 5

Located on the VAST Trail network this property might be used as an Air B&B, possible Bed & Breakfast, Multi-Generation, Multi-Family, Lecture, Workshop , Club or Retreat Center on 30+/- acre. It has a large living room room and dining area, kitchen, 12 bedrooms. 5 Bathrooms, various sitting areas, lofts, multi-use room and full lower level walk-out (1BR private apartment already exits, along with a craft room, family room, utility room w/ full sprinkler system and work shop). The whole building can be nicely divided into 3 different living areas if desired. Chicken coop, garden area, woodshed. beautiful covered porches, 2 car garage, walking trails and a pond. Easy walk to the village center. This would make a wonderful full time home, vacation home, Yoga, Snow Mobile Club, Meditation or Family retreat center. Must be seen to be believed 7,400 sq. ft. located at the end of a dead end road close to golf courses, slopes and lakes!!!

Listed by Janet Boyd of Boyd Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

3358 Vt Route 100 Whitingham VT 05342

Whitingham, VT3358 Vt Route 100

Price$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4980389

  • Residential Single Family
  • Village Jacksonville Village
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5

Stunningly renovated 1850s farmhouse boasting expansive space and versatility. 5 beds, 5 baths, additional den on lower level with ¾ bath and loft of its own! The kitchen and dining areas are perfect for hosting guests or cherished family gatherings. Open space, good flow, work stations, coffee bar, buffet, walk-in pantry, complete with extra refrigerator. Professional grade appliances, built-in ice machine, chefs gas stove with pot filler. This is an entertainer's dream! Elegance meets functionality with a formal living room and gorgeous wood floors grace much of the house. Uniquely designed multi-use spaces encompass heated and partially finished garages & workshop areas w/exposed beams & high ceilings that seamlessly convert into excellent recreational zones. A formal entry for guests,mudroom for practicality. Back deck with pergola & privacy wall covering an inviting 6-person hot tub. Overlook the field, pond, and Christmas Tree Farm while you soak or sip your way into relaxation. Front porch wraps around and is equipped w/ built-in Bluetooth speakers for seamless entertainment inside and out. The grounds are an oasis, showcasing pond with a little dock, gazebo, and a covered pavilion with a fire pit area. Notably, the property boasts hundreds of evergreen trees lining the back of the 3.5 acres. Sell them, cut your own or just enjoy for privacy. Experience the epitome of fine country living in this magnificent property, where historic allure meets modern comforts.

Listed by Jacki Murano of Southern Vermont Realty Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1084 Cyrus Road Whitingham VT 05361

Whitingham, VT1084 Cyrus Road

Price$625,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4960302

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,905

Carefully constructed by the renowned Southern Vermont builder Howard Dix, this log home should be at the top of your list. Welcome the change of seasons in comfort here with radiant, efficient oil heat on two levels of the home and an automatic whole house generator. It's just a short drive to stores and restaurants in the nearby villages of Jacksonville and Wilmington. Skiers and riders will love the easy drive (30 short minutes) to the Mount Snow base lodge while you can access the VAST trail one mile away. All this from a private, pastoral spot. Enter the convenient mudroom opening into the kitchen with a unique live edge wooden counter, new range/dishwasher and stainless refrigerator/freezer. The dramatic great room enjoys light pouring in from the skylights and large windows highlight the cathedral ceiling, the expansive living and dining areas and the shining hardwood floors. Included on the main level are the primary bedroom with full bath and a hallway half- bath with laundry/new washing machine. The impressive staircase leads to a loft area, full bath and two charming bedrooms. The walk-out lower level was updated in 2021 to include an in-house gym/gathering space with light pine paneling and a double door entry to the outside. And the unfinished remainder of the lower level includes a utility room, half-bath and plenty of storage space. Other improvements include a radon mitigation system, all new skylights, a new well pressure tank and recent well fracking.

Listed by Meg Streeter of Meg Streeter Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

371 Butler Brook Road Whitingham VT 05342

Whitingham, VT371 Butler Brook Road

Price$559,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4973209

  • Residential Single Family
  • Village Jacksonville Village
  • Construction Existing
  • Bedrooms 5
  • Bathroom 3

This spacious 5-bedroom colonial sits in a serene country setting with a babbling brook on the land. Best yet, it is situated on a town-maintained, paved, dead-end road. The house has been well kept by the current owner with improvements such as a new roof, refreshed paint, new well pump etc. The home has an in-law suite or apartment for friends, Airbnb or simply for use as an extension of the house to make a 5 bedroom single family residence. The entrance allows for separate access if you would like to utilize the in-law suite. The spacious living room of the main home boasts a gorgeous fieldstone fireplace, hardwood floors and plenty of natural light. Spacious, roomy deck on the back overlooking the nicely manicured lawn which leads to the small brook. There is a large, heated, attached garage to park out of the elements. Brand new oil tank recently installed. This is a beautiful home in a great location, offering peace and quiet. Yet, it is less then 5 minutes to the village of Jacksonville for stores, a restaurant and a bakery. Another 20 minutes and you can reach Mount Snow or Lake Whitingham.

Listed by Monica Sumner of BHG Masiello Brattleboro

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

31 Brook Street Whitingham VT 05361

Whitingham, VT31 Brook Street

Price$350,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4984249

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,783

Best and Final by 5pm 2/13/24. Experience the joy of living in this warm and enchanting custom-built 4-bedroom, 1 1/2 bathroom Peter Vandertuin home nestled on just over 4 acres in the picturesque town of Whitingham, Vermont! Perched on a gentle rolling hill, this home boasts a spacious deck, 1 car garage, and a private yard, perfect for relaxation, recreation, and outdoor gatherings. Known for its outstanding efficiency, abundant natural light streaming through large windows, charming exposed beams and natural wood, this home promises a delightful living experience. Wood stove, open floor plan, large kitchen/dining room with double door pantry, built in buffet and breakfast bar. First floor laundry and mudroom and wonderful enclosed porch with passive solar ( and excellent view! ) making it enjoyable to use most days of the year. Embrace the beauty of the home's surroundings, with convenient access to three lakes-one just around the bend, a welcoming town park, boat launch on beautiful Harriman Reservoir , and close to an array of snowmobiling and hiking trails for endless outdoor adventures! Meticulously cared for by one loving family since it was built, it features a relatively new heating system and roof, ensuring years of comfort and happiness. This home is ready to fill your days with warmth, laughter, and cherished memories!

Listed by Melissa Ellis of Southern Vermont Realty Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

962 Chapel Hill Road Whitingham VT 05361

Whitingham, VT962 Chapel Hill Road

Price$339,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 4986148

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,963

Unique tetradecagon-shaped home boasts character & distinction in excellent condition setting itself apart from the ordinary offering. Situated on a 2 acre lot w/ 3 spacious bedrooms & 2 full baths- this residence offers comfort, relaxation & style in equal measure. Inside to the mudroom w/full laundry, seating & room for your gear. Continue further to discover inviting open plans on both levels-lofty ceilings, expansive windows, natural light & views of wooded and landscaped surroundings. Renovated kitchen-a culinary haven, maple cabinets, gas cooktop, double ovens and farmhouse sink! The kitchen is open to the lounge- perfect for dining & entertaining w/access to the deck and yard. Main floor also has a bedroom and bath. The 2nd floor hosts a great room perfect for large gatherings or as multipurpose space. 2 more beds & full bath are also on this level. Warmth and comfort abound with propane hot water baseboard and two wood stoves, while the generator transfer switch provides peace of mind. Nestled on 2 acres of land, offering a perfect blend of open yard space and wooded tranquility. Outdoor activities year-round w/access ( at the far back of the lot) to a class 4 town road, ideal for hiking, cross-country skiing, snowshoeing, and accessing the snowmobile trails. 2-car insulated garage, complete with a second-floor bonus space. Excellent maintenance history, two-year-old roof on both the home & garage, this property is as practical and fit as it is enchanting.

Listed by Jacki Murano of Southern Vermont Realty Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

188 Ginny Morse Road Whitingham VT 05361

Whitingham, VT188 Ginny Morse Road

Price$299,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4971867

  • Land
  • Acreage 40
  • Utilities None
  • PricePerSqFt 7475
  • Zoning whitingham

Serene 40-acre Haven w/Panoramic Views! Escape to your own paradise in the heart of the Green Mountains. This exceptional property combines privacy, accessibility, and breathtaking natural beauty. Situated just off a paved road w/gated entrance offering both convenience and exclusivity. Bordering farmland protected by the Vermont Land Trust to the west, ensuring forever-preserved pastoral views and mountain vistas w/captivating sunsets. To the north, ski enthusiasts will delight in gazing upon Mount Snow Ski Trails. To the east, w/clearing, potential to capture views of Mount Monadnock in New Hampshire. Two meticulously planned house sites- Soil testing indicates that the main house site can accommodate a 4-bedroom residence, while a private guest house location offers the potential for a 3-bedroom retreat. Alternatively, you can capitalize on the town's 3-acre zoning rules, allowing for potential subdivision according to Zoning Regulations. The natural beauty of the land will captivate you with charming stonewalls, hiking trails, fields, and forests. For winter enthusiasts, direct access to snowmobile trails, strategically situated away from the house to ensure tranquility. Proximity to lakes, skiing, state & national forests, conveniently located just 2.25 hrs to Boston, 1.5 hrs to Albany, 3.75 hours to NYC, & only 30 min to the Berkshires. A legacy property to pass down through generations or an investment opportunity, this land provides the canvas for your dreams

Listed by Jacki Murano of Southern Vermont Realty Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1148 Chapel Hill Road Whitingham VT 05361

Whitingham, VT1148 Chapel Hill Road

Price$249,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4966829

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,152

Looking for a country get-away, situated on a peaceful, one-acre lot close to Mount Snow, Lake Raponda and all that downtown Wilmington has to offer? Look no further. The house features a bright open concept with hardwood floors and exposed beams throughout. The bedrooms and bathrooms are conveniently located on each end of the house allowing for plenty of privacy. Kick back in the living area around a wood & coal stove encased in stone after a long day on the slopes. The large loft is a true bonus: overlooking the living area, it would make a great home office, den or extra room for sleeping. Take your morning coffee outside to the covered porch along the front of the house and listen to the birds while admiring the flower garden. As ideal as this location is as a second home, it would also be perfect as a primary residence. This property has been well cared for and is ready for someone to bring their personal touch. Delayed showings until Tuesday 8/29/23.

Listed by Kassie Rubico of Berkley & Veller Greenwood Country

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

739 Chapel Hill Road Whitingham VT 05361

Whitingham, VT739 Chapel Hill Road

Price$239,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4984621

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,256

This home in Chapel Hill offers 2,5 levels on 2 Acres, Decks overlooking a nice flowing mountain stream. 2 bedrooms and a loft. Easy to heat with propane hot air heat and a Vermont Casting wood stove. Open kitchen and dining, vaulted ceiling. full unfinished basement walk out. Gas cooking, Ample parking, drilled well, 1,000 gallon septic tank. Needs refinish

Listed by Mark Yule of Heritage Associates

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

341 Chapel Hill Road Whitingham VT 05361

Whitingham, VT341 Chapel Hill Road

Price$159,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4982824

  • Land
  • Acreage 10.93
  • Area Rural
  • Utilities None
  • PricePerSqFt 14547.12

Pretty lot with 10.93 acres. Cleared spot toward the upper area that has a large 5th Wheel RV. This summer you can start enjoying your own private campground. Forget about paying high campground fees! There is a large storage shed to park the camper in during the winter months if you desire. A small old camp is also on the property plus another little building. Currently there is no septic, well or electric. A blank canvas for the dreamer in you. Come to Vermont where the air is fresh, and the 4 seasons offer so much.

Listed by Monica Sumner of BHG Masiello Brattleboro

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Lot 2 Kentfield Road Whitingham VT 05361

Whitingham, VTLot 2 Kentfield Road

Price$126,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4973528

  • Land
  • Acreage 14.54
  • PricePerSqFt 8665.75
  • Zoning Rural Res

This beautiful 14+ acre lot located in the heart of the Green Mountains just a very short drive to Lake Sadawga and Harriman Reservoir where you can go motor boating, kayaking, swimming, or fishing. The VAST snowmobile trail crosses Kentfield Rd in two places. The land is mostly wooded area with some open meadow. It is situated on a paved public road where you won't have to worry about mud season driving. There is high speed internet available and the utilities are at the front of the lot at the road. Town Hill Park is only 2 miles away making it an easy to enjoy the playground, picnic area and ball field. You're just a short drive to skiing at Mount Snow and Wilmington center for shopping and restaurants. With thousands of acres Hydro land, National Forest, and Atherton Meadows close by, there are endless opportunities for camping, hunting, fishing and hiking. Easy commute to Brattleboro and I-91.

Listed by Donald Koelsch of Deerfield Valley Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4 Murdock Lane Whitingham VT 05361

Whitingham, VT4 Murdock Lane

Price$44,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 4867161

  • Land
  • Acreage 5.66
  • Utilities None
  • PricePerSqFt 7932.86
  • Zoning Whitingham

Build your dream home on this surveyed 5.66 acre lot with deeded rights to Ryder Pond! A great location for primary or vacation living, situated between down town Wilmington VT and Greenfield MA with easy access to scenic Rt 100. Lakes, ski resorts and out door recreation abound with Mount Snow Resort, Lake Whitingham, Lake Sadawga, Lake Raponda and Molly Stark State Park all close by. To stick closer to home, access the snowmobile trails right from your property or take a walk across the street to fish or kayak in Ryder Pond. Accessible from Murdock Lane or Rt 100, power at street. Roughed in driveway. Perk test results and design for 4 bedroom waste water system included in sale.

Listed by Jacki Murano of Southern Vermont Realty Group

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.9% last updated on 2024-02-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 February 27, 2024 10:23 PM EST

 

100 Acres in Burke

5 BR, Near Jay Peak, $1,999,000 Details

1852 Classic Farmhouse

6 BR, 204 +/- AC $1,995,000 Details

 

127 Acres, Barn @ Okemo

5BR Renovated Rustic $9,995,595 Details