20

Whitingham, VT Homes for Sale

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  • /44

    $400,000

    • 2 Beds
    • 3 Baths
    • 1,696 Sq Ft

    399 Laurel Lake Rd, Jacksonville, VT 05342

    Turnkey 2-Bedroom Home with Lake Access & Extra Garage – Laurel Lake Living! Welcome to this meticulously maintained 2-bedroom, 3-bathroom home, offering turnkey convenience and year-round comfort just steps from beautiful Laurel Lake. Boasting an open and inviting floor plan, this home features a spacious living area with a cozy pellet stove for energy-efficient warmth, perfect for chilly

    Claire Renaud Berkley & Veller Greenwood Country

    399 Laurel Lake Rd, Jacksonville, VT 05342
  • /34

    $699,000

    • 3 Beds
    • 4 Baths
    • 3,596 Sq Ft

    233 Poverty Row, Whitingham, VT 05361

    What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful

    Adam Palmiter Berkley & Veller Greenwood/Dover

    233 Poverty Row, Whitingham, VT 05361
  • /45

    $749,000

    • 2 Beds
    • 1.5 Baths
    • 1,600 Sq Ft

    679 Burrington Hill Rd, Whitingham, VT 05361

    Welcome to a truly one-of-a kind property-a modern Barndominium thoughtfully reimagined from its original barn like beginnings into a stunning architectural masterpiece. Designed by an award-winning architect and brought to life by a meticulous local builder, this home perfectly balances rustic charm with high-end sophistication. Expansive windows throughout invite in the natural beauty of the

    Monica Sumner BHG Masiello Brattleboro

    679 Burrington Hill Rd, Whitingham, VT 05361
  • /55

    $589,000

    • 3 Beds
    • 2.5 Baths
    • 2,438 Sq Ft

    456 Poverty Row, Whitingham, VT 05361

    Lovely country setting on Poverty Row, a road name steeped in history, this builder’s home showcases quality craftsmanship and thoughtful design throughout. Set on 2.66 beautifully manicured acres with wild blueberry bushes and apple trees. Located on a paved public road, this property is less than five minutes from Lake Sadawga and Harriman Reservoir—perfect for boating, kayaking, and swimming.

    Erica Reynolds Southern Vermont Realty Group

    456 Poverty Row, Whitingham, VT 05361
  • /12

    $469,000 New Construction

    • 4 Beds
    • 2 Baths

    442 Mcmillan Rd, Whitingham, VT 05342

    New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three

    Mark Yule BHG Masiello Brattleboro

    442 Mcmillan Rd, Whitingham, VT 05342
  • /38

    $472,500 Sold Jul 08, 2025

    • 1,750 Sq Ft
    • $270/SF
    • 54 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1975

    1452 Maple Hill Ln, Whitingham, VT 05361

    Discover the perfect blend of rustic charm and modern updates in this beautiful two-bedroom, two-and-a-half-bath log home tucked away in a peaceful, private setting. Whether you're looking for a serene full-time residence, a weekend getaway, or an investment opportunity, this home offers comfort, character, and convenience. Inside, you’ll find a spacious layout with warm wood accents and

    Claire Renaud Berkley & Veller Greenwood Country

    1452 Maple Hill Ln, Whitingham, VT 05361
  • /46

    $449,999 Sold Jun 16, 2025

    • 1,438 Sq Ft
    • $313/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    1448 Cyrus Rd, Whitingham, VT 05361

    Welcome to your perfect escape. This home has been beautifully maintained by the owners for 34 years. It has 3-bedrooms and 2-bathrooms. The homes nestled on a sprawling 15.2 acres complete with private hiking and ATV trails, a tranquil pond just steps from your front door, and breathtaking sunrise views from the porch, along with a large horse barn that has been partially converted into a

    Peggy Winchester ACORN REAL ESTATE GROUP LLC

    1448 Cyrus Rd, Whitingham, VT 05361
  • /54

    $665,000 Sold May 29, 2025

    • 4,881 Sq Ft
    • $136/SF
    • 40 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1840

    201 Vermont 112, Whitingham, VT 05342

    Experience endless enjoyment in this charming 4-bedroom converted winery, where every room promises relaxation & excitement. Nestled amidst serene surroundings, discover hiking trails in the backyard, a picturesque pond inhabited by a beaver, a gazebo and a flowing river with a quaint wooden bridge leading to an expansive parking lot accommodating up to 10 cars.  Indoors, an inviting barn houses

    Steve Goldfarb Deerfield Valley Real Estate

    201 Vermont 112, Whitingham, VT 05342
  • /40

    $540,000 Sold Oct 18, 2024

    • 3,700 Sq Ft
    • $146/SF
    • 129 Days On Market
    • 3 Beds
    • 4 Baths
    • Built 2005

    1084 Cyrus Rd, Whitingham, VT 05361

    Country living meets modern amenities in this well built and meticulously maintained log cabin. Nestled on a hill off a quiet country road, it is the perfect place for rest and respite from the hustle and bustle of city life. The kitchen is a chef's delight, equipped with modern appliances, ample counter space, and plenty of storage. Boasting a generous primary bedroom with ensuite on the first

    Kristen Breeden Southern Vermont Realty Group

    1084 Cyrus Rd, Whitingham, VT 05361
  • /40

    $462,440 Sold Aug 29, 2024

    • 2,435 Sq Ft
    • $190/SF
    • 21 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1970

    152 Town Hill Rd, Whitingham, VT 05361

    Beautifully and privately located on 5 acres near Lake Sadawga, this contemporary home offers 4 bedrooms, 3 bathrooms, an inviting living room with a two-sided wood burning fireplace also open into the adjacent sitting area, a spacious kitchen with island seating, a full hall bath, an extensive deck, a separate wood-beamed dining room and a main level primary bedroom with a large

    Meg Streeter Meg Streeter Real Estate

    152 Town Hill Rd, Whitingham, VT 05361
  • /7

    $499,000

    • Land
    • 30 Acres
    • $16,633 per Acre

    Lot X Tyanoga Rd, Whitingham, VT 05361

    Spectacular opportunity to own a rare waterfront building lot on Lake Sadawga in Southern Vermont. This lot sits on a private dead end corner with southern exposure, private lake frontage including an earthen dam, and easy access along this pristine, natural lake. There is additional frontage along Stimpson Hill Road. The lake offers tremendous fishing, kayaking, canoeing, water sports, and

    Adam Palmiter Berkley & Veller Greenwood/Dover

    Lot X Tyanoga Rd, Whitingham, VT 05361
  • /50

    $339,000

    • 7 Beds
    • 4 Baths
    • 3,000 Sq Ft

    89 Gates Pond Rd, Whitingham, VT 05342

    This rare multi-family home presents a unique investment opportunity, featuring four well-designed units. Nestled in the charming town of Jacksonville you're just 23 minutes from the exhilarating slopes of Mount Snow ski resort. The property offers two one-bedroom units on the first floor, alongside a spacious two-bedroom unit and a generous three-bedroom unit on the second floor. Enjoy the large

    Monique White Deerfield Valley Real Estate

    89 Gates Pond Rd, Whitingham, VT 05342
  • /17

    $39,900

    • Land
    • 6 Acres
    • $7,049 per Acre

    4 Murdock Ln, Whitingham, VT 05361

    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

    Jacki Murano Southern Vermont Realty Group

    4 Murdock Ln, Whitingham, VT 05361
  • /49

    $310,000 Sold Jun 20, 2025

    • 1,513 Sq Ft
    • $205/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1893

    6699 Vermont Route 100, Whitingham, VT 05361

    Welcome to this charming historic home that has been lovingly brought back to life by its current owners! Featuring beautifully restored plaster walls, high ceilings, and stunning refinished wide plank flooring. Step inside and you’ll be greeted by a spacious mudroom and cozy sitting area—there’s plenty of room to relax before you move into the bright and inviting living space. The large eat-in

    Michelle O'Neil Deerfield Valley Real Estate

    6699 Vermont Route 100, Whitingham, VT 05361
  • /40

    $280,000 Sold Jun 20, 2025

    • 1,680 Sq Ft
    • $167/SF
    • 268 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1992

    427 Vermont 112, Whitingham, VT 05342

    Discover this turnkey 3-bedroom Cape-style home, charmingly nestled on the edge of the village of Jacksonville. A babbling brook borders the property, flowing gracefully under a quaint bridge. Recently transformed by the current owners, this lovely residence features a new drilled well, new efficient propane furnace, an electric hot water heater, ensuring all major systems are up to date. Enjoy

    Monica Sumner BHG Masiello Brattleboro

    427 Vermont 112, Whitingham, VT 05342
  • /27

    $86,700 Sold Apr 18, 2025

    • 2,428 Sq Ft
    • $36/SF
    • 49 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1840

    1871 Wilmington Cross Rd, Whitingham, VT 05361

    This charming 2,400 sq. ft. Colonial home, dating back to the 1840s, is nestled on 2.1 acres in Whitingham, Vermont. The property is ready for a new owner with a vision to restore it to its original grandeur. The spacious living room showcases the home's historic character, with soaring ceilings and a large fireplace. The kitchen is generously sized, and a screened-in porch at the back of the

    Kim Meeker Southern Vermont Realty Group

    1871 Wilmington Cross Rd, Whitingham, VT 05361
  • /16

    $240,000 Sold Dec 06, 2024

    • 1,652 Sq Ft
    • $145/SF
    • 2 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1935

    1338 Vermont 8a, Whitingham, VT 05342

    Welcome to your new home, a delightful transformation of a historic schoolhouse into a sweet and inviting home! This single-level, 3-bedroom, 1-bath residence is perfect for first-time homebuyers, those looking to downsize, or anyone seeking a peaceful getaway. Nestled on a sprawling 2-acre lot, this property boasts ample sunny space surrounded by lush plantings and vibrant flowering shrubs.

    Karen Hoppe Berkley & Veller Greenwood Country

    1338 Vermont 8a, Whitingham, VT 05342
  • /57

    $240,000 Sold Dec 05, 2024

    • 1,700 Sq Ft
    • $141/SF
    • 18 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1860

    292 Parsons Rd, Jacksonville, VT 05342

    Discover the charm of this 1860 farmhouse set on 17 stunning acres in Jacksonville, VT. Perfect for horses, farming, or creating your family compound, this property offers endless possibilities. Just minutes from Mount Snow, with boating, hiking, fly fishing, and more nearby, it’s an outdoor enthusiast’s dream. The south-facing land includes rolling pastures and a year-round brook, ideal for

    Donald Koelsch Deerfield Valley Real Estate

    292 Parsons Rd, Jacksonville, VT 05342
  • /23

    $285,000 Sold Aug 08, 2024

    • 1,224 Sq Ft
    • $233/SF
    • 19 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1971

    123 Birdville Rd, Whitingham, VT 05361

    This newly painted and furnished 2 bed/2bath chalet is situated on over 7 acres in all the beauty Southern Vermont has to offer. Only 25 minutes to Mt. Snow, 10 minutes to the lake and hiking all around. The many windows afford plenty of light in both living areas, which boasts nice new flooring, throughout the main level as well as the upstairs. Plenty of room to fence in a place for your

    Regina Perrotto Skihome Realty

    123 Birdville Rd, Whitingham, VT 05361
  • /31

    $184,000 Sold Nov 18, 2024

    • 1,537 Sq Ft
    • $120/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    302 Number 9 Rd, Charlemont, MA 01339

    This secluded home comes with 9.2 acres of land including a 4-5 acre (approx.) grazing field and large 2-story 3-bay barn garage w/ separate electric. The home was built in 1987 and never fully finished. Priced to sell with plenty of potential and the perfect opportunity to implement your own finishing touches. First floor includes a solarium with 8 ft of deep small river stone, wrap around porch

    Jocelyn O'Shea Coldwell Banker Community REALTORS®

    302 Number 9 Rd, Charlemont, MA 01339

Home Trends in Whitingham, VT

Housing Trends

Median Sale Price
$295,000
Median Single Family Sale Price
$310,000
Average Price Per Sq Ft
$171
Number of Homes for Sale
1
Last 12 months Home Sales
6
Months of Supply
2.00
Median List Price
$349,900
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
31%
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