Windham, VT Homes

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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
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  /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
• 

  

  

  /35

  Est $361,532 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,783 Sq Ft

  31 Brook St, Whitingham, VT 05361

  31 Brook St, Whitingham, VT 05361
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  /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
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  /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
• 

  

  /31

  Est $376,809 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,963 Sq Ft

  962 Chapel Hill Rd, Whitingham, VT 05361

  962 Chapel 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
• 

  

  /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
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  /31

  Est $82,547 Not Listed For Sale

  1124 Chapel Hill Rd, Whitingham, VT 05361

  1124 Chapel Hill Rd, 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
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  /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
• 

  

  /26

  Est $251,885 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  2815 Burrington Hill Rd, Whitingham, VT 05361

  2815 Burrington Hill 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
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  /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
• 

  

  /12

  Est $274,394 Not Listed For Sale

  2027 Burrington Hill Rd, Whitingham, VT 05361

  2027 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
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  /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
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  /29

  Est $537,250 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft

  960 Holbrook Rd, Jacksonville, VT 05342

  960 Holbrook Rd, Jacksonville, VT 05342
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  /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
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  /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
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  /40

  Est $432,246 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  656 Allard Rd, Whitingham, VT 05361

  656 Allard Rd, 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
• 

  

  /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
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  /33

  Est $259,400 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  754 Allard Rd, Whitingham, VT 05361

  754 Allard Rd, Whitingham, VT 05361
• 

  

  /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
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  /32

  Est $241,542 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  329 Deer Hill Rd, Whitingham, VT 05361

  329 Deer Hill 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
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  /39

  Est $585,320 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,300 Sq Ft

  3358 Vt Route 100, Whitingham, VT 05361

  3358 Vt Route 100, Whitingham, VT 05361
• 

  

  /27

  Est $376,669 Not Listed For Sale

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

  540 Fowler Rd, Whitingham, VT 05361

  540 Fowler Rd, Whitingham, VT 05361
• 

  

  /40

  Est $586,854 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,296 Sq Ft

  371 Butler Brook Rd, Jacksonville, VT 05342

  371 Butler Brook Rd, Jacksonville, VT 05342
• 

  

  /17

  Est $177,511 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft

  813 Gates Pond Rd, Jacksonville, VT 05342

  813 Gates Pond Rd, Jacksonville, VT 05342
• 

  

  /23

  Est $271,092 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  123 Birdville Rd, Whitingham, VT 05361

  123 Birdville Rd, Whitingham, VT 05361
• 

  

  /40

  Est $419,832 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,248 Sq Ft

  4840 Vt Route 100, Whitingham, VT 05361

  4840 Vt Route 100, Whitingham, VT 05361
• 

  

  /38

  Est $790,418 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  1793 Faulkner Rd, Whitingham, VT 05361

  1793 Faulkner Rd, Whitingham, VT 05361
• 

  

  /29

  Est $945,125 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,400 Sq Ft

  2329 Faulkner Rd, Whitingham, VT 05361

  2329 Faulkner Rd, Whitingham, VT 05361
• 

  

  /14

  Est $61,697 Not Listed For Sale

  232 Deer Hill Rd, Whitingham, VT 05361

  232 Deer Hill Rd, Whitingham, VT 05361
• 

  

  /8

  Est $141,168 Not Listed For Sale

  341 Chapel Hill Rd, Whitingham, VT 05361

  341 Chapel Hill Rd, Whitingham, VT 05361
• 

  

  /40

  Est $535,311 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,582 Sq Ft

  39 Mcmillan Rd, Whitingham, VT 05342

  39 Mcmillan Rd, Whitingham, VT 05342
• 

  

  /17

  Est $295,274 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  402 Burrington Hill Rd, Whitingham, VT 05361

  402 Burrington Hill Rd, Whitingham, VT 05361
• 

  

  /40

  Est $608,701 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,592 Sq Ft

  255 Brick House Rd, Whitingham, VT 05361

  255 Brick House Rd, Whitingham, VT 05361

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