Whitingham Homes

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  $599,000

  • 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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  /35

  Est $347,970 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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  /40

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  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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  /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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  /31

  Est $353,607 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
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  /8

  $189,900

  • 3 Beds
  • 2 Baths
  • 2,098 Sq Ft

  843 Kentfield Rd, Whitingham, VT 05361

  Location! Location! Location! Only 15 minutes to Wilmington and all that winter fun...Lake Whitingham and parks and ponds right around the corner...yet, a country property with ample parking for all the toys! This 1865 home has been made ready for the next level of renovation. Use it as it is currently used as a 2 family or with minor changes return it to the original cape upstairs, downstairs.

  Christine Lewis Brattleboro Area Realty

  843 Kentfield Rd, Whitingham, VT 05361
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  /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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  /26

  Est $239,286 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
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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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  /29

  $590,000 Sold Oct 28, 2024

  • 2,732 Sq Ft
  • $216/SF
  • 35 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1840

  55 Reed Hill Rd, Jacksonville, VT 05342

  Originally a centerpiece of a thriving farm in 1840, this farmhouse now stands amidst lush forests on what was once grazing land. Nestled alongside a 20-acre pond, it boasts a dam that historically powered downstream mills. Extensively renovated, the home offers five bedrooms and three full baths. The barn, reconstructed on its original foundation, includes a two-car garage with a spacious studio

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  55 Reed Hill Rd, Jacksonville, VT 05342
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  /12

  Est $246,000 Not Listed For Sale

  2027 Burrington Hill Rd, Whitingham, VT 05361

  2027 Burrington Hill Rd, Whitingham, VT 05361
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  /46

  $449,999 Pending

  • 3 Beds
  • 2 Baths
  • 1,438 Sq Ft

  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
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  /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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  /29

  Est $540,010 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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  /54

  $679,000 Pending

  • 4 Beds
  • 3 Baths
  • 4,881 Sq Ft

  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
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  /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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  /40

  Est $416,969 Not Listed For Sale

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

  656 Allard Rd, Whitingham, VT 05361

  656 Allard Rd, Whitingham, VT 05361
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  /49

  $310,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft

  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
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  /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
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  /33

  Est $272,147 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  754 Allard Rd, Whitingham, VT 05361

  754 Allard Rd, Whitingham, VT 05361
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  /17

  $335,000 Sold Jul 31, 2024

  • 900 Sq Ft
  • $372/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  402 Burrington Hill Rd, Whitingham, VT 05361

  WHAT A VIEW!!!!!! Imagine sitting on your covered porch taking in the spectacular sunsets from your 180 degree vista. Off in the distance you'll see Lake Sadawga, The Berkshires, Mt. Snow and Haystack. The yard is a bird lover's paradise with abundant wildlife, lupin and flowering trees galore. If that isn't enough you can take a swim in your very own pond or sit out in the open meadow and

  Karen Hoppe Berkley & Veller Greenwood Country

  402 Burrington Hill Rd, Whitingham, VT 05361
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  /32

  Est $239,331 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
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  /40

  $600,000 Sold Jul 30, 2024

  • 2,582 Sq Ft
  • $232/SF
  • 5 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1989

  39 Mcmillan Rd, Whitingham, VT 05342

  Quintessential charming Vermont log cabin nestled amongst the trees on 10+acres in the foothills of the Green Mountains just south of Jacksonville village. Once resided upon by the Carthusian monks, old stone walls and many artifacts can still be found around the property. This home comes w/ an oversized garage, a classic barn, and a darling sleeping/writing cottage. Property has open space as

  Mary M. Wallace Berkley & Veller Greenwood Country

  39 Mcmillan Rd, Whitingham, VT 05342
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  /27

  Est $372,133 Not Listed For Sale

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

  540 Fowler Rd, Whitingham, VT 05361

  540 Fowler Rd, Whitingham, VT 05361
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  /8

  $225,000 Sold Jul 26, 2024

  • 1,256 Sq Ft
  • $179/SF
  • 120 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  739 Chapel Hill Rd, Whitingham, VT 05361

  This home in Chapel Hill offers 2.5 levels on 1.9 Acres located on a quiet Town maintained Country Road, Decks overlooking a nice flowing mountain stream that is close to Shippee Pond. 2 bedrooms and a loft. Easy to heat with propane gas hot air heat and a Vermont Casting wood stove. Open kitchen and dining, vaulted ceiling. full unfinished walk out basement. New roof in 2022 and 2 new pressure

  Mark Yule Heritage Associates

  739 Chapel Hill Rd, Whitingham, VT 05361
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  /35

  Est $297,994 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,860 Sq Ft

  159 Reed Hill Rd, Jacksonville, VT 05342

  159 Reed Hill Rd, Jacksonville, VT 05342
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  /22

  $366,000 Sold Jul 23, 2024

  • 2,600 Sq Ft
  • $141/SF
  • 56 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  7451 Vermont Route 100, Whitingham, VT 05361

  New construction! Originally built in 1964 and completely re-built in 2023. This 3 story home sits across the road from Harriman Reservoir and is only a short walk to a small boat (Canoe or Kayak) access and approx. 1/2 mile to the larger boat launch. There is also a small, wooded section with a trail to the lake edge directly across the street for a summer swim or fishing. Located within 20

  Chris Long BHG Masiello Brattleboro

  7451 Vermont Route 100, Whitingham, VT 05361
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  /40

  Est $570,487 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
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  /31

  $20,000 Sold Jun 25, 2024

  • Land
  • 1.00 Acre
  • $20,000 per Acre

  • 64 Days On Market

  1124 Chapel Hill Rd, Whitingham, VT 05361

  This 1+/- acre lot of mostly softwoods offers a level topography and a peaceful setting on a private road in Whitingham, VT. Located near the eastern edge of the Green Mountain National Forest, the mountains, and Harriman Reservoir (Vermont’s second largest lake), all the year-round recreational opportunities will be at your fingertips! Establish your recreational basecamp with a cabin or camper

  Curtis Trousdale Preferred Properties

  1124 Chapel Hill Rd, Whitingham, VT 05361
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  /17

  Est $173,743 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
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  /40

  $620,000 Sold Jun 24, 2024

  • 1,592 Sq Ft
  • $389/SF
  • 22 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1965

  255 Brick House Rd, Whitingham, VT 05361

  Location is the thing and properties like this do not come along often! Two sides of this 2 lot, 6+ acre property abut the Great River Hydro Conservation Easement that surrounds nearly all of Harriman Reservoir. Water sports are just a short walk from your doorstep. Whether you boat (Sawyer’s Boat Launch is just down the road), kayak, canoe, fish or just love relaxing by the water, this property

  Bill Hickok Berkley & Veller Greenwood Country

  255 Brick House Rd, Whitingham, VT 05361
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  /40

  Est $606,966 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
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  /4

  $22,500 Sold Jun 18, 2024

  • Land
  • 1.00 Acre
  • $22,500 per Acre

  • 8 Days On Market

  986 Chapel Hill Rd, Whitingham, VT 05361

  In a well-established country neighborhood, this one acre lot has good road frontage, is relatively level and has had numerous trees and flowering shrubs added over the past decades. No soils testing has been done. Buyers should confirm with the Whitingham Zoning department that the lot is grandfathered for development provided a VT wastewater permit is obtained. This lot is currently included

  Meg Streeter Meg Streeter Real Estate

  986 Chapel Hill Rd, Whitingham, VT 05361
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  /40

  Est $431,123 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft

  756 Wilmington Cross Rd, Whitingham, VT 05361

  756 Wilmington Cross Rd, Whitingham, VT 05361
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  /5

  $22,500 Sold Jun 13, 2024

  • Land
  • 1.00 Acre
  • $22,500 per Acre

  • 8 Days On Market

  982 Chapel Hill Rd Unit lot 28, Whitingham, VT 05361

  An attractive one acre lot in the Chapel Hill neighborhood. There is good road frontage and wonderful landscaping featuring flowering shrubs and many trees planted by a green-thumb owner over the past 40 years. The rhododendron shrubs are stunning! No soils testing has been done. Buyers should confirm with the Whitingham Zoning department that the lot is grandfathered for development with a

  Meg Streeter Meg Streeter Real Estate

  982 Chapel Hill Rd Unit lot 28, Whitingham, VT 05361
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  /38

  Est $771,662 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
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  /8

  $129,900 Sold May 31, 2024

  • Land
  • 11 Acres
  • $11,885 per Acre

  • 75 Days On Market

  341 Chapel Hill Rd, Whitingham, VT 05361

  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,

  Monica Sumner BHG Masiello Brattleboro

  341 Chapel Hill Rd, Whitingham, VT 05361
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  /29

  Est $952,962 Not Listed For Sale

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

  2329 Faulkner Rd, Whitingham, VT 05361

  2329 Faulkner Rd, Whitingham, VT 05361
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  /38

  $695,000 Sold May 13, 2024

  • 7,400 Sq Ft
  • $94/SF
  • 188 Days On Market

  • 12 Beds
  • 5 Baths
  • Built 2007

  267 Academy Rd, Jacksonville, VT 05342

  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

  Janet Boyd Boyd Real Estate

  267 Academy Rd, Jacksonville, VT 05342

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