Whitingham, VT Homes

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  /58

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  1192 Chapel Hill Rd, Whitingham, VT 05361

  Discover Vermont living at its finest in this architecturally unique round home, set on a 1-acre lot. Included in the sale is an additional 1-acre parcel directly across the street, offering potential for a garage, guest house, or Airbnb. Buyers should perform their own due diligence, as seller and broker make no representation on buildability. Step inside and walk into the welcoming lower level,

  Cliff Leinonen Four Seasons Sotheby's Int'l Realty

  1192 Chapel Hill Rd, Whitingham, VT 05361
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  /22

  $69,000 Sold Oct 03, 2025

  1051 Maple Hill Ln, Whitingham, VT 05342

  • Land
  • 10.01 Acres
  • $6,893 per Acre

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Kelly Agrillo Southern Vermont Realty Group

  1051 Maple Hill Ln, Whitingham, VT 05342
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  /40

  Est $542,833 Not Listed For Sale

  1084 Cyrus Rd, Whitingham, VT 05361

  • 3 Beds
  • 4 Baths
  • 2,200 Sq Ft
  • Built 2005

  1084 Cyrus Rd, Whitingham, VT 05361

  Last Sold Summary

  • 1% Above List Price
  • $245/SF
  • 129 Days On Market

  Last Sold Price $540,000

  Last Listing Agent Kristen Breeden Southern Vermont Realty Group
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  /43

  $425,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,872 Sq Ft

  1587 Upper Holbrook Rd, Whitingham, VT 05361

  Set on 3 beautiful acres, this well-maintained 3-bedroom plus loft, 2 1/2 bath home is truly move-in ready. Enter through a spacious mudroom with a convenient back opening for bringing in firewood for the cozy wood stove in the living room. The open-concept kitchen and dining area provide plenty of room for entertaining, while a den/game room just off the living room with a bar area (4X8) offers

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1587 Upper Holbrook Rd, Whitingham, VT 05361
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  /45

  $429,500 Sold Feb 20, 2026

  210 Burrington Hill Rd, Whitingham, VT 05361

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Below List Price
  • $275/SF
  • 35 Days On Market

  Current Estimated Value $431,286

  Last Listing Agent Jacki Murano Southern Vermont Realty Group

  210 Burrington Hill Rd, Whitingham, VT 05361
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  /35

  Est $341,622 Not Listed For Sale

  31 Brook St, Whitingham, VT 05361

  • 4 Beds
  • 1.5 Baths
  • 1,783 Sq Ft
  • Built 1987

  31 Brook St, Whitingham, VT 05361

  Last Sold Summary

  • 2% Above List Price
  • $188/SF
  • 6 Days On Market

  Last Sold Price $334,650

  Last Listing Agent Melissa Ellis Southern Vermont Realty Group
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  /45

  $380,000

  • 5 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  1033 Burrington Hill Rd, Whitingham, VT 05361

  Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's

  Monique White Deerfield Valley Real Estate

  1033 Burrington Hill Rd, Whitingham, VT 05361
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  /44

  $359,350 Sold Sep 26, 2025

  399 Laurel Lake Rd, Jacksonville, VT 05342

  • 2 Beds
  • 3 Baths
  • 1,696 Sq Ft
  • Built 1930

  Last Sold Summary

  • 10% Below List Price
  • $212/SF
  • 17 Days On Market

  Current Estimated Value $341,076

  Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  399 Laurel Lake Rd, Jacksonville, VT 05342
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  /31

  Est $370,007 Not Listed For Sale

  962 Chapel Hill Rd, Whitingham, VT 05361

  • 3 Beds
  • 2 Baths
  • 1,963 Sq Ft
  • Built 1988

  962 Chapel Hill Rd, Whitingham, VT 05361

  Last Sold Summary

  • 8% Above List Price
  • $174/SF
  • 7 Days On Market

  Last Sold Price $342,000

  Last Listing Agent Jacki Murano Southern Vermont Realty Group
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  /20

  $179,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  7139 Vermont Route 100, Whitingham, VT 05361

  This cozy two bedroom, one bath cottage with vaulted wood ceilings is just steps away from Lake Whitingham! Enjoy a low maintenance get-away with an inviting living room and kitchen. This charming property offers the perfect escape for summer and winter enjoyment! The heart of the home is open and inviting where cold winter nights are made comfortable with an efficient propane heater. The simple,

  Casey Scott Southern Vermont Realty Group

  7139 Vermont Route 100, Whitingham, VT 05361
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  /27

  $475,000 Sold Nov 07, 2025

  0 Lake Hill Rd, Whitingham, VT 05361

  • Land
  • 36.7 Acres
  • $12,943 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 3 Days On Market

  Last Listing Agent Chad Lackey Deerfield Valley Real Estate

  0 Lake Hill Rd, Whitingham, VT 05361
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  /31

  Est $106,520 Not Listed For Sale

  1124 Chapel Hill Rd, Whitingham, VT 05361

  1124 Chapel Hill Rd, Whitingham, VT 05361

  Last Sold Summary

  • 433% Above List Price
  • 64 Days On Market

  Last Sold Price $20,000

  Last Listing Agent Curtis Trousdale Preferred Properties
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  /23

  $189,000

  • Land
  • 3.6 Acres
  • $52,500 per Acre

  00 Lake Hill Rd, Whitingham, VT 05361

  Rare opportunity to own the “Spring Lot,” a beautiful 3.6-acre building site overlooking private Laurel Lake in Southern Vermont. This peaceful 17-acre lake is reserved exclusively for landowners—no motorboats allowed—perfect for kayaking, canoeing, fishing, and swimming, with the ability to add your own private dock. With preliminary soil testing & septic design showing positive results,

  Chad Lackey Deerfield Valley Real Estate

  00 Lake Hill Rd, Whitingham, VT 05361
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  /46

  $449,999 Sold Jun 16, 2025

  1448 Cyrus Rd, Whitingham, VT 05361

  • 3 Beds
  • 2 Baths
  • 1,438 Sq Ft
  • Built 1978

  Last Sold Summary

  • $313/SF
  • 15 Days On Market

  Current Estimated Value $476,901

  Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC

  1448 Cyrus Rd, Whitingham, VT 05361
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  /26

  Est $255,879 Not Listed For Sale

  2815 Burrington Hill Rd, Whitingham, VT 05361

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1982

  2815 Burrington Hill Rd, Whitingham, VT 05361

  Last Sold Summary

  • 11% Above List Price
  • $329/SF
  • 6 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Jacki Murano Southern Vermont Realty Group
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  /12

  $399,000 New Construction

  • 4 Beds
  • 2 Baths
  • 3,700 Sq Ft

  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 levels.

  Mark Yule BHG Masiello Brattleboro

  442 Mcmillan Rd, Whitingham, VT 05342
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  /49

  $310,000 Sold Jun 20, 2025

  6699 Vermont Route 100, Whitingham, VT 05361

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft
  • Built 1893

  Last Sold Summary

  • $205/SF
  • 50 Days On Market

  Last Listing Agent Michelle O'Neil Deerfield Valley Real Estate

  6699 Vermont Route 100, Whitingham, VT 05361
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  /12

  Est $345,500 Not Listed For Sale

  2027 Burrington Hill Rd, Whitingham, VT 05361

  2027 Burrington Hill Rd, Whitingham, VT 05361

  Last Sold Summary

  • 47% Above List Price
  • 262 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Kristen Breeden Southern Vermont Realty Group
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  /12

  $99,900 Pending

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

  843 Kentfield Rd, Whitingham, VT 05361

  Step back in time with this 1865 home, currently used as a two-family residence, which could easily be restored to its original layout. The ceiling beams have been exposed, allowing you to keep their rustic charm or cover them for a more traditional look. The attached barn would be ideal for a studio, workshop, or bonus room, offering numerous options to suit your needs. Many projects are left to

  Linda Benoit Highland Realty

  843 Kentfield Rd, Whitingham, VT 05361
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  /36

  $380,000 Sold Nov 21, 2025

  871 Streeter Hill Rd, Whitingham, VT 05361

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft
  • Built 1989

  Last Sold Summary

  • 20% Below List Price
  • $261/SF
  • 79 Days On Market

  Current Estimated Value $375,070

  Last Listing Agent Chris Long BHG Masiello Brattleboro

  871 Streeter Hill Rd, Whitingham, VT 05361
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  /29

  Est $517,326 Not Listed For Sale

  960 Holbrook Rd, Jacksonville, VT 05342

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft
  • Built 1968

  960 Holbrook Rd, Jacksonville, VT 05342

  Last Sold Summary

  • 1% Below List Price
  • $202/SF
  • 14 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover
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  /3

  $275,000

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

  2173 Vermont 8a, Whitingham, VT 05361

  4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

  Mark Yule BHG Masiello Brattleboro

  2173 Vermont 8a, Whitingham, VT 05361
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  /55

  $624,000 Sold Oct 30, 2025

  456 Poverty Row, Whitingham, VT 05361

  • 3 Beds
  • 2.5 Baths
  • 2,438 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $256/SF
  • 234 Days On Market

  Current Estimated Value $609,184

  Last Listing Agent Erica Reynolds Southern Vermont Realty Group

  456 Poverty Row, Whitingham, VT 05361
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  /40

  Est $421,441 Not Listed For Sale

  656 Allard Rd, Whitingham, VT 05361

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1949

  656 Allard Rd, Whitingham, VT 05361

  Last Sold Summary

  • 9% Above List Price
  • $192/SF
  • 56 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Craig Ruggless EXP Realty
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  /2

  $325,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  292 Deer Hill Rd, Whitingham, VT 05361

  Tucked amongst trees with a great deck. This rural location is not far from great skiing, shopping and all kinds of great dining and entertainment. Over an acre of mostly wooded lot. Property is occupied. No drive by's please..

  Susan Bellville Bellville Realty

  292 Deer Hill Rd, Whitingham, VT 05361
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  /27

  $86,700 Sold Apr 18, 2025

  1871 Wilmington Cross Rd, Whitingham, VT 05361

  • 5 Beds
  • 2.5 Baths
  • 2,428 Sq Ft
  • Built 1840

  Last Sold Summary

  • 33% Below List Price
  • $36/SF
  • 49 Days On Market

  Current Estimated Value $255,447

  Last Listing Agent Kim Meeker Southern Vermont Realty Group

  1871 Wilmington Cross Rd, Whitingham, VT 05361
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  /33

  Est $258,874 Not Listed For Sale

  754 Allard Rd, Whitingham, VT 05361

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1963

  754 Allard Rd, Whitingham, VT 05361

  Last Sold Summary

  • 8% Above List Price
  • $256/SF
  • 21 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Jon Tourville
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  /34

  $699,000

  • 3 Beds
  • 4 Baths
  • 3,796 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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  /5

  $92,500 Sold Jan 09, 2026

  1153 Faulkner Rd, Whitingham, VT 05361

  • Land
  • 13.6 Acres
  • $6,801 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 5 Days On Market

  Current Estimated Value $92,786

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  1153 Faulkner Rd, Whitingham, VT 05361
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  /32

  Est $233,530 Not Listed For Sale

  329 Deer Hill Rd, Whitingham, VT 05361

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft
  • Built 1968

  329 Deer Hill Rd, Whitingham, VT 05361

  Last Sold Summary

  • 2% Above List Price
  • $241/SF
  • 6 Days On Market

  Last Sold Price $229,900

  Last Listing Agent Jon Tourville
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  /38

  $472,500 Sold Jul 08, 2025

  1452 Maple Hill Ln, Whitingham, VT 05361

  • 2 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Below List Price
  • $270/SF
  • 54 Days On Market

  Current Estimated Value $458,487

  Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  1452 Maple Hill Ln, Whitingham, VT 05361
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  /39

  Est $557,185 Not Listed For Sale

  3358 Vt Route 100, Whitingham, VT 05361

  • 5 Beds
  • 5 Baths
  • 3,300 Sq Ft
  • Built 1900

  3358 Vt Route 100, Whitingham, VT 05361

  Last Sold Summary

  • 7% Below List Price
  • $182/SF
  • 118 Days On Market

  Last Sold Price $599,000

  Last Listing Agent Jacki Murano Southern Vermont Realty Group
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  /11

  $78,000 Sold Dec 22, 2025

  1154 Vermont 8a, Whitingham, VT 05361

  • Land
  • 3 Acres
  • $26,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 20 Days On Market

  Last Listing Agent Kerry Mulverhill

  1154 Vermont 8a, Whitingham, VT 05361
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  /40

  Est $517,783 Not Listed For Sale

  371 Butler Brook Rd, Jacksonville, VT 05342

  • 5 Beds
  • 2.5 Baths
  • 2,296 Sq Ft
  • Built 1976

  371 Butler Brook Rd, Jacksonville, VT 05342

  Last Sold Summary

  • 7% Below List Price
  • $242/SF
  • 152 Days On Market

  Last Sold Price $555,000

  Last Listing Agent Monica Sumner BHG Masiello Brattleboro
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  /50

  $310,000 Sold Jan 29, 2026

  89 Gates Pond Rd, Whitingham, VT 05342

  • 7 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • Built 1880

  Last Sold Summary

  • 9% Below List Price
  • $103/SF
  • 176 Days On Market

  Current Estimated Value $269,576

  Last Listing Agent Monique White Deerfield Valley Real Estate

  89 Gates Pond Rd, Whitingham, VT 05342
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  /17

  Est $166,175 Not Listed For Sale

  813 Gates Pond Rd, Jacksonville, VT 05342

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft
  • Built 1846

  813 Gates Pond Rd, Jacksonville, VT 05342

  Last Sold Summary

  • 4% Above List Price
  • $194/SF
  • 5 Days On Market

  Last Sold Price $160,000

  Last Listing Agent Melissa Nebelski Real Broker LLC
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  /47

  $555,000 Sold Oct 31, 2025

  149 Dix Ln, Whitingham, VT 05361

  • 4 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 1850

  Last Sold Summary

  • 3% Below List Price
  • $287/SF
  • 35 Days On Market

  Current Estimated Value $532,382

  Last Listing Agent Sandy Reavill

  149 Dix Ln, Whitingham, VT 05361
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  /23

  Est $267,873 Not Listed For Sale

  123 Birdville Rd, Whitingham, VT 05361

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1971

  123 Birdville Rd, Whitingham, VT 05361

  Last Sold Summary

  • 6% Below List Price
  • $233/SF
  • 19 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Regina Perrotto Skihome Realty
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  /40

  $580,000 Sold Jan 05, 2026

  166 Taylor Ln, Whitingham, VT 05361

  • 3 Beds
  • 2.5 Baths
  • 2,516 Sq Ft
  • Built 2009

  Last Sold Summary

  • 10% Above List Price
  • $231/SF
  • 21 Days On Market

  Current Estimated Value $551,390

  Last Listing Agent Flex Realty Group Flex Realty

  166 Taylor Ln, Whitingham, VT 05361
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  /40

  Est $361,296 Not Listed For Sale

  4840 Vt Route 100, Whitingham, VT 05361

  • 5 Beds
  • 3.5 Baths
  • 2,248 Sq Ft
  • Built 1845

  4840 Vt Route 100, Whitingham, VT 05361

  Last Sold Summary

  • 32% Below List Price
  • $236/SF
  • 216 Days On Market

  Last Sold Price $530,000

  Last Listing Agent Jacki Murano Southern Vermont Realty Group

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