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 $572,482 Not Listed For Sale

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

  1084 Cyrus Rd, Whitingham, VT 05361

  1084 Cyrus Rd, Whitingham, VT 05361
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  /45

  $439,000 Under Contract

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

  210 Burrington Hill Rd, Whitingham, VT 05361

  Impeccably maintained 2007 residence in like-new condition, offering quality construction and thoughtful design throughout. The home features vinyl siding and a full concrete walk-out basement with high ceilings—an outstanding opportunity for adding 1000+ future finished living space customized to your needs. The main level showcases an open-concept living, kitchen, and dining area with natural

  Jacki Murano Southern Vermont Realty Group

  210 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 $361,648

  Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  399 Laurel Lake Rd, Jacksonville, VT 05342
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  /35

  Est $364,323 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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  /43

  $425,000

  • 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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  /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 $375,044 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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  /22

  $199,000

  • Land
  • 3.6 Acres
  • $55,278 per Acre

  00 Lake Hill Rd Unit "Spring Lot", 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 showing positive results, utilities at the road,

  Chad Lackey Deerfield Valley Real Estate

  00 Lake Hill Rd Unit "Spring Lot", 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 $443,184

  Last Listing Agent Peggy Winchester ACORN REAL ESTATE GROUP LLC

  1448 Cyrus Rd, Whitingham, VT 05361
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  /31

  Est $96,488 Not Listed For Sale

  1124 Chapel Hill Rd, Whitingham, VT 05361

  1124 Chapel Hill Rd, Whitingham, VT 05361
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  /17

  $39,900

  • Land
  • 5.66 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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  /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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  /26

  Est $254,623 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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  /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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  /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

  Last Listing Agent Chris Long BHG Masiello Brattleboro

  871 Streeter Hill Rd, Whitingham, VT 05361
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  /12

  Est $293,000 Not Listed For Sale

  2027 Burrington Hill Rd, Whitingham, VT 05361

  2027 Burrington Hill Rd, Whitingham, VT 05361
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  /12

  $99,900

  • 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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  /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

  Last Listing Agent Erica Reynolds Southern Vermont Realty Group

  456 Poverty Row, Whitingham, VT 05361
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  /29

  Est $534,485 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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  /50

  $339,000 Pending

  • 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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  /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 $226,244

  Last Listing Agent Kim Meeker Southern Vermont Realty Group

  1871 Wilmington Cross Rd, Whitingham, VT 05361
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  /40

  Est $428,478 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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  /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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  /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

  Last Listing Agent Adam Palmiter Berkley & Veller Greenwood/Dover

  1153 Faulkner Rd, Whitingham, VT 05361
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  /33

  Est $279,613 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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  /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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  /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 $467,348

  Last Listing Agent Claire Renaud Berkley & Veller Greenwood Country

  1452 Maple Hill Ln, Whitingham, VT 05361
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  /32

  Est $249,478 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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  /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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  /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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  /39

  Est $608,098 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
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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

  Last Listing Agent Sandy Reavill Real Broker LLC

  149 Dix Ln, Whitingham, VT 05361
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  /40

  Est $525,866 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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  /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

  Last Listing Agent Flex Realty Group Flex Realty

  166 Taylor Ln, Whitingham, VT 05361
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  /17

  Est $184,477 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

  $280,000 Sold Jun 20, 2025

  427 Vermont 112, Whitingham, VT 05342

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1992

  Last Sold Summary

  • 20% Below List Price
  • $167/SF
  • 268 Days On Market

  Last Listing Agent Monica Sumner BHG Masiello Brattleboro

  427 Vermont 112, Whitingham, VT 05342
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  /23

  Est $290,466 Not Listed For Sale

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

  123 Birdville Rd, Whitingham, VT 05361

  123 Birdville Rd, Whitingham, VT 05361
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  /54

  $665,000 Sold May 29, 2025

  201 Vermont 112, Whitingham, VT 05342

  • 4 Beds
  • 3 Baths
  • 4,881 Sq Ft
  • Built 1840

  Last Sold Summary

  • 2% Below List Price
  • $136/SF
  • 40 Days On Market

  Last Listing Agent Steve Goldfarb Deerfield Valley Real Estate

  201 Vermont 112, Whitingham, VT 05342

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