Cavendish, VT Homes

• 

  

  

  /46

  $750,000

  • 3 Beds
  • 3 Baths
  • 1,432 Sq Ft

  58 Greenbush Rd, Cavendish, VT 05142

  Charming Cape Cod Home in a Serene Country Setting – 10.10 Acres Welcome to this beautifully transformed Cape Cod-style home, nestled on just over 10 acres of picturesque countryside. Offering a perfect blend of classic charm and modern convenience, this inviting property is ideal for those seeking tranquility and space. Step onto the welcoming front porch, where you can relax and take in the

  Katie Ladue Gilbert KW Vermont Woodstock

  58 Greenbush Rd, Cavendish, VT 05142
• 

  

  

  /13

  $1,750 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  214 Main St, Cavendish, VT 05153

  NOT AVAILABLE UNTIL AUGUST 18, 2025. Fully furnished & outfitted, including kitchen pots/pans/plates/etc. Convection oven, microwave/hood fan over. Full sized fridge. Front loading W/D. Walkable to shopping, restaurant. 10 minutes to Okemo, 25 minutes to the Killington Skyeship. School right up the street, so no amount of snow will keep you from the Mountains! VAST trail right up the street too!

  Robert Balewicz Evergreen Realty of Vermont

  214 Main St, Cavendish, VT 05153
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  /40

  $410,000 Sold Nov 25, 2025

  • 1,445 Sq Ft
  • $284/SF
  • 5 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  45 Carriage Ln Unit D-3, Cavendish, VT 05153

  If royalty is how you'd like to be treated then you've found your Castle. This two bedroom condominium is located at the Castle Hill Resort and Spa with amenities that any king and queen would appreciate. Just 3 miles to Okemo and all Ludlow has to offer. And around the corner from charming, vibrant Proctorsville Green. With two bedrooms, a den, and lock out capabilities, you'll have plenty of

  Frank Provance Diamond Realty

  45 Carriage Ln Unit D-3, Cavendish, VT 05153
• 

  

  

  /11

  Est $191,209 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,104 Sq Ft

  995 Knapp Pond Rd, Cavendish, VT 05142

  995 Knapp Pond Rd, Cavendish, VT 05142
• 

  

  

  /41

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  115 Prior Rd, Cavendish, VT 05142

  Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral

  Glenn Olney Barrett and Valley Associates Inc.

  115 Prior Rd, Cavendish, VT 05142
• 

  

  /34

  $110,000 Sold Nov 21, 2025

  • 560 Sq Ft
  • $196/SF
  • 2 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  51 Depot St Unit 8, Proctorsville, VT 05153

  If you looking for an affordable comfy condo in the Village of Proctorsville less than 10 Minutes to Okemo you've found it! Come take a look at this recently renovated two bedroom one full bath condo that is walking distance to all of what the village has to offer. The new café, right next door, Murdoch's On The Green a two minute walk, Singletons Country Store a four minute walk, and after a

  Frank Provance Diamond Realty

  51 Depot St Unit 8, Proctorsville, VT 05153
• 

  

  /35

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,445 Sq Ft

  41 Parkhurst Unit L1, Cavendish, VT 05153

  41 Parkhurst Unit L1, Cavendish, VT 05153
• 

  

  /60

  $799,000

  • 11 Beds
  • 12 Baths
  • 5,102 Sq Ft

  329 Main St, Cavendish, VT 05153

  Step into history with this beautifully maintained property in the heart of Proctorsville — formerly the Okemo Lantern Lodge and now a thriving short-term rental and family vacation retreat. Rich with character, this historic home showcases timeless woodwork, period details, and plenty of charm, while offering all the updates needed for today’s modern use.Located directly along the Okemo

  Benjamin Cote EXP Realty

  329 Main St, Cavendish, VT 05153
• 

  

  /46

  $250,000 Sold Nov 18, 2025

  • 1,250 Sq Ft
  • $200/SF
  • 53 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  2665 Brook Rd, Cavendish, VT 05142

  Country home ready for your vision. This 2 level, 2 bedroom, 2 bath home is located in a very pretty spot on Brooks Road in Cavendish. You are welcomed by a screened-in porch, wrap around deck,and an open kitchen/living area, with warming pellet stove. A bedroom exists on the main level and a full bath. The laundry is also located on the main level. The lower level will need your TLC to finish.

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  2665 Brook Rd, Cavendish, VT 05142
• 

  

  /40

  Est $677,479 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,434 Sq Ft

  621 Main St, Proctorsville, VT 05153

  621 Main St, Proctorsville, VT 05153
• 

  

  /58

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft

  615 Old County Rd, Cavendish, VT 05142

  In need of the perfect ski cabin just 15 minutes from Okemo Mountain? Set on over ten private acres, this home offers the perfect mix of comfort and country charm. The main living room features cathedral ceilings, a propane stove, and access to the deck with a hot tub—ideal for relaxing after a day on the slopes. The kitchen, finished with Vermont soapstone counters and updated appliances, opens

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  615 Old County Rd, Cavendish, VT 05142
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  /60

  $997,500 Sold Nov 14, 2025

  • 4,420 Sq Ft
  • $226/SF
  • 109 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1834

  2941 Twenty Mile Stream Rd, Cavendish, VT 05142

  Experience timeless elegance and modern luxury in this exquisitely renovated 1834 farmhouse, gracefully sited on one of Cavendish’s most sought-after country roads. Thoughtfully updated while preserving its historic charm, this extraordinary residence features a state-of-the-art chef’s kitchen, whole house a/c and an expansive open-concept main level adorned with original hand-hewn beams and

  Joseph Karl William Raveis Real Estate Vermont Properties

  2941 Twenty Mile Stream Rd, Cavendish, VT 05142
• 

  

  /23

  Est $708,717 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,922 Sq Ft

  632 East Rd, Cavendish, VT 05142

  632 East Rd, Cavendish, VT 05142
• 

  

  /36

  $895,000

  • 3 Beds
  • 5 Baths
  • 3,590 Sq Ft

  1104 Main St, Cavendish, VT 05142

  Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuite, 5 bath log home. The Great Room boasts a floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is

  Frank Provance Diamond Realty

  1104 Main St, Cavendish, VT 05142
• 

  

  /19

  $120,000 Sold Nov 14, 2025

  • 700 Sq Ft
  • $171/SF
  • 40 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  51 Depot St Unit 1, Proctorsville, VT 05153

  This 3-bedroom, 1-bath condo offers easy living in a cozy, convenient setting. Enjoy first-floor living with an open kitchen, dining, and living area that’s perfect for gathering after a day of adventure. Hike scenic Hawks Mountain or access the VAST snowmobile trails just minutes from your door, and enjoy a short drive to area golf courses and the beautiful lakes region for boating, swimming,

  Frank Provance Diamond Realty

  51 Depot St Unit 1, Proctorsville, VT 05153
• 

  

  /36

  Est $204,667 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,172 Sq Ft

  2186 Main St, Cavendish, VT 05142

  2186 Main St, Cavendish, VT 05142
• 

  

  /51

  $674,000

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft

  35 Stevens Rd, Cavendish, VT 05142

  Winter, Spring, Summer or Fall, this is a bit of heaven for the nature lover! Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The back yard has lawn area with room for

  Betty McEnaney Diamond Realty

  35 Stevens Rd, Cavendish, VT 05142
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  /44

  $430,000 Sold Nov 11, 2025

  • 1,445 Sq Ft
  • $298/SF
  • 49 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2005

  110 Spaulding Rd Unit G-3, Cavendish, VT 05153

  If royalty is how you'd like to be treated then you've found your Castle. This two bedroom condominium is located at the Castle Hill Resort and Spa with unsurpassed amenities that any king and queen would appreciate. Just 3 miles to Okemo and all Ludlow has to offer and around the corner from charming, vibrant Proctorsville Green. This impeccable condo has been updated, well cared for and loved

  Frank Provance Diamond Realty

  110 Spaulding Rd Unit G-3, Cavendish, VT 05153
• 

  

  /35

  Est $371,207 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 968 Sq Ft

  599 High St, Cavendish, VT 05142

  599 High St, Cavendish, VT 05142
• 

  

  /27

  $539,000

  • 6 Beds
  • 2 Baths
  • 2,304 Sq Ft

  81 High St, Cavendish, VT 05142

  Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

  Tyleen Murray Kelley Real Estate, Inc.

  81 High St, Cavendish, VT 05142
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  /33

  $97,500 Sold Nov 03, 2025

  • 192 Sq Ft
  • $508/SF
  • 51 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 2021

  1150 Tarbell Hill Rd, Cavendish, VT 05142

  Have you been waiting for your own piece of Vermont? Something affordable and easy to maintain? Whether you are looking for a getaway for skiing, relaxing, or a cozy place to call home, this tiny home might be just what you need. This Jamaica Cottage Shop timber frame camp is awaiting new owners to put their own touches on this tiny home. The current owner would be happy to explain all about the

  Tyleen Murray Kelley Real Estate, Inc.

  1150 Tarbell Hill Rd, Cavendish, VT 05142
• 

  

  /40

  Est $567,756 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,226 Sq Ft

  2092 Cavendish Gulf Rd, Cavendish, VT 05142

  2092 Cavendish Gulf Rd, Cavendish, VT 05142
• 

  

  /47

  $549,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft

  127 Pleasant St, Cavendish, VT 05142

  This lovingly restored Arts and Crafts style home is located just 10 minutes from Okemo Mountain. Built in 1928, this home sits on a peaceful, elevated street in Cavendish, just steps from the town’s sledding hill. Owned by the same family for 20 years, the memories made here are priceless. The children learned to ski at Okemo and with everyone grown, the family is ready to pass along this

  Tyleen Murray Kelley Real Estate, Inc.

  127 Pleasant St, Cavendish, VT 05142
• 

  

  /41

  $330,000 Sold Oct 30, 2025

  • 1,798 Sq Ft
  • $184/SF
  • 94 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1880

  109 High St, Cavendish, VT 05142

  Upgraded, updated, and ready for you! Discover the perfect blend of small-town charm and four-season adventure in the heart of Cavendish. Perched on a sunny corner lot with views of Hawks Mountain, this classic Vermont home offers easy access to everything from skiing at Okemo to hiking, biking, and swimming nearby. Step inside through the thoughtfully planned mudroom and enter a warm, updated

  Dana Haley Diamond Realty

  109 High St, Cavendish, VT 05142
• 

  

  /31

  Est $963,972 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft

  129 Carlton Rd, Cavendish, VT 05142

  129 Carlton Rd, Cavendish, VT 05142
• 

  

  /38

  $525,000

  • 3 Beds
  • 3.5 Baths
  • 2,023 Sq Ft

  98 Spaulding Rd Unit H-4, Cavendish, VT 05153

  The Castle Hill Resort & Spa is your place to enjoy and relax. Top floor end unit has 2 levels of living spaces. There are three spacious bedrooms, 3.5 baths, a second level loft area (den) and a lock out area with a bedroom, 3/4 bath and den that can be rented out if you choose. Cathedral ceilings, air conditioning, gas fireplace with an open kitchen/dining/living room. A private main level

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  98 Spaulding Rd Unit H-4, Cavendish, VT 05153
• 

  

  /15

  $55,000 Sold Oct 10, 2025

  • Land
  • 0.35 Acre
  • $157,143 per Acre

  • 16 Days On Market

  150 Parker Ave, Proctorsville, VT 05153

  Tucked among mature maples and just a short drive from Ludlow and Chester,this classic New England barn offers a rare opportunity to own a piece of Vermont history. With its weathered wood siding, original beams, and classic gable roofline, the structure stands as a testament to traditional craftsmanship. Inside, exposed timber framing and a partial stone foundation highlight its old-world

  Frank Provance Diamond Realty

  150 Parker Ave, Proctorsville, VT 05153
• 

  

  /40

  Est $596,878 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,908 Sq Ft

  366 Knapp Pond Rd, Cavendish, VT 05142

  366 Knapp Pond Rd, Cavendish, VT 05142
• 

  

  /48

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft

  228 Cavendish Gulf Rd, Cavendish, VT 05142

  Brand new custom renovated 3bedroom/2bath home in the charming and desirable town of Cavendish, close to Okemo and four-season recreation. From the outside, this home exudes classic New England charm, but step inside through the mudroom to witness a breathtaking, top-to-bottom modern renovation. Inside, discover a bright, open floor plan with gleaming variegated hardwood floors, and recessed

  Michael Gilman 3GEN Real Estate Inc

  228 Cavendish Gulf Rd, Cavendish, VT 05142
• 

  /2

  $299,000 Sold Oct 03, 2025

  • 1,526 Sq Ft
  • $196/SF
  • 70 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  996 Cavendish Gulf Rd, Cavendish, VT 05142

  Its time to escape to your own peaceful retreat in the heart of Cavendish, Vermont. Set on 10 private, wooded acres along a quiet town road, this warm and welcoming cabin-style home offers the perfect blend of comfort and rustic charm. A beautiful pond shimmers in the sunlight, adding to the magical feel of the setting. The home features four bedrooms and two baths, including a first-floor

  Daire Gibney Barrett and Valley Associates Inc.

  996 Cavendish Gulf Rd, Cavendish, VT 05142
• 

  

  /44

  Est $469,791 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,709 Sq Ft

  20 Chubb Hill Rd, Cavendish, VT 05142

  20 Chubb Hill Rd, Cavendish, VT 05142
• 

  

  /50

  $249,000

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  58 Depot St, Cavendish, VT 05153

  Step back in time with this charming brick Colonial home, built in 1830 and beautifully situated in the heart of Proctorsville Village. Rich in history and character, this residence offers the perfect blend of classic New England architecture and convenient village living—just steps from shops, schools, restaurants, and the village green that adds to its timeless charm. The main level welcomes

  Sarah Sheehan William Raveis Real Estate Vermont Properties

  58 Depot St, Cavendish, VT 05153
• 

  

  /52

  $355,000 Sold Sep 30, 2025

  • 5,984 Sq Ft
  • $59/SF
  • 60 Days On Market

  • Built 1820

  643 Main St, Cavendish, VT 05153

  After owning this property for more than 50 years, the Seller is ready to relocate and pass along this classic brick home with lots of square footage and potential. Once having 4 apartments in the main house and an attached barn, the Seller made the upper level of the barn into her own unit. The kitchen was removed from one of the house units and made into a laundry room, so there are currently

  Tyleen Murray Kelley Real Estate, Inc.

  643 Main St, Cavendish, VT 05153
• 

  

  /40

  Est $413,975 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,105 Sq Ft

  581 Brook Rd, Cavendish, VT 05142

  581 Brook Rd, Cavendish, VT 05142
• 

  

  /24

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,800 Sq Ft

  50 Bates Rd, Cavendish, VT 05142

  Bring your vision to this charming 3-bedroom, 1-bath farmhouse in the heart of Cavendish, a true opportunity for those looking to restore or reimagine a home with character. Set on a generous 1.6-acre lot, the property offers endless potential with plenty of space to expand, garden, or create your dream outdoor retreat. Inside, you’ll find original hardwood floors throughout and good bones that

  Daniel Preston KW Vermont Woodstock

  50 Bates Rd, Cavendish, VT 05142
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  /57

  $845,000 Sold Sep 26, 2025

  • 2,906 Sq Ft
  • $291/SF
  • 187 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2002

  903 Old County Rd, Cavendish, VT 05142

  BACK ON THE MARKET after prior buyer’s financial constraints. Don’t miss your chance to own the Perfect Mountain House - fully furnished and ready for your enjoyment! Perched overlooking the Hawks Mountain Range, at the base of Star Mountain, this secluded haven offers the perfect escape with a babbling brook and breathtaking mountain views. Set at the end of a winding, tree-lined drive, the

  Frank Provance Diamond Realty

  903 Old County Rd, Cavendish, VT 05142
• 

  

  /36

  Est $677,886 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,215 Sq Ft

  662 Moriglioni Rd, Cavendish, VT 05142

  662 Moriglioni Rd, Cavendish, VT 05142
• 

  

  /58

  $415,000

  • 5 Beds
  • 3 Baths
  • 1,976 Sq Ft

  198 Depot St, Cavendish, VT 05153

  Welcome to this charming home nestled in a small neighborhood along the scenic Black River in Cavendish, Vermont. This inviting property combines classic Vermont character with versatile living spaces, all within walking distance of the town green, shops, restaurants, and more. Step inside through the mudroom. The kitchen offers a warm, welcoming space with a sunny dining area perfect for morning

  Katherine Burns William Raveis Real Estate Vermont Properties

  198 Depot St, Cavendish, VT 05153
• 

  

  /24

  $234,000 Sold Sep 24, 2025

  • 1,288 Sq Ft
  • $182/SF
  • 2 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1965

  126 Parker Ave, Proctorsville, VT 05153

  Looking for a comfortable, affordable home with one-level living? This 3-bedroom, 1-bath raised ranch is a great option for first-time buyers, downsizers, or anyone seeking a more manageable space. The layout is practical and inviting, a spacious eat-in kitchen, and a bright living room featuring large windows welcoming warm sunshine for added comfort. Hardwood floors through out most of the

  Frank Provance Diamond Realty

  126 Parker Ave, Proctorsville, VT 05153
• 

  

  /40

  Est $587,494 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,119 Sq Ft

  1521 Brook Rd, Cavendish, VT 05142

  1521 Brook Rd, Cavendish, VT 05142

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