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8 Little Bend Wilmington VT 05363

MLS Number 5063727

  • Residential Single Family
  • Full Bath 2
  • Address 8 Little Bend
  • Construction Existing
  • Bedrooms 4

Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook below, and living room with wood-burning fireplace for taking the chill off. Second level has two bedrooms and a half bath. Lower level has a family room with a gas fired stove for added warmth, full bath and guest room. Furnishings included! Enjoy all the amenities Chimney Hill offers including pickleball, tennis, hiking, biking, cross country skiing, ice skating, sledding, our exclusive member-only Clubhouse located at 2,000' in elevation on our 1,200 Acre Resort Campus and features indoor and outdoor heated pools for year-round swimming, hot tub, fitness room, arcade room, playroom, community room, fully-equipped kitchen, playground, and on-site management. World Class skiing and shredding are minutes away, as well as fine dining golf, boating, shopping, music, breweries, distilleries, wineries, antiques, flea markets, festivals, the Green Mountain National Forest, and more!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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118 Chimney Hill Road Wilmington VT 05363

Wilmington, VT118 Chimney Hill Road

Price$125,000

Est. Mortgage: $/month

MLS Number 5048056

  • Land
  • Acreage 1.31
  • Area VT-Windham
  • PricePerSqFt 95419.85
  • Zoning R1

Brand new Quad Lot right on Chimney Hill Road! Former lots M118 & M119 have had two additional parcels added on each end to form a 1.31-Acre Lot suitable for a three-bedroom single family home. Build your dream home and live the all-season resort lifestyle. Chimney Hill Owners Association is located on 1,200 acres adjacent to the Green Mt. National Forest, with 550 acres owned in common by the HOA members. HOA Members enjoy more recreational amenities for less dues than other associations because the homes and land are individually owned. Three tennis courts, pickleball in season, ice skating in season, 2 playgrounds, a fishing pond, a multi-use trail network, a members only exclusive Club House featuring indoor and outdoor heated pools, hot tub, fitness, arcade, playroom, community room, fully equipped kitchen, members lounge, reading nook and more! Enjoy world class skiing and shredding within a 10-minute drive, and all the Deerfield Valley offers including boating, golf, hiking, biking, shopping, fine dining, pickleball, antiquing, flea market, breweries, distilleries, festivals, music, and more!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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408 Fox Mount Road Wilmington VT 05363

Wilmington, VT408 Fox Mount Road

Price$125,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5035898

  • Land
  • Address 408 Fox Mount Road
  • Acreage 1.58
  • Area VT-Windham
  • PricePerSqFt 79113.92

Top of the Hill at the end of the Road! Triple building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sacon Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Club House. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, the CHOA exclusive members-only Clubhouse located near the top of Chimney Hill at 2.000' in elevation, with year-round swimming in our heated pools, hot tub, lounge, arcade, fitness room, community room, fully equipped kitchen, reading nook, and toddler playroom. The CHOA Resort covers 1,200-Acres, with 300-Acres owned in common by the HOA. The common land has 3 tennis courts, seasonal pickleball and ice skating, an extensive trail system for hiking, snowmobiling, and playing, a fishing pond, and the trailhead to Haystack Mountain. Music festivals, theater, arts and crafts tours, flea market, fine dining, unique shopping, antiques, breweries, distilleries, wineries, boating, golf, bicycling and more - heck, you can hike from Chimney Hill to Mt Snow on the Valey Trail too!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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402 Fox Mount Road Wilmington VT 05363

Wilmington, VT402 Fox Mount Road

Price$85,000

Est. Mortgage: $/month

MLS Number 5035426

  • Land
  • Address 402 Fox Mount Road
  • Acreage 1.04
  • Area VT-Windham
  • PricePerSqFt 81730.77

Top of the Hill at the end of the Road! Double building lot with a current 3-bedroom septic design! Be part of the new 5-Lot Cul de Sac on Fox Mt Road. These Lots have a SW orientation and sit at about 2,400' in elevation and adjoin the National Forest - yet are within walking distance to the Clubhouse. If you've been thinking of building your dream home, this is a great opportunity! Enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, the CHOA exclusive members-only Clubhouse located near the top of Chimney Hill at 2.000' in elevation, with year-round swimming in our heated pools, hot tub, lounge, arcade, fitness room, community room, fully equipped kitchen, reading nook, and toddler playroom. The CHOA Resort covers 1,200-Acres, with 300-Acres owned in common by the HOA. The common land has 3 tennis courts, seasonal pickleball and ice skating, an extensive trail system for hiking, snowmobiling, and playing, a fishing pond, and the trailhead to Haystack Mountain. Music festivals, theater, arts and crafts tours, flea market, fine dining, unique shopping, antiques, breweries, distilleries, wineries, boating, golf, bicycling and more - heck, you can hike from Chimney Hill to Mt Snow on the Valey Trail too!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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404 Fox Mount Road Wilmington VT 05356

Wilmington, VT404 Fox Mount Road

Price$55,000

Est. Mortgage: $/month

MLS Number 5082241

  • Land
  • Address 404 Fox Mount Road
  • Acreage 0.5
  • Area VT-Windham
  • PricePerSqFt 110000

Top of the Hill. Build your dream home! One of 2 remaining lots on the new Fox Mt. Cul de Sac, and the only single lot. These have had recent soil tests showing the lot is suitable for a 3-bedroom home. The Lot is oriented to the Southwest, towards Bennington. Plus, enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, fine dining, music, flea markets, festivals, hiking, biking, golfing, breweries, distilleries, wineries, unique shops, artisans, fine artists, theater, boating, snowmobiling, year-round swimming between CHOA's exclusive members-only Clubhouse located at 2,000' on the1,200 Acre Resort Campus, and beach access to Lake Raponda. Pickleball, tennis, basketball, arcade, playground, fishing pond, grill by the outdoor heated pool, or enjoy the hot tub, and fitness room. Chimney Hill just had its 50th anniversary, and has a multi-generational following, something that is rare these days.

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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564 Upper Dam Road Wilmington VT 05363-0253

Wilmington, VT564 Upper Dam Road

Price$50,000

Est. Mortgage: $/month

MLS Number 5019824

  • Land
  • Address 564 Upper Dam Road
  • Acreage 0.93
  • Area VT-Windham
  • PricePerSqFt 53763.44

Double lot on top of the Hill! Recent soil tests say this looks good for a 3-bedroom home! If you've been thinking of building your dream home, this is a great spot. Walk to the Clubhouse, seasonal views, about 2,400' in elevation, facing SE. Enjoy all the amenities Chimney Hill offers including year-round swimming, in-season tennis, basketball, pickleball, ice skating, pond fishing, hiking, biking, snowmobiling, and more on our 1,200-acre resort campus featuring the exclusive members-only Clubhouse located at 2,000' in elevation, and members enjoy 300 acres of common land with an extensive trail network. Plus, the Deerfield Valley, and southern Vermont boast world class skiing and shredding at Vail's Mt Snow Resort, or the private Hermitage Club, Boating on Lake Whitingham or Lake Raponda, the Green Mt National Forest, shopping, fine dining, golf, breweries, distilleries, antiques, music, theater, arts and crafts, flea markets, and more!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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CH #B033

B033 83 West Road Wilmington VT 05363

Wilmington, VTB033 83 West Road

Rental Price$28,500
Long Term Winter Rental

Rented

Listing Number LTW-B033

  • Exclusive Long-Term Rentals Long Term Winter Rentals
  • Bathroom 3
  • Maximum Occupants 10
  • Bedrooms 5
  • Property Name CH #B033

 *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington and fifteen minutes from Mount Snow. INCLUDED: Rubbish, TV, and Clubhouse. TENANT PAYS: Heat, Electric, & Internet. State of Vermont, Department of Taxes, Meals and Rooms Tax Account #10024438

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

30 Upper Howes Way Wilmington VT 05363

Wilmington, VT30 Upper Howes Way

Price$25,000

Est. Mortgage: $/month

MLS Number 5052334

  • Land
  • Address 30 Upper Howes Way
  • Acreage 0.5
  • Area VT-Windham
  • PricePerSqFt 50000

Affordable Single Lot with favorable soil tests for a 3-bedroom single family home in Chimney Hill. Surrounded on two sides by common land, this lot is in a quiet section of the Main Hill. Buyer is responsible or securing a septic permit. Join a community of over 560 homes sited on 1,200-Acres adjoining the Green Mt. National Forest, with 550-Acres owned in common by the membership of the HOA. Chimney Hill offers the most recreational amenities for the least amount in annual dues because it is a Homeowners Association, so each member owns their own home and the land it sits on. Amenities include the exclusive members-only Club House, located at 2,000' in elevation, with sweeping seasonal views of the ridgeline and Deerfield Valey, indoor and outdoor heated pools, fitness room, hot tub, arcade, small child playroom, members-only lounge, fully-equipped kitchen for members to use, community room, reading nook, outdoor grill by the outdoor pool, playground, tennis, basketball, and more! A network of trails, and common recreation areas for hiking, biking, playing, snowmobiling, dog walking, and more. Plus, Southern Vermont and the Deerfield Valley offer world class skiing and shredding, boating, golf, pickleball, fine dining, unique shopping, festivals, flea markets, theater, music, and even more!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28 Upper Howes Way Wilmington VT 05363

Wilmington, VT28 Upper Howes Way

Price$25,000

Est. Mortgage: $/month

MLS Number 5081925

  • Land
  • Address 28 Upper Howes Way
  • Acreage 0.6
  • Area VT-Windham
  • PricePerSqFt 41666.67

Sweet Spot tucked away in a quiet corner of the Hill, ready for you to build your vacation getaway. Recent soil tests are favorable for a 3-bedroom house. Enjoy all the amenities Chimney Hill offers on its 1,200 Acre Resort Campus, including year-round swimming, seasonal tennis and pickleball, ice skating with a warming hut full of skates to use, hiking, biking, snowmobiling right from your house in some sections, the fishing pond that is stocked with trout for the annual fishing derby, the members-only exclusive Clubhouse with fitness, arcade, hot tub, indoor and out-door heated pools, community room, table tennis, fully-equipped kitchen for members to use, reading nook, aprs ski lounge, outdoor grill by the pool in summer, and so much more!

Listed by Sigrid Pickering of Chimney Hill Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

254 8 Deer Run

254 8 Deer Run Wilmington VT 05363

Wilmington, VT254 8 Deer Run

Rental Price$22,500
Long Term Winter Rental

Rented

Listing Number LTW-254

  • Exclusive Long-Term Rentals House - 4 Bedroom,Long Term Winter Rentals,Vacation Rental
  • Village Chimney Hill
  • Bathroom 4
  • Bedrooms 4
  • Property Name 254 8 Deer Run

Pet Friendly (1 Dog)   *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington and fifteen minutes from Mount Snow. INCLUDED: Rubbish, TV, and Clubhouse. TENANT PAYS: Heat, Electric, & Internet. State of Vermont, Department of Taxes, Meals and Rooms Tax Account #10024438

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

670 Murray's Cabin

670 9 Greer Court Wilmington VT 05363

Wilmington, VT670 9 Greer Court

Rental Price$20,500
Long Term Winter Rental

For Rent

Listing Number LTW-670

  • Exclusive Long-Term Rentals Log Cabin,Long Term Summer Rentals,Long Term Winter Rentals
  • Village Chimney Hill
  • Bathroom 3
  • Maximum Occupants 6
  • Bedrooms 3

     *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** Combination tub/shower, jetted tub, queen, shower, sleep sofa /futon, library, playground, pond, restaurants, Heating, Internet, Parking, Wood Stove, Wifi, Coffee Maker, Dishes & Utensils, Kitchen, Microwave, Oven, Refrigerator, Stove, Toaster, Dining Table, antiquing, scenic drives, sight seeing, sledding, walking, ATM/bank, fitness center, laundromat, Mountain View, Resort, Rural, Communal Pool, bedroom, cycling, fishing, hiking, ice skating, mountain biking, skiing, swimming, tennis, children welcome, flexible, necessary, Staff, Adventure, Away From It All, Budget, Family, Sports & Activities All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington, ten minutes from The Hermitage, and fifteen minutes from Mount Snow. INCLUDED: Rubbish, Plowing, TV, and Clubhouse. TENANT PAYS: Heat, Electric, & Internet. State of Vermont, Department of Taxes, Meals and Rooms Tax Account #10024438

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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#532 9 Scattered Timber Road

532 9 Scattered Timber Wilmington VT 05363

Wilmington, VT532 9 Scattered Timber

Rental Price$20,000
Winter seasonal rental

Rented

Listing Number LTW-532

  • Exclusive Long-Term Rentals House - 4 Bedroom,Log Home,Long Term,Long Term Furnished,Long Term Winter Rentals,Seasonal - Negotiable,Single Family Home,Ski Season Rental,Vacation Rental,Winter Rental,Winter Seasonal
  • Village Chimney Hill
  • Bathroom 2
  • Maximum Occupants 9
  • Bedrooms 4

Rented for the 2024 - 2025 Season   *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** This immaculate log home is perfect for making winter memories with your family and has plenty of room for the friends, guests and extended family! With a beautifully renovated kitchen and large dining area, entertaining the crowd is no problem and with two separate living areas (one in the lower level), the kids can have their own space while the adults have theirs. Offering 4bedrooms and 2.5bathrooms on three levels, this home is warm and comfortable.  Included with your winter rental is a cord of wood for the woodstove, plowing, curbside trash pickup and access to all of Chimney Hill's top notch amenities including the Clubhouse. Pets will be considered and we do require that you bring your personal choice of sheets, towels and pillowcases. WiFi is available.   

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

CH#908

908 12 Fawn Run Wilmington VT 05363

Wilmington, VT908 12 Fawn Run

Rental Price$20,000
Long Term Winter Rental

Rented

Listing Number LTW-908

  • Exclusive Long-Term Rentals 3 Bedroom Home,Long Term Winter Rentals
  • Village Chimney Hill
  • Location Chimney Hill
  • Bathroom 2
  • Maximum Occupants 6

Rented for the 2025-2026 Winter Season   Available Long Term and Short Term   Beautiful updated ski chalet on a private cul de sac in the Chimney Hill resort. Sleeps 9+ guests. New owner has provided all new bedding,kitchen small appliances, dishes, cookware, wine glasses, coffee maker with pot and k-cup etc. Entryway includes storage area for boots, skis, and boards. Plenty of seating areas, upstairs separate loft area for kids. All new Smart TVs. Roaring fireplace, and grand picturesque windows to watch the snow fall.  Minutes to Mount snow and historic downtown Wilmington. Many area attractions, restaurants and shops.              Your stay includes amenities at Chimney Hill club house. Amenities include hiking trails, outdoor skating rink, indoor heated pool, sauna, hot tub, fully equipped gym, showers and locker room , game room for kids, fireplaces and luxury couches to unwind and enjoy your own food and wine.    Master-sleeps 2-queen size bed, his and her full size closets, dresser, sitting area, and Smart tv   Bedroom-1-sleeps 2, twin beds, closet, dresser, Smart tv   Bedroom -2-sleeps 4,  full size beds, full closet, dresser, Smart tv, sliders to outdoor deck   Loft-sleeps 2, pullout leather sleeper sofa, twin size daybed. Smart TV   Laundry Room -washer and dryer on main floor   Bathrooms-2- main floor and upstairs, tubs/shower  

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

CH #909

909 8 Fawn Run Wilmington VT 05363

Wilmington, VT909 8 Fawn Run

Rental Price$20,000
Long Term Winter Rental

Rented

Listing Number LTW-909

  • Exclusive Long-Term Rentals 3 Bedroom Home,Long Term Winter Rentals
  • Village Chimney Hill
  • Location On Hill
  • Bathroom 2
  • Maximum Occupants 8

Long Term Winter Rental 25/26   "We would like to welcome you in our happy place to get away, located part-way up the hill on Fawn Run.  We are a quick walk to the fishing pond and many trails connecting you to additional amenities, including the club house. Whether you have spent many vacations in Chimney Hill or if this is your first visit, we think you’ll love our serene house, with picturesque views year-round, from snow-covered mountains in the winter to the lush green leaf-cover that turns to bright colors in the Fall. The house has 3 bedrooms and 2.5 bathrooms, providing plenty of space for a group to gather. You’ll enter the house through our mudroom that has space to store your gear for all those outdoor adventures.  If you find you still need more storage space, there is ample space in the garage on the basement level. The master bedroom is on the upper level and has a queen bed, large skylight with lots of sunlight during the day and beautiful stars at night, flat-screen smart TV, and an ensuite full bathroom. The master bedroom exits onto a loft that overlooks the main room and has views out the large picture windows on the front of the house.  The loft is a wonderful spot to curl up with a book and take in the views.  The main level includes two more bedrooms, one with a queen bed and another larger room with 2 twins and a queen.  The large main room includes the living room, well-equipped kitchen, and dining area so you can spend time together.  The living room has lots of comfy seating, another large flat-screen smart TV, and a gas stove to provide ambiance and warmth at the flip of a switch without the hassle of hauling wood. There is another full bath on the main floor.  Step right outside from the main room onto the large deck where you can take in the views from our seating and dining space or the relaxing hot tub (4-6 person, year-round) while also listening to your favorite music on our outdoor stereo.  For those times when you want to gather outside by the fire, we also have an old Vermont Castings wood stove that has been converted into an outdoor fireplace with Adirondack chairs on the back lawn. For those times when part of the group wants to get away, there is also a bonus room in the basement with another large sectional and a large flat-screen smart TV with DVD player as well as a half bath.  The laundry is also located in the basement."   *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington, ten minutes from The Hermitage, and fifteen minutes from Mount Snow. Rent Includes: Plowing, Rubbish, 1 Cord Firewood, TV, and Clubhouse. Tenant Pays:  Electric, heat, and Internet.

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

CH #573

573 22 Reservoir Lane Wilmington VT 05363

Wilmington, VT573 22 Reservoir Lane

Rental Price$18,500
Winter Seasonal Rental

Rented

Listing Number LTW-573

  • Exclusive Long-Term Rentals House,Long Term Winter Rentals,Seasonal,Ski Season Rental,Winter Rental,Winter Seasonal
  • Village Chimney Hill
  • Bathroom 3
  • Maximum Occupants 10
  • Bedrooms 5

    Sorry, no pets allowed. *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington, ten minutes from The Hermitage, and fifteen minutes from Mount Snow. INCLUDED: Rubbish, Plowing, TV, and Clubhouse. TENANT PAYS: Heat, Electric, & Internet.

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

CH #A115

#A115 34 Three Streams Way Wilmington VT 05363

Wilmington, VT#A115 34 Three Streams Way

Rental Price$18,500
Long Term Winter Rental

Rented

Listing Number LTW-A115

  • Exclusive Long-Term Rentals Long Term Winter Rentals,Seasonal,Ski Season Rental,Winter Rental,Winter Seasonal
  • Village Chimney Hill
  • Location Upper Hill
  • Bathroom 2
  • Maximum Occupants 6

  *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** A sweet little cape tucked away on a quiet corner on the edge of the Green Mountain National Forest located in Southern Vermont.3 / 4 bedroom, 2 bath home with an open floor plan. Come enjoy the foliage (or snowfall) from the large front deck or just sit back and watch the snow fall and leaves change from the large windows and sliding glass doors from inside. It’s also the perfect spot to catch the sunrise in the Winter months. The open concept living makes it easy to enjoy fires in the wood burning fireplace from the dining room or breakfast bar as well. The vaulted ceilings, large windows, beautiful woodland vistas, white-washed pine walls provide the quintessential Vermont experience. The loft provides a separate living space perfect for a game, puzzle, reading, watching a movie or just taking a quick snooze on the couch or reclining love seat. Activities await you! Hiking trails just outside your door, nearby lakes, boutique shopping or just relax by an outdoor fire pit under the stars. Come Winter – Mount Snow is just a quick 10/15 min drive, snowshoe, sled on the nearby trails, nearby ice skating. Inside there is a Smart TV, family friendly laptop workspace, board games, & amp; puzzles. Our home is near the top of Chimney Hill on a quiet tree lined cul-de-sac, just a 20 min walk to the Club House. The drive up is quite steep, 4WD/AWD is recommended during the Winter months. Give us a follow on Instagram @three.streams for an inside look   All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington, ten minutes from The Hermitage, and fifteen minutes from Mount Snow. State of Vermont, Department of Taxes, Meals and Rooms Tax Account #10024438

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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CH #B127

B127 34 High Top Road Wilmington VT 05363

Wilmington, VTB127 34 High Top Road

Rental Price$18,000
Mid-November through mid April

Rented

Listing Number LTW-B127

  • Exclusive Long-Term Rentals 3 Bedroom Home,House,Long Term,Long Term Winter Rentals,Seasonal,Vacation Rental,Winter Rental,Winter Seasonal
  • Village Chimney Hill
  • Bathroom 2
  • Maximum Occupants 6
  • Bedrooms 3

  Welcome to our home where you’ll feel like you’re retreating, not camping! Light fills the living areas on both sides of the house.  Your master bedroom (king) and bath are on the first floor. The kitchen is generously equipped with cookware and matching dinnerware with plenty of room for meal prep.  Eight of you can easily fit at the dining room table.  We’ve converted our antique musket cabinet into a storage space for your “spirits” and other items.  The new gas fireplace, easy to operate with remote, provides extra heat and ambiance after a day on the slopes. If you’re inclined to grill out, you’ll be protected from snow and wind on the screened-in porch.  The loft upstairs with a queen sleeper sofa provides the perfect spot for reading, games and TV.  One bedroom has twin beds with brand new mattresses and a walk-in closet, the other has a very comfortable queen sized bed and two ample closets.   You are welcome to use our mix and match bed sheets and pillow cases.  At the time of this writing (July 8, 2018) we are in the process of building a large deck accessible from the downstairs living area and the screened-in porch where you can continue to enjoy Vermont’s sun and fresh air.  Flat screen TV’s are located in the master bedroom, living room and loft.   Roku internet connection is available in the living room -Owners   All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington and fifteen minutes from Mount Snow. INCLUDED: Linens, Sheets, Rubbish, Plowing, TV, and Clubhouse. TENANT PAYS: Heat, Electric, & Internet.

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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CH #416

416 6 Shincracker Way Wilmington VT 05363

Wilmington, VT416 6 Shincracker Way

Rental Price$17,500
Long Term Winter Rental

For Rent

Listing Number LTW-416

  • Exclusive Long-Term Rentals Long Term Summer Rentals,Long Term Winter Rentals,Monthly Rental,Short Term Rental
  • Village Chimney Hill
  • Location Chimney Hill
  • Bathroom 2
  • Maximum Occupants 6

Chimney Hill House, 15 Mins to Mt Snow, Clubhouse access w/ indoor pool, hot tub *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** Fully equipped 3 bedroom 2 bathroom house located near the top of Chimney Hill. Just bring your sports gear, clothes and food and everything else is there. Fully equipped kitchen with everything needed to prepare meals, including *condiments, *cooking oils, *spices, ete…….. *Kitchen cleaning supplies Premium beds with duvets (down comforter inside washable cover) for great night’s sleep – previous guest have said “it’s like sleeping in cloud”. (**All bedding is supplied with this home) High quality sheets, pillowcases and comforter cover are all white and are washed with bleached to disinfect after every guest/renter change over by housekeeping. Bathrooms are stocked with linens, *toiletries, *soaps, *shampoo and *cleaning supplies. Blazing fast 1 Gb/S fiber to home internet/Wi-Fi Land line phone with unlimited calling to the US and Canada (3) 4K Smart TVs all with access to premium on demand services Netflix and Prime Video and hundreds of ad supported services/channels on Xumo, Tubi and You Tube and broadcast services from the Hartford/ Springfield area i.e. ABC HD, CBS HD, NBC HD, FOX HD…….. High quality 5.1 Surround Sound system in the living room for the best movie experience or listening to your favorite music (smart phone input for audio) Large woodstove in the living room for warming up after a cold day on the slopes or out the snowmobiles Washer and Dryer – *with clothes detergent supplied Programmable heat control (24/7) in every room Security System and advanced interconnected smoke/CO alarms Generator for back-up power Location features The house is about a 15 minute drive to Mount Snow (Carinthia base area) and from house 19 minutes to main base lodge area. Direct access to the VAST snowmobile trail system from the house (ride right out of the driveway onto trail system) Walkable distance to the clubhouse For hiking the trailhead to the Haystack Mountain trail to summit is walking distance from the house. The Chimney Hill trail and Valley trail are also nearby. The Harriman Reservoir is about 3 miles from the house for motor boating, water skiing and tubing, PWC’s, sailing, canoeing and kayaking, picnicking and swimming. Boat/water toy rentals are available at the reservoir. Minutes to downtown Wilmington and Dover for shopping and dining out (*) For longer term rentals home will be stocked at the beginning of the stay and renter will need to purchase item as needed during their stay. (**) Renter/Guest is responsible for any damages i.e. tears, stains that cannot be removed.(Deposit required) State of Vermont, Department of Taxes, Meals and Rooms Tax Account #10024438

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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CH #C199

C199 9 Low Land Loop Wilmington VT 05363

Wilmington, VTC199 9 Low Land Loop

Rental Price$16,500
Long Term Winter Rental

Rented

Listing Number LTW-C199

  • Exclusive Long-Term Rentals Chalet,Long Term Winter Rentals
  • Bathroom 2
  • Maximum Occupants 8
  • Bedrooms 4
  • Half Baths 1

Coming soon!!   Wilmington is waiting for you! With 2 queen beds, 3 twin beds, and 1 full bed, this amazing 4 bedroom property is perfect for families or groups of friends. You'll find everything you need, from an open living/dining room space for adults to a separate TV room for the kids. There is even a spacious mudroom entryway to store your ski and snowboard equipment. Plenty of space in the 3 bathrooms (2 full, 1 half) available. Kick back and relax with a cozy indoor fire after a day at the slopes, or be adventurous and build a fire outdoors in the fire pit. Take a 2 minute drive to the skating pond or a 5 minute drive to our association's clubhouse. Enjoy everything our clubhouse has to offer- indoor and outdoor swimming pool, game room, gym and communal recreation space. The property is also located steps from the VAST snowmobile trails, A skier's dream, Mt Snow is just a short ride away from this Chimney Hill property.  Our Place in VT is waiting for you!   All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington and fifteen minutes from Mount Snow. INCLUDED: Rubbish, TV, and Clubhouse. TENANT PAYS: Heat, Electric, & Internet. State of Vermont, Department of Taxes, Meals and Rooms Tax Account #10024438

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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CH #B072

B72 33 North Road Wilmington VT 05363

Wilmington, VTB72 33 North Road

Rental Price$16,000
Long Term Winter Rental

Rented

Listing Number LTW-B072

  • Exclusive Long-Term Rentals Long Term Winter Rentals
  • Village Chimney Hill
  • Bathroom 2
  • Maximum Occupants 6
  • Bedrooms 3

Rented for the 2023 - 2024 Season *****HOME IS FULLY EQUIPPED EXCEPT FOR SHEETS, PILLOWCASES, TOWELS,  SHAMPOO ETC.***** All rentals through Chimney Hill Rental Management include use and access to all of the Chimney Hill amenities. This includes use of the Chimney Hill Clubhouse. At the Clubhouse, you will find: a fitness room, arcade games, ping pong table, pool table, theater, sitting/reading rooms, BYO Bar, summer BBQ, horseshoe court, kids play area, indoor hot tub, indoor pool, outdoor pool, lighted tennis court, lighted basket ball court, bocce court, and volleyball court. Other amenities include a fishing pond, picnic areas, more tennis courts, skating rink and warming hut, VAST snowmobile trails, and hiking trails. Chimney Hill is located five minutes from downtown Wilmington, ten minutes from The Hermitage, and fifteen minutes from Mount Snow. HOME IS PET FRIENDLY INCLUDED: Rubbish, Plowing, TV, and Clubhouse. TENANT PAYS: Heat, Electric, & Internet.

Listed by of Chimney Hill (802-464-2181)

$
$
%
$/month over payments
Federal 30-year interest rate: 6.37% last updated on Apr 9, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated April 12, 2026 9:37 AM EDT