Our Listings

MLS Number 5051532

• Residential Single Family
• Full Bath 2
• Address 22 Lower Howes Road
• Construction Existing
• Bedrooms 3

Section A - end of the road, low on the Hill, this Chalet style home has a lot of desirable features you have been looking for, including a mudroom entry with custom live edge bench, ski, coat and storage racks, three levels of living space, view rail deck, fire pit, family room, laundry, bunk room and full bath on ground level, 2 bedrooms, a full bath and cathedral ceiling open concept living, dining and kitchen with island, sliders to the deck, plus a loft for extra entertaining or guest quarters. Start living your dream! Plus, enjoy all the amenities that Chimney Hill offers in its 1,200-Acre All Season Resort Campus, including the exclusive members-only Club House, located at 2,000' in elevation on the Main Hill, with indoor and outdoor heated pools, hot tub, arcade room small child playroom, members-only lounge, fully-equipped kitchen for HOA members to use, community room, reading nook, outdoor grill, playground, basketball, tennis, and the extensive multi-use trail system for snowmobiling, hiking, biking, x-country skiing, seasonal pickleball and ice skating, fishing pond, lookout, Haystack Mt trail access, and more. Southern Vermont and the Deerfield Valley offer golf, boating, hiking, paddleboarding, world-class skiing and shredding, the Green Mt National Forest, music, festivals, breweries, distilleries, unique shopping, flea markets, fine dining, casual dining, and so much more!

Listed by Sigrid Pickering of Chimney Hill Realty

MLS Number 5056974

• Residential Single Family
• Full Bath 1
• Address 47 Upper Howes Way
• Construction Existing
• Bedrooms 3

On the Hill, end of the Road, double lot, brand new house with attached garage. If this is what you have been waiting for, wait no more! 2024 modular construction home with 3 bedrooms, 2 baths, one bedroom has an ensuite bath, the other 2 bedrooms share a full bath. Dining area has a slier to the deck out back, and it has a secluded feel of almost complete privacy. Enjoy all the amenities Chimney Hill Resort offers including the Clubhouse located at 2,000' in elevation featuring year-round swimming in the indoor/outdoor heated pools, hot tub, fitness, arcade, playroom, playground, patio, community room, tennis, pickleball, ice skating, 550 acres of land owned in common by the HOA, all on our beautiful 1,200-acre campus adjoining the Gren Mt National Forest. Plus there is so much more to the Deerfield Valley of Southern VT including fine dining, unique shopping, festivals, music, arts and crafts, breweries, distilleries, artisan and craft tours, hiking, biking, boating, golfing, flea markets, antiques, paddleboarding, kayaking, jet and water skiing, world class alpine skiing and shredding, and so much more!

Listed by Sigrid Pickering of Chimney Hill Realty

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

MLS Number 5049562

• Residential Single Family
• Full Bath 2
• Address 96 E Brook Crossing
• Construction Existing
• Bedrooms 3

New Listing in Section C! Quiet corner of the Resort features this Classic Chalet with a mudroom entry, bedroom with slider to the deck, a full bath, open concept kitchen with wood cabinets and breakfast bar, dining area with a bay window, living area with vaulted ceiling, wood burning fireplace and slider to the deck. Upstairs has a full bath with skylight and two bedrooms, one with a skylight and lock-off storage closet. Full walk-out basement could be finished. If you've been thinking about a Vermont getaway, this house has a lot of potential and attributes, including radiant heat flooring as one of 3 sources of heat. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous multi-use trail system for biking, hiking, snowmobiling, 3 areas with tennis courts, seasonal pickleball and ice skating, year-round swimming at the Exclusive Members-Only Club House located at 2,000' in elevation with indoor and outdoor in-ground pools, hot tub, fitness room, arcade room, small child playroom, community room, table tennis, basketball, fully-equipped kitchen for HOA members use, outdoor grill by the outdoor pool, along with a playground for young children, and members lounge. Plus, world class skiing and shredding just minutes away, golf, boating, fishing, paddleboarding, unique shops, fine dining, flea markets, festivals, music, and all the Deerfield Valley and Southern Vermont have to offer!

Listed by Sigrid Pickering of Chimney Hill Realty

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

MLS Number 5035688

• Land
• Address 406 Fox Mount Road
• Acreage 1.52
• Area VT-Windham
• PricePerSqFt 82236.84

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 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

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

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

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

MLS Number 5019848

• Land
• Address 566 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 getaway 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-acreresort 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

MLS Number 5008125

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

BUILD your dream home in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200' with fitness, year-round swimming, arcade, fully equipped kitchen for member use, aprs ski lounge, hot tub indoor and outdoor heated pools, pickleball, tennis, playground, trails, snowmobiling and more! Plus, get out and see what Southern Vermont offers including year-round skiing and shredding at the world-class Vail Mt Snow Resort, or private Hermitage Club, both within a few minutes' drive, boating on Lake Whitingham or Raponda, hiking the Valley Trail or Green Mt National Forest, biking on the Southern VT Trail Assoc system, numerous concerts, festivals, flea markets, events, yoga, music, theater, and not to leave out - fine dining, shopping, arts and craft tours, artisanal cheese, farmers markets, breweries, wineries, distilleries, chocolatiers, bakeries, equestrian events, kayaking, tubing, paddle boarding, and so much more!

Listed by Sigrid Pickering of Chimney Hill Realty

MLS Number 5008126

• Land
• Address 25 Upper Howes Way
• Acreage 0.56
• Area VT-Windham
• Utilities None

BUILD your Getaway Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200' with fitness, year-round swimming, arcade, fully equipped kitchen for member use, aprs ski lounge, hot tub indoor and outdoor heated pools, pickleball, tennis, playground, trails, snowmobiling and more! Plus, get out and see what Southern Vermont offers including year-round skiing and shredding at the world-class Vail Mt Snow Resort, or private Hermitage Club, both within a few minutes' drive, boating on Lake Whitingham or Raponda, hiking the Valley Trail or Green Mt National Forest, biking on the Southern VT Trail Assoc system, numerous concerts, festivals, flea markets, events, yoga, music, theater, and not to leave out - fine dining, shopping, arts and craft tours, artisanal cheese, farmers markets, breweries, wineries, distilleries, chocolatiers, bakeries, equestrian events, kayaking, tubing, paddle boarding, and so much more!

Listed by Sigrid Pickering of Chimney Hill Realty

MLS Number 5039354

• Land
• Address 139 Big Bend Loop
• Acreage 0.3
• Area VT-Windham
• PricePerSqFt 83333.33

One of a handful of single lots remaining on the Hill! Septic design needs updating, Power is at the street. The lot is buffered by common land on both sides, and there is a drop off at the back. Access is best at the left end of the property, where a gentle slope takes you to this level plateau. View with clearing and in non-leaf seasons. Build your dream home and enjoy all the amenities Chimney Hill, the Deerfield Valley and Southern Vermont offer including year-round swimming and hot tub in the exclusive members-only clubhouse located at 2,000' in elevation on the Hill, fitness, arcade, playroom and playground for little tykes, lounge, fully-equipped kitchen for members to use, grill for chillin' by the outdoor pool in summer, tennis, hiking, biking, golf, world class skiing and shredding, boating ice skating, festivals, breweries, distilleries, flea markets, music, fine dining antiques, unique shops, theater, arts and crafts, art, and more! The resort campus is 1,200-acres, with 300 acres owned by the members, adjoining the Green Mountain National Forest.

Listed by Sigrid Pickering of Chimney Hill Realty

MLS Number 5008127

• Land
• Address 26 Upper Howes Way
• Acreage 0.6
• Area VT-Windham
• Utilities None

BUILD your dream home in this Lot in Section A! Buyer assumes responsibility for pursuing a septic plan and permit, and all costs associated with permitting and building. Lots 25 & 26 are also available and can be combined for a double or triple lot at the end of the road/world. Enjoy the wellness VT lifestyle and all the 1,200-acre resort with our exclusive member-only clubhouse located at 200' with fitness, year-round swimming, arcade, fully equipped kitchen for member use, aprs ski lounge, hot tub indoor and outdoor heated pools, pickleball, tennis, playground, trails, snowmobiling and more! Plus, get out and see what Southern Vermont offers including year-round skiing and shredding at the world-class Vail Mt Snow Resort, or private Hermitage Club, both within a few minutes' drive, boating on Lake Whitingham or Raponda, hiking the Valley Trail or Green Mt National Forest, biking on the Southern VT Trail Assoc system, numerous concerts, festivals, flea markets, events, yoga, music, theater, and not to leave out - fine dining, shopping, arts and craft tours, artisanal cheese, farmers markets, breweries, wineries, distilleries, chocolatiers, bakeries, equestrian events, kayaking, tubing, paddle boarding, and so much more!

Listed by Sigrid Pickering of Chimney Hill Realty

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

MLS Number 5019786

• Land
• Address 452 Two Wall Way
• Acreage 0.53
• Area VT-Windham
• PricePerSqFt 47169.81

Single Lot on top of the Hill! Walk to the clubhouse from your very own vacation home, designed by you. Survey required and septic design. Lot is unimproved but has had recent favorable soil tests. 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! Soil tests show favorable conditions for a 3-bedroom home.

Listed by Sigrid Pickering of Chimney Hill Realty