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$1,350,000

A rare 110-acre offering in Sherman, CT, where open skies and eastern-facing views create a truly peaceful setting. Whether you're envisioning a private estate, family compound, or future development, this property offers endless potential. Ideally located close to town and just a short drive to NYC, it strikes the perfect balance between seclusion and accessibility. With subdivision potential for up to 18 lots, this is an exceptional opportunity in one of Fairfield County's most desirable towns.

24170921 MLS

A rare 110-acre offering in Sherman, CT, where open skies and eastern-facing views create a truly peaceful setting. Whether you're envisioning a private estate, family compound, or future development, this property offers endless potential. Ideally located close to town and just a short drive to NYC, it strikes the perfect balance between seclusion and accessibility. With subdivision potential for up to 18 lots, this is an exceptional opportunity in one of Fairfield County's most desirable towns.

00 Anderson Rd, Sherman

$869,999

A true waterfront retreat with direct frontage on Candlewood Lake, this hidden gem is tucked away behind a perimeter of mature trees, offering a private and peaceful setting within the private Holiday Point Association. The community invites an active lifestyle with scenic opportunities for walking, hiking, and biking. Outdoor living shines here, featuring an expansive 107' x 12' deck and a heated in-ground pool. A gentle path leads to the water's edge, where a private dock accommodates you. Designed for both entertaining and flexible, multi-generational living, this fully remodeled home is spacious and filled with natural light. Most rooms feature sliding doors that open to decks or balconies. The main level includes a living room with fireplace and deck access, flowing into a dining room and kitchen. A den/additional bedroom with French doors to the deck, along with fully remodeled bath completes this level. Upstairs, the impressive vaulted primary suite offers a gas fireplace, private balcony, oversized walk-in closet, and spa-like bath. An additional vaulted bedroom with its own balcony and loft, along with a full bath, provides ample space. The finished lower level expands the living area even further, with a family room featuring a wet bar a media/game room, a full bath, and plenty of storage. This opportunity will not last long, schedule your showing today!

4 Beds ⋅ 4 Baths ⋅ 24168886 MLS

A true waterfront retreat with direct frontage on Candlewood Lake, this hidden gem is tucked away behind a perimeter of mature trees, offering a private and peaceful setting within the private Holiday Point Association. The community invites an active lifestyle with scenic opportunities for walking, hiking, and biking. Outdoor living shines here, featuring an expansive 107' x 12' deck and a heated in-ground pool. A gentle path leads to the water's edge, where a private dock accommodates you. Designed for both entertaining and flexible, multi-generational living, this fully remodeled home is spacious and filled with natural light. Most rooms feature sliding doors that open to decks or balconies. The main level includes a living room with fireplace and deck access, flowing into a dining room and kitchen. A den/additional bedroom with French doors to the deck, along with fully remodeled bath completes this level. Upstairs, the impressive vaulted primary suite offers a gas fireplace, private balcony, oversized walk-in closet, and spa-like bath. An additional vaulted bedroom with its own balcony and loft, along with a full bath, provides ample space. The finished lower level expands the living area even further, with a family room featuring a wet bar a media/game room, a full bath, and plenty of storage. This opportunity will not last long, schedule your showing today!

25 Hillside Dr, Sherman

$1,495,000

Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes it equally suited for fireside evenings or lively gatherings. At its center lies the kitchen, beautifully reimagined for today while honoring its past. Soapstone countertops, custom cabinetry, and high-end appliances meet the warmth of an original fireplace and the practicality of a walk-in laundry room. Beyond the doors, your private world awaits. A heated, in-ground saltwater Gunite pool with automatic cover and outdoor shower sits tucked among lush gardens and gentle breezes, home abuts valley pond adding a hush of serenity. Extensive upgrades have been completed, from new mechanical systems to refined details throughout, ensuring comfort in every season. With central air, steam/hot air heating, and a standby generator, every modern convenience is in place. For Sale and or Lease.

6 Beds ⋅ 6 Baths ⋅ 24167831 MLS

Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes it equally suited for fireside evenings or lively gatherings. At its center lies the kitchen, beautifully reimagined for today while honoring its past. Soapstone countertops, custom cabinetry, and high-end appliances meet the warmth of an original fireplace and the practicality of a walk-in laundry room. Beyond the doors, your private world awaits. A heated, in-ground saltwater Gunite pool with automatic cover and outdoor shower sits tucked among lush gardens and gentle breezes, home abuts valley pond adding a hush of serenity. Extensive upgrades have been completed, from new mechanical systems to refined details throughout, ensuring comfort in every season. With central air, steam/hot air heating, and a standby generator, every modern convenience is in place. For Sale and or Lease.

201 Rte 37 S, Sherman

$2,250,000

TABER ACRES -This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 7.4 acres means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation, and have hiking trails, a bridge, and boardwalks! This is your chance to partner with an award-winning local design-build firm to create the home of your dreams! House plans shown are just a sample; this firm can do whatever fit your needs. Check out Sherman Building Design LLC on the web or on Instagram-extraordinary blend of superior craftsmanship and refined modern design. This is the only lot left in this small country 3 Lot subdivision; The sale price listed represents a land conveyance at 369K, and a building allowance starting at $500/ sf. Ease & proximity 5M-Metro North Train Station/4M-quaint small Town Center, Community Park w/Basketball, Tennis & Pickle Ball Courts, jogging path/Town Boat Slips/Kayak-Canoe Racks & Sandy Beach on CANDLEWOOD LAKE/2M to private golf club (The Club @ River Oaks) / 3.5M to Quaker Hill Country Club. 4M to 835 Acres Deer Pond Farm Sanctuary-Audubon Center w/its 20M of trails. 60M to NYC-makes for a perfect weekend retreat or year round living. Welcome to Small Town USA! Builder available to meet and walk land.

4 Beds ⋅ 5 Baths ⋅ 24167303 MLS

TABER ACRES -This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 7.4 acres means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation, and have hiking trails, a bridge, and boardwalks! This is your chance to partner with an award-winning local design-build firm to create the home of your dreams! House plans shown are just a sample; this firm can do whatever fit your needs. Check out Sherman Building Design LLC on the web or on Instagram-extraordinary blend of superior craftsmanship and refined modern design. This is the only lot left in this small country 3 Lot subdivision; The sale price listed represents a land conveyance at 369K, and a building allowance starting at $500/ sf. Ease & proximity 5M-Metro North Train Station/4M-quaint small Town Center, Community Park w/Basketball, Tennis & Pickle Ball Courts, jogging path/Town Boat Slips/Kayak-Canoe Racks & Sandy Beach on CANDLEWOOD LAKE/2M to private golf club (The Club @ River Oaks) / 3.5M to Quaker Hill Country Club. 4M to 835 Acres Deer Pond Farm Sanctuary-Audubon Center w/its 20M of trails. 60M to NYC-makes for a perfect weekend retreat or year round living. Welcome to Small Town USA! Builder available to meet and walk land.

8 Taber Rd, Sherman

$369,000

TABER ACRES-last lot in 3 lot subdivision. This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 400 AMP ELECTRIC SERVICE INSTALLED. 7.4 ACRES means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation, and have hiking trails, a bridge, and boardwalks! This is your chance to partner with an award-winning local design-build firm to create the home of your dreams! House plans shown are just a sample; this firm can do anything! Check out Sherman Building Design on the web or on Instagram to see their amazing work. The sale price listed represents a building allowance starting at $500/ sf. Ease & proximity 5M-Metro North Train Station/4M-quaint small Town Center, Community Park w/Basketball, Tennis & Pickle Ball Courts, jogging path/Town Boat Slips/Kayak-Canoe Racks & Sandy Beach on CANDLEWOOD LAKE/2M to private golf club (The Club @ River Oaks) / 3.5M to Quaker Hill Country Club. 4M to 835 Acres Deer Pond Farm Sanctuary-Audubon Center w/its 20M of trails. 60M to NYC-makes for a perfect weekend retreat or year round living. Welcome to Small Town USA! Builder available to meet and walk land.

24166929 MLS

TABER ACRES-last lot in 3 lot subdivision. This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 400 AMP ELECTRIC SERVICE INSTALLED. 7.4 ACRES means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation, and have hiking trails, a bridge, and boardwalks! This is your chance to partner with an award-winning local design-build firm to create the home of your dreams! House plans shown are just a sample; this firm can do anything! Check out Sherman Building Design on the web or on Instagram to see their amazing work. The sale price listed represents a building allowance starting at $500/ sf. Ease & proximity 5M-Metro North Train Station/4M-quaint small Town Center, Community Park w/Basketball, Tennis & Pickle Ball Courts, jogging path/Town Boat Slips/Kayak-Canoe Racks & Sandy Beach on CANDLEWOOD LAKE/2M to private golf club (The Club @ River Oaks) / 3.5M to Quaker Hill Country Club. 4M to 835 Acres Deer Pond Farm Sanctuary-Audubon Center w/its 20M of trails. 60M to NYC-makes for a perfect weekend retreat or year round living. Welcome to Small Town USA! Builder available to meet and walk land.

8a Taber Rd, Sherman

$390,000

Circa 1900 antique property offering character, history, and opportunity, set on a picturesque parcel with a babbling brook. The home has seen additions over the years and features 3 bedrooms and 2 full baths, ready for restoration and updating. A detached twocar barn/garage includes a spacious loft and a basement workshop-ideal for hobbyists, storage, or future conversion possibilities. Both the house and outbuildings are in need of work, making this an excellent project for contractors, investors, or buyers looking to create their dream country retreat. Centrally located in desirable Sherman, close to town amenities, schools, and outdoor recreation. A charming setting with tremendous potential awaits. Property being sold "AS IS"

3 Beds ⋅ 2 Baths ⋅ 24164142 MLS

Circa 1900 antique property offering character, history, and opportunity, set on a picturesque parcel with a babbling brook. The home has seen additions over the years and features 3 bedrooms and 2 full baths, ready for restoration and updating. A detached twocar barn/garage includes a spacious loft and a basement workshop-ideal for hobbyists, storage, or future conversion possibilities. Both the house and outbuildings are in need of work, making this an excellent project for contractors, investors, or buyers looking to create their dream country retreat. Centrally located in desirable Sherman, close to town amenities, schools, and outdoor recreation. A charming setting with tremendous potential awaits. Property being sold "AS IS"

2 Sawmill Rd, Sherman

$1,595,000

This impeccable 4 bedroom home is sited on 7.7 private acres w/four fenced paddocks and a 3/4 stall stable for horses at the end of a quiet country lane.The home has a sought after open floor plan on the 1st level. The large, eat-in kitchen has a vast granite center island & includes a 6 burner/two oven range w/egress to the outdoor stone terrace. The open flow to the family room and dining room is ideal for today's lifestyle. The family room features built-ins & an Extraordinaire Fireplace capable of heating the entire home! It is back to back with the outdoor fireplace on the expansive stone terrace. A convenient first floor bedroom with a newly renovated full bath can also be used as a gym, office or library. There is an additional room at that end of the home that is perfect for a home office, den or music room. The upper level has 3 bedrooms including the primary ensuite bedroom w/3 walk-in closets. There is a hall bath for the other two bedrooms to share. The walk-out lower level/basement has high ceilings & a poured concrete foundation. The beautifully appointed 4 stall/3 stalls plus tack room, center aisle stable has large stalls with a stone aisle. The stalls have rubber matting & the 4 fenced paddocks are all adjacent to the barn. There is a fenced round pen as well as access to the Naromi trail system. The in-ground pool is heated and fenced with lovely gardens surrounding it. A charming, in character garage/storage building graces the property as well.

4 Beds ⋅ 4 Baths ⋅ 24159584 MLS

This impeccable 4 bedroom home is sited on 7.7 private acres w/four fenced paddocks and a 3/4 stall stable for horses at the end of a quiet country lane.The home has a sought after open floor plan on the 1st level. The large, eat-in kitchen has a vast granite center island & includes a 6 burner/two oven range w/egress to the outdoor stone terrace. The open flow to the family room and dining room is ideal for today's lifestyle. The family room features built-ins & an Extraordinaire Fireplace capable of heating the entire home! It is back to back with the outdoor fireplace on the expansive stone terrace. A convenient first floor bedroom with a newly renovated full bath can also be used as a gym, office or library. There is an additional room at that end of the home that is perfect for a home office, den or music room. The upper level has 3 bedrooms including the primary ensuite bedroom w/3 walk-in closets. There is a hall bath for the other two bedrooms to share. The walk-out lower level/basement has high ceilings & a poured concrete foundation. The beautifully appointed 4 stall/3 stalls plus tack room, center aisle stable has large stalls with a stone aisle. The stalls have rubber matting & the 4 fenced paddocks are all adjacent to the barn. There is a fenced round pen as well as access to the Naromi trail system. The in-ground pool is heated and fenced with lovely gardens surrounding it. A charming, in character garage/storage building graces the property as well.

27 Osborn Rd, Sherman

$3,200,000

Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a two-car detached garage, a sauna and spa room, Tabacco Barn & an expansive horse barn with fully operational paddocks complete with water and electricity. The artist's extraordinary vision brings the estate to life, creating a museum-quality residence that embodies elegance and sophistication. Rare materials and uncompromising attention to detail are evident throughout, including white oak hardwood floors sourced from MOMA, custom handmade mahogany windows fitted with imported wavy German glass, and advanced argon gas insulation. The chef's kitchen is thoughtfully designed with gnarled brass pulls, leathered limestone marble countertops, and a handmade, hand-painted tile backsplash. The retreat was constructed using Pennsylvania Lichen Stone, with stone walls and pillars carefully built to replicate the craftsmanship of centuries past. Bronze metal seamed-heated roofs, snow guards, and cupolas crown each structure, providing both durability and architectural distinction. The grounds are beautifully landscaped with rows of English dwarf boxwoods.

3 Beds ⋅ 2 Baths ⋅ 24069608 MLS

Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a two-car detached garage, a sauna and spa room, Tabacco Barn & an expansive horse barn with fully operational paddocks complete with water and electricity. The artist's extraordinary vision brings the estate to life, creating a museum-quality residence that embodies elegance and sophistication. Rare materials and uncompromising attention to detail are evident throughout, including white oak hardwood floors sourced from MOMA, custom handmade mahogany windows fitted with imported wavy German glass, and advanced argon gas insulation. The chef's kitchen is thoughtfully designed with gnarled brass pulls, leathered limestone marble countertops, and a handmade, hand-painted tile backsplash. The retreat was constructed using Pennsylvania Lichen Stone, with stone walls and pillars carefully built to replicate the craftsmanship of centuries past. Bronze metal seamed-heated roofs, snow guards, and cupolas crown each structure, providing both durability and architectural distinction. The grounds are beautifully landscaped with rows of English dwarf boxwoods.

6 Hoyt Rd, Sherman

$279,000

This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities, including an 18-hole, par-70 golf course, tennis courts, a heated swimming pool, fitness center, and both fine and casual dining options. Located just 60 miles from NYC, 45 miles from White Plains, and only minutes to the Wingdale Metro-North station, this property combines serenity with convenience. Enjoy Sherman's charming town center nearby, offering a library, parks, sandy beach, town boat slips, and easy access to Candlewood Lake. A builder is available to discuss custom home designs that integrate seamlessly with this stunning setting.

24141352 MLS

This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities, including an 18-hole, par-70 golf course, tennis courts, a heated swimming pool, fitness center, and both fine and casual dining options. Located just 60 miles from NYC, 45 miles from White Plains, and only minutes to the Wingdale Metro-North station, this property combines serenity with convenience. Enjoy Sherman's charming town center nearby, offering a library, parks, sandy beach, town boat slips, and easy access to Candlewood Lake. A builder is available to discuss custom home designs that integrate seamlessly with this stunning setting.

41 Long River Rd, Sherman

$1,195,000

River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have full baths. Awesome lot on with golf course view. Gated community. 18 hole golf course, community pool, tennis, restaurant, gym is optional.

4 Beds ⋅ 5 Baths ⋅ 24112249 MLS

River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have full baths. Awesome lot on with golf course view. Gated community. 18 hole golf course, community pool, tennis, restaurant, gym is optional.

60 Long River Rd, Sherman