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Steeped in history and natural beauty, the Charles Ives House (ca. 1913) is a masterfully restored 18-acre West Redding summer retreat where the famed modernist composer lived and created his signature works. Designed and built by Ives himself, this iconic Arts and Crafts estate seamlessly pairs vintage authenticity with ultra-luxury modern updates. Inside, original architectural integrity shines. The spectacular great room features a double-height wood-beamed ceiling, a stunning original paned picture window, and custom staircase balusters subtly crafted to resemble musical staff notes. A country-chic chef's kitchen boasts elite appliances (La Cornue, Miele, Bosch), a cozy built-in banquette, and a fireplace inset with original vintage tile. The second-level primary suite offers panoramic views of the lush, pastoral grounds, a luxurious marble bath, and an expansive walk-in closet. Retain your own inspiration in the original music studio/office where Ives composed, complete with untouched original hardwood floors. The extraordinary 18-acre grounds double as a private resort, featuring a charming 1BR guest cottage (ca. 1900), a heated Gunite infinity-edge pool and spa, a tennis court, and a classic century-old timber frame barn with a new foundation and roof. Effortlessly sophisticated, enchantingly rustic, a rare opportunity and an absolute masterpiece of living history.

6 Beds ⋅ 6 Baths ⋅ 24181754 MLS

Steeped in history and natural beauty, the Charles Ives House (ca. 1913) is a masterfully restored 18-acre West Redding summer retreat where the famed modernist composer lived and created his signature works. Designed and built by Ives himself, this iconic Arts and Crafts estate seamlessly pairs vintage authenticity with ultra-luxury modern updates. Inside, original architectural integrity shines. The spectacular great room features a double-height wood-beamed ceiling, a stunning original paned picture window, and custom staircase balusters subtly crafted to resemble musical staff notes. A country-chic chef's kitchen boasts elite appliances (La Cornue, Miele, Bosch), a cozy built-in banquette, and a fireplace inset with original vintage tile. The second-level primary suite offers panoramic views of the lush, pastoral grounds, a luxurious marble bath, and an expansive walk-in closet. Retain your own inspiration in the original music studio/office where Ives composed, complete with untouched original hardwood floors. The extraordinary 18-acre grounds double as a private resort, featuring a charming 1BR guest cottage (ca. 1900), a heated Gunite infinity-edge pool and spa, a tennis court, and a classic century-old timber frame barn with a new foundation and roof. Effortlessly sophisticated, enchantingly rustic, a rare opportunity and an absolute masterpiece of living history.

240 Umpawaug Rd, Redding

$1,400,000

Set on over 2 private acres in a coveted neighborhood in SW Redding, this sun-filled 4 BR Colonial blends timeless style, scale and effortless living. Designed for both entertaining and daily life, the main level centers around a spacious EIK w/center island, all-new appliances and seamless flow to the adjoining family room w/gas fireplace. Sliders open to the deck and grounds beyond, creating an easy indoor-outdoor flow. A formal dining room is ideal for gatherings, while a second living room w/fireplace provides an inviting retreat. A dedicated home office with a wall of custom built-ins & a powder room complete the main floor. Upstairs, the expansive primary suite is a sanctuary, featuring dual walk-in closets and a large bath w/soaking tub. 3 additional bedrooms share an updated hall bath, while 2nd floor laundry adds convenience. The finished lower level adds versatility with a spacious recreation/media room, dedicated gym & half bath. Outside, the property truly shines. A level, usable yard is anchored by a heated gunite saltwater pool w/travertine surrounds, creating a private resort-like setting for summer entertaining and quiet afternoons. The charming barn has outstanding potential to become a pool house or studio. Minutes from Route 7, downtown Ridgefield, MetroNorth, and Topstone Park, this home delivers the rare combination of neighborhood living, privacy and convenience, just in time for summer.

4 Beds ⋅ 4 Baths ⋅ 24171032 MLS

Set on over 2 private acres in a coveted neighborhood in SW Redding, this sun-filled 4 BR Colonial blends timeless style, scale and effortless living. Designed for both entertaining and daily life, the main level centers around a spacious EIK w/center island, all-new appliances and seamless flow to the adjoining family room w/gas fireplace. Sliders open to the deck and grounds beyond, creating an easy indoor-outdoor flow. A formal dining room is ideal for gatherings, while a second living room w/fireplace provides an inviting retreat. A dedicated home office with a wall of custom built-ins & a powder room complete the main floor. Upstairs, the expansive primary suite is a sanctuary, featuring dual walk-in closets and a large bath w/soaking tub. 3 additional bedrooms share an updated hall bath, while 2nd floor laundry adds convenience. The finished lower level adds versatility with a spacious recreation/media room, dedicated gym & half bath. Outside, the property truly shines. A level, usable yard is anchored by a heated gunite saltwater pool w/travertine surrounds, creating a private resort-like setting for summer entertaining and quiet afternoons. The charming barn has outstanding potential to become a pool house or studio. Minutes from Route 7, downtown Ridgefield, MetroNorth, and Topstone Park, this home delivers the rare combination of neighborhood living, privacy and convenience, just in time for summer.

8 Windy Hill Rd, Redding

$1,250,000

Exceptional custom designed and built 4 bedroom Colonial, bathed in natural sunlight, is nestled perfectly on 2 lush level manicured acres at the end of a small quiet cul-de-sac in a coveted area of town, a perfect tranquil oasis. The open floor plan provides timeless functionality and effortless living with dramatic high ceilings and extensive walls of glass. The special landscaped entrance porch opens into the welcoming 2-story foyer which leads into the gracious living room flowing into the banquet sized dining room. The spacious chef's kitchen with center island enjoys new stainless-steel appliances, granite counters, and an adjacent dining area which steps out onto a large deck, patio and extensive lawn; ideal for everyday peaceful enjoyment, activities, entertaining as well as ample room for a pool. Directly next to the kitchen is the comfortable family room with fireplace and access to the big deck. Upstairs is the primary suite with generous bath providing a comfortable retreat, 3 family bedrooms and a hall bathroom. Come to Redding, the "Vermont of Fairfield County", and enjoy the peaceful privacy yet convenience to Topstone Park's hiking and swimming, activities at New Pond Farm, NY Metro train, commuting roads and shopping. Move-in, just in time for Summer! AGENTS PLEASE SEE SIGNIFICANT PUBLIC ADDENDUM REMARKS

4 Beds ⋅ 3 Baths ⋅ 24171692 MLS

Exceptional custom designed and built 4 bedroom Colonial, bathed in natural sunlight, is nestled perfectly on 2 lush level manicured acres at the end of a small quiet cul-de-sac in a coveted area of town, a perfect tranquil oasis. The open floor plan provides timeless functionality and effortless living with dramatic high ceilings and extensive walls of glass. The special landscaped entrance porch opens into the welcoming 2-story foyer which leads into the gracious living room flowing into the banquet sized dining room. The spacious chef's kitchen with center island enjoys new stainless-steel appliances, granite counters, and an adjacent dining area which steps out onto a large deck, patio and extensive lawn; ideal for everyday peaceful enjoyment, activities, entertaining as well as ample room for a pool. Directly next to the kitchen is the comfortable family room with fireplace and access to the big deck. Upstairs is the primary suite with generous bath providing a comfortable retreat, 3 family bedrooms and a hall bathroom. Come to Redding, the "Vermont of Fairfield County", and enjoy the peaceful privacy yet convenience to Topstone Park's hiking and swimming, activities at New Pond Farm, NY Metro train, commuting roads and shopping. Move-in, just in time for Summer! AGENTS PLEASE SEE SIGNIFICANT PUBLIC ADDENDUM REMARKS

7 Jeremiah Sanford Rd, Redding

$1,245,000

Exceptional Colonial Farmhouse Retreat: Set on 2 private acres in a sought-after cul-de-sac and neighborhood off prestigious Umpawaug Road, this ~4,000 sq ft residence offers a perfect blend of charm, comfort, and convenience in West Redding. The grounds are truly captivating, with a gunite pool, rolling lawn, mature gardens, three barn-style garages, split-rail fencing, and inviting stone patios, an ideal setting for relaxation or gatherings. Inside, the main level is bright and welcoming. The open kitchen with breakfast bar and stainless steel appliances flows into the family room with exposed beams, shiplap walls, and a cozy fireplace, as well as into the sun-filled three-season porch. Additional highlights include a private office with rich wood paneling and built-ins, a formal dining room, and a generous living room with a second hearth. Upstairs, the primary suite features a spa-inspired bath with double vanity and expansive walk-in closets. Three well-proportioned bedrooms share a recently updated hall bath, while a walk-up extra room offers flexible space for work, play, or guests. Designed for both daily living and memorable celebrations, this home shines with its resort-style pool area, stone patios, and sweeping backyard. All set in a prime West Redding setting, close to shopping, dining, schools, train, and only 60 miles from Manhattan. Recent updates include Hot Water Heater, HVAC, Refrigerator, Attic insulation, W/D.

4 Beds ⋅ 4 Baths ⋅ 24123232 MLS

Exceptional Colonial Farmhouse Retreat: Set on 2 private acres in a sought-after cul-de-sac and neighborhood off prestigious Umpawaug Road, this ~4,000 sq ft residence offers a perfect blend of charm, comfort, and convenience in West Redding. The grounds are truly captivating, with a gunite pool, rolling lawn, mature gardens, three barn-style garages, split-rail fencing, and inviting stone patios, an ideal setting for relaxation or gatherings. Inside, the main level is bright and welcoming. The open kitchen with breakfast bar and stainless steel appliances flows into the family room with exposed beams, shiplap walls, and a cozy fireplace, as well as into the sun-filled three-season porch. Additional highlights include a private office with rich wood paneling and built-ins, a formal dining room, and a generous living room with a second hearth. Upstairs, the primary suite features a spa-inspired bath with double vanity and expansive walk-in closets. Three well-proportioned bedrooms share a recently updated hall bath, while a walk-up extra room offers flexible space for work, play, or guests. Designed for both daily living and memorable celebrations, this home shines with its resort-style pool area, stone patios, and sweeping backyard. All set in a prime West Redding setting, close to shopping, dining, schools, train, and only 60 miles from Manhattan. Recent updates include Hot Water Heater, HVAC, Refrigerator, Attic insulation, W/D.

14 Guardhouse Dr, Redding

$1,028,000

Charming Colonial in Sought-After Cul-de-Sac Neighborhood. Welcome to this light-filled Colonial nestled on a quiet cul-de-sac in a highly desirable neighborhood. A newly repaved circular driveway, framed by professionally designed landscaping, sets a gracious tone as you arrive. Inside, fresh paint and refinished hardwood floors create a bright and inviting atmosphere. Elegant details abound, including classic dental molding in the formal living room. The heart of the home is the spacious kitchen, which opens to an expansive great room featuring picture windows, a cozy fireplace, and soaring vaulted ceilings - the perfect space for everyday living and entertaining. This home offers four bedrooms, including a generously sized en-suite primary bedroom. Two additional bedrooms are located on the second level, while the fourth bedroom - featuring a large picture window - is conveniently situated on the main floor. A private office above the garage provides a quiet retreat for working from home or creative pursuits. From the kitchen, sliding doors lead to a large deck overlooking a private, tree-lined backyard - ideal for outdoor dining or relaxing in a tranquil setting. On the lower level, a walk-out finished family room opens to a brand-new patio area, extending your living space and providing a great spot for gatherings or quiet evenings outdoors.

4 Beds ⋅ 3 Baths ⋅ 24129285 MLS

Charming Colonial in Sought-After Cul-de-Sac Neighborhood. Welcome to this light-filled Colonial nestled on a quiet cul-de-sac in a highly desirable neighborhood. A newly repaved circular driveway, framed by professionally designed landscaping, sets a gracious tone as you arrive. Inside, fresh paint and refinished hardwood floors create a bright and inviting atmosphere. Elegant details abound, including classic dental molding in the formal living room. The heart of the home is the spacious kitchen, which opens to an expansive great room featuring picture windows, a cozy fireplace, and soaring vaulted ceilings - the perfect space for everyday living and entertaining. This home offers four bedrooms, including a generously sized en-suite primary bedroom. Two additional bedrooms are located on the second level, while the fourth bedroom - featuring a large picture window - is conveniently situated on the main floor. A private office above the garage provides a quiet retreat for working from home or creative pursuits. From the kitchen, sliding doors lead to a large deck overlooking a private, tree-lined backyard - ideal for outdoor dining or relaxing in a tranquil setting. On the lower level, a walk-out finished family room opens to a brand-new patio area, extending your living space and providing a great spot for gatherings or quiet evenings outdoors.

7 Guardhouse Dr, Redding

$950,000

Located in the highly desirable Umpawaug section of West Redding, this exceptional home offers privacy, character, and convenience just minutes to shopping, dining, schools, train and only 60 miles from Manhattan. Set on over 2.5 acres abutting 85 acres of town owned open space, the property provides a rare combination of usable land and protected natural surroundings in a prime location. The chef's kitchen features white shaker cabinets with crown molding, butcher block counters, a dark gray island accented with a dark stone top complete with a farmhouse sink. It opens to a living room with stone fireplace and reclaimed wood mantel. The formal dining room w/ second fireplace showcases a brand-new 16' wide wall of floor-to-ceiling glass sliders that flood the space w/ natural light & open to a new composite deck w/ black rail system and brand-new patio with fieldstone knee walls. Extensive hardscape improvements create ideal outdoor living and entertaining space. The exterior showcases striking stonework accents, newer roof and a contrasting color scheme that enhances curb appeal. Updated baths offer modern finishes. The 2nd floor includes 2 bedrooms plus office/nursery; the main level features a spacious primary bedroom with walk-in closet. Per town, septic updated in '22 supports 4 bedrooms, offering expansion potential. Experience the rare blend of privacy, natural beauty & timeless New England charm that makes Redding one of Fairfield County's most treasured towns!

3 Beds ⋅ 3 Baths ⋅ 24154748 MLS

Located in the highly desirable Umpawaug section of West Redding, this exceptional home offers privacy, character, and convenience just minutes to shopping, dining, schools, train and only 60 miles from Manhattan. Set on over 2.5 acres abutting 85 acres of town owned open space, the property provides a rare combination of usable land and protected natural surroundings in a prime location. The chef's kitchen features white shaker cabinets with crown molding, butcher block counters, a dark gray island accented with a dark stone top complete with a farmhouse sink. It opens to a living room with stone fireplace and reclaimed wood mantel. The formal dining room w/ second fireplace showcases a brand-new 16' wide wall of floor-to-ceiling glass sliders that flood the space w/ natural light & open to a new composite deck w/ black rail system and brand-new patio with fieldstone knee walls. Extensive hardscape improvements create ideal outdoor living and entertaining space. The exterior showcases striking stonework accents, newer roof and a contrasting color scheme that enhances curb appeal. Updated baths offer modern finishes. The 2nd floor includes 2 bedrooms plus office/nursery; the main level features a spacious primary bedroom with walk-in closet. Per town, septic updated in '22 supports 4 bedrooms, offering expansion potential. Experience the rare blend of privacy, natural beauty & timeless New England charm that makes Redding one of Fairfield County's most treasured towns!

74 Seventy Acre Rd, Redding

$250,000

Highest and best Tuesday at noon. Great chance to build your dream home or renovate barn in to dream home. Small cottage and gristmill in addition to Large Barn on sloping property with pond. House (#53)across street can be bought together with this land. This land is in a trust which was included in Saltbox across Street. There are not plans, perk or maps for the property so buyers please do you due dilegence. Property is being sold as is with all contents to transfer with the sale.

24208124 MLS

Highest and best Tuesday at noon. Great chance to build your dream home or renovate barn in to dream home. Small cottage and gristmill in addition to Large Barn on sloping property with pond. House (#53)across street can be bought together with this land. This land is in a trust which was included in Saltbox across Street. There are not plans, perk or maps for the property so buyers please do you due dilegence. Property is being sold as is with all contents to transfer with the sale.

58 Umpawaug Rd, Redding

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