Homeswithjeremy.com Search Results

$899,000

Exceptional opportunity in a prime Lower Weston location directly bordering Westport - just minutes to both Weston and Westport town centers, award-winning schools, shopping, dining, trains and commuting routes. Privately set on a beautiful 2-acre lot on a quiet country lane, this property offers endless potential for buyers with vision. Whether you choose to renovate, customize, expand, or build your dream home from the ground up, the setting and location are truly outstanding. Existing features include a freeform in-ground pool, expansive patio, underground utilities, and a remarkable 12-car barn/garage ideal for car enthusiasts, hobbyists, storage, or creative use. Surrounded by nature and offering exceptional privacy, this is a rare chance to create something truly special in one of Fairfield County's most desirable locations. Property being sold as-is. Pool hasn't been open in a few years.

4 Beds ⋅ 2 Baths ⋅ 24172740 MLS

Exceptional opportunity in a prime Lower Weston location directly bordering Westport - just minutes to both Weston and Westport town centers, award-winning schools, shopping, dining, trains and commuting routes. Privately set on a beautiful 2-acre lot on a quiet country lane, this property offers endless potential for buyers with vision. Whether you choose to renovate, customize, expand, or build your dream home from the ground up, the setting and location are truly outstanding. Existing features include a freeform in-ground pool, expansive patio, underground utilities, and a remarkable 12-car barn/garage ideal for car enthusiasts, hobbyists, storage, or creative use. Surrounded by nature and offering exceptional privacy, this is a rare chance to create something truly special in one of Fairfield County's most desirable locations. Property being sold as-is. Pool hasn't been open in a few years.

27 Huckleberry Ln, Weston

$1,695,000

Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary suite offers its own stone fireplace and a luxurious bath with radiant heated floors. The kitchen is equipped with Wolf, Bosch, and Liebherr appliances. The dining room features a hidden dry bar and a glassware cabinet, with sliders to the top deck for outdoor dining if desired. Upstairs, there are three additional bedroom suites with updated baths, plus a smaller third-floor bedroom ideal for an office or flex space. The finished walk-out lower level includes radiant heat, a bedroom, a full bath, an office, a gym, laundry, and a kitchenette. Outdoors, enjoy a heated Gunite pool and spa with a bluestone patio, surrounded by serene woodland views. Additional features include the Sonos system, whole-house generator, and air purification. Minutes to town and top-rated schools, this move-in-ready retreat is ideal for weekend or year-round living.

4 Beds ⋅ 4 Baths ⋅ 24171415 MLS

Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary suite offers its own stone fireplace and a luxurious bath with radiant heated floors. The kitchen is equipped with Wolf, Bosch, and Liebherr appliances. The dining room features a hidden dry bar and a glassware cabinet, with sliders to the top deck for outdoor dining if desired. Upstairs, there are three additional bedroom suites with updated baths, plus a smaller third-floor bedroom ideal for an office or flex space. The finished walk-out lower level includes radiant heat, a bedroom, a full bath, an office, a gym, laundry, and a kitchenette. Outdoors, enjoy a heated Gunite pool and spa with a bluestone patio, surrounded by serene woodland views. Additional features include the Sonos system, whole-house generator, and air purification. Minutes to town and top-rated schools, this move-in-ready retreat is ideal for weekend or year-round living.

129 Davis Hill Rd, Weston

$3,149,000

Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with apartment, and converted barn, largely by architect Jack Franzen. The main residence offers over 11,000 square feet with 7 bedrooms, 6 full and 2 half baths. The two-story media wing includes a home theater, library, office, and billiard room. The conservatory overlooks stone terraces, a waterfall and pond, and gardens. The primary suite and office have private balconies. The estate is further distinguished by multiple auxiliary structures: a carriage house with guest accommodations, a separate guest residence, and a heated party barn dating to circa 1850. A pool with spa, pergola, and outdoor kitchen complete the grounds. Original architectural details such as leaded glass windows, rich hardwood paneling and window seats and doors, five stone and brick fireplaces, and other features have been preserved. Modern additions introduce light-filled living spaces. New appliances and updated mechanicals service the buildings. Rock Ledge offers luxury and privacy rare in this area, and promises a lifetime of enjoyment for a buyer who appreciates its beauty.

7 Beds ⋅ 8 Baths ⋅ 24168594 MLS

Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with apartment, and converted barn, largely by architect Jack Franzen. The main residence offers over 11,000 square feet with 7 bedrooms, 6 full and 2 half baths. The two-story media wing includes a home theater, library, office, and billiard room. The conservatory overlooks stone terraces, a waterfall and pond, and gardens. The primary suite and office have private balconies. The estate is further distinguished by multiple auxiliary structures: a carriage house with guest accommodations, a separate guest residence, and a heated party barn dating to circa 1850. A pool with spa, pergola, and outdoor kitchen complete the grounds. Original architectural details such as leaded glass windows, rich hardwood paneling and window seats and doors, five stone and brick fireplaces, and other features have been preserved. Modern additions introduce light-filled living spaces. New appliances and updated mechanicals service the buildings. Rock Ledge offers luxury and privacy rare in this area, and promises a lifetime of enjoyment for a buyer who appreciates its beauty.

214 Good Hill Rd, Weston

$2,449,000

Set on three private acres of serene woodland along the banks of the Saugatuck River, this extraordinary Riverfront Retreat offers a rare opportunity to live immersed in nature in a modern masterpiece. Creating a seamless connection between the stunning interiors and the tranquil beauty of the surrounding landscape, experience breathtaking river views from the rooftop deck with succulent gardens, from the heated gunite pool surrounded by an oversized terrace and through the walls of glass throughout the home. From the moment you enter, prepared to be wowed by this concrete, glass and bamboo structure, as you flow through the stunning open living spaces into the private first floor Primary Bedroom, then up to the well thought out second floor. Rare and remarkable, this noteworthy home was designed by Specht Harpman and artfully built in 2010 by Michael Greenberg in the bucolic setting of Weston, CT. Enjoy best of both worlds- living in secluded waterfront serenity with effortless access to the areas shopping, restaurants and beaches in Westport and neighboring communities.

2 Beds ⋅ 3 Baths ⋅ 24167448 MLS

Set on three private acres of serene woodland along the banks of the Saugatuck River, this extraordinary Riverfront Retreat offers a rare opportunity to live immersed in nature in a modern masterpiece. Creating a seamless connection between the stunning interiors and the tranquil beauty of the surrounding landscape, experience breathtaking river views from the rooftop deck with succulent gardens, from the heated gunite pool surrounded by an oversized terrace and through the walls of glass throughout the home. From the moment you enter, prepared to be wowed by this concrete, glass and bamboo structure, as you flow through the stunning open living spaces into the private first floor Primary Bedroom, then up to the well thought out second floor. Rare and remarkable, this noteworthy home was designed by Specht Harpman and artfully built in 2010 by Michael Greenberg in the bucolic setting of Weston, CT. Enjoy best of both worlds- living in secluded waterfront serenity with effortless access to the areas shopping, restaurants and beaches in Westport and neighboring communities.

52 Valley Forge Rd, Weston

$2,595,000

A RARE property. The 28- year owners lovingly restored their 18th century antique and expanded it to 6,050 SF of modern comfort on its 4 acres including a 11/4 ac. pond. Albeit, the renovation of the property's antique 1,100 SF, 2 BR continually-rented cottage may be the financial coup for 42% marginal tax bracket (Fed+CT) buyers who assume a 6.25%, 80% ($2,080,000 of 2.6M asking) 30 yr. fixed mortgage. The rent, presently $30,000/yr., and tax advantaged deductions will contribute funds that amortize $915,000 of the 2.080M. Accordingly, the effective purchase price could be $1,685,000. High-quality finishes aside, consider the setting: brook-fed pond for large-mouth-bass anglers and visiting egrets; stunning fall foliage surrounding the pond; 450 ft. long, bleached-stone, maple tree-lined driveway to the main house; just a 2-minute drive to the Weston Town Center and K-12 school campus; 150 SF of veggie-intensive raised beds along with wild blackberries, and Concord grapes where you meander; pool site plans rendered and readied for the buyer; oversized-windows and 3rd floor balcony offering sweeping views; and a massive front lawn for that Great Tent celebration. Inside, a 2025-new heating system slashes the gas bill; a home office space w/ fireplace has its own private entrance; and the former, acclaimed NYC chef/owner's professionally equipped kitchen is central to the home's 5 entertaining areas, while a 600 SF bonus room with its own full kitchen invites countless uses.

6 Beds ⋅ 7 Baths ⋅ 24160708 MLS

A RARE property. The 28- year owners lovingly restored their 18th century antique and expanded it to 6,050 SF of modern comfort on its 4 acres including a 11/4 ac. pond. Albeit, the renovation of the property's antique 1,100 SF, 2 BR continually-rented cottage may be the financial coup for 42% marginal tax bracket (Fed+CT) buyers who assume a 6.25%, 80% ($2,080,000 of 2.6M asking) 30 yr. fixed mortgage. The rent, presently $30,000/yr., and tax advantaged deductions will contribute funds that amortize $915,000 of the 2.080M. Accordingly, the effective purchase price could be $1,685,000. High-quality finishes aside, consider the setting: brook-fed pond for large-mouth-bass anglers and visiting egrets; stunning fall foliage surrounding the pond; 450 ft. long, bleached-stone, maple tree-lined driveway to the main house; just a 2-minute drive to the Weston Town Center and K-12 school campus; 150 SF of veggie-intensive raised beds along with wild blackberries, and Concord grapes where you meander; pool site plans rendered and readied for the buyer; oversized-windows and 3rd floor balcony offering sweeping views; and a massive front lawn for that Great Tent celebration. Inside, a 2025-new heating system slashes the gas bill; a home office space w/ fireplace has its own private entrance; and the former, acclaimed NYC chef/owner's professionally equipped kitchen is central to the home's 5 entertaining areas, while a 600 SF bonus room with its own full kitchen invites countless uses.

32 Steep Hill Rd, Weston

$369,000

Rare oppotunity to purchase a magical 2 acre parcel of land w/ a little slice of frontage on Aspetuck River in coveted Stonybrook Association. Beautiful lot with fabulous views in true lower Weston on Westport border! Stonybrook is a unique enclave of homes in Weston and offers swimming, boating, tennis, zipline, basketball court, playground, picnic benches and more, all for the use of homeowners in this beloved neighborhood! See addendum for additional info.

24161293 MLS

Rare oppotunity to purchase a magical 2 acre parcel of land w/ a little slice of frontage on Aspetuck River in coveted Stonybrook Association. Beautiful lot with fabulous views in true lower Weston on Westport border! Stonybrook is a unique enclave of homes in Weston and offers swimming, boating, tennis, zipline, basketball court, playground, picnic benches and more, all for the use of homeowners in this beloved neighborhood! See addendum for additional info.

B Bridge Rd, Weston

$3,450,000

In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every turn, including a coffered ceiling living room, a banquet sized dining room with a curved wall of windows, and an octagonal office. French doors create a natural flow to two stone patios and sweeping lawns. The gourmet kitchen, appointed with four Wolf ovens, dual Sub Zeros and dishwashers, and extensive custom cabinetry, is designed for both comfortable daily living and memorable entertaining. The serene primary suite offers a private sitting room, balcony, barrel-ceiling dressing room, and an inspiring octagonal bathroom, while additional en-suite bedrooms and a full in-law suite provide exceptional comfort. The finished lower level includes a custom cherry wet bar, gym, and flexible space for a media room or wine cellar. Two full-size laundry rooms and a pool bath w/exterior access offer flexibility. Outdoors, a heated Gunite pool with auto cover and spa create a private resort experience. Convenient to the Merritt Parkway and Westport, this rare offering blends timeless sophistication with modern livability in one of Fairfield County's most sought-after settings.

6 Beds ⋅ 11 Baths ⋅ 24151746 MLS

In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every turn, including a coffered ceiling living room, a banquet sized dining room with a curved wall of windows, and an octagonal office. French doors create a natural flow to two stone patios and sweeping lawns. The gourmet kitchen, appointed with four Wolf ovens, dual Sub Zeros and dishwashers, and extensive custom cabinetry, is designed for both comfortable daily living and memorable entertaining. The serene primary suite offers a private sitting room, balcony, barrel-ceiling dressing room, and an inspiring octagonal bathroom, while additional en-suite bedrooms and a full in-law suite provide exceptional comfort. The finished lower level includes a custom cherry wet bar, gym, and flexible space for a media room or wine cellar. Two full-size laundry rooms and a pool bath w/exterior access offer flexibility. Outdoors, a heated Gunite pool with auto cover and spa create a private resort experience. Convenient to the Merritt Parkway and Westport, this rare offering blends timeless sophistication with modern livability in one of Fairfield County's most sought-after settings.

76 Lords Hwy, Weston

$1,300,000

The Oasis at Richmond Hill is a rare mid-century modern retreat nestled at the end of a quiet cul-de-sac in Weston. Set on 2 acres of landscaped grounds bordered by towering spruce, elms, and rhododendrons, this 1956 residence offers a seamless blend of architecture and nature. Inspired by the Harvard Five, its design features clean lines, warm materials, and walls of glass that frame the changing seasons. A dramatic stone fireplace anchors the main living space, while French doors from the granite-appointed kitchen open to a stone terrace overlooking tiered lawns and a gunite pool with cabana. A winding path leads through mature gardens to the pool, creating a private, resort-like setting perfect for entertaining. The home offers three bedrooms and two full baths, including a serene primary suite with en-suite bath, private deck, and tranquil views. Custom built-ins in the secondary rooms allow for flexible use as bedrooms, offices, or studios. Additional highlights include central air, updated systems, and a detached garage once used as an artist's studio. Located near nature preserves, walking trails, and Weston's beloved dog park, this property offers a rare opportunity to live within architecture - not just inside it.

3 Beds ⋅ 2 Baths ⋅ 24147378 MLS

The Oasis at Richmond Hill is a rare mid-century modern retreat nestled at the end of a quiet cul-de-sac in Weston. Set on 2 acres of landscaped grounds bordered by towering spruce, elms, and rhododendrons, this 1956 residence offers a seamless blend of architecture and nature. Inspired by the Harvard Five, its design features clean lines, warm materials, and walls of glass that frame the changing seasons. A dramatic stone fireplace anchors the main living space, while French doors from the granite-appointed kitchen open to a stone terrace overlooking tiered lawns and a gunite pool with cabana. A winding path leads through mature gardens to the pool, creating a private, resort-like setting perfect for entertaining. The home offers three bedrooms and two full baths, including a serene primary suite with en-suite bath, private deck, and tranquil views. Custom built-ins in the secondary rooms allow for flexible use as bedrooms, offices, or studios. Additional highlights include central air, updated systems, and a detached garage once used as an artist's studio. Located near nature preserves, walking trails, and Weston's beloved dog park, this property offers a rare opportunity to live within architecture - not just inside it.

17 Richmond Hill Rd, Weston

$1,779,000

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.

5 Beds ⋅ 6 Baths ⋅ 24079433 MLS

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.

28 Old Orchard Dr, Weston

$1,149,000

Reminiscent of an European Estate this 4420 square-foot home features, four bedrooms, two full bathrooms and two half bathrooms on an open acre of land. It's extensive outdoor patio and entertainment areas wrap around the rear of the property, a cobblestone lined driveway, and specimen landscaping are all situated on a cul-de-sac in an easy to get to everything location. The gourmet kitchen features high end appliances, and the house is served by radiant heat as well as central air.

4 Beds ⋅ 4 Baths ⋅ 24122214 MLS

Reminiscent of an European Estate this 4420 square-foot home features, four bedrooms, two full bathrooms and two half bathrooms on an open acre of land. It's extensive outdoor patio and entertainment areas wrap around the rear of the property, a cobblestone lined driveway, and specimen landscaping are all situated on a cul-de-sac in an easy to get to everything location. The gourmet kitchen features high end appliances, and the house is served by radiant heat as well as central air.

15 Mountain View Dr, Weston