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Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensuite bedrooms with fireplaces, and a playroom. A private ensuite studio bedroom sits above the heated three-car garage, offering perfect accommodations for staff or guests.

6 Beds ⋅ 8 Baths ⋅ 24192442 MLS

Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensuite bedrooms with fireplaces, and a playroom. A private ensuite studio bedroom sits above the heated three-car garage, offering perfect accommodations for staff or guests.

210 Doolittle Dr, Norfolk

Stunning European-style mini-estate where rolling golf course greens meet breathtaking views of the Long Island Sound. Crafted with a timeless stone exterior, cedar roof, hardwood floors, and exquisite granite surfaces, this home offers an unparalleled lifestyle of privacy and sophistication. The heart of the home is an open-concept layout featuring a soaring 2-story family room with dramatic French doors that open to a backyard oasis. The chef's kitchen is equipped with high-end appliances, custom cabinetry, and a massive center island. The main floor boasts a formal dining room, a dedicated office with built-in bookshelves, and a luxurious primary suite featuring vaulted ceilings, a private screened porch overlooking the golf course, and a spa-like bath with a soaking tub and custom walk-in closet. Upstairs, a stunning balcony looks out to the Sound, leading to 4 generous bedrooms: 2 en-suites and 2 sharing a Jack-and-Jill bath. The lower level is the ultimate entertainment hub, offering 3,000 sq ft of finished space designed as a private club with a state-of-the-art gym, connoisseur's wine room, spacious billiards room, and full bath. Step outside to a private paradise with manicured gardens, a sparkling gunite pool, and a pool house with a full bath. A fully equipped outdoor kitchen makes summer hosting an absolute breeze. Do not miss this rare opportunity to own a resort-style masterpiece.

5 Beds ⋅ 7 Baths ⋅ 24187690 MLS

Stunning European-style mini-estate where rolling golf course greens meet breathtaking views of the Long Island Sound. Crafted with a timeless stone exterior, cedar roof, hardwood floors, and exquisite granite surfaces, this home offers an unparalleled lifestyle of privacy and sophistication. The heart of the home is an open-concept layout featuring a soaring 2-story family room with dramatic French doors that open to a backyard oasis. The chef's kitchen is equipped with high-end appliances, custom cabinetry, and a massive center island. The main floor boasts a formal dining room, a dedicated office with built-in bookshelves, and a luxurious primary suite featuring vaulted ceilings, a private screened porch overlooking the golf course, and a spa-like bath with a soaking tub and custom walk-in closet. Upstairs, a stunning balcony looks out to the Sound, leading to 4 generous bedrooms: 2 en-suites and 2 sharing a Jack-and-Jill bath. The lower level is the ultimate entertainment hub, offering 3,000 sq ft of finished space designed as a private club with a state-of-the-art gym, connoisseur's wine room, spacious billiards room, and full bath. Step outside to a private paradise with manicured gardens, a sparkling gunite pool, and a pool house with a full bath. A fully equipped outdoor kitchen makes summer hosting an absolute breeze. Do not miss this rare opportunity to own a resort-style masterpiece.

95 Old Saugatuck Rd, Norwalk

Rare beachfront opportunity at 40 Pond Rd in Old Lyme featuring two homes on one lot with incredible views of Long Island Sound. This exclusive coastal property includes one beautifully remodeled home and one brand-new construction home nearing completion, offering exceptional flexibility for guests, rental potential, or multi-generational use. Designed with modern coastal living in mind, the new construction features sleek concrete floors, open floor plans, abundant natural light, stylish bathrooms, and seamless indoor-outdoor living. Enjoy breathtaking water views from the expansive beachside deck, perfect for relaxing, entertaining, and taking in the shoreline setting. A private exclusive mooring adds tremendous value for boating enthusiasts, with direct access to the water. A truly unique Long Island Sound beachfront compound combining modern design, luxury finishes, and an unmatched coastal lifestyle 365 days of the year.

6 Beds ⋅ 9 Baths ⋅ 24176656 MLS

Rare beachfront opportunity at 40 Pond Rd in Old Lyme featuring two homes on one lot with incredible views of Long Island Sound. This exclusive coastal property includes one beautifully remodeled home and one brand-new construction home nearing completion, offering exceptional flexibility for guests, rental potential, or multi-generational use. Designed with modern coastal living in mind, the new construction features sleek concrete floors, open floor plans, abundant natural light, stylish bathrooms, and seamless indoor-outdoor living. Enjoy breathtaking water views from the expansive beachside deck, perfect for relaxing, entertaining, and taking in the shoreline setting. A private exclusive mooring adds tremendous value for boating enthusiasts, with direct access to the water. A truly unique Long Island Sound beachfront compound combining modern design, luxury finishes, and an unmatched coastal lifestyle 365 days of the year.

40 Pond Rd, Old Lyme

A Historic Masterpiece, Reimagined for Modern Living Originally crafted in 1931 by renowned architect Frazier Forman Peters, this iconic stone residence has been completely reinvented-expanded, redesigned, and redefined for today's luxury lifestyle. The newly completed home now offers over 9,000 square feet of exquisite living space with 6 bedrooms, 7.5 baths, and every modern comfort imaginable, all while preserving the timeless character of its hand-cut fieldstone construction. Inside, soaring ceilings, a dramatic double staircase, and elegant living and dining spaces create a perfect blend of grandeur and warmth. Five fireplaces anchor inviting gathering areas, while French doors lead to light-filled suites and sweeping terraces overlooking the serene landscape. From its architectural heritage to its meticulous, top-to-bottom reinvention, this residence stands as a true work of art-a rare fusion of history, craftsmanship, and modern sophistication-just minutes from downtown New Canaan. SQ FT REFLECTS TO BE BUILT RENDERINGS 9000 SQ FT+-

6 Beds ⋅ 8 Baths ⋅ 24116481 MLS

A Historic Masterpiece, Reimagined for Modern Living Originally crafted in 1931 by renowned architect Frazier Forman Peters, this iconic stone residence has been completely reinvented-expanded, redesigned, and redefined for today's luxury lifestyle. The newly completed home now offers over 9,000 square feet of exquisite living space with 6 bedrooms, 7.5 baths, and every modern comfort imaginable, all while preserving the timeless character of its hand-cut fieldstone construction. Inside, soaring ceilings, a dramatic double staircase, and elegant living and dining spaces create a perfect blend of grandeur and warmth. Five fireplaces anchor inviting gathering areas, while French doors lead to light-filled suites and sweeping terraces overlooking the serene landscape. From its architectural heritage to its meticulous, top-to-bottom reinvention, this residence stands as a true work of art-a rare fusion of history, craftsmanship, and modern sophistication-just minutes from downtown New Canaan. SQ FT REFLECTS TO BE BUILT RENDERINGS 9000 SQ FT+-

760 Valley Rd, New Canaan

$4,199,000

New construction from foundation up and ready for 2026! On a coveted Darien cul-de-sac, this modern colonial boasts 6500sf of elegance and comfort. Step through the welcoming foyer, complete with a coat room and powder room, and into a spacious, light-flooded living room, perfect for gatherings that stretch into the evening. The custom kitchen is a true centerpiece, with a grand stone island, Thermador appliances, an oversized range, and abundant cabinetry. Surrounded by windows, the sunlit breakfast room flows effortlessly to the kitchen/great room, where a gas fireplace and beamed ceiling create warmth and character and flow out to an huge deck overlooking 1.2 private acres. A first-floor office with full bath offers flexibility for work, guests, or a quiet retreat. Everyday ease continues with a mudroom, half bath with stunning, floating quartz vanity, and an attached two-car garage. Upstairs, the primary suite is a serene escape with vaulted ceilings, a walk-in closet, and a private balcony overlooking the lush and private yard. Three additional en-suite bedrooms each feature custom walk-in closets, blending function with elegance. The partially finished third floor and lower level invite endless possibilities - a home gym, playroom, creative spaces, etc. This home has privacy and space for all and is only minutes from town, shops, the beach, golf, the train and all amenities. A new home for the new year!

5 Beds ⋅ 8 Baths ⋅ 24082353 MLS

New construction from foundation up and ready for 2026! On a coveted Darien cul-de-sac, this modern colonial boasts 6500sf of elegance and comfort. Step through the welcoming foyer, complete with a coat room and powder room, and into a spacious, light-flooded living room, perfect for gatherings that stretch into the evening. The custom kitchen is a true centerpiece, with a grand stone island, Thermador appliances, an oversized range, and abundant cabinetry. Surrounded by windows, the sunlit breakfast room flows effortlessly to the kitchen/great room, where a gas fireplace and beamed ceiling create warmth and character and flow out to an huge deck overlooking 1.2 private acres. A first-floor office with full bath offers flexibility for work, guests, or a quiet retreat. Everyday ease continues with a mudroom, half bath with stunning, floating quartz vanity, and an attached two-car garage. Upstairs, the primary suite is a serene escape with vaulted ceilings, a walk-in closet, and a private balcony overlooking the lush and private yard. Three additional en-suite bedrooms each feature custom walk-in closets, blending function with elegance. The partially finished third floor and lower level invite endless possibilities - a home gym, playroom, creative spaces, etc. This home has privacy and space for all and is only minutes from town, shops, the beach, golf, the train and all amenities. A new home for the new year!

20 Marianne Rd, Darien

$4,000,000

A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one of Old Greenwich's most sought after waterfront settings. The .28 acre property sits within a private association that includes sandy beach access, a boat launch ramp for paddle boarding, kayaking and boating and a large communal waterfront lawn. The current home features a large living room with direct Sound views, a formal dining room, a kitchen and family room opening to a stone patio facing Long Island Sound, and a primary bedroom suite with private bath. Three additional bedrooms and full bath occupy the upper level, sharing the same water views. Gas heating, central air conditioning and an attached 2-car garage are in place. A beautiful and serene location in a private waterfront association, Long Island Sound views and steps to Tod's Point - all within minutes of the Old Greenwich train station, Old Greenwich shops and dining and schools.

4 Beds ⋅ 3 Baths ⋅ 24205297 MLS

A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one of Old Greenwich's most sought after waterfront settings. The .28 acre property sits within a private association that includes sandy beach access, a boat launch ramp for paddle boarding, kayaking and boating and a large communal waterfront lawn. The current home features a large living room with direct Sound views, a formal dining room, a kitchen and family room opening to a stone patio facing Long Island Sound, and a primary bedroom suite with private bath. Three additional bedrooms and full bath occupy the upper level, sharing the same water views. Gas heating, central air conditioning and an attached 2-car garage are in place. A beautiful and serene location in a private waterfront association, Long Island Sound views and steps to Tod's Point - all within minutes of the Old Greenwich train station, Old Greenwich shops and dining and schools.

14 Shoreham Club Rd, Greenwich

$4,000,000

Welcome to a property where a collector's garden of Japanese maples, rhododendrons, and azaleas - in every shade from gold to crimson to blush pink - announces something extraordinary before you've even reached the front door. A circular drive leads to this classic New England white Colonial, set on nearly three and a half acres on prestigious Turtle Back Road, where grounds shaped with the care of a private arboretum unfold: flagstone terraces, fieldstone walls, and specimen plantings set against a canopy of mature trees. From its copper roof to its storied gardens, every element of this five-bedroom, six-bath New Canaan property feels distinctive. With nearly 5,200 square feet of living space, the home offers generous accommodations while maintaining real warmth and character. Positioned to embrace its surroundings, sun-filled interiors and tranquil views from nearly every room create a seamless connection between indoors and out. Whether entertaining on a grand scale or savoring the simple pleasures of everyday life, the property offers a rare sense of space, comfort, and retreat. Just minutes from the heart of New Canaan, this exceptional home provides easy access to downtown amenities, award-winning schools, parks, and Metro-North - while feeling worlds away from it all. Seldom does a property offer such a rare combination of privacy, beauty, and one of Fairfield County's most sought-after addresses.

5 Beds ⋅ 6 Baths ⋅ 24178727 MLS

Welcome to a property where a collector's garden of Japanese maples, rhododendrons, and azaleas - in every shade from gold to crimson to blush pink - announces something extraordinary before you've even reached the front door. A circular drive leads to this classic New England white Colonial, set on nearly three and a half acres on prestigious Turtle Back Road, where grounds shaped with the care of a private arboretum unfold: flagstone terraces, fieldstone walls, and specimen plantings set against a canopy of mature trees. From its copper roof to its storied gardens, every element of this five-bedroom, six-bath New Canaan property feels distinctive. With nearly 5,200 square feet of living space, the home offers generous accommodations while maintaining real warmth and character. Positioned to embrace its surroundings, sun-filled interiors and tranquil views from nearly every room create a seamless connection between indoors and out. Whether entertaining on a grand scale or savoring the simple pleasures of everyday life, the property offers a rare sense of space, comfort, and retreat. Just minutes from the heart of New Canaan, this exceptional home provides easy access to downtown amenities, award-winning schools, parks, and Metro-North - while feeling worlds away from it all. Seldom does a property offer such a rare combination of privacy, beauty, and one of Fairfield County's most sought-after addresses.

248 Turtle Back Rd, New Canaan

$4,000,000

This exquisite Frank Lloyd Wright Usonian-inspired lakefront home offers a rare opportunity on the serene shores of Lake Waramaug. Known for its pristine waters, natural beauty, and timeless appeal, Lake Waramaug is one of Connecticut's most beautiful and well-preserved natural lakes. Set in the charming village of New Preston, the to-be-built residence is presented by Viridian Custom Homes and Lindal Cedar Homes, with a masterful design by Aris Georges, a leading authority on Frank Lloyd Wright's design principles. Finishes by Kathleen Goodwin Interiors reflect a sophisticated blend of Connecticut and New York City design sensibilities. This 4-bedroom, 3.5-bath, 3,285 SF home features airy rooms, dramatic ceiling heights, organic materials, broad roof overhangs, abundant natural light, and a seamless connection to the land. Set on 1.85 acres with 500 ft of private waterfront and dock rights, the property offers spectacular westerly views. A rare opportunity to create a modern lakefront retreat that blends architectural elegance, natural beauty, and timeless Wright-inspired design.

4 Beds ⋅ 4 Baths ⋅ 24182872 MLS

This exquisite Frank Lloyd Wright Usonian-inspired lakefront home offers a rare opportunity on the serene shores of Lake Waramaug. Known for its pristine waters, natural beauty, and timeless appeal, Lake Waramaug is one of Connecticut's most beautiful and well-preserved natural lakes. Set in the charming village of New Preston, the to-be-built residence is presented by Viridian Custom Homes and Lindal Cedar Homes, with a masterful design by Aris Georges, a leading authority on Frank Lloyd Wright's design principles. Finishes by Kathleen Goodwin Interiors reflect a sophisticated blend of Connecticut and New York City design sensibilities. This 4-bedroom, 3.5-bath, 3,285 SF home features airy rooms, dramatic ceiling heights, organic materials, broad roof overhangs, abundant natural light, and a seamless connection to the land. Set on 1.85 acres with 500 ft of private waterfront and dock rights, the property offers spectacular westerly views. A rare opportunity to create a modern lakefront retreat that blends architectural elegance, natural beauty, and timeless Wright-inspired design.

31a June Rd, Washington

$3,999,999

Subdivision Potential! One of the Largest Land Parcels in Bethel - Over 61 Acres! A rare opportunity for investors, developers, and visionaries to own more than 61 acres in the highly sought-after Codfish Hill area. This former farmland, once a thriving homestead, offers a unique combination of development potential and the charm of an existing colonial farmhouse with multiple outbuildings. The property includes an oversized 3-bay garage/barn with a full second level, and a nearly 4,500 sq. ft. farmhouse filled with character and possibility. Inside, you'll find a grand great room with a soaring floor-to-ceiling stone fireplace featuring French doors leading to an expansive deck-perfect for entertaining. The home features 5 bedrooms (potentially 6), 3.5 baths, and 3 stone fireplaces, including a first-floor primary suite with separate office/nursery, its own fireplace and spa-like bath, plus a walk-out lower-level in-law suite with private entrance, stone fireplace, and separate laundry hookups. This is truly a diamond in the rough-whether you're looking to restore the farmhouse to its former glory or envisioning a subdivision project on one of the largest parcels left in Bethel. Opportunities like this are few and far between-don't miss it! Buyer use due diligence in possible subdivision and zoning requirements per town of Bethel. Property is part of an estate and sold as-is and subject to probate approval.

6 Beds ⋅ 4 Baths ⋅ 24128777 MLS

Subdivision Potential! One of the Largest Land Parcels in Bethel - Over 61 Acres! A rare opportunity for investors, developers, and visionaries to own more than 61 acres in the highly sought-after Codfish Hill area. This former farmland, once a thriving homestead, offers a unique combination of development potential and the charm of an existing colonial farmhouse with multiple outbuildings. The property includes an oversized 3-bay garage/barn with a full second level, and a nearly 4,500 sq. ft. farmhouse filled with character and possibility. Inside, you'll find a grand great room with a soaring floor-to-ceiling stone fireplace featuring French doors leading to an expansive deck-perfect for entertaining. The home features 5 bedrooms (potentially 6), 3.5 baths, and 3 stone fireplaces, including a first-floor primary suite with separate office/nursery, its own fireplace and spa-like bath, plus a walk-out lower-level in-law suite with private entrance, stone fireplace, and separate laundry hookups. This is truly a diamond in the rough-whether you're looking to restore the farmhouse to its former glory or envisioning a subdivision project on one of the largest parcels left in Bethel. Opportunities like this are few and far between-don't miss it! Buyer use due diligence in possible subdivision and zoning requirements per town of Bethel. Property is part of an estate and sold as-is and subject to probate approval.

62 Codfish Hill Rd, Bethel

$3,999,500

Rarely does a property offer frontage on both Long Island Sound and Pine Creek. Positioned along a naturally elevated stretch of Fairfield Beach framed by protective dunes, the property enjoys a broad sandy beach at both high and low tide. Located within a residential section of Fairfield Beach away from many public beach access points, the setting offers a unique combination of beach, creek, and open water frontage. Across the street, the South Pine Creek frontage offers water views, sunsets, a detached two-car garage, and remnants of a former dock, offering potential boating opportunities subject to due diligence and approvals. Designed by renowned architect Jack Franzen and featured in Westport Magazine, the home reflects timeless neoclassical design. The thoughtful floor plan places the primary suite on the first floor, while the main living level is elevated above to maximize light and views. A sweeping staircase and interior elevator lead to open-concept living spaces overlooking Long Island Sound. An in-ground spa completes this exceptional waterfront offering. Agent/Owner Related Owner/Broker. Agents: Additional information is available in the disclosure section. Ask about the extremely low cost and transferable flood insurance policy.

3 Beds ⋅ 5 Baths ⋅ 24174562 MLS

Rarely does a property offer frontage on both Long Island Sound and Pine Creek. Positioned along a naturally elevated stretch of Fairfield Beach framed by protective dunes, the property enjoys a broad sandy beach at both high and low tide. Located within a residential section of Fairfield Beach away from many public beach access points, the setting offers a unique combination of beach, creek, and open water frontage. Across the street, the South Pine Creek frontage offers water views, sunsets, a detached two-car garage, and remnants of a former dock, offering potential boating opportunities subject to due diligence and approvals. Designed by renowned architect Jack Franzen and featured in Westport Magazine, the home reflects timeless neoclassical design. The thoughtful floor plan places the primary suite on the first floor, while the main living level is elevated above to maximize light and views. A sweeping staircase and interior elevator lead to open-concept living spaces overlooking Long Island Sound. An in-ground spa completes this exceptional waterfront offering. Agent/Owner Related Owner/Broker. Agents: Additional information is available in the disclosure section. Ask about the extremely low cost and transferable flood insurance policy.

1681 Fairfield Beach Rd, Fairfield

$3,999,000

This exceptional residence, one of Sharon's most historic properties, occupies much of the original 1812 Georgian mansion, home to a notable family, including William F. Buckley, Jr., for over a century. The layout is spacious & flexible, offering multiple options for purchase: 1) purchase in its current layout as a spacious, 6-bedroom residence, 2) divide the current 6-bedroom residence into two spacious 3-bedroom residences, 3) additionally acquire the north wing to recreate a more complete version of the original mansion for use as an expansive single-family residence, a family compound, or separate residences for rental income. The current 6,716 sq ft home has been thoughtfully restored & offers 6 bedrooms with primary suites on both levels, 7 full baths, and 2 powder rooms. The kitchen opens to a stunning library & informal dining area, complemented by formal living & dining rooms, a family room, office, gym, den, laundry room and 7 fireplaces. At the center of the home, a dramatic three-story 1250 sq foot glass atrium (the 1,250 sq ft is not included in the 6,716 sq ft) - enclosing the 1929 courtyard - creates a year-round living space that brings light & openness into the core of the home. This is estate living with the ease of a managed community. Enjoy beautifully maintained grounds with specimen trees & beautiful plantings. Amenities include: junior Olympic-sized heated pool, pool house, tennis court & separate paddle/pickle courts and more. More info below.

6 Beds ⋅ 9 Baths ⋅ 24173869 MLS

This exceptional residence, one of Sharon's most historic properties, occupies much of the original 1812 Georgian mansion, home to a notable family, including William F. Buckley, Jr., for over a century. The layout is spacious & flexible, offering multiple options for purchase: 1) purchase in its current layout as a spacious, 6-bedroom residence, 2) divide the current 6-bedroom residence into two spacious 3-bedroom residences, 3) additionally acquire the north wing to recreate a more complete version of the original mansion for use as an expansive single-family residence, a family compound, or separate residences for rental income. The current 6,716 sq ft home has been thoughtfully restored & offers 6 bedrooms with primary suites on both levels, 7 full baths, and 2 powder rooms. The kitchen opens to a stunning library & informal dining area, complemented by formal living & dining rooms, a family room, office, gym, den, laundry room and 7 fireplaces. At the center of the home, a dramatic three-story 1250 sq foot glass atrium (the 1,250 sq ft is not included in the 6,716 sq ft) - enclosing the 1929 courtyard - creates a year-round living space that brings light & openness into the core of the home. This is estate living with the ease of a managed community. Enjoy beautifully maintained grounds with specimen trees & beautiful plantings. Amenities include: junior Olympic-sized heated pool, pool house, tennis court & separate paddle/pickle courts and more. More info below.

1 Great Elm Dr, Sharon

$3,998,000

WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern additions: radiant heat, elevator, sun-filled library, luminous sunroom overlooking formal gardens and 4-acre spring-fed pond. The 227 acres aren't just land-they're composition. Meadow unfolding to pond positioned where morning & evening light catch it. Mature forest giving way to unbroken views. Trails looping you gently home by blue hour. Stone walls, pool, tennis court, greenhouse. Magnificent 3,550sf hand-hewn barn moved here. Northern land borders State Forest; southern abuts conservation land-permanent privacy. Guest house (6,668sf): 4 residences replete with possibilities-multigenerational living, art studios, writing spaces, media rooms, yoga, creative sanctuary. Cathedral ceilings, fireplaces, soaring light. The quiet money cannot buy: depth of silence settling at dusk, Milky Way stretching clear across valley, no light pollution. Architecture, land, and sky speaking the same language. Where hosting feels like breathing, completely natural. 5 families in 227 years. You'll be 5th. 5 min to dining, 20 min to Great Barrington, 2.5 hrs to Boston/NYC. Complete and irrepla

5 Beds ⋅ 6 Baths ⋅ 24142076 MLS

WHERE THE WORLD FALLS AWAY 227 acres. 227 years. At East Hill Road's summit, East Hill Farm is a fully realized estate where infrastructure, land, and possibility are complete and in place. The 1798 Thomas Shepard House-museum-quality restoration featuring 5 bedrooms, 5.5 baths, 5 fireplaces, original King's board floors, hand-blown glass windows-awaits your vision for kitchens and baths. Modern additions: radiant heat, elevator, sun-filled library, luminous sunroom overlooking formal gardens and 4-acre spring-fed pond. The 227 acres aren't just land-they're composition. Meadow unfolding to pond positioned where morning & evening light catch it. Mature forest giving way to unbroken views. Trails looping you gently home by blue hour. Stone walls, pool, tennis court, greenhouse. Magnificent 3,550sf hand-hewn barn moved here. Northern land borders State Forest; southern abuts conservation land-permanent privacy. Guest house (6,668sf): 4 residences replete with possibilities-multigenerational living, art studios, writing spaces, media rooms, yoga, creative sanctuary. Cathedral ceilings, fireplaces, soaring light. The quiet money cannot buy: depth of silence settling at dusk, Milky Way stretching clear across valley, no light pollution. Architecture, land, and sky speaking the same language. Where hosting feels like breathing, completely natural. 5 families in 227 years. You'll be 5th. 5 min to dining, 20 min to Great Barrington, 2.5 hrs to Boston/NYC. Complete and irrepla

764 E Hill Rd, New Marlborough

$3,997,000

Welcome to Greystone, a masterpiece of modern architecture. Bordered by a protected wildlife area, this 4500 sf smart home offers peace and privacy. The main level features an open living room, dining area and kitchen, den, office, half bath, laundry room and primary bedroom suite. Two ensuite bedrooms and a rooftop deck comprise the upper level. The lower level affords access to the backyard and has finished space for a gym or home office as well as a rough-in for a full bath. The kitchen boasts a 10' x 4' island and large walk-in pantry and is well appointed with Wolf and Sub-Zero appliances. An expansive white limestone wrap-around deck and spacious lawn---with an irrigation system---are perfect for relaxing or entertaining. The attached two-car garage is heated. White oak radiant-heated flooring complements the oak Unilux windows and exterior doors. Interior pocket doors and custom cabinetry continue the sleek contemporary look. Kitchen and bathroom countertops are quartzite, some with waterfall edging. Bathrooms feature limestone floors and unique tadelakt plaster walls. Designed with energy efficiency in mind, Greystone uses a geothermal system for heating and cooling. Smart home technology includes programmable LED lighting, motorized shades, security system, and wiring for audio and AI systems. A whole-house generator connects automatically during power outages.

3 Beds ⋅ 4 Baths ⋅ 24151511 MLS

Welcome to Greystone, a masterpiece of modern architecture. Bordered by a protected wildlife area, this 4500 sf smart home offers peace and privacy. The main level features an open living room, dining area and kitchen, den, office, half bath, laundry room and primary bedroom suite. Two ensuite bedrooms and a rooftop deck comprise the upper level. The lower level affords access to the backyard and has finished space for a gym or home office as well as a rough-in for a full bath. The kitchen boasts a 10' x 4' island and large walk-in pantry and is well appointed with Wolf and Sub-Zero appliances. An expansive white limestone wrap-around deck and spacious lawn---with an irrigation system---are perfect for relaxing or entertaining. The attached two-car garage is heated. White oak radiant-heated flooring complements the oak Unilux windows and exterior doors. Interior pocket doors and custom cabinetry continue the sleek contemporary look. Kitchen and bathroom countertops are quartzite, some with waterfall edging. Bathrooms feature limestone floors and unique tadelakt plaster walls. Designed with energy efficiency in mind, Greystone uses a geothermal system for heating and cooling. Smart home technology includes programmable LED lighting, motorized shades, security system, and wiring for audio and AI systems. A whole-house generator connects automatically during power outages.

314 Ferry Rd, Old Lyme

Tucked behind mature landscaping on a beautifully private 1 acre setting, this extraordinary Southport residence is a home that reveals itself slowly, filled with warmth, character, and timeless craftsmanship. Designed for both everyday living and effortless entertaining, the nearly 6,000 SF home offers 6 bedrooms, 5.5 baths, soaring beamed ceilings, reclaimed wood, antique doors, wide-plank floors, and an exceptional collection of gathering spaces. The heart of the home is an inviting chef's kitchen that opens seamlessly to the family room, while the dramatic great room, lined with floor-to-ceiling bookcases and a library ladder, creates a space unlike anything else on the market. A private 1st floor guest suite, elegant library, and luxurious primary suite with fireplace complete the home's thoughtful design. Outside, the property feels more like a private resort than a backyard. Stone terraces surround a spectacular Gunite pool and spa with 3 cascading fountains, complemented by a beautifully appointed pool house, covered outdoor dining beneath a bamboo canopy, built-in grilling area, fire pit, and integrated sound system, creating an unforgettable setting for summer gatherings or quiet evenings at home. Located just minutes from Southport Village, beaches, Metro-North, restaurants, shopping, and top-rated public and private schools, 1061 Cedar Road offers the rare combination of architectural distinction, exceptional privacy, and an effortless Connecticut lifestyle.

6 Beds ⋅ 6 Baths ⋅ 24198399 MLS

Tucked behind mature landscaping on a beautifully private 1 acre setting, this extraordinary Southport residence is a home that reveals itself slowly, filled with warmth, character, and timeless craftsmanship. Designed for both everyday living and effortless entertaining, the nearly 6,000 SF home offers 6 bedrooms, 5.5 baths, soaring beamed ceilings, reclaimed wood, antique doors, wide-plank floors, and an exceptional collection of gathering spaces. The heart of the home is an inviting chef's kitchen that opens seamlessly to the family room, while the dramatic great room, lined with floor-to-ceiling bookcases and a library ladder, creates a space unlike anything else on the market. A private 1st floor guest suite, elegant library, and luxurious primary suite with fireplace complete the home's thoughtful design. Outside, the property feels more like a private resort than a backyard. Stone terraces surround a spectacular Gunite pool and spa with 3 cascading fountains, complemented by a beautifully appointed pool house, covered outdoor dining beneath a bamboo canopy, built-in grilling area, fire pit, and integrated sound system, creating an unforgettable setting for summer gatherings or quiet evenings at home. Located just minutes from Southport Village, beaches, Metro-North, restaurants, shopping, and top-rated public and private schools, 1061 Cedar Road offers the rare combination of architectural distinction, exceptional privacy, and an effortless Connecticut lifestyle.

1061 Cedar Rd, Fairfield

BELL ISLAND CONNECTICUT. Experience the best of waterfront living on sought-after Bell Island. Perfectly perched to capture beautiful water views, this exceptional home offers peace of mind and an unmatched coastal lifestyle. Featuring 3 spacious bedrooms, 3 full baths and 1 half bath, the home is designed for both comfortable everyday living and effortless entertaining. The expansive great room with cozy fireplace serves as the heart of the home, while large windows capture the scenic water views. Step outside to two private decks, perfect for enjoying your morning coffee, hosting friends, or taking in spectacular sunsets over the water. Whether you are looking for a year-round residence or the perfect coastal retreat, this Bell Island gem combines timeless charm, generous living spaces, and an enviable location just moments from the shoreline including two private park/beach areas.

3 Beds ⋅ 4 Baths ⋅ 24192999 MLS

BELL ISLAND CONNECTICUT. Experience the best of waterfront living on sought-after Bell Island. Perfectly perched to capture beautiful water views, this exceptional home offers peace of mind and an unmatched coastal lifestyle. Featuring 3 spacious bedrooms, 3 full baths and 1 half bath, the home is designed for both comfortable everyday living and effortless entertaining. The expansive great room with cozy fireplace serves as the heart of the home, while large windows capture the scenic water views. Step outside to two private decks, perfect for enjoying your morning coffee, hosting friends, or taking in spectacular sunsets over the water. Whether you are looking for a year-round residence or the perfect coastal retreat, this Bell Island gem combines timeless charm, generous living spaces, and an enviable location just moments from the shoreline including two private park/beach areas.

14 Rocky Point Rd, Norwalk

A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms and five full bathrooms and one powder room. A grand living room, complete with a two-story fireplace and windows on three sides, opens to two decks overlooking the rear yard. The spacious formal dining room, equipped with a gas fireplace and soft indirect lighting, is ideal for hosting formal gatherings. The chef's-eat-in kitchen, generously furnished with ample cabinetry, marble countertops, connects to a large deck and a granite patio, facilitating seamless outdoor dining. The primary level's main suite features French doors to the gardens, a luxurious bath, two walk-in closets, and a private sitting room. Three additional ensuite bedrooms complete the main level. The lower level offers a media room, a game room, a bunk room with built-in beds, a spa bath, and a laundry facility. A separate guest cottage provides a cozy retreat with two bedrooms, two bathrooms, a vaulted great room, a kitchenette, a fireplace, and a wrap-around deck. A must see!

5 Beds ⋅ 6 Baths ⋅ 24177581 MLS

A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms and five full bathrooms and one powder room. A grand living room, complete with a two-story fireplace and windows on three sides, opens to two decks overlooking the rear yard. The spacious formal dining room, equipped with a gas fireplace and soft indirect lighting, is ideal for hosting formal gatherings. The chef's-eat-in kitchen, generously furnished with ample cabinetry, marble countertops, connects to a large deck and a granite patio, facilitating seamless outdoor dining. The primary level's main suite features French doors to the gardens, a luxurious bath, two walk-in closets, and a private sitting room. Three additional ensuite bedrooms complete the main level. The lower level offers a media room, a game room, a bunk room with built-in beds, a spa bath, and a laundry facility. A separate guest cottage provides a cozy retreat with two bedrooms, two bathrooms, a vaulted great room, a kitchenette, a fireplace, and a wrap-around deck. A must see!

47 Squire Rd, Roxbury

Ideally located on a private lot in close proximity to public and private schools, 25 Hillcrest Rd. is located on a low traffic street on New Canaan's lower west side within minutes of the Merritt Parkway, Talmadge Hill train station and down town New Canaan. Spanning close to 8,000 sq ft, the transitional floor plan masterfully blends open concept spaces with more intimate, private spaces. Featuring 9' ceilings throughout and a clean, contemporary design aesthetic, the gracious home is perfect for entertaining large crowds while at the same time comfortable for everyday living. Entering through the custom designed front door, you are welcomed by a grand foyer with unobstructed views through the living room to the private backyard. As you move through the home, the centrally located family room is connected to both the large formal dining room and the gourmet kitchen which is flooded with natural light through six over sized windows. Featuring a clean, white design aesthetic the kitchen is as functional as it is beautiful. With a large 8.5' island coupled with two sinks and two dishwashers, prep and clean-up is easy. The adjacent pantry with lots of cabinetry and mudroom provide a place for everything, keeping the main living area neat and tidy. Not to be missed on the 1st floor is the large en suite guest bedroom (which could also serve as the primary bedroom) and a large private office.

6 Beds ⋅ 7 Baths ⋅ 24169909 MLS

Ideally located on a private lot in close proximity to public and private schools, 25 Hillcrest Rd. is located on a low traffic street on New Canaan's lower west side within minutes of the Merritt Parkway, Talmadge Hill train station and down town New Canaan. Spanning close to 8,000 sq ft, the transitional floor plan masterfully blends open concept spaces with more intimate, private spaces. Featuring 9' ceilings throughout and a clean, contemporary design aesthetic, the gracious home is perfect for entertaining large crowds while at the same time comfortable for everyday living. Entering through the custom designed front door, you are welcomed by a grand foyer with unobstructed views through the living room to the private backyard. As you move through the home, the centrally located family room is connected to both the large formal dining room and the gourmet kitchen which is flooded with natural light through six over sized windows. Featuring a clean, white design aesthetic the kitchen is as functional as it is beautiful. With a large 8.5' island coupled with two sinks and two dishwashers, prep and clean-up is easy. The adjacent pantry with lots of cabinetry and mudroom provide a place for everything, keeping the main living area neat and tidy. Not to be missed on the 1st floor is the large en suite guest bedroom (which could also serve as the primary bedroom) and a large private office.

25 Hillcrest Rd, New Canaan

Set behind stone walls on nearly 2 acres, this exceptional 5-bedroom home offers over 5,000 SF of refined living in a truly extraordinary setting. A dramatic 2-story foyer w/circular staircase and exquisite herringbone floors sets the tone for elegance throughout. Walls of windows fill the gracious interiors with natural light and frame manicured grounds and lush gardens. The formal living room, w/classic wood-burning fireplace, is complemented by a handsome library w/fireplace and wet bar, while an elegant dining room, detailed w/wainscoting and custom built-ins, sets the stage for memorable gatherings. At the heart of the home, a gourmet kitchen with custom cabinetry and oversized island flows into a sun-drenched family room w/fireplace and a wall of glass opening to the expansive terrace - perfect for indoor/outdoor entertaining. The luxurious primary suite features generous walk-in closets and spa-like bath with dual vanities, soaking tub and radiant-heated floors. Four additional bedrooms each enjoy private baths. A separate wing with bedroom, bath and playroom offers an ideal retreat for guests. Additional amenities include a private vaulted-ceiling office, first-floor gym, mudroom, laundry, two-car garage and generator. Beyond the interiors lies a secluded oasis: a level lawn, tranquil pond and fountain, charming footbridge, and secret garden, w/protected land-trust property beyond. A rare expression of privacy, beauty, space, and enduring distinction

5 Beds ⋅ 6 Baths ⋅ 24198712 MLS

Set behind stone walls on nearly 2 acres, this exceptional 5-bedroom home offers over 5,000 SF of refined living in a truly extraordinary setting. A dramatic 2-story foyer w/circular staircase and exquisite herringbone floors sets the tone for elegance throughout. Walls of windows fill the gracious interiors with natural light and frame manicured grounds and lush gardens. The formal living room, w/classic wood-burning fireplace, is complemented by a handsome library w/fireplace and wet bar, while an elegant dining room, detailed w/wainscoting and custom built-ins, sets the stage for memorable gatherings. At the heart of the home, a gourmet kitchen with custom cabinetry and oversized island flows into a sun-drenched family room w/fireplace and a wall of glass opening to the expansive terrace - perfect for indoor/outdoor entertaining. The luxurious primary suite features generous walk-in closets and spa-like bath with dual vanities, soaking tub and radiant-heated floors. Four additional bedrooms each enjoy private baths. A separate wing with bedroom, bath and playroom offers an ideal retreat for guests. Additional amenities include a private vaulted-ceiling office, first-floor gym, mudroom, laundry, two-car garage and generator. Beyond the interiors lies a secluded oasis: a level lawn, tranquil pond and fountain, charming footbridge, and secret garden, w/protected land-trust property beyond. A rare expression of privacy, beauty, space, and enduring distinction

700 Hollow Tree Ridge Rd, Darien

A rare modern retreat - where extraordinary design meets an unexpected sense of warmth and ease. Privately set above the Connecticut River, 274 Joshuatown Road is remarkable for how beautifully it lives; intimate, inviting, and deeply connected to its natural surroundings. A long, private drive creates a profound sense of arrival, revealing a residence thoughtfully positioned to capture sweeping river views and changing light. Designed by acclaimed architect Stephen Jacobs with interiors by Andi Pepper, this residence was created with a singular vision: to live within the landscape, not simply look upon it. Here, architecture doesn't compete with nature-it frames it. Inside, soaring spaces, natural stone, warm wood, and walls of glass bring the outdoors into nearly every experience. The dramatic living room is anchored by an 18' natural stone wall and fireplace opposite an equally impressive wall of glass, capturing changing light and river views throughout the day. An open kitchen with high-end appliances and substantial center island flows effortlessly into the dining area with seating for twelve, creating a natural gathering place for both intimate evenings and larger-scale entertaining. The main-level primary suite offers privacy & ease,

4 Beds ⋅ 6 Baths ⋅ 24186404 MLS

A rare modern retreat - where extraordinary design meets an unexpected sense of warmth and ease. Privately set above the Connecticut River, 274 Joshuatown Road is remarkable for how beautifully it lives; intimate, inviting, and deeply connected to its natural surroundings. A long, private drive creates a profound sense of arrival, revealing a residence thoughtfully positioned to capture sweeping river views and changing light. Designed by acclaimed architect Stephen Jacobs with interiors by Andi Pepper, this residence was created with a singular vision: to live within the landscape, not simply look upon it. Here, architecture doesn't compete with nature-it frames it. Inside, soaring spaces, natural stone, warm wood, and walls of glass bring the outdoors into nearly every experience. The dramatic living room is anchored by an 18' natural stone wall and fireplace opposite an equally impressive wall of glass, capturing changing light and river views throughout the day. An open kitchen with high-end appliances and substantial center island flows effortlessly into the dining area with seating for twelve, creating a natural gathering place for both intimate evenings and larger-scale entertaining. The main-level primary suite offers privacy & ease,

274 Joshuatown Rd, Lyme

Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

4 Beds ⋅ 7 Baths ⋅ 24192621 MLS

Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury

Here is your opportunity to own an extraordinary Connecticut River waterfront estate complete with a deep-water dock! This exceptional 5 bedroom, 5.5 bath residence offers unparalleled privacy and stunning panaromic views across protected conservation land, creating a setting of remarkable beauty and tranquility. Thoughtfully designed to embrace its spectacular surroundings, every room is filled with natural light and captures river views, seamlessly blending the ever-changing beauty of the water with miles of pristine, undeveloped landscape. Whether watching boats glide along the river, bald eagles and ospreys soar overhead, or vibrant sunsets reflect across the water, the connection to nature is simply unrivaled. The luxurious primary suite is a private sanctuary, perfectly positioned to showcase the breathtaking riverfront setting and spectacular sunset views. Inside, three fireplaces create warmth and ambiance, offering intimate gathering spaces for cozy evenings and seasonal get-togethers. This unique Deep River property is conveniently located to Essex Village, which is recognized as one of America's "Best Small Towns" where one can enjoy boutique shopping, restaurants, marinas and quintessential New England charm, all while returning to the peace and privacy of your own waterfront retreat. This stunning property is situated two hours from Boston and New York City, and offers convenient access to airports in New haven, Hartford and Providence.

5 Beds ⋅ 6 Baths ⋅ 24192020 MLS

Here is your opportunity to own an extraordinary Connecticut River waterfront estate complete with a deep-water dock! This exceptional 5 bedroom, 5.5 bath residence offers unparalleled privacy and stunning panaromic views across protected conservation land, creating a setting of remarkable beauty and tranquility. Thoughtfully designed to embrace its spectacular surroundings, every room is filled with natural light and captures river views, seamlessly blending the ever-changing beauty of the water with miles of pristine, undeveloped landscape. Whether watching boats glide along the river, bald eagles and ospreys soar overhead, or vibrant sunsets reflect across the water, the connection to nature is simply unrivaled. The luxurious primary suite is a private sanctuary, perfectly positioned to showcase the breathtaking riverfront setting and spectacular sunset views. Inside, three fireplaces create warmth and ambiance, offering intimate gathering spaces for cozy evenings and seasonal get-togethers. This unique Deep River property is conveniently located to Essex Village, which is recognized as one of America's "Best Small Towns" where one can enjoy boutique shopping, restaurants, marinas and quintessential New England charm, all while returning to the peace and privacy of your own waterfront retreat. This stunning property is situated two hours from Boston and New York City, and offers convenient access to airports in New haven, Hartford and Providence.

323 River Rd, Deep River