Luxury Homes for Sale in Connecticut

/39
$45,000,000
- 6 Beds
- 8 Baths
- 12,492 Sq Ft
545 Indian Field Rd, Greenwich, CT 06830

A rare waterfront estate of true scale and presence, this reimagined coastal masterpiece commands 1.6 acres on the Long Island Sound with sweeping, unobstructed horizon views. Rebuilt from the foundation up, the home delivers level beachfront living with powerful architectural lines, floor-to-ceiling glass, and a seamless connection to the water at every turn. The approach opens to a 19-foot

Jesse Marinak Serhant Connecticut LLC

545 Indian Field Rd, Greenwich, CT 06830
/14
$35,000,000
- Land
- 66 Acres
- $530,303 per Acre
10 Cliffdale Rd, Greenwich, CT 06831

Spanning approximately 66 acres, this exceptional parcel on Cliffdale Road in Greenwich features a harmonious blend of open pastures, mature woodlands, and cultivated areas. The landscape is rich and varied, with gently rolling fields giving way to dense forest and scenic natural trails, ideal for walking, horseback riding, or enjoying the serene surroundings. Measuring roughly half a mile in

Peter Janis BHHS New England Properties

10 Cliffdale Rd, Greenwich, CT 06831
/31
$35,000,000
- 8 Beds
- 9 Baths
- 9,300 Sq Ft
10 Cliffdale Rd, Greenwich, CT 06831

Nestled on 66 acres of picturesque pastures and woods, the historic Beinecke estate features a stunning 9,300 sq. ft. Georgian Colonial home. The main floor includes a grand entry hall, a cozy library with custom wood paneling, and a spacious living room with two fireplaces. A large screened porch offers sweeping views. The second floor boasts a luxurious primary suite with a fireplace, along

Peter Janis BHHS New England Properties

10 Cliffdale Rd, Greenwich, CT 06831
/40
$35,000,000
- 6 Beds
- 4.5 Baths
- 5,354 Sq Ft
215 Uncas Point Rd, Guilford, CT 06437

Waterfront.. Sachems Head - Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House.

Joseph Piscitelli Coldwell Banker Realty

215 Uncas Point Rd, Guilford, CT 06437
/28
$34,500,000
- 10 Beds
- 16 Baths
- 15,820 Sq Ft
7 John St, Greenwich, CT 06831

'Robin Hill Farm' and 'Smokey Hill Farm' are situated at one of the highest points in Greenwich in bucolic backcountry. This magnificent estate encompasses the main house, represented in this listing data sheet, two cottages, stables and gorgeous paddocks, Indoor and outdoor pools, tennis house, tennis court, and two ethereal fountains. Originally designed in 1937 by Augusta L.Noel (designer of

Shelly Tretter Lynch Compass Connecticut, LLC

7 John St, Greenwich, CT 06831
/40
$29,995,000
- 10 Beds
- 8 Baths
- 10,662 Sq Ft
0 Rogers Island, Branford, CT 06405

Dazzling summer resort-like oasis on the private, 7.65-acre Rogers Island in the idyllic Thimble Islands archipelago. Surrounded by cinematic 360-degree views of Long Island Sound, this spectacular compound is comprised of a c.1902 10-bedroom Tudor house set amidst beautifully mature landscaping with a waterfront pool with spa, tennis court, putting green, formal gardens and a koi pond.

Joseph Barbieri Sotheby's International Realty

0 Rogers Island, Branford, CT 06405
/46
$29,995,000
- 10 Beds
- 8 Baths
- 8,746 Sq Ft
0 Rogers Island Unit 122749, Branford, CT 06405

Dazzling summer resort-like oasis on the private, 7.65-acre Rogers Island in the Thimble Islands archipelago. Surrounded by cinematic 360-degree views of Long Island Sound, this spectacular compound is comprised of a c.1902 10-bedroom Tudor house set amidst beautifully mature landscaping with a waterfront pool w/ spa, tennis court, putting green, formal gardens and koi pond. Outbuildings include

Joseph Barbieri Sotheby's International Realty

0 Rogers Island Unit 122749, Branford, CT 06405
/37
$27,500,000
- 8 Beds
- 8 Baths
- 11,536 Sq Ft
276 Otter Rock Dr, Greenwich, CT 06830

Magnificent formal gardens by renowned landscape architect Paul Gazerwitz set the stage for this historic 1890 Queen Anne with a pool and carriage house in the coveted Belle Haven Association. Blending historic elegance with modern sophistication, the 11,536 sq ft house was exquisitely restored and renovated by Markham Roberts, one of Architectural Digest's AD100 top interior designers. Featuring

Joseph Barbieri Sotheby's International Realty

276 Otter Rock Dr, Greenwich, CT 06830
/40
$25,500,000
- 9 Beds
- 14 Baths
- 14,266 Sq Ft
104 Dans Hwy, New Canaan, CT 06840

Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a

Leslie Razook William Pitt Sotheby's Int'l

104 Dans Hwy, New Canaan, CT 06840
/40
$25,000,000
- 6 Beds
- 11 Baths
- 19,569 Sq Ft
1131 Sasco Hill Rd, Fairfield, CT 06824

Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

Andrew Whiteley Brown Harris Stevens

1131 Sasco Hill Rd, Fairfield, CT 06824
/43
$24,950,000
- 10 Beds
- 19 Baths
- 17,878 Sq Ft
97 Pecksland Rd, Greenwich, CT 06831

Truly unique 19 Acre estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the

Robert Johnson Brown Harris Stevens CT, LLC

97 Pecksland Rd, Greenwich, CT 06831
/28
$24,000,000
- 10 Beds
- 16 Baths
- 15,820 Sq Ft
5 & 7 John St, Greenwich, CT 06831

Robin Hill Farm' and 'Smokey Hill Farm' are situated at one of the highest points in Greenwich in bucolic backcountry. This magnificent estate encompasses the main house, represented in this listing data sheet, two cottages, stables and gorgeous paddocks, Indoor and outdoor pools, tennis house, tennis court, and two ethereal fountains. Originally designed in 1937 by Augusta L.Noel (designer of

Shelly Tretter Lynch Compass Connecticut, LLC

5 & 7 John St, Greenwich, CT 06831
/34
$22,000,000
- 7 Beds
- 5.5 Baths
- 6,166 Sq Ft
36, 38, 0 Game Cock Rd, Greenwich, CT 06830

36, 38 and 0 Game Cock Road make up this 1.1+ acre island property that has been enjoyed as a multi generational family compound. One of only a few Island properties in Greenwich, let alone the Connecticut shoreline, to have it's own private bridge for access. The property boasts a 7 bedroom, 5 bath 6166 SQ FT main house, 3 en-suite bedroom 3238 SQ FT guest house, boathouse for entertaining,

Brett Smith Brown Harris Stevens CT, LLC

36, 38, 0 Game Cock Rd, Greenwich, CT 06830
/28
$19,800,000
- 8 Beds
- 8.5 Baths
- 9,995 Sq Ft
92 Beachside Ave, Westport, CT 06880

Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of

Cyd Hamer William Pitt Sotheby's Int'l

92 Beachside Ave, Westport, CT 06880
/37
$18,500,000
- 6 Beds
- 9 Baths
- 10,275 Sq Ft
41 Meadow Wood Dr, Greenwich, CT 06830

With breathtaking views of Long Island Sound, this custom-built Mediterranean-style home is nestled in an exclusive gated community known as Quarry Farm in Belle Haven. Featuring a terracotta-tiled roof, this luxurious home boasts 6-bedrooms and 6.3 baths on 4.7 acres of land. The central courtyard, which serves as the heart of the home, is surrounded by common living areas with extra-height

Jennifer Ho Douglas Elliman of Connecticut

41 Meadow Wood Dr, Greenwich, CT 06830
/38
$17,000,000
- 6 Beds
- 9 Baths
- 10,197 Sq Ft
865 Hollow Tree Ridge Rd, Darien, CT 06820

Blending refined elegance with complete privacy, this 9.5-acre estate is a true sanctuary for those seeking a sophisticated lifestyle. At the end of a Bradford Pear-lined gravel drive, the compound features a 10,000 sq. ft. main house, pool and pool house, two-bedroom guest cottage, and a breathtaking field house by architect Louise Brooks. The main home marries historic charm with sleek, modern

Ashley Dineen Compass Connecticut, LLC

865 Hollow Tree Ridge Rd, Darien, CT 06820
/17
$16,750,000
- 8 Beds
- 11 Baths
- 16,300 Sq Ft
90 Oneida Dr, Greenwich, CT 06830

Build your legacy in one of Greenwich, CT's most sought-after downtown gated communities. Approved plans and ready to break ground with local Award winning developer, Greenwich Custom Homes. A magnificent estate will be built with precision and finished with elegance, continuing to raise the bar for the finest living in Greenwich CT. This waterfront Georgian Colonial blends timeless elegance with

Brian Milton Compass Connecticut, LLC

90 Oneida Dr, Greenwich, CT 06830
/64
$16,750,000
- 5 Beds
- 9 Baths
- 13,031 Sq Ft
50 Dingletown Rd, Greenwich, CT 06830

Peace and tranquility amid 7.37 lush acres, just minutes from Downtown Greenwich: this is Harkaway Farm, a distinguished Georgian Colonial estate set behind stately stone pillars and impressive gates. A meandering drive carries you over a stone bridge fording a gentle stream, to the recently transformed home. Built exceptional craftsmanship the facade of the stately manner was preserved and

Francine Ehrlich Sotheby's International Realty

50 Dingletown Rd, Greenwich, CT 06830
/18
$15,000,000
- 8 Beds
- 10.5 Baths
- 10,171 Sq Ft
16 Windrose Way, Greenwich, CT 06830

Waterfront estate in coveted Mead Point, one of a few gated communities in Greenwich, ready for the next chapter. Prominently sited on 2 glorious acres with 225' of shorefront, luxurious pool and expansive open lawns. Amazing privacy with the Windrose Association 5-acre park next door, which has dock with electricity & water. Seven ensuite bedrooms; main floor primary suite. Grand reception hall

Amanda Miller Houlihan Lawrence

16 Windrose Way, Greenwich, CT 06830
/40
$15,000,000
- 7 Beds
- 10 Baths
- 9,129 Sq Ft
4800 Congress St, Fairfield, CT 06824

The Ultimate East Coast Sanctuary-Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning icons who demand seclusion with proximity to NYC. This 38.91-acre compound is a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music,

Leslie Razook William Pitt Sotheby's Int'l

4800 Congress St, Fairfield, CT 06824
/39
$13,995,000
- 6 Beds
- 8 Baths
- 10,286 Sq Ft
7 Parsonage Rd, Greenwich, CT 06830

An extraordinary newly constructed residence in the heart of Greenwich, Seven Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously designed living

Leslie McElwreath Sotheby's International Realty

7 Parsonage Rd, Greenwich, CT 06830
/50
$13,750,000
- 6 Beds
- 8 Baths
- 9,418 Sq Ft
52 Carriglea Dr, Riverside, CT 06878

Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

Stephen Archino Sotheby's International Realty

52 Carriglea Dr, Riverside, CT 06878
/39
$12,995,000
- 9 Beds
- 12 Baths
- 7,528 Sq Ft
Unlisted Address

A once in a lifetime opportunity to own over 230 acres overlooking Lake Waramaug. Nestled high in the hills overlooking the pristine beauty of the lake, this offering comprises six parcels of open fields and forest with exceptional views. Owned by the same family for the last 70 years, dignitaries from the worlds of art, politics, and industry have been entertained here while the stables,

Pat Lahoud William Pitt Sotheby's Int'l

Unlisted Address
/40
$12,000,000
- 7 Beds
- 6.5 Baths
- 8,119 Sq Ft
260 Willow St, Southport, CT 06890

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

Elizabeth Tritschler William Raveis Real Estate

260 Willow St, Southport, CT 06890
/6
$11,795,000
- 5 Beds
- 7 Baths
- 6,050 Sq Ft
14 Owenoke Park, Westport, CT 06880

Bluewater Home Owenoke Opportunity Knocks Again! Another beach masterpiece is underway and this 6050 sqft 5BR/3Car garage designed home with private yard, pool with spa, pond views and walking distance to Compo Beach will be ready Spring 2026. Enjoy this new beach construction living in the heart of Westport while peacefully tucked away on a private cul-de-sac.

Deirdre Andreoli Compass Connecticut, LLC

14 Owenoke Park, Westport, CT 06880
/23
$10,350,000
- 5 Beds
- 4 Baths
- 8,223 Sq Ft
111 Byram Shore Rd, Greenwich, CT 06830

Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage

Joseph Barbieri Sotheby's International Realty

111 Byram Shore Rd, Greenwich, CT 06830
/32
$10,000,000
- 5 Beds
- 8 Baths
- 7,021 Sq Ft
153 Ferry Rd, Lyme, CT 06439

Introducing Highover-a 25-acre hilltop estate overlooking the lower Connecticut River, designed by renowned architect Alfred Hopkins. With over half a mile of frontage, this property offers one of the most private and naturally protected waterfront settings in Connecticut, along with direct access to Long Island Sound and the Atlantic Ocean. The estate has welcomed legendary visitors, including

Edward Hillyer William Raveis Real Estate

153 Ferry Rd, Lyme, CT 06439
/18
$9,995,000 New Construction
- 7 Beds
- 10 Baths
- 10,800 Sq Ft
688 Hulls Farm Rd, Southport, CT 06890

This is the iconic property everyone is talking about! Introducing an extraordinary new custom residence set in the beloved estate area of Upper Southport near private equestrian facilities and public trails, beaches, restaurants, train, and shopping. Masterfully designed and customized to YOUR every whim with exquisite main house, separate party barn and/or guest house, pool with spa, tennis

Jaclyn Picarillo Higgins Group Bedford Square

688 Hulls Farm Rd, Southport, CT 06890
/40
$9,900,000
- 21 Beds
- 40 Baths
- 51,830 Sq Ft
50 Poplar Hill Dr, Farmington, CT 06032

Once home to both Mike Tyson and 50 Cent, this extraordinary estate sits on more than 17 private acres in Farmington, Connecticut-a historic town just 10 miles west of Hartford and ideally positioned between Boston and New York City. Spanning an impressive 51,000 square feet, the residence embodies unmatched opulence, with over $3 million in recent renovations elevating it to a world-class

Sherry Borgeson Berkshire Hathaway NE Prop.

50 Poplar Hill Dr, Farmington, CT 06032
/71
$9,870,000
- 6 Beds
- 6.5 Baths
- 7,456 Sq Ft
546 Lake Ave, Greenwich, CT 06830

PRIME MID-COUNTRY with 2.83 acres on Lake Avenue in GREENWICH, CT. This impressive stone home has undergone a complete gut renovation. Original architectural details are retained and enhanced with a new chic aesthetic of expansive living areas, sun-drenched rooms and soaring ceilings. The incredible Chef's Kitchen opens through two dramatic stone arched doorways to the family room w/fireplace and

Mary Jones Sotheby's International Realty

546 Lake Ave, Greenwich, CT 06830
/13
$9,500,000
- Land
- 426.5 Acres
- $22,274 per Acre
0 South Rd, Marlborough, CT 06447

426.5 beautiful acres, ready to be developed into a remarkable golfing retreat with homesites looking over the rolling 18-hole 7,010-yard course designed by the Roger Rulewich Group. There will be 120 acres designated to open space with ponds and scenic meadow views. This entire project was approved by the Town of Marlborough Open Space Conservation Area Regulation (OSCAR)., but several of the

R. Dean Eubank William Pitt Sotheby's Int'l

0 South Rd, Marlborough, CT 06447
/52
$9,350,000
- 6 Beds
- 8.5 Baths
- 9,845 Sq Ft
3 Anderson Rd, Greenwich, CT 06830

2025 Modern New Const. residence sits on 0.78 acres combines privacy with elegant design. Moments from Greenwich Ave. built by Hobi Award winner, RA Land Development, interiors by the acclaimed Laura Michael Design. This home features soaring 10ft ceilings, light filled rooms, and seamless indoor-outdoor living. Highlights are a Rooftop deck with Long Island Sound views that crowns the residence,

Sabrina Adorno William Raveis Real Estate

3 Anderson Rd, Greenwich, CT 06830
/36
$9,350,000
- 7 Beds
- 10 Baths
- 9,649 Sq Ft
18 Tokeneke Trail, Darien, CT 06820

This magnificent Round Meadows estate with a fantastic 9700 sf house on 5.346 acres of private property is now on the market for the first time in more than 54 years. Located in the private Tokeneke Association with protected land trust property to the East and West of it, Round Meadows is the ultimate in privacy and natural beauty. The owners had the vision to preserve, restore and ultimately

Robin Stineman William Pitt Sotheby's Int'l

18 Tokeneke Trail, Darien, CT 06820
/14
$8,995,000
- 6 Beds
- 7.5 Baths
- 10,400 Sq Ft
11 Winterset Rd, Greenwich, CT 06830

Ring in the New Year At Your New House — where modern luxury meets timeless Mid-Country living. This 10,000+ sq ft new construction is the latest offering by Ritzzo Development. Highlights include six en-suite bedrooms, 3rd floor room ready for a golf simulator, a custom Sub-Zero/Wolf kitchen w breakfast area, family room w striking wood burning hearth, oversized primary suite + seamless

Amanda Bates Houlihan Lawrence

11 Winterset Rd, Greenwich, CT 06830
/37
$8,950,000
- 7 Beds
- 8 Baths
- 13,056 Sq Ft
19 Seherr Thoss Dr, Litchfield, CT 06759

Butternut Brook House is a luxurious Litchfield County estate nestled in the heart of the Litchfield Hills, offering a rare combination of privacy, sophistication, and natural beauty. Set on over 36 acres of pristine Connecticut countryside, this stunning property features sweeping 360-degree views, a private pond, walking trails, and professionally landscaped grounds-all just five minutes from

Elyse Morris Elyse Harney Real Estate

19 Seherr Thoss Dr, Litchfield, CT 06759
/38
$8,875,000
- 6 Beds
- 8 Baths
- 8,334 Sq Ft
406 Wells Hill Rd, Lakeville, CT 06039

Perched on more than seventy acres of rolling meadows and sculpted gardens, Linden Hill Farm stands as one of the most distinguished country estates in the region. A tree-lined allee of Linden trees leads to the Georgian Revival residence, built in 1929, where timeless architecture is seamlessly paired with modern luxury. The six-bedroom main residence opens with a dramatic double-height entrance

Elyse Morris Elyse Harney Real Estate

406 Wells Hill Rd, Lakeville, CT 06039
/30
$8,750,000
- 5 Beds
- 8 Baths
- 9,619 Sq Ft
10 Birch Ln, Greenwich, CT 06830

Impeccably constructed colonial in Greenwich's Golden Triangle on 1.35 acres with pool bordered by a scenic pond. A double-height foyer leads to the formal living room and library, both with fireplaces. Chef's kitchen adjoins the family room with fireplace, butler's pantry, and formal dining room. French doors open to terrace with heated pool, barbecue and firepit. Mudroom and attached 4-car

Joseph Barbieri Sotheby's International Realty

10 Birch Ln, Greenwich, CT 06830
/39
$8,750,000
- 5 Beds
- 4.5 Baths
- 8,240 Sq Ft
841 Winchester Rd, Norfolk Historic District, CT 06058

Gracefully nestled at water's edge among lofty pines on over 115 utterly private and unspoiled woodland acres, this breathtaking lakefront country home features five bedrooms and four-and-a-half bathrooms and over 8,000 sq ft of luxurious living space. With extraordinary craftsmanship and exceptional materials, this custom built contemporary residence harmoniously integrates with its natural

Jennifer Leahy Compass Connecticut, LLC

841 Winchester Rd, Norfolk Historic District, CT 06058
/40
$8,600,000
- 7 Beds
- 6.5 Baths
- 9,420 Sq Ft
63 Turney Rd, Redding, CT 06896

Another Day in Paradise! Timeless grandeur, architectural mastery, and opportunity define this exceptional plantation-style colonial set on 39.23 acres bordered by 100+ acres of protected forestland-a rare opportunity for stately country living in a singular setting.For the sportsman, pristine woodlands and abundant wildlife offer boundless opportunities for hunting, hiking, and connecting with

Roni Agress William Pitt Sotheby's Int'l

63 Turney Rd, Redding, CT 06896
/40
$8,595,000 Open Sat 1PM - 3PM
- 7 Beds
- 9 Baths
- 11,494 Sq Ft
928 West Rd, New Canaan, CT 06840

BRAND NEW CONSTRUCTION completed on 11/15/25. IMMEDIATE OCCUPANCY. The Ultimate Compound! Exceptional new construction by custom home builder, Woodcrest Homes. Ultra-Prime West Road Location on 6.5 flat & dry private acres with room for a Pool, Pool House, Sports Court and Guest House (with special permit application). Seven ensuite bedrooms, transitional style throughout with beautiful finishes

Jaime Sneddon William Pitt Sotheby's Int'l

928 West Rd, New Canaan, CT 06840

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