Luxury Homes for Sale in Connecticut

/50
$75,000,000
- 8 Beds
- 14 Baths
- 15,944 Sq Ft
1233 Rock Rimmon Rd, Stamford, CT 06903

An extraordinary 268-acre legacy estate spanning the New York-Connecticut border, Hillandale offers unrivaled privacy and timeless grandeur. Once owned by the Sulzberger family of the New York Times, the 15,000+ sq ft, eight-bedroom European-inspired manor has been meticulously restored and features magnificent formal entertaining rooms, 11 fireplaces, two elevators, a paneled library, sun-filled

Leslie McElwreath Sotheby's International Realty

1233 Rock Rimmon Rd, Stamford, CT 06903
/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
/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
/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
/37
$24,900,000
- 7 Beds
- 8 Baths
- 18,217 Sq Ft
44 & 40 Mayo Ave, Greenwich, CT 06830

Nestled within the prestigious Belle Haven, Fairholme Estate is a magnificent English Manor that exudes timeless elegance and grandeur. Set on 2.74 beautifully landscaped acres, this seven-bedroom masterpiece features a spectacular pool, gracious wraparound porch, formal gardens, and expansive lawns, complemented by a charming coachman's cottage. Meticulously preserved to honor its historic

Joanne Mancuso Houlihan Lawrence

44 & 40 Mayo Ave, Greenwich, CT 06830
/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
/6
$22,825,000
- 8 Beds
- 10 Baths
- 12,946 Sq Ft
11 Beachside Common, Westport, CT 06880

Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island

Andrew Whiteley Brown Harris Stevens

11 Beachside Common, Westport, CT 06880
/20
$21,000,000
- 8 Beds
- 12 Baths
- 14,071 Sq Ft
8 Fox Run Ln, Greenwich, CT 06831

Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls of

James Hoffman Houlihan Lawrence

8 Fox Run Ln, Greenwich, CT 06831
/21
$19,000,000
- 6 Beds
- 9 Baths
- 9,565 Sq Ft
25 Field Point Cir, Greenwich, CT 06830

FIELD POINT CIRCLE: Grandly proportioned French-inspired manor set within the prestigious 24-hour guard-gated private Association. Sited on 2.2 level parklike acres, this limestone-clad residence with a 2014 new slate roof offers exceptional privacy for outdoor living, featuring a pool and spa. The elegant six-bedroom residence, with 7 full and two half bathrooms, is distinguished by a flexible

Leslie McElwreath Sotheby's International Realty

25 Field Point Cir, Greenwich, CT 06830
/8
$18,999,000 New Construction
- 6 Beds
- 12 Baths
- 17,197 Sq Ft
528 Round Hill Rd, Greenwich, CT 06831

Stunning New Construction. A Grand Estate of Architectural Distinction. This Incredible new build was Conceived and will be Constructed without Compromise. A build of enduring significance beautifully set on 4 acres. Spanning 17,197 square feet, this residence achieves extraordinary vertical volume with 11-foot ceilings on the main level and a breathtaking two-and-a-half-story family room framed

Kathryn Bates Compass Connecticut, LLC

528 Round Hill Rd, Greenwich, CT 06831
/44
$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
/31
$15,995,000
- 6 Beds
- 8 Baths
- 8,962 Sq Ft
44 Khakum Wood Rd, Greenwich, CT 06831

Located in Khakum Wood Association, a premier Greenwich location. The extensive 3 year expansion & renovation completed in 2025 is the collaboration of Top 100 Architectural Digest designers and architects: McAlpine House,Studio Mellone, Mario Neivera,with construction by the Tallman Builders.Reimagined for today's living.Pool, Carriage house with apartment, gym, infrared sauna, Savant smart

Robin Kencel Compass Connecticut, LLC

44 Khakum Wood Rd, Greenwich, CT 06831
/40
$15,945,000
- 6 Beds
- 10 Baths
- 11,211 Sq Ft
30 Meadowcroft Ln, Greenwich, CT 06830

Sited on over two acres of private, west-facing land in the heart of Greenwich's coveted Golden Triangle, this architectural modern masterpiece commands attention. Designed in collaboration with renowned architect William D. Earls, this 11,000+ sq ft six-bedroom estate showcases timeless design, masterful craftsmanship, and refined sophistication. Completed in 2018, the residence blends bold

Jeffrey Jackson Corcoran Centric Realty

30 Meadowcroft Ln, Greenwich, CT 06830
/67
$15,600,000
- 8 Beds
- 14 Baths
- 17,121 Sq Ft
164 Round Hill Rd, Greenwich, CT 06831

Unrivaled in its beauty, design, build and landscape, this unparalleled Mid-Country estate showcases an extensive 4 year restoration and renovation by leading industry visionaries Sam Mitchell and Nordic Builders. This stunning eight-bedroom English Manor sits at the end of a long, gated driveway on Round Hill Road with spectacular European-inspired gardens, sparkling pool and three bed/three

Julie Church Houlihan Lawrence

164 Round Hill Rd, Greenwich, CT 06831
/39
$15,000,000
- 5 Beds
- 10 Baths
- 10,197 Sq Ft
865 Hollow Tree Ridge Rd, Darien, CT 06820

Set on 9.4 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, a two-bedroom guest cottage, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house

Ashley Dineen Compass Connecticut, LLC

865 Hollow Tree Ridge Rd, Darien, CT 06820
/37
$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 engineered for the world's most discerning icons who demand seclusion with proximity to NYC. This 38.91-acre compound ,is the mid century former home of Richard Rodgers, composer of The Sound of Music. Restored and expanded to incorporate 7 bedrooms and 7

Leslie Razook William Pitt Sotheby's Int'l

4800 Congress St, Fairfield, CT 06824
/40
$14,995,000
- 11 Beds
- 17 Baths
- 15,479 Sq Ft
326 Stanwich Rd, Greenwich, CT 06830

Welcome to An Extraordinary Lakeside Retreat in GreenwichEncompassing an incredible assemblage of 9.4 lakeside acres ideally situated within the Greenwich mid country, Frye Lake Compound is the ultimate sanctuary for those seeking a world of elevated privacy, scenery and architecture. Nestled around the serene 11-acre Frye Lake, this incomparable park-like estate represents an idyllic

Kevin Sneddon Compass Connecticut, LLC

326 Stanwich Rd, Greenwich, CT 06830
/42
$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
/12
$13,850,000 New Construction
- 7 Beds
- 9 Baths
- 10,496 Sq Ft
133 Doubling Rd, Greenwich, CT 06830

Stunning 6-bedroom Colonial in Mid-Country currently underway (Summer '26 completion). Designed to impress by the renowned Alex Kaali-Nagy Architect AIA with a traditional exterior look, quintessential Greenwich, but a transitional interior with 4 finished levels and thoughtful design touches throughout, including extensive millwork. Exceptional primary suite with walk-in dressing rooms, plus 5

Amanda Miller Houlihan Lawrence

133 Doubling Rd, Greenwich, CT 06830
/33
$13,000,000
- 5 Beds
- 10 Baths
- 9,564 Sq Ft
10 Shorehaven Rd, Norwalk, CT 06855

Rarely does an opportunity arise to own a home in the coastal enclave of Shorehaven, and 10 Shorehaven Road is a true masterpiece. This Nantucket-inspired estate blends timeless elegance with relaxed coastal charm, offering unmatched luxury and tranquility. Set along the serene waterfront, the lush, landscaped grounds feature a sparkling pool, spa, and private dock-perfect for boating adventures

Laurie Morris Compass Connecticut, LLC

10 Shorehaven Rd, Norwalk, CT 06855
/37
$13,000,000
- 5 Beds
- 10 Baths
- 10,197 Sq Ft
865 Hollow Tree Ridge Rd, Darien, CT 06820

Set on 7 acres, this exceptional estate offers a private, sophisticated retreat at the end of a Bradford pear-lined gravel drive. The property includes a 10,000-square-foot main residence with pool and pool house, and a remarkable field house designed by architect Louise Brooks. The main house blends timeless elegance with modern design, while the field house delivers a one-of-a-kind recreational

Ashley Dineen Compass Connecticut, LLC

865 Hollow Tree Ridge Rd, Darien, CT 06820
/27
$12,495,000
- 6 Beds
- 11 Baths
- 10,421 Sq Ft
537 North St, Greenwich, CT 06830

Exquisite six-bedroom stone manor, executed to the highest standards, and sited atop a majestic knoll on 2.97 picturesque acres in the heart of Mid-Country Greenwich. Chic, sophisticated interiors by Amy Hirsch unfold across three levels of light-filled living space, highlighted by soaring ceilings, oversized custom windows, and every modern amenity. An elegant double-height entry hall with

Leslie McElwreath Sotheby's International Realty

537 North St, Greenwich, CT 06830
/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

Libby Tritschler

William Raveis Real Estate

(203) 350-0943

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

Ready for SUMMER 2026! Bluewater Home's newest luxury creation is close to completion. This 6050 sqft 5BR/3Car garage designed home with private yard, pool with spa, pond & LI sound views and walking distance to Compo Beach offers privacy and multiple balconies and indoor/outdoor spaces. Oversized rooms and expansive kitchen with double islands, scullery kitchen, elevator and private primary

Deirdre Andreoli Compass Connecticut, LLC

14 Owenoke Park, Westport, CT 06880
/33
$11,500,000
- 6 Beds
- 7 Baths
- 8,081 Sq Ft
19 Hawkwood Ln, Greenwich, CT 06830

Set on 2 private, gated acres off North Street, this exceptional Greenwich mid-country estate offers rare privacy, timeless architecture & refined modern luxury. Originally designed in 1938 by renowned architect Nora Stanton Barney and completely rebuilt & expanded in 2005, the stately brick residence features elegant formal rooms plus relaxed indoor & outdoor living spaces. A 2021 renovation

Kevin Sneddon Compass Connecticut, LLC

19 Hawkwood Ln, Greenwich, CT 06830
/30
$11,250,000
- 5 Beds
- 6.5 Baths
- 6,966 Sq Ft
188 Round Hill Rd, Greenwich, CT 06831

Spanning 11 remarkable Mid-Country acres on Round Hill Road, this exceptional property offers sweeping western exposures over rolling meadow land framed by mature specimen trees--an increasingly rare and investment-worthy setting. The five bedroom main residence, designed by renowned architect Mott B. Schmidt, showcases elegant formal spaces, an eat-in kitchen, and a tranquil primary suite with

Leslie McElwreath Sotheby's International Realty

188 Round Hill Rd, Greenwich, CT 06831
/28
$10,950,000
- 6 Beds
- 7 Baths
- 9,834 Sq Ft
174 Round Hill Rd, Greenwich, CT 06831

Spectacular lifestyle - this custom built handsome Colonial is set up high on 2 exceptional acres in the coveted Golden Triangle and just minutes from town and schools. This sun-filled 6-bedroom home with 10' ceilings is designed for seamless indoor-outdoor living. Gracious formal and informal rooms, a gourmet eat-in kitchen, and family room open to an expansive terrace with outdoor fireplace and

B.K. Bates Houlihan Lawrence

174 Round Hill Rd, Greenwich, CT 06831
/38
$10,950,000
- 4 Beds
- 4 Baths
- 4,262 Sq Ft
189 Shore Rd, Old Greenwich, CT 06870

An extraordinary waterfront residence in Old Greenwich, offers a rare opportunity for sophisticated coastal living with spectacular, unobstructed water views from virtually every room. Meticulously redesigned by renowned architect Rick Swann, this exceptional home is defined by dramatic architectural details, soaring ceilings, and an open, light-filled floor plan that seamlessly blends indoor

Joy Kim Metalios Houlihan Lawrence

189 Shore Rd, Old Greenwich, CT 06870
/7
$10,650,000 New Construction
- 6 Beds
- 8 Baths
- 9,100 Sq Ft
11 Dogwood Ln, Westport, CT 06880

Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

Jen Kass Higgins Group Bedford Square

11 Dogwood Ln, Westport, CT 06880
/11
$10,350,000
- 6 Beds
- 8 Baths
- 7,072 Sq Ft
12 Woodside Rd, Greenwich, CT 06830

DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive,

Leslie McElwreath Sotheby's International Realty

12 Woodside Rd, Greenwich, CT 06830
/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

Welcome to 'Highover,' a 25-acre hilltop estate on the Connecticut River, voted the WSJ House of the Month nationwide. Over half a mile of waterfront, with natural barriers, ensures unmatched privacy and security. Accommodation for extended family and live-in help. Uniquely poised between New York and Boston, and less than an hour by helicopter from JFK, Logan, and Bradley. The home, designed by

Edward Hillyer William Raveis Real Estate

153 Ferry Rd, Lyme, CT 06439
/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
/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
/40
$8,999,000
- 7 Beds
- 9 Baths
- 10,482 Sq Ft
19 Beachside Common, Westport, CT 06880

Like-new custom modern home with open-concept living designed for comfort and entertaining. The main level connects the family room, dining room, office, and chef's kitchen featuring Sub-Zero and Wolf appliances, invisible speakers, quartzite countertops, custom cabinetry, two large islands and multiple sliding glass doors leading to an outdoor oasis. The spacious pantry includes custom shelving,

Gina Hackett Compass Connecticut, LLC

19 Beachside Common, Westport, CT 06880
/8
$8,995,000 New Construction
- 6 Beds
- 10 Baths
- 10,216 Sq Ft
2 Stillman Ln, Greenwich, CT 06831

Exceptional 2026 new construction offering resort-style living across a main residence + pool house on a private one-acre lot close to town. Designed by Schettino, the main house features 5 bedrooms, 7 full baths + 2 powder rooms with a seamless, light-filled floor plan ideal for entertaining and everyday living. The second floor incl a luxurious primary suite w balcony, dual walk-in closets, +

Amanda Bates Houlihan Lawrence

2 Stillman Ln, Greenwich, CT 06831
/26
$8,995,000 Coming Soon
- 8 Beds
- 10 Baths
- 15,172 Sq Ft
2 Judy Point Ln, Westport, CT 06880

Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house.

Daniel Kramp Christie's International Real Estate

2 Judy Point Ln, Westport, CT 06880

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