Luxury Homes for Sale in Connecticut

/49
$100,000,000
- 8 Beds
- 14 Baths
- 13,163 Sq Ft
108 Cedar Cliff Rd, Riverside, CT 06878

Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside's prestigious Indian Head Association, this storied property occupies the historic grounds of

Leslie McElwreath Sotheby's International Realty

108 Cedar Cliff Rd, Riverside, CT 06878
/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
/39
$42,995,000
- 6 Beds
- 9 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
/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
/40
$29,995,000
- 10 Beds
- 8 Baths
- 8,378 Sq Ft
0 Rogers Island, Branford, CT 06405

A truly unforgettable and exceptionally rare offering-Rogers Island presents an exciting opportunity to own a private island paired with a mainland residence, delivering the perfect balance of seclusion and convenience. The mainland property includes its own dock, parking, and support space, making access to the island with a 5-minute boat ride, seamless and effortless. Just offshore, the island

Alicia Hale

Coldwell Banker Realty

(475) 259-2473

0 Rogers Island, Branford, CT 06405
/16
$28,500,000

New Construction
- 7 Beds
- 12 Baths
- 18,370 Sq Ft
39 Brookridge Dr, Greenwich, CT 06830

Set along a quiet street 3 mins from town, this exceptional 2027 new construction blends timeless architecture w modern livability. A striking white brick façade, steep gables, and dark-framed windows create a refined yet welcoming presence. Warm interior light highlights expansive living spaces, including a dramatic kitchen and family room designed for both everyday living and elevated

Amanda Bates Houlihan Lawrence

39 Brookridge 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
/39
$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
/86
$23,000,000
- 5 Beds
- 7 Baths
- 7,400 Sq Ft
58 Shore Rd, Old Greenwich, CT 06870

You don't look at your home...you look out from it.Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering and execution where every material, finish and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a façade clad in premium Thermory wood siding beneath a

Danielle Malloy

Serhant Connecticut LLC

(475) 253-5714

58 Shore Rd, Old Greenwich, CT 06870
/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
/43
$21,000,000
- 8 Beds
- 12 Baths
- 14,071 Sq Ft
8 Fox Run Ln, Greenwich, CT 06831

Perfectly sited on a quiet lane minutes from Greenwich Avenue, this 2024 SBP home offers serenity on nearly 5.5 gated acres. Walls of glass flood the interiors with natural light, highlighting 7'' white oak floors, a dramatic foyer, Calacatta marble fireplaces and Bocci lighting across 11,000+ sq ft. The open plan features a Bulthaup kitchen, living room with bar, and main-level bedroom suite or

Megan Sullivan

Douglas Elliman of Connecticut

(475) 260-5961

8 Fox Run Ln, Greenwich, CT 06831
/6
$19,950,000

$5M PRICE DROP
- 9 Beds
- 13 Baths
- 16,154 Sq Ft
16 Doubling Rd, Greenwich, CT 06830

GREAT INVESTMENT OPPORTUNITY-Bellavista is a 16,000+sf estate designed by architect Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus Long Island Sound views from the 2nd and 3rd floors, A truly

Jill Kelly Sotheby's International Realty

16 Doubling Rd, Greenwich, CT 06830
/51
$19,900,000
- 7 Beds
- 10 Baths
- 18,000 Sq Ft
37 Burying Hill Rd, Greenwich, CT 06831

Custom designed and built to exacting standards, this phenomenal back country lakefront compound was built to exacting standards offering fabulous privacy and flexibility for families, guests and staff. Prominent local design build firm created a masterpiece that combines a pre war elegance with substantial entertaining and modern lifestyle amenities. Multiple structures, including a large pool

Robert Johnson Brown Harris Stevens CT, LLC

37 Burying Hill Rd, Greenwich, CT 06831
/25
$19,000,000
- 5 Beds
- 8.5 Baths
- 8,248 Sq Ft
207 Long Neck Point Rd, Darien, CT 06820

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned

Shelly Tretter Lynch Compass Connecticut, LLC

207 Long Neck Point Rd, Darien, CT 06820
/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
/39
$17,995,000
- 7 Beds
- 10 Baths
- 15,216 Sq Ft
19 Khakum Dr, Greenwich, CT 06831

Privately set on more than 6 extraordinary acres within the prestigious Khakum Wood Association, this award-winning estate offers distinction, privacy, and architectural excellence in an A+ location. Clad in limestone, fieldstone, and stucco and crowned by a graduated slate roof, the residence is defined by timeless elegance and exceptional quality. Bright interiors feature soaring ceilings,

Deborah Ward Sotheby's International Realty

19 Khakum Dr, Greenwich, CT 06831
/25
$15,000,000
- 6 Beds
- 11 Baths
- 10,523 Sq Ft
4 Rockwood Lane Spur, Greenwich, CT 06830

Modern planning, superior craftsmanship and bespoke details define this extraordinary newly built Transitional home by visionary leaders Christopher Pagliaro Architects, East Coast Structures and M&N Development. Private 1.64 acres showcase resort style amenities indoors and out. Brick and cast stone facade home offers 10,573 sq. ft. on four customized levels with oversized European Klar windows,

Deborah Needle Houlihan Lawrence

4 Rockwood Lane Spur, Greenwich, CT 06830
/40
$15,000,000
- 7 Beds
- 6.5 Baths
- 6,215 Sq Ft
4 Sherwood Island Ln, Westport, CT 06880

Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected

Andrew Whiteley Brown Harris Stevens

4 Sherwood Island Ln, Westport, CT 06880
/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 buyers 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

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
/43
$14,900,000
- 5 Beds
- 8 Baths
- 9,546 Sq Ft
279 Saugatuck Ave, Westport, CT 06880

Panoramic vistas of Long Island Sound extend from this gated, resort-style estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with

Joseph Barbieri Sotheby's International Realty

279 Saugatuck Ave, Westport, CT 06880
/43
$14,890,000
- 5 Beds
- 7 Baths
- 6,069 Sq Ft
4 Little Cove Ln, Old Greenwich, CT 06870

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree unobstructed water views from every bedroom and living space, with beautiful NYC skyline views. Designed for modern coastal living, the home spans three levels with six decks and seamless indoor-outdoor flow. Walls of glass and

Alexandra Robinson Corcoran Centric Realty LLC

4 Little Cove Ln, Old Greenwich, CT 06870
/10
$14,750,000

New Construction $900K PRICE INCREASE
- 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
/67
$14,600,000

$1M PRICE DROP
- 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
/40
$14,500,000
- 6 Beds
- 8 Baths
- 8,738 Sq Ft
379 Ocean Dr W, Stamford, CT 06902

Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal

Joshua Weisman William Raveis Real Estate

379 Ocean Dr W, Stamford, CT 06902
/14
$14,495,000
- 7 Beds
- 11 Baths
- 14,000 Sq Ft
532 Round Hill Rd, Greenwich, CT 06831

Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and

Danielle Malloy

Serhant Connecticut LLC

(475) 270-5264

532 Round Hill Rd, Greenwich, CT 06831
/13
$14,450,000

New Construction
- 6 Beds
- 10 Baths
- 10,731 Sq Ft
137 Doubling Rd Unit A, Greenwich, CT 06830

*Complete this Summer* Privately gated on 1.65 acres in Greenwich's coveted mid-country, this home blends timeless architecture by Alex Kaali-Nagy AIA with modern elegance. Over 10,000 sq ft features 10-ft ceilings, white oak floors, and custom millwork throughout. The main level includes a library, formal dining room, butler's pantry, and a chef's kitchen opening to an expansive family room and

Megan Sullivan

Douglas Elliman of Connecticut

(475) 269-4447

137 Doubling Rd Unit A, Greenwich, CT 06830
/17
$13,950,000
- Land
- 7.2 Acres
- $1,937,500 per Acre
122 Round Hill Rd, Greenwich, CT 06831

Seven-plus acres on Round Hill Road, brought to market after six decades in one family. An existing approximately 8,000 SF Connecticut Colonial sits on the parcel -- livable today and easily occupied during the planning and entitlement phase. Additional improvements include a nearly one-acre pond at the back of the property, a resort-style pool, tennis court, two-bedroom guest cottage, and

Leslie McElwreath Sotheby's International Realty

122 Round Hill Rd, Greenwich, CT 06831
/39
$13,500,000
- 4 Beds
- 7 Baths
- 7,142 Sq Ft
16 Indian Point Ln, Riverside, CT 06878

Presenting a rare Riverside home, this SBP Homes masterpiece, custom-built in 2009, is now on the market for the first time. Designed to capture breathtaking water views and stunning sunsets. Situated in a peaceful private association within the desirable 1-acre zone off Indian Head Road. Manhattan skyline in the distance, regular Summer firework displays can be seen from Rye Playland as the

Robert Johnson Brown Harris Stevens CT, LLC

16 Indian Point Ln, Riverside, CT 06878
/41
$13,500,000
- 5 Beds
- 4 Baths
- 3,330 Sq Ft
22 Northway, Old Greenwich, CT 06870

Live like you're on vacation all year round in Old Greenwich with spectacular 200 feet of waterfront with stunning views of Manhattan. Amazing vistas from every room of this 5 bedroom designer house. Sliding doors open to expansive deck, both covered and uncovered overlooking private pier with ramp to floating dock. Dine al fresco with stunningly beautiful sunsets, and enjoy sailing, boating,

Megan Epand Houlihan Lawrence

22 Northway, Old Greenwich, CT 06870
/51
$13,495,000
- 6 Beds
- 10 Baths
- 11,373 Sq Ft
7 Loch Ln, Greenwich, CT 06830

Privately tucked away at the end of a tranquil lane in prestigious Mid-Country Greenwich, this custom built stone manor is a rare offering of timeless architecture, exceptional craftsmanship, and resort-like amenities. Encompassing more than 11,373 square feet and set upon 3.2 exquisitely landscaped level acres, the estate is surrounded by sweeping lawns, mature specimen plantings, and

Leslie McElwreath Sotheby's International Realty

7 Loch Ln, Greenwich, CT 06830
/47
$13,100,000
- 6 Beds
- 8 Baths
- 10,286 Sq Ft
7 Parsonage Rd, Greenwich, CT 06830

SUMMER FUN BEGINS HERE! An extraordinary newly constructed residence in the heart of Greenwich,7 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

Leslie McElwreath Sotheby's International Realty

7 Parsonage Rd, Greenwich, CT 06830
/40
$13,000,000
- 61 Beds
- 81 Baths
- 75,075 Sq Ft
35 Union St, New London, CT 06320

Rare opportunity to own The Crocker House, a landmark mixed-use investment property anchoring the corner of Union and State Streets in downtown New London. Originally constructed in 1872 as a five-story luxury hotel and thoughtfully maintained over the years, this iconic red-brick building offers three distinct income streams under one roof: 81 residential apartments (studios, one- and

Lisa Cozzi Century 21 AllPoints Realty

35 Union St, New London, CT 06320
/57
$12,900,000
- 8 Beds
- 13 Baths
- 13,268 Sq Ft
550 Round Hill Rd, Greenwich, CT 06831

Nestled on 4.09 acres in Greenwich, CT, this breathtaking 8-bedroom Georgian Colonial estate offers unparalleled elegance and privacy. Commanding spectacular big sky views from its perch 560' above sea level, the property features exquisite formal gardens, and pool. Inside, grand-scale rooms with soaring ceilings, masterful stonework, elegant millwork, and arches create a luxurious atmosphere.

Stephen Archino Sotheby's International Realty

550 Round Hill Rd, Greenwich, CT 06831
/48
$12,100,000
- 5 Beds
- 5.5 Baths
- 5,560 Sq Ft
123 Saddle Rock Rd, Stamford, CT 06902

Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance.Designed by Hunt & Hunt Architects and completed in

Leslie McElwreath Sotheby's International Realty

123 Saddle Rock Rd, Stamford, CT 06902
/38
$12,100,000
- 6 Beds
- 13 Baths
- 11,668 Sq Ft
524 Lake Ave, Greenwich, CT 06830

A gated drive opens to this elegant six-bedroom Mid-Country Manor overlooking tranquil views of Horseneck Brook. A stone courtyard introduces the dramatic four-story residence with elegant foyer, where sweeping butterfly staircases and limestone floors create a striking architectural welcome. From the gracious gallery hall, beautifully proportioned formal and informal rooms unfold-including

Leslie McElwreath Sotheby's International Realty

524 Lake Ave, Greenwich, CT 06830
/13
$12,000,000
- Land
- 20.21 Acres
- $593,765 per Acre
1405-1445 Boston Post Rd, Old Saybrook, CT 06475

Bushnell Farm presents a rare opportunity to acquire one of the Connecticut shoreline's most unique and historically significant properties. Located on Boston Post Road in Old Saybrook, this 20.21-acre property offers an exceptional combination of history, character, visibility, and development potential. The property features open meadows, mature trees, historic New England stone walls, and the

Casey Fisher Houlihan Lawrence WD

1405-1445 Boston Post Rd, Old Saybrook, CT 06475
/12
$12,000,000
- 4 Beds
- 1 Bath
- 2,059 Sq Ft
1445 Boston Post Rd, Old Saybrook, CT 06475

A rare opportunity to acquire a historic Connecticut landmark. The Bushnell Farm House and Barn offer a unique chance to restore and reimagine an important piece of Old Saybrook history. Featuring the historic Elisha Bushnell House and accompanying barn, the property showcases classic New England architecture, mature landscaping, stone walls, and the timeless character that has made this site a

Casey Fisher Houlihan Lawrence WD

1445 Boston Post Rd, Old Saybrook, CT 06475

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