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
/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
/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
/7
$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
/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 Georgian Colonial, with LI Sound waterfront access, blends

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
/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
/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
/13
$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
/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
/40
$10,995,000
- 7 Beds
- 9 Baths
- 8,232 Sq Ft
19 Beachside Common, Westport, CT 06880

Experience the ultimate in luxury with this custom-designed Bluewater Home, nestled on a sought after Greens Farms cul-de-sac. This exceptional waterfront property offers panoramic water views from nearly every room, creating a serene and picturesque setting. The bright and modern home features seven bedrooms across four expansive levels, offering ample space for living, working, and

Gina Hackett Compass Connecticut, LLC

19 Beachside Common, Westport, CT 06880
/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
/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

VOTED WALL STREET JOURNAL HOME OF THE MONTH AND NOW IN CONTENTION FOR THE WSJ HOME OF THE YEAR. Welcome to 'Highover,' a 25-acre hilltop estate on the Connecticut River. 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

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
/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
/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
/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

(203) 717-5061

63 Turney Rd, Redding, CT 06896
/12
$8,495,000
- Land
- 9.3 Acres
- $913,441 per Acre
65 John St, Greenwich, CT 06831

Rare opportunity to create your own sophisticated country retreat comprising 9.3 private, peaceful acres overlooking Closes Pond and bordering the Audubon Preserve with miles of scenic trails in the heart of bucolic Backcountry. This extraordinary parcel is steeped in natural beauty with an allee of crab apple trees, grove of Linden trees and sweeping views. Tucked away behind a gated entry and

James Hoffman Houlihan Lawrence

65 John St, Greenwich, CT 06831
/34
$8,250,000
- 6 Beds
- 9 Baths
- 9,295 Sq Ft
34 Dublin Hill Dr, Greenwich, CT 06830

Ideally located on a picture-perfect cul-de sac, this Shingle Style house has had just one owner since it was built in 2005. A well-conceived 9,295 +/-SF floor plan comprises six bedrooms, seven full bathrooms and two powder rooms, plus five fireplaces. High ceilings invite an abundance of light, while exquisite millwork, rich hardwood floors and a desirable layout highlight the appealing

Leslie McElwreath Sotheby's International Realty

34 Dublin Hill Dr, Greenwich, CT 06830
/40
$8,200,000
- 6 Beds
- 9 Baths
- 8,457 Sq Ft
62 Big Bear Hill Rd, New Milford, CT 06776

A Legacy Estate Where Natural Beauty and Serenity Meet Sophisticated Living. Discover an extraordinary private retreat where nature's magic meets world-class refinement. Once owned by mineral magnate Ferdinand Julius Fohs and later donated to establish a camp for underprivileged NYC youth, this 100-acre sanctuary with 15-acre private lake and over 23,000 sq ft of living space has been extensively

Pat Lahoud William Pitt Sotheby's Int'l

62 Big Bear Hill Rd, New Milford, CT 06776
/56
$8,000,000
- 5 Beds
- 5 Baths
- 3,669 Sq Ft
640 Round Hill Rd, Greenwich, CT 06831

This is an opportunity to own a piece of Greenwich history. A fully restored antique farmhouse offering approximately 3,669 square feet of refined living space, set on extraordinary level acreage with sweeping meadow views and an irreplaceable country setting across from protected conservation land with direct access to the Greenwich Riding Trails. The residence blends historic authenticity with

Monica Webster Douglas Elliman of Connecticut

640 Round Hill Rd, Greenwich, CT 06831
/25
$8,000,000
- Land
- 122.65 Acres
- $65,226 per Acre
0 Frost Bridge Rd Unit 24118953, Watertown, CT 06795

Big beautiful land for sale in the Watertown Business Park area. Total of 8 land parcels that equal 122.65 acres of record. See map on file for visual of the large parcels that abut. See the Rt 262 frontage, Echo Lake Road frontage, Dinunzio Road and Ledge Road access. Wonderful curb appeal and very close Route 8 highway on/off access. Land is currently zoned for office, industrial, retail &

Laurie Lukasavage Showcase Realty, Inc.

0 Frost Bridge Rd Unit 24118953, Watertown, CT 06795

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