Luxury Homes for Sale in Connecticut

/40
$10,500,000

$5M PRICE DROP
- 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
/24
$10,495,000
- 4 Beds
- 5.5 Baths
- 6,045 Sq Ft
7 Rowayton Ave, Norwalk, CT 06853

Set prominently along the coveted shoreline of Rowayton, this extraordinary residence is a true architectural masterpiece that defies the standard coastal trope. Designed by award-winning Cardello Architects, the home is a fortress of design-a structural marvel built with an uncompromising integrity that feels as permanent as the tides. The silhouette is bold and commanding, yet every element

Libby Mattson Houlihan Lawrence

7 Rowayton Ave, Norwalk, CT 06853
/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
/39
$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
/46
$9,875,000
- 5 Beds
- 5.5 Baths
- 6,852 Sq Ft
203 Shore Rd, Old Greenwich, CT 06870

Hamptons-Inspired Elegance in Waterfront Lucas PointExperience the ease of coastal living just one hour from New York City in the coveted private waterfront association of Lucas Point in Old Greenwich. Residents enjoy an exceptional lifestyle anchored by a private sandy beach, dock, and boat storage, while the neighborhood's charming privet-lined lanes foster a true sense of community--where

Tracey Koorbusch Sotheby's International Realty

203 Shore Rd, Old Greenwich, CT 06870
/8
$9,860,000

New Construction
- 6 Beds
- 9 Baths
- 9,200 Sq Ft
9 Over Rock Ln, Westport, CT 06880

Newly completed by Compo Luxury Homes, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating

Danna Rogers Higgins Group Bedford Square

9 Over Rock Ln, Westport, CT 06880
/40
$9,850,000
- 5 Beds
- 7.5 Baths
- 9,481 Sq Ft
20 Saltus Dr, Old Saybrook, CT 06475

YOUR OWN PRIVATE COUNTRY CLUB! Enjoy the expansive 3500 sf granite terrace, a heated saltwater swimming pool, a deep water dock and a pool house with a full kitchen and seating for 10! This modern masterpiece, sited to take full advantage of a private 1.6 acre waterfront location overlooking North Cove and the Connecticut River has been constructed with the best curated materials. 20 Saltus Drive

Margaret Muir William Pitt Sotheby's Int'l

20 Saltus Dr, Old Saybrook, CT 06475
/37
$9,750,000
- 6 Beds
- 8 Baths
- 11,567 Sq Ft
31 Sawmill Ln, Greenwich, CT 06830

Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated and expanded, this warmly inviting residence offers 10,664± square feet with six bedrooms, six full and two half baths, plus eight fireplaces. Above the three-bay detached garage is a renovated two-bedroom, 903-square-foot

Joseph Barbieri Sotheby's International Realty

31 Sawmill Ln, Greenwich, CT 06830
/15
$9,495,000
- 4 Beds
- 4.5 Baths
- 5,500 Sq Ft
3 Manatook Way, Nantucket, MA 02554

Tucked just moments from the village, this exceptional 'Sconset residence pairs privacy with refined, resort-caliber living. A private pool, expansive outdoor entertaining space, and a thoughtfully composed indoor-outdoor flow set the tone throughout, while high-end custom finishes carry the same level of craft into every room. With four spacious bedrooms plus additional office/sleeping space, a

Jeffrey Lee Lee Real Estate

3 Manatook Way, Nantucket, MA 02554
/7
$9,350,000
- 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
/37
$9,250,000

New Construction
- 6 Beds
- 8.5 Baths
- 11,314 Sq Ft
175 Brookside Rd, Darien, CT 06820

Exceptional new construction estate by K&C Builders Inc., set on over 2.5 private acres on coveted Brookside Road. Offering approximately 11,000 SF across four finished levels, this stunning residence features 6 bedrooms, 8 full baths, and 1 half bath. Designed for elegant entertaining and everyday living, the home showcases a spectacular great room, gourmet chef's kitchen, private study,

Sylwia Kozlowski William Raveis Real Estate

175 Brookside Rd, Darien, CT 06820
/10
$9,200,000

New Construction
- 6 Beds
- 9 Baths
- 8,623 Sq Ft
38 Prospect Rd, Westport, CT 06880

A bold expression of sculptural architecture and modern organic design, this exceptional Green's Farms estate is set on 1.19 artfully layered acres with stacked stone walls, gardens, and a striking stone and white stucco facade. Walls of glass flood the interiors with natural light, seamlessly connecting the home to the private grounds and heated pool. Every space is composed with architectural

Jaclyn Picarillo Higgins Group Bedford Square

38 Prospect Rd, Westport, CT 06880
/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
/40
$8,795,000
- 6 Beds
- 10 Baths
- 8,273 Sq Ft
55 Calhoun Dr, Greenwich, CT 06831

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors

Barbara Wells Houlihan Lawrence

55 Calhoun Dr, Greenwich, CT 06831
/38
$8,750,000

$2M PRICE DROP
- 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
/40
$8,747,000

New Construction Open Sun 6PM - 8PM $250K PRICE DROP
- 7 Beds
- 9.5 Baths
- 13,026 Sq Ft
259 Frogtown Rd, New Canaan, CT 06840

FrogPond Estate is a modern Scandinavian masterpiece unlike anything New Canaan has ever seen - an architecturally rare achievement set on 2.25 pristine, private acres, moments from the train and village. Spanning 11,836 plus square feet of sleek, sun-drenched living space, this 7-bedroom, nine-and-a-half-bath residence is defined by its 12-foot ceilings, bespoke millwork, and designer lighting -

Mar Jennings Higgins Group Bedford Square

259 Frogtown Rd, New Canaan, CT 06840
/14
$8,696,000

New Construction
- 7 Beds
- 8 Baths
- 9,422 Sq Ft
688 Hulls Farm Rd, Southport, CT 06890

Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury

Jaclyn Picarillo Higgins Group Bedford Square

688 Hulls Farm Rd, Southport, CT 06890
/35
$8,500,000
- 6 Beds
- 8 Baths
- 9,081 Sq Ft
174 Round Hill Rd, Greenwich, CT 06831

Set high on two exceptional acres in the coveted Golden Triangle, this custom-built home offers a great lifestyle just minutes from town and schools. The sun-filled six-bedroom residence features 10-foot ceilings and is designed for effortless indoor-outdoor living. Elegant formal rooms, casual living spaces, a gourmet eat-in kitchen, and family room open to an expansive terrace with an outdoor

Julie Church Houlihan Lawrence

174 Round Hill Rd, Greenwich, CT 06831
/40
$8,495,000

$500K PRICE DROP
- 9 Beds
- 10 Baths
- 8,188 Sq Ft
16 East Trail, Darien, CT 06820

Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the

Ashley Dineen Compass Connecticut, LLC

16 East Trail, Darien, CT 06820
/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
/40
$8,450,000

New Construction
- 6 Beds
- 8 Baths
- 9,893 Sq Ft
10 Beltas Farm Ln, Westport, CT 06880

Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling

Linda Skolnick Coldwell Banker Realty

10 Beltas Farm Ln, Westport, CT 06880
/39
$8,250,000
- 6 Beds
- 9 Baths
- 9,440 Sq Ft
34 Carrington Dr, Greenwich, CT 06831

A rare offering in back-country Greenwich, this timeless estate is set on 3.58 exquisitely landscaped and gated acres, masterfully blending classic architecture with contemporary luxury. Designed for both grand-scale entertaining and intimate everyday living, the residence offers a sun-filled interior with soaring ceilings, custom millwork, and modern, bespoke finishes throughout. The grand foyer

Carissa Larriuz Houlihan Lawrence

34 Carrington Dr, Greenwich, CT 06831
/13
$8,250,000

$1M PRICE DROP
- Land
- 426.5 Acres
- $19,343 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
/14
$8,250,000

New Construction
- 6 Beds
- 8 Baths
- 10,495 Sq Ft
190 Brookwood Ln, New Canaan, CT 06840

190 Brookwood Lane is set in one of New Canaan's most unique and desirable residential settings - a bucolic landscape of rolling meadows, mature woodlands, and gently flowing streams set on just over 3 acres of quintessential New England beauty. Situated in the heart of New Canaan, the property offers a peaceful and established neighborhood setting where quiet roads, mature trees, and

James Hoffman Houlihan Lawrence

190 Brookwood Ln, New Canaan, CT 06840
/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 Lahoud William Pitt Sotheby's Int'l

62 Big Bear Hill Rd, New Milford, CT 06776
/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
/40
$7,995,000
- 8 Beds
- 9 Baths
- 8,934 Sq Ft
236 & 250 Main St, Ridgefield, CT 06877

Unprecedented opportunity to purchase two landmark, historic residences, situated side by side on Ridgefield's beloved Main St., which have been developed into an unparalleled lifestyle compound. This once in a lifetime sale includes the treasured Hawley House at 236 Main St. - Ridgefield's oldest home, on its original lot (5) which was built by the proprietors in 1713 for the Rev. Thomas Hawley,

Laura Ancona William Pitt Sotheby's Int'l

236 & 250 Main St, Ridgefield, CT 06877
/13
$7,990,000

New Construction
- 6 Beds
- 8 Baths
- 6,000 Sq Ft
4 Compo Pkwy, Westport, CT 06880

Build your coastal dream home on a rare, full acre* property along one of Compo Beach's most coveted cul-de-sacs, where opportunities of this caliber seldom become available. Ideally positioned just across from Longshore and moments from the shoreline, this extraordinary setting places Westport's most treasured amenities at your fingertips: golf, tennis, swimming, boating, beaches, playgrounds,

Jaclyn Picarillo Higgins Group Bedford Square

4 Compo Pkwy, Westport, CT 06880
/4
$7,950,000

New Construction
- 6 Beds
- 8 Baths
- 8,650 Sq Ft
197 Tinker Hill Rd, New Preston Marble Dale, CT 06777

New Construction BY Ritzzo Development a premier builder! Situated on a country road among luxury estates, this 8,050 sq. ft., to be built new construction strikes the perfect balance of secluded privacy and commanding views. The 8.18 acre lot is bordered by state forest on 3 sides. The welcoming front porch sets a sophisticated tone, leading into an interior defined by 5" white oak flooring,

Sharon McGuire William Pitt Sotheby's Int'l

197 Tinker Hill Rd, New Preston Marble Dale, CT 06777
/17
$7,926,000

New Construction
- 6 Beds
- 7 Baths
- 7,200 Sq Ft
0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880

Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan,

Brett Lieberman

The Riverside Realty Group

0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880
/40
$7,900,000
- 7 Beds
- 9 Baths
- 8,100 Sq Ft
246 Brookside Rd, Darien, CT 06820

Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and

Keiley Fuller Compass Connecticut, LLC

246 Brookside Rd, Darien, CT 06820
/40
$7,900,000
- 7 Beds
- 8 Baths
- 13,056 Sq Ft
19 Seherr Thoss Dr, Litchfield, CT 06759

Introducing Butternut Brook House; a Majestic, Luxurious Country Estate commanding stunning 360-degree views of the Litchfield Hills. Representing a masterful fusion of absolute privacy, consummate sophistication and breathtaking natural beauty, this legacy property spans over 36 pristine acres of rolling countryside. The palatial main residence encompasses an impressive 13,056 square feet,

Alan O'Doherty William Pitt Sotheby's Int'l

19 Seherr Thoss Dr, Litchfield, CT 06759
/40
$7,893,000
- 4 Beds
- 8 Baths
- 9,605 Sq Ft
7 Equestrian Ridge, Newtown, CT 06470

Commandingly sited above the Aspetuck River, this exceptional 9,600+ sq ft cut stone manor offers sweeping views of a 40 acre horse farm and an estate setting rarely available. A long, stately driveway sets a grand first impression, opening to a large courtyard framed by manicured boxwoods. As you enter the home, a grand hall and great room with a dramatic view of the outdoor waterfall

Mary Ann Hebert

BHGRE Gaetano Marra Homes

7 Equestrian Ridge, Newtown, CT 06470
/40
$7,889,000
- 3 Beds
- 5 Baths
- 4,664 Sq Ft
175 River Rd, Essex, CT 06426

Set along one of Essex's most coveted stretches of River Road, this exceptional waterfront estate offers a rare blend of understated elegance, privacy, and Connecticut River waterfront. Privately sited on nearly three acres, the property enjoys a serene, tucked-away feel while remaining just minutes from the heart of Essex Village. Custom-built and thoughtfully designed by its original owner, the

Susan Malan William Pitt Sotheby's Int'l

175 River Rd, Essex, CT 06426
/40
$7,725,000
- 7 Beds
- 13 Baths
- 13,094 Sq Ft
206 Umpawaug Rd, Redding, CT 06896

Exquisite Nantucket-style country estate magnificently sited on seven sprawling acres in Redding, CT's coveted Umpawaug neighborhood. Comprised of three extraordinary residences, this masterfully crafted 2008 HOBI award-winning compound offers 13,904 sf of carefully constructed living space with meticulous architectural details, effortlessly balancing timeless elegance with modern function. The

Lauren Parr Houlihan Lawrence

206 Umpawaug Rd, Redding, CT 06896
/42
$7,599,000
- 5 Beds
- 9 Baths
- 9,716 Sq Ft
24 Stillman Ln, Greenwich, CT 06831

Sport Lovers Dream - Set at end of a quiet cul-de-sac on Stillman Lane, this custom-built 2013 residence offers 4 finished levels of thoughtfully designed living space on 1.2 level acres w putting green. High ceilings, abundant natural light and seamless flow define the main level, where formal living and dining rooms connect effortlessly to an expansive open-concept kitchen and family room with

Amanda Bates Houlihan Lawrence

24 Stillman Ln, Greenwich, CT 06831
/27
$7,599,000

$396K PRICE DROP
- 5 Beds
- 8 Baths
- 9,716 Sq Ft
24 Stillman Ln, Greenwich, CT 06831

Sport lovers dream - Set on a quiet cul-de-sac within Sherwood Farms, this custom-built 2013 residence offers four finished levels of thoughtfully designed living space paired with exceptional recreational and lifestyle amenities. High ceilings, abundant natural light and seamless flow define the main level, where formal living and dining rooms connect effortlessly to an expansive open-concept

Amanda Bates Houlihan Lawrence Inc.

24 Stillman Ln, Greenwich, CT 06831
/40
$7,500,000
- 4 Beds
- 4.5 Baths
- 5,475 Sq Ft
620 Colonial Rd, Guilford, CT 06437

This is not simply waterfront living. This is a waterfront lifestyle unlike any other. Tucked within the coveted enclave of Sachem's Head, this extraordinary estate commands direct Long Island Sound frontage with unobstructed harbor views and breathtaking sunsets. Masterfully crafted in 2003 and transformed by the current owners with uncompromising quality, the 6,000 SF+ residence is defined by

Susan Santoro William Pitt Sotheby's Int'l

620 Colonial Rd, Guilford, CT 06437
/40
$7,500,000

$500K PRICE DROP
- 6 Beds
- 9 Baths
- 8,933 Sq Ft
33 Nodine Pasture Rd, Kent, CT 06757

West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open

Jill Sloane Brown Harris Stevens

33 Nodine Pasture Rd, Kent, CT 06757
/5
$7,499,000

New Construction
- 6 Beds
- 10 Baths
- 9,429 Sq Ft
46 Norholt Dr, New Canaan, CT 06840

NEW CONSTRUCTION - Set on a quiet cul-de-sac just minutes from the heart of New Canaan, this custom-built estate by renowned builder V&A Construction reflects the superior craftsmanship, attention to detail and refined finishes for which the company is known. Currently in the final stages of construction, the home is designed for both everyday living and effortless entertaining. A gracious floor

Katherine Kuras BHHS Darien/New Canaan

46 Norholt Dr, New Canaan, CT 06840

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home

Connecticut Types of Homes for Sale

Connecticut Real Estate

More About Living in Connecticut

Connecticut Homes for Sale by Style

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage