Luxury Homes for Sale in Connecticut

/40
$8,995,000
- 6 Beds
- 6.5 Baths
- 7,456 Sq Ft
546 Lake Ave, Greenwich, CT 06830

Situated on prestigious Lake Avenue in the coveted Greenwich mid-country, the storied Chadeline is a reimagined English Manor estate evoking a private European retreat. Set on 2.83 majestic riverfront acres, this fieldstone Tudor blends historic elegance with a full modern renovation. Sunlit interiors feature soaring ceilings, original details & refined finishes. At the home's epicenter, the

Kevin Sneddon Compass Connecticut, LLC

546 Lake Ave, Greenwich, CT 06830
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/26
$8,995,000
- 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
/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
/37
$8,895,000
- 8 Beds
- 10 Baths
- 8,391 Sq Ft
212 Bedford Rd, Greenwich, CT 06831

Step into the reimagined 'Sunset Farm,' where historic charm meets modern luxury. Originally a Dutch Colonial from 1840, this landmarked property was completely rebuilt in 2006, blending timeless craftsmanship with contemporary elegance. The grand living and dining rooms, showcasing custom moldings and bespoke details, are perfect for entertaining, while the spacious chef's kitchen flows into a

Yashmin Lloyds Compass Connecticut, LLC

212 Bedford Rd, Greenwich, CT 06831
/31
$8,880,000
- 6 Beds
- 8 Baths
- 7,718 Sq Ft
15 Vineyard Ln, Greenwich, CT 06831

Location, location, location! This stunning stone colonial sits on 2 park like acres just minutes from downtown Greenwich. With over 9,000 sq ft of beautiful living space, this 6-bedroom, 6.5-bath home offers graciously scaled rooms and an exceptional floor plan. The luxurious primary suite features a fireplace, dual bathrooms, and walk-in closets. Enjoy the spacious playroom over the garage, a

Megan Sullivan

Douglas Elliman of Connecticut

(475) 265-6175

15 Vineyard Ln, Greenwich, CT 06831
/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
/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
/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
/36
$8,500,000
- 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
/30
$8,495,000
- 6 Beds
- 10 Baths
- 10,887 Sq Ft
44 Hunting Ridge Rd, Greenwich, CT 06831

Masterfully conceived in the French country tradition and completed in 2006, this magnificent stone manor with a slate roof blends European elegance with modern luxury. Spanning 11,687 sq ft across 4 levels, the home features sun-filled formal & casual living spaces including a grand remodeled chef's kitchen with seamless indoor-outdoor flow to a flagstone patio. The 1st floor offers formal and

Kevin Sneddon Compass Connecticut, LLC

44 Hunting Ridge Rd, Greenwich, CT 06831
/27
$8,495,000
- 6 Beds
- 7.5 Baths
- 9,113 Sq Ft
13 Wyckham Hill Ln, Greenwich, CT 06831

Framed by mature trees, this brick Georgian-style home overlooks sweeping lake views on 4.26 sylvan acres with a pool and squash court. Custom-built by the current owners, the house blends traditional design with contemporary finishes and offers a sophisticated floor plan with six bedrooms, seven bathrooms, three double-sided fireplaces. Exquisite Christopher Peacock kitchen, walk-out lower level

Leslie McElwreath Sotheby's International Realty

13 Wyckham Hill Ln, Greenwich, CT 06831
/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 Lahoud William Pitt Sotheby's Int'l

62 Big Bear Hill Rd, New Milford, CT 06776
/40
$8,000,000
- 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
/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
/26
$7,995,000
- 5 Beds
- 7.5 Baths
- 10,981 Sq Ft
38 Partridge Hollow Rd, Greenwich, CT 06831

Set on 8 private acres in one of Greenwich's most prestigious enclaves, 38 Partridge Hollow Road offers luxury and tranquility. This five-bedroom, 7.5-bath home blends timeless elegance with modern sophistication, featuring a first-floor primary suite with dual baths, separate closets, and access to a private office and gym. Bright, sunlit interiors and a chef's kitchen flow into inviting living

Brittany Baity Compass Connecticut, LLC

38 Partridge Hollow Rd, Greenwich, CT 06831
/17
$7,995,000
- Land
- 1.9 Acres
- $4,207,895 per Acre
2 Vista Dr, Greenwich, CT 06830

Stunning waterfront building lot in the private downtown Indian Harbor Association with 24-hour security. This gated community has many luxury waterfront homes in the district. The expansive lot has 1.9 acres in a 1/2 zone, allowing for a substantial home to be built. This lot is not subdividable. There is 290 feet of waterfront on Long Island Sound with its own pier and dock. The owners had

Barbara Wells Houlihan Lawrence

2 Vista Dr, Greenwich, CT 06830
/17
$7,995,000
- Land
- 1.9 Acres
- $4,207,895 per Acre
2 Vista Dr, Greenwich, CT 06830

Stunning waterfront building lot in the private downtown Indian Harbor Association with 24-hour security. This gated community has many luxury waterfront homes in the district. The expansive lot has 1.9 acres in a 1/2 zone, allowing for a substantial home to be built. This lot is not subdividable. There is 290 feet of waterfront on Long Island Sound with its own pier and dock. The owners had

Barbara Wells Houlihan Lawrence

2 Vista Dr, Greenwich, CT 06830
/8
$7,995,000 New Construction
- 8 Beds
- 11.5 Baths
- 10,646 Sq Ft
68 Dearfield Dr, Greenwich, CT 06831

Perched high on a hill in downtown Greenwich, 66 Dearfield is unparalleled in its grandeur with 10,646 square feet of luxury living spanning 4 floors. Walk to Greenwich Library, Greenwich Avenue, the train and all downtown amenities. This exquisite colonial boasts stone chimneys with extra height ceilings on each floor. Upon entry, the 2 story foyer nestled between the living room and dining room

Nina Frandson Berkshire Hathaway NE Prop.

68 Dearfield Dr, Greenwich, CT 06831
/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
/49
$7,750,000
- 4 Beds
- 4.5 Baths
- 6,600 Sq Ft
52 Ridge St, Greenwich, CT 06830

Welcome to this custom Charles Hilton-designed stone Georgian style masterpiece in the heart of downtown Greenwich. Completed in 2018, this exceptional custom home perfectly balances classic architecture with modern luxury across four levels served by an elevator. Set on .33 acres, it offers sweeping views of downtown and glimpses of the Long Island Sound. A dramatic central staircase connects

Megan Sullivan

Douglas Elliman of Connecticut

(475) 471-1130

52 Ridge St, Greenwich, CT 06830
/35
$7,750,000
- 6 Beds
- 10 Baths
- 15,399 Sq Ft
119 Proprietors Crossing, New Canaan, CT 06840

119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere.

Molly Rubins NestSeekers International

119 Proprietors Crossing, New Canaan, CT 06840
/31
$7,500,000
- 9 Beds
- 8 Baths
- 12,057 Sq Ft
138 Amenia Rd, Sharon, CT 06069

Seize the rare opportunity to own Filston, one of Litchfield County's most distinguished Gilded Age estates. Designed in 1903 by renowned architect William Cromwell, Jr. for Mr. and Mrs. Romulus Colgate, this Neoclassical treasure seamlessly blends Italianate Renaissance Revival, Palladian, Neo-Gothic, and French Empire influences, creating a singularly breathtaking country estate. Every original

Dan Kessler Compass Connecticut, LLC

138 Amenia Rd, Sharon, CT 06069
/40
$7,500,000 Open Sat 1PM - 3PM
- 6 Beds
- 9 Baths
- 9,576 Sq Ft
8 Loretta Ct, Westport, CT 06880

Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning three and a half levels, this six-bedroom home features an airy layout with refined finishes

Lianne Owen Coldwell Banker Realty

8 Loretta Ct, Westport, CT 06880
/34
$7,495,000
- 6 Beds
- 11 Baths
- 7,528 Sq Ft
229 Umpawaug Rd, Redding, CT 06896

Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor plan, formal and informal rooms, embracing the incredibly private 6.5 acres of hand-stacked walls, privacy gates and

Stacy Young William Raveis Real Estate

229 Umpawaug Rd, Redding, CT 06896
/18
$7,450,000
- 4 Beds
- 5.5 Baths
- 5,140 Sq Ft
47 Husted Ln, Greenwich, CT 06830

Elegant Regency style single-level living in a fabulous Greenwich location. This beautifully designed four-bedroom, five-and-one-half bath Home offers approximately 5,100 square feet of sun-filled living space with refined finishes and gracious proportions throughout. Expansive living and entertaining rooms, a stunning dining room, and a beautifully appointed kitchen create an effortless flow for

Salley Maloney Houlihan Lawrence

47 Husted Ln, Greenwich, CT 06830
/40
$7,400,000
- 7 Beds
- 7 Baths
- 6,844 Sq Ft
102 Melius Rd, Warren, CT 06754

Reverie Farm is an exceptionally rare late 18th century stone and shingle estate, on more than one hundred acres, located in one of the highest and most private parts of Connecticut. Situated in the heart of Litchfield County, the property rises more than 1,200 feet in elevation across four distinct tax parcels, among which are several estate quality building sites. The setting is dreamlike in

Andrew Gates Houlihan Lawrence, Inc.

102 Melius Rd, Warren, CT 06754
/39
$7,395,000
- 6 Beds
- 10 Baths
- 9,051 Sq Ft
33 Highland Farm Rd, Greenwich, CT 06831

Tucked away on over seven quiet acres off prestigious Round Hill Road, this private estate offers a serene blend of luxury, space, and style. The main residence is complemented by a beautiful pool/guest house designed for effortless entertaining and resort-style living. At the heart of the home, a Christopher Peacock kitchen showcases statuary marble countertops and backsplash, double islands,

Joy Kim Metalios Houlihan Lawrence

33 Highland Farm Rd, Greenwich, CT 06831
/30
$7,250,000
- 5 Beds
- 4.5 Baths
- 4,423 Sq Ft
16 Juniper Rd, Norwalk, CT 06853

Masterpiece in Rowayton. Originally designed by legendary architect Bruce Beinfield, this exceptional home was expanded by its current owners, who merged two properties to create one of Rowayton's truly one-of-a-kind residences. Pool. Yard. Privacy. Just steps from the beach and a short stroll to town. Tucked behind 30-foot evergreen hedges lies a true sanctuary: a 35-foot gunite pool, outdoor

Amanda Spatola Houlihan Lawrence

16 Juniper Rd, Norwalk, CT 06853
/21
$6,999,999
- 7 Beds
- 10 Baths
- 6,010 Sq Ft
132 Curtiss Rd, Warren, CT 06777

A once in a lifetime opportunity to own a significant estate overlooking Lake Waramaug. Nestled high in the hills overlooking the pristine beauty of the lake, this offering features 40 acres with exceptional views. Owned by the same family for the last 70 years, dignitaries from the worlds of art, politics, and industry have been entertained here while the stables, paddocks and trails have been

Pat Lahoud Lahoud William Pitt Sotheby's Int'l

132 Curtiss Rd, Warren, CT 06777
/2
$6,999,999 New Construction
- 6 Beds
- 9 Baths
- 10,521 Sq Ft
32 Narrow Rocks Rd, Westport, CT 06880

NEW CONSTRUCTION BY RENOWNED LUXURY BUILDER MATTERA CONSTRUCTION - STEPS TO COMPO BEACH! A rare opportunity to own a brand-new, architecturally refined home in one of Westport's most coveted coastal locations-just steps to Compo Beach, Longshore Club, downtown Westport, the train, and schools. Currently under construction, this impeccably designed 6-bedroom residence spans four finished levels

Judy Michaelis Coldwell Banker Realty

32 Narrow Rocks Rd, Westport, CT 06880
/15
$6,995,826 New Construction
- 6 Beds
- 10 Baths
- 8,417 Sq Ft
24 Edgemarth Hill Rd, Westport, CT 06880

This Beauty will be ready Summer 2026! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted

Jaclyn Picarillo Higgins Group Bedford Square

24 Edgemarth Hill Rd, Westport, CT 06880
/36
$6,995,000
- 6 Beds
- 9 Baths
- 7,292 Sq Ft
105 Woodside Dr, Greenwich, CT 06830

105 Woodside Drive captures the very best of Country Club Living in Greenwich. Chic stone classic set within the gated Milbrook community, home to the coveted Milbrook Club, with the opportunity to apply for private membership--creating a lifestyle where recreation, relaxation, and social life are just moments from your front door. Perfectly sited overlooking the lake with incredible water view

Ellen Mosher Houlihan Lawrence

105 Woodside Dr, Greenwich, CT 06830
/40
$6,995,000
- 4 Beds
- 5.5 Baths
- 5,400 Sq Ft
23 Mauwee Brook Rd, Kent, CT 06757

"The Falls." Prominent Modernist Architect, Charles Gwathmey of Guggenheim Museum renovation fame, designed this masterpiece in one of the most beautiful locations, offering dramatic views, cascading waterfall, nestled on 40+ acres of beautifully landscaped grounds with serene stream and extensive stonework. The property boasts a breathtaking western view of the Litchfield Hills. Just minutes to

Kathryn Clair William Pitt Sotheby's Int'l

23 Mauwee Brook Rd, Kent, CT 06757
/9
$6,950,000
- Land
- 7.42 Acres
- $936,658 per Acre
549 Round Hill Rd, Greenwich, CT 06831

A unique opportunity to build a home on a site of over 7 acres atop one of the highest elevations in Greenwich with distant Long Island Sound views. Fully approved site is offered with Rich Granoff plans for an elegant 6-bedroom, 10-bath, 11,000 sq. ft. residence. Design features: 4,000 sq. ft. walk-out lower level with a home theater, spa, and golf simulator, a 4-car garage; and over 2,000 sq.

Francine Ehrlich Sotheby's International Realty

549 Round Hill Rd, Greenwich, CT 06831
/46
$6,895,000
- 6 Beds
- 8 Baths
- 6,117 Sq Ft
Unlisted Address

Sensational resort-style amenities enhance this architecturally stunning six-bedroom Colonial on 2.29 level acres with pool, pool house, outdoor Kalamazoo kitchen, screened-in porch with heaters, sandbox and garden near schools, shops and trains. Built in 2014, the luxurious interior features wood floors, high coffered ceilings and four fireplaces. Three finished levels reveal chef's kitchen

Spencer Sodokoff

Houlihan Lawrence

(475) 244-6867

Unlisted Address
/40
$6,790,000
- 7 Beds
- 9 Baths
- 14,066 Sq Ft
4 Cowdray Park Dr, Greenwich, CT 06831

Situated within the gated enclave of Conyers Farm in backcountry Greenwich, this elegant French Chateau embodies architectural distinction, privacy, and resort-style living. Here, heritage and pastoral elegance converge, framed by rolling polo grounds, preserved countryside, and an atmosphere defined by quiet exclusivity. Set gracefully on more than 13 acres, comprised of mature woodlands, and

Vickie Kelley Camelot Real Estate

4 Cowdray Park Dr, Greenwich, CT 06831

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