5-Bedroom Homes for Sale in Fairfield County CT

/10
$7,995,000
- 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. Close 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

Nina Frandson BHHS New England Properties

68 Dearfield Dr, Greenwich, CT 06831
/11
$4,350,000
- Land
- 2.30 Acres
- $1,891,304 per Acre
121 Round Hill Rd, Greenwich, CT 06831

Rare find - property on one of Greenwich' estate roads, Round Hill Rd. Oversized,2.3 acres of private estate level property, pool, stable, with a perfect blend of tranquil, manicured and natural landscapes. Enjoy your morning coffee gazing across beautiful east-facing rear vistas. Property can't be appreciated from the street. This custom-designed 10,000 SF home (plan only)

Sabine Schoenberg PrimeSites, Inc.

121 Round Hill Rd, Greenwich, CT 06831
/37
$589,999
- 5 Beds
- 2 Baths
- 2,052 Sq Ft
30 Grove Place, Danbury, CT 06810

Prestine updated home. Location, nestled on a corner lot, close to everything near center of town, updated pristine home Dutch Colonial fenced in with lots of room, spacious, beautiful floors, spectacular cherry wood kitchen cabinets, with lots of lighting, and top of the line refrigerator, stove, dishwasher and Brazilian granite counters. The home presents itself with five bedrooms, two

Edwin Rivera Nationwide Homes

30 Grove Place, Danbury, CT 06810
/43
$24,950,000
- 10 Beds
- 19 Baths
- 17,878 Sq Ft
97 Pecksland Rd, Greenwich, CT 06831

Truly unique 19 Acre estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the

Robert Johnson Brown Harris Stevens CT, LLC

97 Pecksland Rd, Greenwich, CT 06831
/38
$5,995,000
- 6 Beds
- 7 Baths
- 6,673 Sq Ft
7 Jones Park Dr, Riverside, CT 06878

Nestled on a beloved tree-lined cul-de-sac, this custom-built residence perfectly blends a traditional coastal Connecticut shingle style with a sun-filled, modern open-plan interior all just steps from Riverside Yacht Club, schools, and train. Thoughtfully designed, the home incorporates bespoke architectural elements including tall ceilings, custom millwork, expansive windows and wide-plank

Ellen Mosher Houlihan Lawrence

7 Jones Park Dr, Riverside, CT 06878
/40
$8,250,000
- 10 Beds
- 9 Baths
- 9,483 Sq Ft
14 Meadow Dr, Greenwich, CT 06831

DISCOVER BREEZEMORE Experience the rare opportunity to own a piece of history with the stunning Breezemore estate located in Greenwich, Connecticut. Built in 1909, this magnificent property with 10,000 square feet of architectural splendor, old-world charm, and modern conveniences. Set high on 3.2 private, park-like acres within close distance of downtown Greenwich, this property stands proudly

Ryan Hoffman Houlihan Lawrence

14 Meadow Dr, Greenwich, CT 06831
/35
$4,300,000
- 7 Beds
- 5 Baths
- 6,000 Sq Ft
378 Penfield Rd, Fairfield, CT 06824

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

378 Penfield Rd, Fairfield, CT 06824
/37
$4,300,000
- 7 Beds
- 5.5 Baths
- 6,000 Sq Ft
394 Penfield Rd, Fairfield, CT 06824

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

394 Penfield Rd, Fairfield, CT 06824
/38
$25,000,000
- 5 Beds
- 5.5 Baths
- 11,450 Sq Ft
122 Beachside Ave, Westport, CT 06880

A GOLD COAST opportunity: 6.6 acres of pristine estate living culminating at 400 ft of direct Long Island Sound waterfront.A winding drive from the famed Beachside Ave enclave leads past the tennis pavilion, through the shaded trees and into a cobblestone courtyard with fountain and perfectly manicured garden entry.Stepping through the front door, the striking view of blue water tops the lush

Leslie Clarke Compass Connecticut, LLC

122 Beachside Ave, Westport, CT 06880
/51
$10,300,000
- 12 Beds
- 16 Baths
- 16,487 Sq Ft
724 North St, Greenwich, CT 06831

Eight private, gated acres showcase a sprawling back-country home with stone terraces, secluded backyard, fountain and resort-style amenities including tennis court, indoor pool, spa, steam room and separate office. Thoughtful floor plan accommodates both grand scale entertaining as well as comfortable everyday living with elegant formal rooms, fireplaces in living, family rooms and library;

Julie Church Houlihan Lawrence

724 North St, Greenwich, CT 06831
/40
$1,550,000 Open Sun 12PM - 2PM
- 5 Beds
- 6 Baths
- 7,833 Sq Ft
34 Fox Run Rd, Redding, CT 06896

Updated Price Drop! This exceptional luxury home has just been completed and is ready to welcome its first owner. Boasting 5 beds, 4 full baths, and 2 half baths, this residence blends elegance with modern convenience, offering a lifestyle of comfort and sophistication. Step inside to a grand 2-story foyer, setting the stage for the home's expansive open floor plan. The sun-drenched family room

Patrick Capobianco Dave Jones Realty, LLC

34 Fox Run Rd, Redding, CT 06896
/29
$2,499,000
- 5 Beds
- 5 Baths
- 3,598 Sq Ft
201 Shore Rd, Greenwich, CT 06830

1st house on Belle Haven peninsula offers bucolic commuter convenience in a most sought-after enclave overlooking Greenwich Harbor. Positioned atop slope with outstanding Harbor views, this 5 bed, 3 full & two half bathroom residence spans 3,598 sqft. Cleverly renovated to maximize water views with upgraded systems & interior improvements, this home marries smart functional privacy with today's

Meg McAuley Kaicher Coldwell Banker Realty

201 Shore Rd, Greenwich, CT 06830
/39
$7,999,999
- 6 Beds
- 10 Baths
- 15,399 Sq Ft
119 Proprietors Crossing, New Canaan, CT 06840

119 Proprietors Crossing is a breathtaking estate by architect James E. Gearity. Set on four acres, this fully restored six-bedroom home blends timeless elegance with modern function. A private drive and grand fountain lead you in to a soaring foyer with a sweeping staircase beneath a dramatic Baccarat chandelier. The parlor, with one of seven fireplaces, flows to a serene terrace. The Blue Room

Ashlei De Souza Serhant Connecticut, LLC

119 Proprietors Crossing, New Canaan, CT 06840
/40
$2,999,000
- 6 Beds
- 6.5 Baths
- 7,649 Sq Ft
29 Rogues Ridge, Weston, CT 06883

This exquisite custom estate with pool site on 4.7+/- acres (poss./potential to divide) will take your breath away. Set atop one of the highest points in the area, this luxurious retreat blends modern luxury, convenience, privacy and treetop vistas into one irresistible package. Sited to capture the incomparable views, every room and multiple terraces have gorgeous panoramas, with a circulating

Alex Chingas Coldwell Banker Realty

29 Rogues Ridge, Weston, CT 06883
/38
$17,000,000
- 6 Beds
- 9 Baths
- 10,197 Sq Ft
865 Hollow Tree Ridge Rd, Darien, CT 06820

Blending refined elegance with complete privacy, this 9.5-acre estate is a true sanctuary for those seeking a sophisticated lifestyle. At the end of a Bradford Pear-lined gravel drive, the compound features a 10,000 sq. ft. main house, pool and pool house, two-bedroom guest cottage, and a breathtaking field house by architect Louise Brooks. The main home marries historic charm with sleek, modern

Ashley Dineen Compass Connecticut, LLC

865 Hollow Tree Ridge Rd, Darien, CT 06820
/28
$13,950,000
- 6 Beds
- 11 Baths
- 15,171 Sq Ft
537 North St, Greenwich, CT 06830

Exquisite six bedroom, 7.4 bathroom stone manor executed to the highest standards sited on 2.97 picturesque acres. Chic and sophisticated interiors by Amy Hirsch throughout three levels of living space with extra high ceilings, oversized custom windows and all modern amenities. Elegant entry hall with a sweeping staircase and 3 stop elevator opens to a floor plan ideal for both formal and casual

Leslie McElwreath Sotheby's International Realty

537 North St, Greenwich, CT 06830
/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
/39
$5,245,000
- 6 Beds
- 9 Baths
- 7,700 Sq Ft
114 Ferris Hill Rd, New Canaan, CT 06840

The beloved 1925 Elmstone Estate situated on over 4 acres in the heart of Ferris Hill has been lovingly restored w/ high-end finishes that blend original charm and modern-day luxury. A gated drive leads to a spectacular iconic stone home anchored by a breathtaking historic elm tree. A welcoming Dutch door leads to the expansive foyer. A second staircase leads to the masterfully designed custom

Marsha Charles Coldwell Banker Realty

114 Ferris Hill Rd, New Canaan, CT 06840
/40
$4,500,000
- 5 Beds
- 9 Baths
- 9,819 Sq Ft
1 Flower Farm Ln, Westport, CT 06880

Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

Heather Fitzgerald YellowBrick Real Estate LLC

1 Flower Farm Ln, Westport, CT 06880
/33
$2,299,000
- 6 Beds
- 9 Baths
- 7,843 Sq Ft
125 Brett Ln, Fairfield, CT 06824

Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 picturesque acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Step into the elegant formal living and dining rooms, both warmed by inviting FPs, setting the stage for memorable moments. The custom gourmet kitchen, designed for

Linna Yuen Coldwell Banker Realty

125 Brett Ln, Fairfield, CT 06824
/40
$4,500,000
- 10 Beds
- 10 Baths
- 6,526 Sq Ft
Unlisted Address

Enter a world of opulent privacy on nearly twenty-five acres of pristine countryside, boasting five acres of serene lakes, elegant stone bridge, and expansive manicured lawns that cradle an entire valley just 45 miles from NYC! Discover a lavish retreat comprising of four distinct residences: a magnificent five-bedroom, four-bathroom main estate, a charming two-bedroom, two-bathroom guest

Dannel Malloy NestSeekers International

Unlisted Address
/34
$22,000,000
- 7 Beds
- 5.5 Baths
- 6,166 Sq Ft
36, 38, 0 Game Cock Rd, Greenwich, CT 06830

36, 38 and 0 Game Cock Road make up this 1.1+ acre island property that has been enjoyed as a multi generational family compound. One of only a few Island properties in Greenwich, let alone the Connecticut shoreline, to have it's own private bridge for access. The property boasts a 7 bedroom, 5 bath 6166 SQ FT main house, 3 en-suite bedroom 3238 SQ FT guest house, boathouse for entertaining,

Brett Smith Brown Harris Stevens CT, LLC

36, 38, 0 Game Cock Rd, Greenwich, CT 06830
/20
$3,995,000
- 5 Beds
- 6.5 Baths
- 4,570 Sq Ft
59 Locust St Unit A, Greenwich, CT 06830

Unparalleled opportunity to own a luxury condo with elevator right in the heart of downtown Greenwich. This is one of the most sought-after locations in Greenwich. This quiet tree lined one way street is walking distance to everything the downtown area has to offer- train, shops, library and restaurants.

Nina Frandson Berkshire Hathaway NE Prop.

59 Locust St Unit A, Greenwich, CT 06830
/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
$6,450,000 Open Sun 2PM - 4PM
- 5 Beds
- 7 Baths
- 5,567 Sq Ft
46 Compo Mill Cove, Westport, CT 06880

Imagine crossing a footbridge into a world without cars, where the scent of salt air lingers and the only sounds are waves and wind. This is Compo Mill Cove—a private beachfront enclave unlike anywhere else. Designed by Brooke Girty, this timeless shingle-style home offers 5,567 SF of coastal elegance with reclaimed French oak floors, a sculptural 3-story spiral stair case, and endless views of

Evangela Brock Douglas Elliman of Connecticut

46 Compo Mill Cove, Westport, CT 06880
/38
$7,995,000
- 6 Beds
- 10 Baths
- 10,796 Sq Ft
230 Taconic Rd, Greenwich, CT 06831

A timeless Connecticut Compound in mid-country Greenwich custom designed and built by a coveted team. Resting on 4.7 private level acres with a two bedroom guest house and barn/accessory garage. The sun-filled stylish interior features 10+foot ceilings, grand front-to-back entrance hall, refined living and dining rooms; large handsome library and five inviting fireplaces all with bespoke

Ellen Mosher Houlihan Lawrence

230 Taconic Rd, Greenwich, CT 06831
/21
$1,200,000
- 8 Beds
- 5.5 Baths
- 5,231 Sq Ft
16 Greenwood Hill St, Stamford, CT 06902

Ideal opportunity for this recently updated Rare find, large multi family home, bring your in-laws! Each side has 5+ bedrooms and 2.5 baths, gas boilers, updated electrical and much more. 48 hour notice.

Mitchell Stevenson William Raveis Real Estate

16 Greenwood Hill St, Stamford, CT 06902
/40
$4,650,000
- 6 Beds
- 11 Baths
- 17,548 Sq Ft
241 Black Rock Turnpike, Redding, CT 06896

Love life? Love it even more when you arrive home to this exquisite Normandy Chateau with all the special attributes you would expect from a luxurious estate. Set on over 19 acres of lush property, the setting is nothing but idyllic with beautiful gardens, wide open pastures, koi ponds and scenic water views. The best surprise is how inviting & comfortable the home truly is. Of course, there are

Jodi Gutierrez Alliance R.E. Consultants

241 Black Rock Turnpike, Redding, CT 06896
/40
$5,495,000
- 6 Beds
- 7.5 Baths
- 12,385 Sq Ft
26 Pequot Ln, New Canaan, CT 06840

THIS MAGNIFICENT ESTATE HAS BEEN FEATURED IN THE N.Y. TIMES MAGAZINE FOR ITS EXTRAORDINARY ENTRY AND CONSTRUCTION. BE IT THE OVERSIZED POOL, RARE CUSTOM ELEVATOR, SPORTS TENNIS COURT, MEDIA ROOM, HIS & HER SEPARATE BATHS, ALSO INCLUDED ARE SEVERAL PRACTICAL AND FUN AMENITIES THAT GRACE THIS ONE OF A KIND HOME. WITH PRIVACY ON ALL FOUR SIDES THIS HOME PRESENTS ONE OF THE BEST LOTS, SCHOOL SYSTEMS

Susan Morelli Coldwell Banker Realty

26 Pequot Ln, New Canaan, CT 06840
/2
$2,350,000
- 18 Beds
- 4 Baths
- 4,744 Sq Ft
1014 Noble Ave, Bridgeport, CT 06608

House #1- 1014-1016 Noble Ave Bridgeport. Incredible income-generating opportunity with this 18-room legal rooming house, fully compliant and positioned for maximum return. Projected annual income at full capacity $168,300. One room occupied rent-free by on-site property manager. Ideal for investors seeking steady cash flow and minimal vacancies features 16 private rooms 2 efficiency units and 2

Latasha Eaddy Eaddy Associates

1014 Noble Ave, Bridgeport, CT 06608
/42
$2,695,000
- 5 Beds
- 5.5 Baths
- 2,885 Sq Ft
65 Sherwood Place, Greenwich, CT 06830

Scott Kelland CLS Group

65 Sherwood Place, Greenwich, CT 06830
/9
$1,949,000 New Construction
- 6 Beds
- 4.5 Baths
- 4,474 Sq Ft
204 Glen Ridge Rd, Fairfield, CT 06825

Available now for Spring occupancy, with the option to select custom touches that make this home distinctly yours. A brand new home that feels rooted in tradition, yet perfectly suited for modern living. With 5/6 bedrooms, 4 full baths, 1 half bath, and 4,474 sq. ft. above grade plus the ability to finish additional space in the unfinished lower level with 9' ceilings, this home sits on a

Jennifer DeLaurentis Compass Connecticut, LLC

204 Glen Ridge Rd, Fairfield, CT 06825
/13
$6,999,000 New Construction
- 6 Beds
- 9 Baths
- 12,781 Sq Ft
1 Element Ln, Greenwich, CT 06831

Exceptional luxury estate inside ELEMENT, Greenwich's newest gated community where modern details meet natural beauty. This south-facing 12,781 sq ft new construction features 6 bedrooms / 9 baths with a transitional minimalist design. Step through the soaring two-story foyer with gorgeous floating stairs into light filled spaces w/ towering ceilings & walls of glass framing the sunset views over

Michael Ferraro Compass Connecticut, LLC

1 Element Ln, Greenwich, CT 06831
/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
/32
$3,999,000 New Construction
- 5 Beds
- 5.5 Baths
- 5,710 Sq Ft
13 Terhune Dr, Westport, CT 06880

Welcome to this beautifully crafted new construction home in the heart of Westport, where timeless design and thoughtful details come together to create a luxurious space. From the moment you step inside, you're welcomed by a bright and open floor plan with high ceilings and wide-plank flooring that runs throughout the main living space. Natural light fills every room, highlighting the custom

Sara Santos Coldwell Banker Realty

13 Terhune Dr, Westport, CT 06880
/26
$3,900,000 New Construction
- 5 Beds
- 4.5 Baths
- 4,100 Sq Ft
1008 Fairfield Beach Rd, Fairfield, CT 06824

Welcome to the pinnacle of luxury coastal living at 1008 Fairfield Beach Road- where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one

Valerie Alvarez Higgins Group Real Estate

1008 Fairfield Beach Rd, Fairfield, CT 06824
/18
$2,000,000 New Construction
- 5 Beds
- 4.5 Baths
- 4,592 Sq Ft
94 Soundview Rd, Ridgefield, CT 06877

Construction has begun! Luxury New Construction just minutes to Downtown Ridgefield! This custom-built 5-bedroom, 4.5-bath home offers 4,592 sq. ft. of thoughtfully designed living space across 3 finished levels. The main floor features an open-concept layout with a grand foyer, formal living room, large family room, stunning kitchen with oversized island, and a sunlit dining area that opens to a

Stephanie Heering Houlihan Lawrence

94 Soundview Rd, Ridgefield, CT 06877
/42
$7,800,000 New Construction
- 8 Beds
- 11 Baths
- 8,567 Sq Ft
148 E Elm St Unit 1&2, Greenwich, CT 06830

Discover an investment opportunity or the perfect setting for multigenerational living at 148 East Elm St, Unit 1 and 2. These luxurious townhomes, together offering over 8,944 square feet of living space, feature a combined total of 8 bedrooms and 8.3 bathrooms. Each unit is thoughtfully designed with high-end amenities: an elevator, a gourmet kitchen with top-tier appliances, and an expansive

Jenny Allen Compass Connecticut, LLC

148 E Elm St Unit 1&2, Greenwich, CT 06830
/37
$3,495,000 New Construction
- 6 Beds
- 5.5 Baths
- 8,000 Sq Ft
52 Garibaldi Ln, New Canaan, CT 06840

Discover sophisticated modern luxury in the heart of New Canaan This stunning, newly constructed 6,500 square foot residence offers a unique blend of modern design, luxurious finishes, convenient location. Overlooking the iconic God's Acre church steeples, this exceptional home is the latest creation by a local designer renowned for crafting one meticulously curated project per year. Step inside

Hannelore Kaplan William Raveis Real Estate

52 Garibaldi Ln, New Canaan, CT 06840
/12
$4,174,840 New Construction
- 6 Beds
- 5.5 Baths
- 4,540 Sq Ft
128 Mariners Way Unit (To Be Built), Fairfield, CT 06824

If you LOVE the idea of Luxury New Construction in Fairfield's Beach Area, but hate all the stairs to get inside, need more privacy, a bigger yard (maybe a pool), and don't want to be threatened with flooding... I have just the property for you! Welcome to 128 Mariners Way. Live life beautifully on this wide, tree-lined, and quiet cul de sac just steps from the beach, town, shopping and

Jaclyn Picarillo Higgins Group Bedford Square

128 Mariners Way Unit (To Be Built), Fairfield, CT 06824

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