Homes for Sale in Fairfield County CT with 5-Bedrooms

/33
$11,500,000
- 6 Beds
- 7 Baths
- 8,081 Sq Ft
19 Hawkwood Ln, Greenwich, CT 06830

Set on 2 private, gated acres off North Street, this exceptional Greenwich mid-country estate offers rare privacy, timeless architecture & refined modern luxury. Originally designed in 1938 by renowned architect Nora Stanton Barney and completely rebuilt & expanded in 2005, the stately brick residence features elegant formal rooms plus relaxed indoor & outdoor living spaces. A 2021 renovation

Kevin Sneddon Compass Connecticut, LLC

19 Hawkwood Ln, Greenwich, CT 06830
/40
$1,000,000 Open Sat 11AM - 1PM
- 5 Beds
- 2.5 Baths
- 3,161 Sq Ft
225 Lordship Rd, Stratford, CT 06615

Welcome to 225 Lordship Road, ideally located in Stratford's highly sought-after Lordship neighborhood. Offering 3,161 square feet of living space plus a large finished lower level, this expansive home presents a rare opportunity to own a true five-bedroom property in one of the area's most desirable coastal communities. The main level features an open-concept layout with generous living and

Ralph Lewis Coldwell Banker Realty

225 Lordship Rd, Stratford, CT 06615
/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
/43
$6,345,000
- 5 Beds
- 5.5 Baths
- 6,233 Sq Ft
164 Stanwich Rd, Greenwich, CT 06830

Welcome to this exquisitely updated Colonial on 1.16 landscaped acres near Greenwich Country Club and minutes from town. A grand foyer with gleaming hardwood floors and sweeping staircase introduces the elegant interior. The main level includes a formal living room, dining room, two studies, and a gourmet kitchen with Wolf appliances, Palissandro marble, Thermador coffee station, a custom wet bar

Jeffrey Jackson Corcoran Centric Realty LLC

164 Stanwich Rd, Greenwich, CT 06830
/40
$2,350,000
- 5 Beds
- 6 Baths
- 6,684 Sq Ft
6 Winthrop Hills, Weston, CT 06883

THANK YOU FOR YOUR INTEREST, SELLER REQUESTS HIGHEST/BEST OFFERS BY 5PM MONDAY 3/30. Welcome to this Modern Colonial, a sanctuary where luxury, comfort & tranquility converge on a premier cul-de-sac, conveniently located to the Merritt Parkway, Weston Center & the campus of award-winning schools and downtown Westport plus beaches. With 5 BRs plus a potential 6th BR/au-pair or in-law suite, this

Alex Chingas Coldwell Banker Realty

6 Winthrop Hills, Weston, CT 06883
/17
$499,900 Open Sat 12PM - 2PM
- 6 Beds
- 2 Baths
- 2,780 Sq Ft
202 James St Unit 204, Bridgeport, CT 06604

Well-maintained 2-family home offering strong income potential and flexibility for both investors and owner-occupants. Each unit is currently rented on a month-to-month basis, providing immediate cash flow with the option to adjust rents or occupy a unit as desired. The property features spacious layouts in both units, with ample natural light and functional floor plans that appeal to long-term

Tyler Amann Social & Co Realty

202 James St Unit 204, Bridgeport, CT 06604
/32
$650,000 Open Sat 12:30PM - 3PM
- 5 Beds
- 3 Baths
- 2,446 Sq Ft
73 Orange St, Bridgeport, CT 06607

Location, location! Don't miss out on this great investment opportunity in Bridgeport's East End, conveniently located right near Route 95 and Metro North stations for fantastic commuter access. This oversized 3 unit building has been tastefully updated and cared for. Units 1 and 2 feature 2 bedrooms/1 bath each, with freshly remodeled kitchens, and large rooms with tall ceilings for space and

John Nigro Keller Williams Realty Prtnrs.

73 Orange St, Bridgeport, CT 06607
/34
$579,000
- 6 Beds
- 3 Baths
- 2,716 Sq Ft
584 Kossuth St, Bridgeport, CT 06608

A charming three-family property is now available in the highly desirable Historic East Side of Bridgeport, ideally situated directly across from scenic Washington Park. This stately residence is set on a charming, tree-lined street, offering a perfect blend of urban convenience and neighborhood appeal. Enjoy relaxing evening strolls through the park or along the peaceful surroundings. Each of

Kathleen Dattilo Lamacchia Realty

584 Kossuth St, Bridgeport, CT 06608
/37
$4,199,000
- 5 Beds
- 10 Baths
- 9,062 Sq Ft
73 Lake Wind Rd, New Canaan, CT 06840

Located in the desirable Lake Wind / Ponus Ridge corridor, this custom Colonial estate offers over 9,000 square feet of living space, thoughtfully rebuilt in 2010 and designed for both scale and comfort. The home features 5 bedrooms, 7 full and 3 half baths, six fireplaces (including one outdoor), and multiple porches, with select rooms showcasing cathedral ceilings. Set on 2.74 acres, the

Gene Shklover AG Prime Realty

73 Lake Wind Rd, New Canaan, CT 06840
/21
$19,000,000
- 6 Beds
- 9 Baths
- 9,565 Sq Ft
25 Field Point Cir, Greenwich, CT 06830

FIELD POINT CIRCLE: Grandly proportioned French-inspired manor set within the prestigious 24-hour guard-gated private Association. Sited on 2.2 level parklike acres, this limestone-clad residence with a 2014 new slate roof offers exceptional privacy for outdoor living, featuring a pool and spa. The elegant six-bedroom residence, with 7 full and two half bathrooms, is distinguished by a flexible

Leslie McElwreath Sotheby's International Realty

25 Field Point Cir, Greenwich, CT 06830
/38
$700,000
- 5 Beds
- 2 Baths
- 2,208 Sq Ft
5940 Main St, Trumbull, CT 06611

Introducing a truly special Antique Colonial, rich in history, thoughtfully updated, and beautifully suited for modern living. Ideally located in the sought-after Long Hill neighborhood, this distinctive residence, built by Lucius Burroughs in 1855, blends timeless character with the comfort and functionality today's buyers seek. From the moment you step inside, the home feels open and welcoming.

Wendy Storms Berkshire Hathaway NE Prop.

5940 Main St, Trumbull, CT 06611
/34
$899,000 Open Sat 1:30PM - 3:30PM
- 5 Beds
- 4.5 Baths
- 4,080 Sq Ft
2 Abbey Ln, Newtown, CT 06470

Welcome to this extraordinary colonial home on 2 Abbey Lane in Newtown, CT! This 4080 SF residence offers five bedrooms and 4 1/2 baths on a beautifully landscaped 2+acre lot at the end of a quiet cul-de-sac. Two primary bedroom suites, one on each floor makes it ideal for multigenerational living or guest/au pair space. The gourmet eat-in kitchen features granite beveled edge counters, custom

Lynda Linley Coldwell Banker Realty

2 Abbey Ln, Newtown, CT 06470
/67
$15,600,000
- 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
/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
/37
$15,995,000
- 6 Beds
- 8 Baths
- 8,962 Sq Ft
44 Khakum Wood Rd, Greenwich, CT 06831

Located in Khakum Wood Association, a premier Greenwich location. The extensive 3 year expansion & renovation completed in 2025 is the collaboration of Top 100 Architectural Digest designers and architects: McAlpine House,Studio Mellone, Mario Neivera,with construction by the Tallman Builders.Reimagined for today's living.Pool, Carriage house with apartment, gym, infrared sauna, Savant smart

Robin Kencel Compass Connecticut, LLC

44 Khakum Wood Rd, Greenwich, CT 06831
/37
$3,990,000
- 5 Beds
- 7 Baths
- 7,409 Sq Ft
13 Rockyfield Rd, Westport, CT 06880

This pristine Colonial offers timeless Westport elegance and effortless living, set on 1.12 flat, manicured acres framed by classic stone walls in a coveted, quiet neighborhood just one hour from NYC. The five-bedroom home features five full and two half baths, two dedicated offices, two versatile bonus spaces, custom millwork throughout, and abundant storage-perfect for today's work-from-home,

Danna Rogers Higgins Group Bedford Square

13 Rockyfield Rd, Westport, CT 06880
/14
$429,900
- 6 Beds
- 2 Baths
- 2,464 Sq Ft
147 Trumbull Ave, Bridgeport, CT 06606

Two family home with convenient location in Bridgeport CT. Oversized two family near parks, highways, and major modes of transportation.

Davis Owen Davis Owen Real Estate

147 Trumbull Ave, Bridgeport, CT 06606
/31
$2,000,000
- 10 Beds
- 4 Baths
- 2,068 Sq Ft
61 Cedar St, Norwalk, CT 06854

61 Cedar Street in Norwalk offers a unique mixed use opportunity featuring a residential multi family building along with a well established restaurant. The residential portion includes a legal multi family unit with apartments on the first floor and second floor, along with a finished basement. The basement and first floor are currently rented per bedroom, while the second floor is rented as a

Jithu Sajeevan Serhant Connecticut, LLC

61 Cedar St, Norwalk, CT 06854
/14
$2,595,000
- 5 Beds
- 4.5 Baths
- 4,998 Sq Ft
433 Belden Hill Rd, Wilton, CT 06897

Offering approximately 6,400 square feet of finished living space across three thoughtfully designed levels, this exceptional residence blends timeless architecture with modern luxury. Expansive interiors are filled with natural light and feature refined craftsmanship, generous room proportions, and a seamless flow ideal for both everyday living and elegant entertaining. The finished lower level

Hernan Benitez VORO CT LLC

433 Belden Hill Rd, Wilton, CT 06897
/32
$5,185,000
- 6 Beds
- 8 Baths
- 8,190 Sq Ft
19 Mortar Rock Rd, Westport, CT 06880

Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

Danna Rogers Higgins Group Bedford Square

19 Mortar Rock Rd, Westport, CT 06880
/37
$1,025,000
- 7 Beds
- 5 Baths
- 3,428 Sq Ft
760 Hope St, Stamford, CT 06907

A Rare Find! Large, well-maintained two-family home in the heart of Springdale. Front unit consists of three bedrooms and two full baths, wood-burning fireplace, hardwood floors throughout and window AC units. Rear unit consists of three/four bedrooms, three full baths, hardwood floors throughout, central air, full finished basement, basement storage and patio. New driveway. Plenty of parking.

Suzanne Cingari William Pitt Sotheby's Int'l

760 Hope St, Stamford, CT 06907
/41
$5,200,000
- 5 Beds
- 6.5 Baths
- 5,428 Sq Ft
2 Potter Dr, Greenwich, CT 06870

Coastal Old Greenwich Village living at its finest! There are very few places where you can go out your front door and have everything you could possibly need within reach - and this is one of them. This stunning new construction by North Star Development sits in the heart of Old Greenwich, moments from the train station, the village shops, incredible restaurants, the library and the sandy shores

Angela Swift Compass Connecticut, LLC

2 Potter Dr, Greenwich, CT 06870
/34
$525,000
- 6 Beds
- 2 Baths
- 2,250 Sq Ft
50 Columbus Ave, Stratford, CT 06615

PRICE FOR A QUICK SALE, 3 BEDROOMS ON EACH FLOOR, EAT IN KITCHEN, FINSHED BASEMENT, STORAGE SHED, LARGE ET LONG DRIVEWAY FOR MULTIPLE CARS. SELLING AS IS, INSPECTION FOR INFORMATIONAL PURPOSES ONLY. FLOOD ELEVATION CERTIFICATE IS AVAILLABLE. EASY TO SHOW, PLEASE SCHEDULE YOUR SHOWINGS, 2 MINUTES FROM I-95, NOT FAR FROM THE STRATFORD SHORELINE AND SHORT BEACH, SIKORSKY AIRPORT.

Dominique Jean Marie Antoine Real Estate Services

50 Columbus Ave, Stratford, CT 06615
/40
$879,000
- 5 Beds
- 4 Baths
- 1,223 Sq Ft
2 & 4 Old Weston Old Weston Rd, Weston, CT 06883

Rare opportunity to own a historic 2-acre compound featuring a circa 1770 home (1223 SF), charming 1930s cottage (1048 SF), classic barn, and a rare surviving corn crib. An exceptional property rich in New England history & character! Step into the heart of the 1770 home where centuries-old craftsmanship is on full display. Massive hand-hewn beams stretch across the ceiling, beautifully preserved

Sandra Calise Cenatiempo Settlers & Traders

2 & 4 Old Weston Old Weston Rd, Weston, CT 06883
/32
$1,295,000
- 5 Beds
- 4 Baths
- 3,537 Sq Ft
26 Hill Farm Rd, Weston, CT 06883

This light-filled contemporary home has been masterfully reimagined and updated. Combining an innovative architectural approach with high-end finishes, this residence offers a sophisticated retreat on 2.27 private acres. The heart of the home is the upper level, featuring a fantastic modern eat-in kitchen flooded with natural light. The adjacent living and dining area is defined by soaring

Peter Depalo William Raveis Real Estate

26 Hill Farm Rd, Weston, CT 06883
/40
$8,999,000
- 7 Beds
- 9 Baths
- 10,482 Sq Ft
19 Beachside Common, Westport, CT 06880

Like-new custom modern home with open-concept living designed for comfort and entertaining. The main level connects the family room, dining room, office, and chef's kitchen featuring Sub-Zero and Wolf appliances, invisible speakers, quartzite countertops, custom cabinetry, two large islands and multiple sliding glass doors leading to an outdoor oasis. The spacious pantry includes custom shelving,

Gina Hackett Compass Connecticut, LLC

19 Beachside Common, 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
/39
$1,825,000
- 5 Beds
- 6 Baths
- 4,595 Sq Ft
140 Signal Hill Rd, Wilton, CT 06897

Tucked away on 2.18 private acres, this beautifully designed 5-bedroom, 6-bathroom home offers exceptional space, natural light, and a layout ideal for both everyday living and entertaining. Discover hardwood floors and a thoughtfully designed main level. The open kitchen flows seamlessly into the family room, anchored by a fireplace that creates a warm gathering space. A sun-filled den with a

Mayra Cardenas Mayorga Berkshire Hathaway NE Prop.

140 Signal Hill Rd, Wilton, CT 06897
/39
$3,449,000
- 5 Beds
- 7 Baths
- 5,515 Sq Ft
2683 Bronson Rd, Fairfield, CT 06824

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family

Tara Hawley Coldwell Banker Realty

2683 Bronson Rd, Fairfield, CT 06824
/39
$2,649,000
- 6 Beds
- 7 Baths
- 8,500 Sq Ft
55 Tanners Dr, Wilton, CT 06897

A rare opportunity to own a custom-designed residence by renowned architect Peter Cadoux, nestled on a private cul-de-sac abutting Quarry Head Park/Harrison Smith Preserve providing direct access to nearly 60 acres of hiking and equestrian trails. Additional privacy is provided by a serene sanctuary of forever green space to the west. This extraordinary home combines architectural artistry,

Sharon Brameier Berkshire Hathaway NE Prop.

55 Tanners Dr, Wilton, CT 06897
/39
$725,000
- 6 Beds
- 3.5 Baths
- 3,397 Sq Ft
5385 Main St, Trumbull, CT 06611

Magnificent opportunity to embrace historic charm. This spacious Victorian home is filled with character and timeless architectural details while offering the comfort of modern updates. A beautifully updated kitchen with a massive island that blends classic charm with modern convenience. The home's signature wrap-around porch provides the perfect spot to relax and enjoy the outdoors. Inside, the

Michael Debiase Keller Williams Realty

5385 Main St, Trumbull, CT 06611
/28
$10,950,000
- 6 Beds
- 7 Baths
- 9,834 Sq Ft
174 Round Hill Rd, Greenwich, CT 06831

Spectacular lifestyle - this custom built handsome Colonial is set up high on 2 exceptional acres in the coveted Golden Triangle and just minutes from town and schools. This sun-filled 6-bedroom home with 10' ceilings is designed for seamless indoor-outdoor living. Gracious formal and informal rooms, a gourmet eat-in kitchen, and family room open to an expansive terrace with outdoor fireplace and

B.K. Bates Houlihan Lawrence

174 Round Hill Rd, Greenwich, CT 06831
/31
$6,495,000
- 5 Beds
- 9 Baths
- 13,474 Sq Ft
386 North St, Greenwich, CT 06830

This magnificent 9,974 sq ft estate seamlessly blends grand scale, craftsmanship, and modern luxury following an extensive 2025-2026 renovation. Set on 2.3 parklike acres in coveted Mid-Country Greenwich, just minutes from town, the home makes an immediate impression with a soaring two-story foyer introducing exquisitely appointed interiors defined by custom details and rich materials. Completed

Jennifer Leahy Compass Connecticut, LLC

386 North St, Greenwich, CT 06830
/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
/40
$3,495,000
- 5 Beds
- 8 Baths
- 9,032 Sq Ft
253 Rivergate Dr, Wilton, CT 06897

Handsomely set on two private, resort-like acres, this timeless Nantucket-style residence offers the feel of a secluded family compound. Adjacent to a 21-acre wildlife preserve along the west bank of the Saugatuck River, the setting invites fishing by the river and peaceful walks along scenic trails through the surrounding natural landscape. Custom built by celebrated architect Tim Geitz, the

Michelle Genovesi William Raveis Real Estate

253 Rivergate Dr, Wilton, CT 06897
/15
$780,000
- 10 Beds
- 4 Baths
- 2,999 Sq Ft
120 Milne St Unit 122, Bridgeport, CT 06604

Excellent investment opportunity at 120 Milne Street. This well-maintained four-unit multifamily property features spacious two-bedroom units, offering a highly desirable layout for tenants and strong rental demand in the area. Two of the units are currently empty and newly renovated, providing a great opportunity for an investor to place tenants at current market rents or for a homebuyer to live

Aharon Cowen Roundtree Realty LLC

120 Milne St Unit 122, Bridgeport, CT 06604
/14
$644,900
- 6 Beds
- 3 Baths
- 2,582 Sq Ft
23-25 Morgan Ave, Bridge Port, CT 06606

This is an excellent opportunity for first-time buyers to live more affordably than renting. It's also a great investment opportunity. The property is conveniently located near shopping centers, restaurants, Boys and Girls clubs, and Central High School.

Mitchell Stevenson William Raveis Real Estate

23-25 Morgan Ave, Bridge Port, CT 06606
/40
$799,000
- 5 Beds
- 3.5 Baths
- 2,651 Sq Ft
240 Highland Ave, Stratford, CT 06614

Spacious colonial just listed in the desirable Paradise Green neighborhood in Stratford! This beautiful home includes a bonus in-law suite with separate entry. There is a total of 5 bedrooms, 3.5 bathrooms, a living room, dining room, family room, laundry room, and two kitchens! Step inside to an airy, open-concept main level with hardwood floors throughout and abundant natural light. The main

Valerie King Keller Williams Realty Prtnrs.

240 Highland Ave, Stratford, CT 06614
/37
$5,350,000
- 5 Beds
- 8 Baths
- 8,035 Sq Ft
473 Hollow Tree Ridge Rd, Darien, CT 06820

Welcome to 473 Hollow Tree Ridge Road in Darien - a custom built, stone and shingle Colonial set on 1.3 professionally landscaped acres offering exceptional indoor and outdoor living. This 5-bedroom smart home blends timeless architecture with extensive upgrades and modern technology throughout. The resort-style backyard features a pool with spa, pool house with nano doors, outdoor shower, custom

Ellen Mccue Houlihan Lawrence

473 Hollow Tree Ridge Rd, Darien, CT 06820
/9
$685,000
- 6 Beds
- 3 Baths
- 1,872 Sq Ft
13 W Wooster St, Danbury, CT 06810

Great Investment Opportunity - home features two spacious 3-bedroom 2 floor , 2-bedroom 1 floor Enjoy many recent updates, including newer kitchens and bathrooms. All utilities are separately ample parking. full basement property to be sold AS-IS

Wilmer Duran Marinablue Realty

13 W Wooster St, Danbury, CT 06810

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