5-Bedroom Homes for Sale in Fairfield County CT

/40
$999,999 Open Sun 12:30PM - 2:30PM
- 5 Beds
- 4.5 Baths
- 4,080 Sq Ft
2 Abbey Ln, Newtown, CT 06470

REDUCED FOR A QUICK SALE! 4,080 SF, 5BR, 4-1/2 Bath Colonial sits on a 2+ acre cul-de-sac street. 2 Primary BR Suites, one on each floor. An amazing gourmet eat-in-Kitchen has granite bevel edge counters, all high-end SS appliances including Subzero refrigerator, Wolf gas range w/red knobs, Bosch dishwasher & microwave, custom built-in cabinetry, pot filler, instant hot water faucets, garbage

Jeanette Politano Coldwell Banker Realty

2 Abbey Ln, Newtown, CT 06470
/5
$1,699,999
- 5 Beds
- 3 Baths
- 2,918 Sq Ft
20 Berkeley St, Norwalk, CT 06850

ATTENTION INVESTORS, DEVELOPERS AND BUILDERS!! Exceptional Investment Opportunity in Norwalk, presenting a prime multi-family property featuring an existing fully occupied 3-family residence, complemented by approved plans for a new 10-unit apartment building (Potential 13 Units total). This development opportunity has received zoning approval from the City of Norwalk, with architectural and site

Maria Palladino William Raveis Real Estate

20 Berkeley St, Norwalk, CT 06850
/40
$2,575,000
- 6 Beds
- 4.5 Baths
- 5,083 Sq Ft
4 the Fenway, Westport, CT 06880

Timeless elegance in Westport's prestigious Old Hill. First time on the market in 29 years! This expansive 5-6 bedroom, 4.5 bath farmhouse is gracefully set on 2.22 serene acres, featuring a heated gunite pool, picturesque pond, and a very rare blend of privacy and proximity to town. The sun-drenched primary suite is a true retreat with a fireplace, spa-like bath, and generous walk-in closet. A

Mary Kate Klemish-Boehm Brown Harris Stevens

4 the Fenway, Westport, CT 06880
/40
$5,200,000
- 5 Beds
- 9 Baths
- 7,070 Sq Ft
294 Maple Rd, Easton, CT 06612

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 6 acres on a cul-de-sac, offering a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered

Linda Toscano Coldwell Banker Realty

294 Maple Rd, Easton, CT 06612
/16
$1,199,000
- 5 Beds
- 4 Baths
- 2,775 Sq Ft
442 Pepper Ridge Rd, Stamford, CT 06905

JUST REDUCED! Move right in to this fully renovated 5-bed, 4-bath Stamford home blending modern luxury with peace of mind. The brand-new primary suite impresses with tray ceilings, dual walk-in closets, and a spa-inspired bath, while vaulted ceilings and a quartzite chef's kitchen create light-filled living and entertaining spaces. All major systems - roof, HVAC, plumbing, and electrical - have

Daniel Morris Keller Williams Realty Group

442 Pepper Ridge Rd, Stamford, CT 06905
/10
$340,000
- 6 Beds
- 2 Baths
- 1,920 Sq Ft
1050 Hancock Ave Unit 1052, Bridgeport, CT 06605

Investment opportunity awaits with this spacious multi-family property featuring two up-and-down units. Offering just under 2,000 square feet of total living space, each unit includes 3 bedrooms and 1 full bathroom ideal for rental income or multi-generational living. Residents will appreciate the convenience of off-street parking and the added bonus of a fully fenced front and backyard,

Jonathan Gineo Silver and Oak Realty

1050 Hancock Ave Unit 1052, Bridgeport, CT 06605
/7
$4,899,000
- 5 Beds
- 8 Baths
- 7,400 Sq Ft
10 Tierney Ln, Westport, CT 06880

This is the second of 2 custom homes in final stages of completion, beautifully sited at the end of a private lane in the heart of Greens Farms. Combining classic design with modern detailing by an established local builder of premier residences, this masterfully crafted home is sure to delight even the most discerning buyer. The main level showcases expert millwork and warm white oak accents

Laurie Crouse Coldwell Banker Realty

10 Tierney Ln, Westport, CT 06880
/40
$4,999,000 Open Sun 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 4,669 Sq Ft
216 Hillspoint Rd, Westport, CT 06880

Compo Beach Coastal Compound+Water Views+Approved Lot! A rare Compo Beach opportunity-beautifully rebuilt, expanded 5 bed/4.5 bath home on a .47-acre parcel-INCLUDES AN APPROVED BUILDABLE .14 ACRE LOT. Enjoy stunning water views, privacy & unmatched lifestyle just steps from Old Mill & Compo Beaches! Discover a rare blend of timeless character & sophisticated living in this coastal estate.

Sarah Fair William Raveis Real Estate

216 Hillspoint Rd, Westport, CT 06880
/22
$819,000
- 11 Beds
- 5 Baths
- 4,188 Sq Ft
49 Dover St, Bridgeport, CT 06610

Investor Alert - Rare Opportunity! This 4-family property at 49 Dover St. brings in the income of FIVE units - a rare find with serious earning potential! Four 2-bedroom units PLUS an additional 3-bedroom unit Strong rental history with long-term, reliable, on-time paying tenants Cash flow from day one With consistent performance and steady income, this is the kind of investment that helps

Lisa Nussbaum Top Tier Realty Group, LLC

49 Dover St, Bridgeport, CT 06610
/40
$3,495,000
- 5 Beds
- 4 Baths
- 5,133 Sq Ft
19 Skymeadow Dr, Stamford, CT 06903

Welcome to The Benjamin Weed House-an extraordinary 5-bed, 4-bath estate set on 3.5 lush acres. Thoughtfully expanded over time, this historic home and property blends timeless charm with modern luxury. High ceilings, wide plank hardwood floors, and exceptional craftsmanship shine throughout. The gourmet kitchen features a Sub-Zero fridge, Wolf cooktop, and granite countertops as well as a large

Laurie Cingari Berkshire Hathaway NE Prop.

19 Skymeadow Dr, Stamford, CT 06903
/37
$4,895,000 Open Sat 1PM - 3PM
- 7 Beds
- 7.5 Baths
- 9,035 Sq Ft
26 Morningside Dr S, Westport, CT 06880

Welcome to 26 Morningside Drive South, the first completed home in Sherwood Estates at Greens Farms. Builder has recently added over $150,000 in exterior upgrades into the final plans!!!! This newly built four-level residence blends timeless design with modern luxury in one of Westport's most desirable neighborhoods. The main level features a chef's kitchen with custom island and pantry, open

John Schiaroli Coldwell Banker Realty

26 Morningside Dr S, Westport, CT 06880
/28
$3,895,000
- 6 Beds
- 7 Baths
- 5,510 Sq Ft
2 Webb Rd, Westport, CT 06880

Welcome to everything you've ever wanted! NEW CONSTRUCTION, Pool, cul-de-sac, in a neighborhood that is great for walking and biking in central Westport. Walk to Post Rd shops/restaurants, Winslow dog park, even Main St., Library, and the Levitt Pavilion! 6 bedrooms/5 full baths/ 2 half baths. 4 finished floors of living space. Gunite Pool w/Automatic Safety Cover and Room for Cabana. HUGE, FLAT

Lori Popkin Coldwell Banker Realty

2 Webb Rd, Westport, CT 06880
/38
$4,350,000
- 5 Beds
- 6.5 Baths
- 5,257 Sq Ft
331 Round Hill Rd, Greenwich, CT 06831

Built in 1758 and masterfully updated, 331 Round Hill Road offers a rare opportunity where historic character and modern comfort exist in perfect balance. Wide-plank floors, hand-hewn beams, and wood-burning fireplaces showcase early American craftsmanship, while a reimagined kitchen with premium appliances and renovated baths provides seamless functionality. The large living room offers a quiet

Jack Sarsen Compass Connecticut, LLC

331 Round Hill Rd, Greenwich, CT 06831
/40
$3,749,000
- 5 Beds
- 4.5 Baths
- 6,661 Sq Ft
2683 Bronson Rd, Fairfield, CT 06824

Located in the heart of Greenfield Hill at the top of Bronson Road, this iconic Connecticut estate sits on 2+ beautifully landscaped acres with distant water views of Long Island Sound. Across from a majestically developed family and horse-farm compound and outside the historic district, this home blends old-world charm with modern comforts. Originally built in 1844 and significantly expanded and

Tara Hawley Coldwell Banker Realty

2683 Bronson Rd, Fairfield, CT 06824
/40
$5,700,000
- 5 Beds
- 9 Baths
- 7,070 Sq Ft
294 Maple Rd, Easton, CT 06612

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood

Linda Toscano Coldwell Banker Realty

294 Maple Rd, Easton, CT 06612
/40
$3,450,000
- 5 Beds
- 5 Baths
- 3,561 Sq Ft
6 Over Rock Ln, Westport, CT 06880

Welcome to 6 Over Rock Lane - a stunning 1920s colonial retreat in the heart of Westport, Connecticut blending timeless New England charm with sophisticated modern living. A unique move-in opportunity with curated designer furniture offered. Set on a quiet, luxurious street in one of Westport's most desirable neighborhoods, this property offers peace, privacy, and proximity - just minutes from

Judy Michaelis Coldwell Banker Realty

6 Over Rock Ln, Westport, CT 06880
/39
$5,995,000
- 7 Beds
- 8 Baths
- 6,057 Sq Ft
40 Oenoke Ridge, New Canaan, CT 06840

You can stroll into town from 40 Oenoke Ridge, one of New Canaan's most admired and iconic properties, stunningly transformed by its current owners into a showpiece of refined elegance and contemporary comfort. Nestled on 2+ acres of breathtaking, park-like grounds, this distinguished 1929 brick Colonial offers the rare combination of historic charm and today's most desired luxuries. Boasting 6/7

John Dunn Compass Connecticut, LLC

40 Oenoke Ridge, New Canaan, CT 06840
/39
$2,200,000 Open Sun 12:30PM - 2:30PM
- 6 Beds
- 4.5 Baths
- 4,191 Sq Ft
50 Harrison Ave, New Canaan, CT 06840

Welcome to this beautifully updated and energy-efficient Cape-style 2-family home, offering 4,191 sq. ft. of elegant living space on a professionally landscaped 0.49-acre lot in a desirable walk-to-town New Canaan location. The home is just minutes away from local shops, top-rated schools, fine dining, public parks and the New Canaan Metro-North train station with direct service to New York

Maria Miller William Raveis Real Estate

50 Harrison Ave, New Canaan, CT 06840
/39
$2,100,000 Open Sat 1PM - 4PM
- 5 Beds
- 7 Baths
- 6,422 Sq Ft
4 Lyons Plain Rd, Weston, CT 06883

Stunning Colonial on a beautifully landscaped 2-acre lot on the corner of Coley Drive, just over the Westport line in Lower Weston! Enjoy the best of both towns with easy access to the Merritt, train, Longshore, The Westport/Weston Y, and Compo beach. Perfectly situated for walking and biking on neighboring streets, the property features an in-ground pool, gorgeous bluestone patio and generous

Julie Vanderblue Higgins Group Real Estate

4 Lyons Plain Rd, Weston, CT 06883
/38
$2,199,999 Open Sun 12PM - 3PM
- 6 Beds
- 5.5 Baths
- 5,256 Sq Ft
59 Thornhill Rd, Fairfield, CT 06824

Located on one of the most coveted cul-de-sacs in Fairfield's University area, this Newly Built Colonial offers a perfect blend of classic charm & modern luxury. A welcoming stone-trimmed front porch sets the stage for quiet mornings with coffee, while inside, 5-7 bedrooms and 5.5 bathrooms provide ample space for comfortable living and entertaining. The gorgeous open-concept Kitchen with eating

Julie Vanderblue Higgins Group Real Estate

59 Thornhill Rd, Fairfield, CT 06824
/12
$5,900,000
- 6 Beds
- 7 Baths
- 7,600 Sq Ft
6 Dorchester Ln, Riverside, CT 06878

Just Completed! 2025 Luxury new construction in a fabulous Riverside location! This beautifully designed home features a double height entrance with front to back views, a sophisticated living room, dining room with tray ceiling, and office with access to a covered terrace and outdoor fireplace. The gourmet kitchen with high-end appliances and breakfast area is next to the family room with a

Gloria Gimenez-Ferrer Berkshire Hathaway HS NE Prop.

6 Dorchester Ln, Riverside, CT 06878
/40
$2,399,000
- 6 Beds
- 3.5 Baths
- 4,032 Sq Ft
708 Ponus Ridge, New Canaan, CT 06840

Welcome to 708 Ponus Ridge! This exceptional 2.53-acre parcel offers the perfect blend of space, serenity, and opportunity. The flat, cleared grounds are framed by classic stone walls and expansive, manicured lawns, creating a peaceful, park-like setting. The backyard is a true retreat, featuring a classic rectangular pool, a enchanting pool house and summer kitchen-ideal for entertaining or

Melissa Jones Houlihan Lawrence

708 Ponus Ridge, New Canaan, CT 06840
/51
$19,900,000
- 7 Beds
- 10 Baths
- 18,000 Sq Ft
37 Burying Hill Rd, Greenwich, CT 06831

Custom designed and built to exacting standards, this phenomenal back country lakefront compound was built to exacting standards offering fabulous privacy and flexibility for families, guests and staff. Prominent local design build firm created a masterpiece that combines a pre war elegance with substantial entertaining and modern lifestyle amenities. Multiple structures, including a large pool

Robert Johnson Brown Harris Stevens CT, LLC

37 Burying Hill Rd, Greenwich, CT 06831
/22
$555,500
- 5 Beds
- 2 Baths
- 3,264 Sq Ft
21 Dayton St, Sandy Hook, CT 06482

Great 4 bedroom home home with a separate 1 bedroom apartment Beautiful home in Newtown with the best schools. Broker Protected. Beautiful home with 4 bedrooms, large private yard and a great income producing separate 1 bedroom apartment, The main house has 4 large rooms on the 1st. LV Rm, new kitchen,dining & den, 2nd fl is 3 bedrooms and a large bathrm with W/D. 3rd fl with a 4th

David White OwnerEntry.com

21 Dayton St, Sandy Hook, CT 06482
/40
$1,325,000 Open Sat 1PM - 4PM
- 5 Beds
- 4 Baths
- 4,830 Sq Ft
108 Northwood Dr, Easton, CT 06612

Welcome to 108 Northwood Drive in Lower Easton. Back on market to no fault of the home - buyers could not perform. Two KEY upgrades to home: BRAND NEW ROOF (INSTALLED AUGUST 2025) AND NEW SEPTIC TANK (SCHEDULED TO BE INSTALLED SHORTLY). Set at end of cul-de-sac offering privacy yet near all amenities, highways. Enjoy 3+acres, expansive gardens including chicken coops, inground heated pool, 2

Erika Portanova Songer William Pitt Sotheby's Int'l

108 Northwood Dr, Easton, CT 06612
/29
$1,600,000
- 5 Beds
- 2.5 Baths
- 3,811 Sq Ft
82 Partrick Rd, Westport, CT 06880

Diamond in the Rough! This stately colonial is brimming with potential and ready to be restored to its former grandeur. Nestled on a private lot, the home offers a peaceful setting with ample space for everyone. Boasting over 3,800 sq ft, this spacious residence features 5 bedrooms and 2.5 bathrooms, along with gleaming hardwood floors and a variety of rooms designed for comfortable living. The

Glenn Stavens Aspen Realty Group

82 Partrick Rd, Westport, CT 06880
/40
$2,950,000
- 8 Beds
- 10 Baths
- 8,716 Sq Ft
134 Nod Rd, Ridgefield, CT 06877

Elegantly situated in one of Fairfield County's most desirable scenic roads, this timeless estate offers luxury and privacy on two acres of park-like grounds. This residence showcases sophisticated charm with custom craftsmanship throughout, boasting tray ceilings, mahogany inlaid floors, and oversized windows that flood the space with natural light. The main level offers formal living and dining

Karla Murtaugh Compass Connecticut, LLC

134 Nod Rd, Ridgefield, CT 06877
/40
$2,200,000
- 5 Beds
- 5 Baths
- 5,713 Sq Ft
7 Jackson Ct, Ridgefield, CT 06877

Best location in Ridgefield with direct sidewalks to restaurants, shopping and the village center! Gorgeous 5 Bedroom custom-built residence on cul-de-sac with amazing level property and western exposure. The new kitchen with large center island and charming breakfast nook is great for everyday living and entertaining. Family room with cathedral ceiling, floor-to-ceiling fireplace, and tons of

Russell Neumann Houlihan Lawrence

7 Jackson Ct, Ridgefield, CT 06877
/31
$1,995,000
- 6 Beds
- 5.5 Baths
- 5,489 Sq Ft
130 Easton Rd, Westport, CT 06880

Unique opportunity to renovate this classic Westport estate on three professionally landscaped acres with a pool. You will love the great room with views of the pond and property. Six bedrooms makes space for everyone with a separate guest wing that is perfect for an au-pair.

David Weber Compass Connecticut, LLC

130 Easton Rd, Westport, CT 06880
/35
$1,950,000
- 5 Beds
- 4.5 Baths
- 3,050 Sq Ft
22 Maplewood Dr, Cos Cob, CT 06807

Where lifestyle, livability, and versatility meet... all your family & friends, too. Set in Cos Cob's tight-knit Loughlin Park, this 5 Bed home is in a prime location. Seconds to the train, a food scene, & the Park. With 3000 sqft of livability this home is a neighborhood hub. A garage & breezeway lead to open living, kitchen, & dining with a fireplace. Easy access to a grill, putting green, &

Mike Parelli Mike Parelli Real Estate LLC

22 Maplewood Dr, Cos Cob, CT 06807
/40
$1,999,000
- 6 Beds
- 5.5 Baths
- 3,847 Sq Ft
45 Robin Cir, Fairfield, CT 06824

Welcome to the epitome of luxury living. A stunning new construction masterpiece nestled in the prestigious enclave of Fairfield's University Neighborhood by local, multi HOBI Award-Winning builder, DeLaurentis Developments. This architectural marvel boasts exquisite craftsmanship, unparalleled attention to detail, & an array of features that redefine modern elegance. Spanning 3,847 sq. ft. this

Jennifer DeLaurentis Compass Connecticut, LLC

45 Robin Cir, Fairfield, CT 06824
/40
$8,850,000
- 6 Beds
- 8 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

Carissa Larriuz Houlihan Lawrence

34 Carrington Dr, Greenwich, CT 06831
/47
$5,995,000
- 6 Beds
- 9 Baths
- 6,520 Sq Ft
25 Dialstone Ln, Riverside, CT 06878

Discover the perfect blend of modern luxury and thoughtful design in this 6-bedroom, 7.2 half-bath home with room for a pool tucked away on a quiet cul-de-sac in Riverside. Just steps from top schools, transportation, parks, and Old Greenwich village, this 6,500 sq. ft. residence spans four finely crafted levels, offering ultimate convenience and comfort. The main level impresses with soaring 10+

Carol Zuckert Sotheby's International Realty

25 Dialstone Ln, Riverside, CT 06878
/37
$8,795,000
- 5 Beds
- 7 Baths
- 6,108 Sq Ft
25 Tokeneke Trail, Darien, CT 06820

Welcome to 25 Tokeneke Trail, an exceptional waterfront residence in the private Tokeneke Association. Perfectly positioned to capture panoramic water views from nearly every room and not in a flood zone, this home blends coastal charm with the finest in modern living. The property offers direct water access via a dock. Mooring available with approved Town application, and permitting for a deeper

Breda Casey Brown Harris Stevens

25 Tokeneke Trail, Darien, CT 06820
/27
$4,975,000 Open Sun 10:30AM - 12:30PM
- 6 Beds
- 6.5 Baths
- 5,970 Sq Ft
52 Breezemont Ave, Riverside, CT 06878

Renovated in 2025 this exquisite home features a grand triple-height foyer and stunning hardwood floors throughout. A bright living room flows seamlessly onto a wraparound porch. Inviting eat- in kitchen includes Viking appliances, a center island, a wine refrigerator and elegant marble countertops. Family room has a wet bar and fireplace while the dining room is adorned with wainscoting and

Jennifer Danzi-glenn Jennifer M Danzi, Broker

52 Breezemont Ave, Riverside, CT 06878
/44
$19,500,000
- 8 Beds
- 17 Baths
- 26,454 Sq Ft
11 Langhorne Ln, Greenwich, CT 06831

Famed architect Boris Baranovich designed this extraordinary stone Georgian estate of 26,000+/- square feet on 8.788 secluded acres off of Round Hill Road. Exquisitely executed, this stately manor home offers eight bedrooms and twelve full and five half bathrooms throughout four levels of living space. Mature trees and lush lawn surround this exceptional estate with two gated entrances: one to

Leslie McElwreath Sotheby's International Realty

11 Langhorne Ln, Greenwich, CT 06831
/39
$2,649,999
- 6 Beds
- 9 Baths
- 6,191 Sq Ft
72 Little Hill Dr, Stamford, CT 06905

72 Little Hill Drive - Stately Colonial in the Heart of Newfield Privately nestled in one of Newfield's most sought-after neighborhoods, this grand colonial offers over 6,300 sq ft of beautifully finished living space, including 6 bedrooms, 5 full and 4 half baths, and a 4-car garage. Built in 1865 and fully renovated, the home blends timeless charm with modern luxury. The expansive backyard is

Anthony Gaglio Jr Hathaway, Inc.

72 Little Hill Dr, Stamford, CT 06905
/40
$2,895,000
- 5 Beds
- 4.5 Baths
- 5,424 Sq Ft
20 Crawford Rd, Westport, CT 06880

Nestled in Westport's coveted Old Hill neighborhood, this stunning residence blends classic Colonial design w/modern amenities. You're greeted by the centerpiece of the home - an impressive foyer w/soaring ceilings. The spacious office w/lacquer-finished built-ins includes a fireplace and access to the veranda. For more intimate gatherings, go through the French doors to a sitting room,

Lisa Tortora Coldwell Banker Realty

20 Crawford Rd, Westport, CT 06880
/50
$13,750,000
- 6 Beds
- 8 Baths
- 9,418 Sq Ft
52 Carriglea Dr, Riverside, CT 06878

Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

Stephen Archino Sotheby's International Realty

52 Carriglea Dr, Riverside, CT 06878
/40
$1,930,000
- 7 Beds
- 10 Baths
- 5,883 Sq Ft
49 Great Ring Rd, Sandy Hook, CT 06482

Welcome to 49 Great Ring Road-an iconic estate with breathtaking views and a classic 1940 built home full of charm and elegance. Step into the front-to-back foyer and take in the sight lines to the expansive stone patio and sparkling pool. At the heart of the home is the great room, featuring a soaring ceiling and a grand fireplace-perfect for gatherings. The custom cherry sunroom is a

Connie Widmann William Raveis Real Estate

49 Great Ring Rd, Sandy Hook, CT 06482

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