5-Bedroom Homes for Sale in Fairfield County CT

/39
$759,900
- 5 Beds
- 3.5 Baths
- 3,168 Sq Ft
65 Cloverdale Ave, Shelton, CT 06484

Located in a prime neighborhood of Huntington in Shelton. Easy access to Rte 8, Rte 25 & Merritt Parkway. It is conveniently located minutes to schools, golf courses, shopping, family farms, community center, hiking trails & restaurants. This home boasts 5 bedrooms, 3 Full Baths/1 half bath and over 3,000 sq ft. Front of house has a covered porch which leads into the tiled foyer. The eat in

Persefone Burnett BHGRE Gaetano Marra Homes

65 Cloverdale Ave, Shelton, CT 06484
/40
$2,795,000
- 5 Beds
- 3.5 Baths
- 5,262 Sq Ft
6 Wahackme Ln, New Canaan, CT 06840

Discover timeless elegance in this beautifully expanded and meticulously renovated Center Hall Colonial, set on two private acres abutting Audubon Society land. Nestled on a coveted cul-de-sac on a private lane in the West School district, this sophisticated home combines classic charm with modern updates and a superb location close to town. Featuring 5 spacious bedrooms and 3.5 well-appointed

Jaime Sneddon William Pitt Sotheby's Int'l

6 Wahackme Ln, New Canaan, CT 06840
/40
$1,250,000
- 5 Beds
- 2.5 Baths
- 2,890 Sq Ft
25 Palmer Place, Easton, CT 06612

Enjoy sophisticated one level living in this breathtaking Serena & Lily inspired home. Located on a popular Lower Easton street this exceptional, totally renovated ranch is a rare find. Drive up the freshly paved driveway and spend hours relaxing on the charming bluestone front porch. Step into the welcoming foyer and see all the way through to the back yard. The sunny living room with its

Gayle Worthington William Raveis Real Estate

25 Palmer Place, Easton, CT 06612
/17
$850,000
- 11 Beds
- 4 Baths
- 4,938 Sq Ft
1621 Stratford Ave, Stratford, CT 06615

Excellent Investment Opportunity with great cash flow. Legal 4 Family with 3 units occupied. Corner Building, Lot of parking space. Some units are recently remodeled. Rents can be higher, Long term tenants. Very Convenient Location - Close to I95 and bus line.

Aziz Seyal William Raveis Real Estate

1621 Stratford Ave, Stratford, CT 06615
/21
$585,000
- 8 Beds
- 3 Baths
- 3,078 Sq Ft
565 Carroll Ave Unit 567, Bridgeport, CT 06607

Amazing investment opportunity with this property that is located very close to the heart of Bridgeport, an evolving area of Bridgeport. Invest smart with this property, starting with a great foundation, the basement. 3 units that you can either use as a primary residence and lease the rest or lease all 3 units for a positive cash flow. Units consisting of 3 bedrooms, 1 bathroom and plenty of

Christian Flores mygoodagent

565 Carroll Ave Unit 567, Bridgeport, CT 06607
/11
$679,000
- 8 Beds
- 3 Baths
- 3,749 Sq Ft
53-55 Fremont St, Bridgeport, CT 06605

Three Family house located in BRIDGEPORT CT . Legal three family fully rented and producing income. Welcome all investors to this great opportunity featuring 12 rooms, 8 bedrooms, three full baths approximately 3,000 sq ft, good sized units. If you are looking for an income investment look no further. Make an appointment for your tour today!

Rosania Melo Century 21 Scala Group

53-55 Fremont St, Bridgeport, CT 06605
/40
$27,950,000
- 8 Beds
- 12 Baths
- 13,428 Sq Ft
45 Binney Ln, Old Greenwich, CT 06870

This unparalleled custom-built modern waterfront estate, winner of 2021 HOBI-award, is a true oasis with 300'+ water frontage, pool, guest house, boat house, spa, expansive terraces integrated with gardens and deep water pier. Joeb Moore + Partners, Arthur Dunnam for Jed Johnson Studio, Reed Hilderbrand & Prutting Custom Builders collaborated on this spectacular LEED certified 13,428 sf compound

Ellen Mosher Houlihan Lawrence

45 Binney Ln, Old Greenwich, CT 06870
/61
$5,595,000
- 6 Beds
- 8 Baths
- 5,634 Sq Ft
44 N Porchuck Rd, Greenwich, CT 06831

Elegantly renovated 6 bed, 6.2 bath Georgian Colonial w/stunning finishes & custom millwork on 4+ acres bordering the Greenwich Audubon providing privacy. The stunning new kitchen & adjacent family rm., opens to spacious outdoor living for entertaining w/expansive terraces, heated pool w/spa, outdoor BBQ, pool house w/kitchen & also a paddock with 3 stall stable. Arched doorways lead into the

Giselle Gibbs BHHS New England Properties

44 N Porchuck Rd, Greenwich, CT 06831
/25
$2,700,000
- 5 Beds
- 3 Baths
- 4,170 Sq Ft
70 Redding Rd, Easton, CT 06612

This magnificent country estate includes the historic Thorp House on 8.8 acres of riverfront property, as well as a charming one bedroom cottage with attached 2 car garage. The main house, built in 1750, is listed on the National Register of Historic Places. Authentic period details grace the home with unique old world charm. Cathedral ceilings in the kitchen and great room make a stately

Charlotte Cotton William Raveis Real Estate

70 Redding Rd, Easton, CT 06612
/37
$789,000
- 6 Beds
- 3 Baths
- 2,935 Sq Ft
525 Courtland Ave Unit 527, Bridgeport, CT 06605

Don't miss this exceptional opportunity to own a multi-family property on one of Black Rock's most desirable streets. This property is truly an investor's dream. With nearly 3,000 square feet of living space, it offers a total of six bedrooms and three bathrooms across three levels, each featuring beautiful hardwood floors and updated HVAC systems. This spacious home features a two-bedroom,

Hillary Waite William Raveis Real Estate

525 Courtland Ave Unit 527, Bridgeport, CT 06605
/11
$4,900,000
- 7 Beds
- 5.5 Baths
- 7,995 Sq Ft
37 Green Acre Ln, Westport, CT 06880

The most private and serene of the remaining multi-acre estates in central-most Westport... Just two minutes from the beach, town center, I-95, and the Saugatuck Hamlet rail station. Located Near several well-regarded school systems in Connecticut. This grand estate offers space for recreation, relaxation, and entertaining. A stone-gated, walled circular driveway marks the end of a private road

Lisa Bortz William Pitt Sotheby's Int'l

37 Green Acre Ln, Westport, CT 06880
/36
$599,500 Open Sat 12PM - 3PM
- 5 Beds
- 2 Baths
- 2,359 Sq Ft
128 Bancroft Ave, Bridgeport, CT 06604

This stunning 5 bed, 2 bath home is located on a corner lot in the highly desirable Brooklawn neighborhood, moments from Fairfield. Blending classic charm, modern elegance, it was thoughtfully redesigned with an emphasis on organic modern & lived-in luxury. With 2 BRs located on the main level & 3 BRs upstairs, the flexible layout is perfect for multigenerational living, guest accommodations, or

Angela Morales Keller Williams Realty Prtnrs.

128 Bancroft Ave, Bridgeport, CT 06604
/31
$6,900,000
- 6 Beds
- 6.5 Baths
- 6,585 Sq Ft
69 Beachside Ave, Westport, CT 06880

Nestled along Westport's prestigious 'Gold Coast,' this architecturally magnificent estate on 4+ acres of park-like grounds with a breathtaking pool and professional-grade Har-Tru tennis court is a haven for luxury living and distinguished entertaining. Surrounded by major estates in one of the most sought-after coastal regions in the Northeast, it boasts access to pristine beaches, sophisticated

Doug Bross Coldwell Banker Realty

69 Beachside Ave, Westport, CT 06880
/40
$970,000
- 5 Beds
- 3 Baths
- 4,455 Sq Ft
3 Huntington Ln, New Fairfield, CT 06812

Discover this impressive 4,455 sq ft Colonial, beautifully sited on 2.04 private acres at the end of a quiet cul-de-sac in one of the area's most coveted neighborhoods. A lush, manicured front lawn and wrap-around driveway set the tone for the inviting elegance within. The main level offers exceptional space for entertaining and everyday living, featuring a bright eat-in kitchen with center

Kristie Perry William Pitt Sotheby's Int'l

3 Huntington Ln, New Fairfield, CT 06812
/39
$2,895,000 Open Sun 2PM - 4PM
- 5 Beds
- 3.5 Baths
- 4,020 Sq Ft
4 Rabbit Ln, Darien, CT 06820

This contemporary Colonial, crafted by Alfieri Enterprises and thoughtfully reimagined in 2025 by Gill & Gill Architects, blends timeless charm with modern sophistication. Nestled on a sought-after cul-de-sac convenient to downtown Darien, this nearly 4,000SF home offers 5 bedrooms, 3.5 bathrooms-perfectly designed for both everyday living and elegant entertaining. The main level boasts open

Becky Munro Brown Harris Stevens

4 Rabbit Ln, Darien, CT 06820
/40
$2,350,000
- 5 Beds
- 4.5 Baths
- 5,445 Sq Ft
20 Silver City Rd, Newtown, CT 06470

Welcome to 20 Silver City, a truly exceptional estate offering magnificent views, total privacy, and effortless luxury. Set on 18.57 secluded acres at the end of a cul-de-sac, this sophisticated ranch-style home combines modern updates with timeless design. Step inside to discover a bright, open floor plan ideal for everyday living and entertaining. The living and dining areas flow seamlessly

Connie Widmann William Raveis Real Estate

20 Silver City Rd, Newtown, CT 06470
/31
$1,300,000
- 6 Beds
- 7 Baths
- 6,493 Sq Ft
106 Wyldewood Rd, Easton, CT 06612

Welcome to your dream retreat! This stunning property offers privacy on a quiet cul-de-sac, with a serene pond in the backyard. Situated on 3+ acres, it features 3 fireplaces, an open concept main floor, a first-floor primary suite with dual showers and a standalone tub, an Inlaw suite with a private entrance and full kitchen, large windows, a lofted great room, and a finished walkout basement.

Jason Saphire www.HomeZu.com

106 Wyldewood Rd, Easton, CT 06612
/38
$2,125,000
- 5 Beds
- 4 Baths
- 3,023 Sq Ft
19 Pond Place, Cos Cob, CT 06807

Welcome to this beautifully expanded and meticulously renovated Cape Cod-style home, nestled on a quiet, family-friendly street in the heart of Cos Cob. Boasting 5 spacious bedrooms including a large primary suite and 4 full bathrooms, this home perfectly blends classic charm with modern amenities. The heart of the home is a stunning custom gourmet kitchen, seamlessly connected to a sun-filled

Catherine Aaron BHHS New England Properties

19 Pond Place, Cos Cob, CT 06807
/32
$5,250,000
- 6 Beds
- 7 Baths
- 5,839 Sq Ft
5 Spring St, Riverside, CT 06878

Welcome to 5 Spring Street, a distinguished 6 bedroom, 5.2 bath residence in picturesque Riverside. This grand estate offers a perfect blend of modern elegance & sophistication, set on an expansive lot, emphasizing privacy & tranquility. Upon entering, you are greeted by a gracious foyer that sets the tone for the thoughtfully expanded home. The main level boasts a chef's kitchen perfect for

Lindsay Sheehy Compass Connecticut, LLC

5 Spring St, Riverside, CT 06878
/40
$2,795,000
- 6 Beds
- 8 Baths
- 5,811 Sq Ft
463 N Salem Rd, Ridgefield, CT 06877

This gracious country estate's idyllic setting is the perfect backdrop for large family gatherings & joyous celebrations. For over 40 years, the Rosenthal family has cherished this sprawling sanctuary, creating a legacy of warmth & hospitality that is unmatched. Now the doors are open for a new owner to create timeless memories - whether poolside; sitting by the outdoor fireplace; cooking in the

Jay Contessa William Pitt Sotheby's Int'l

463 N Salem Rd, Ridgefield, CT 06877
/5
$799,900
- 8 Beds
- 4 Baths
- 2,390 Sq Ft
56 Calhoun Ave, Bridgeport, CT 06604

Four Family house located in BRIDGEPORT CT . Legal 4 family fully rented and producing income. Welcome all investors to this great opportunity featuring 16 rooms, 8 bedrooms, three full baths approximately 3,000 sq ft, good sized units. If you are looking for an income investment look no further. Make an appointment for your tour today!

Rosania Melo Century 21 Scala Group

56 Calhoun Ave, Bridgeport, CT 06604
/30
$1,699,000
- 5 Beds
- 5 Baths
- 6,177 Sq Ft
811 Rock Rimmon Rd, Stamford, CT 06903

Stunning Modern completely redone colonial set in a quiet North Stamford location. Completely re-imagined in 2025 with well crafted & stylish design elements through out. This designer chic modern home features a first floor plan w/an open concept. A two story foyer welcomes you to the many elements of this sophisticated home. The oversized kitchen is the center of the home; featuring abundant

Tom Vozzella Berkshire Hathaway NE Prop.

811 Rock Rimmon Rd, Stamford, CT 06903
/40
$2,400,000
- 5 Beds
- 3.5 Baths
- 4,619 Sq Ft
57 Main St, Ridgefield, CT 06877

Welcome to a timeless gem at 57 Main Street, Ridgefield, CT. This fabulous vintage Farmhouse Colonial has been completely renovated to the highest standards, blending sophistication with a casual, inviting vibe. The attention to detail is remarkable and features the latest design finishes and designer lighting. Nestled on a prime 1-acre level parcel, this home offers a highly desirable Main

Karla Murtaugh Compass Connecticut, LLC

57 Main St, Ridgefield, CT 06877
/35
$799,000
- 5 Beds
- 2.5 Baths
- 2,240 Sq Ft
9 Jean Ave, Norwalk, CT 06850

Stunning 5 bedroom, 2.5 bath colonial in West Norwalk! - Totally renovated kitchen featuring white shaker-style cabinets, quartz counters, subway tile backsplash, range hood, and stainless steel appliances! - Large island in kitchen features wine chiller / beverage fridge - Great entertaining space on 1st floor with open dining room, leading into family room + additional den / playroom - 5

Todd Turcotte Milligan Realty.com

9 Jean Ave, Norwalk, CT 06850
/39
$2,799,000
- 5 Beds
- 4.5 Baths
- 6,400 Sq Ft
433 Belden Hill Rd, Wilton, CT 06897

Exceptional Custom Designed Contemporary Colonial Farmhouse Style Estate in South Wilton. Set on 3.1 pristine acres of flat, manicured land in coveted South Wilton, this newly constructed 6,400 +/- square foot masterpiece sets a new standard for luxury living. No expense has been spared in creating this exceptional residence, where thoughtful design meets uncompromising quality. The home's grand

Alison Mark Coldwell Banker Realty

433 Belden Hill Rd, Wilton, CT 06897
/38
$2,475,000
- 6 Beds
- 4.5 Baths
- 6,015 Sq Ft
212 Fence Row Dr, Fairfield, CT 06824

Welcome to your custom built gem at The Ridge, a gated community where luxury meets comfort. This Contemporary Cape Cod is located on a premier two acre lot with graceful landscaping. Inside, the vaulted foyer sets the expansive tone, opening up to a sunken living room bathed in natural light from a wall of windows. Picture hosting elegant dinners in the formal dining room, where tray ceilings

Sara Melendez-Hossain Compass Connecticut, LLC

212 Fence Row Dr, Fairfield, CT 06824
/40
$1,779,000
- 5 Beds
- 5.5 Baths
- 7,611 Sq Ft
28 Old Orchard Dr, Weston, CT 06883

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer.

Barbara Bross Coldwell Banker Realty

28 Old Orchard Dr, Weston, CT 06883
/37
$1,375,000 Open Sat 12PM - 2PM
- 5 Beds
- 3.5 Baths
- 3,327 Sq Ft
64 Old Kings Hwy S, Darien, CT 06820

Own a piece of history with the Quintard-Frost House, a stunning antique Dutch Colonial home built in 1715 that seamlessly blends historic charm with modern comfort. This 5-bedroom, 3.5-bathroom residence showcases timeless craftsmanship, including original wide-plank floors, exposed beams, and period details throughout. At the heart of the home is a true antique bar with fireplace, a rare and

Seema Dohil Brown Harris Stevens

64 Old Kings Hwy S, Darien, CT 06820
/32
$1,295,000
- 5 Beds
- 2 Baths
- 2,983 Sq Ft
85 Indian Field Rd, Greenwich, CT 06830

First time on the market since 1971!This bright and sunny five-bedroom, 2 bath home, situated on a spacious 0.36-acre lot, boasts great bones and awaits someone with creative vision to make it their own. Featuring high ceilings, fireplaces in both the living room and lower level, a sauna, and a two-car garage, this property offers ample potential. Conveniently located near the train, schools,

Kelly Feda Coldwell Banker Realty

85 Indian Field Rd, Greenwich, CT 06830
/9
$739,900
- 9 Beds
- 3 Baths
- 3,688 Sq Ft
139 Whitney Ave Unit 141, Bridgeport, CT 06606

Very well-cared large 3-family house located in the northern Bridgeport, offering all the amenities that the city offers, such as public transportation, restaurants, stores, and highways. This house is perfect for owner-occupied or investors. 2-car detached garage and long shared driveway. Do not miss this opportunity, make your reservation today! Subject to the seller finding suitable housing.

Arbis Faustin Faustin Realty Group

139 Whitney Ave Unit 141, Bridgeport, CT 06606
/40
$2,495,000
- 5 Beds
- 5.5 Baths
- 7,225 Sq Ft
32 Steep Hill Rd, Weston, CT 06883

This country estate,commanding views of three acres of natural beauty centered by a 1.2 acre pond, masterfully blends 18th century farmhouse charm with newly-built modern luxury. Original features include chestnut posts and beams, wide-plank pine floors, and a flued brick oven. Gather in the spacious chef's kitchen, sunroom, and family room anchored by a semi-circular fireplace crafted from the

Michelle Genovesi William Raveis Real Estate

32 Steep Hill Rd, Weston, CT 06883
/24
$998,500
- 14 Beds
- 8 Baths
- 5,052 Sq Ft
40-42 Jane St, Bridgeport, CT 06608

Welcome to 40-42 Jane St. in Bridgeport, Connecticut. Opportunity to own a spacious six family property with two large four bedroom one and a half bathroom apartments, two spacious two bedroom and one full bathroom apartments, and two large one bedroom one full bathroom apartments. Each apartment comes with an updated kitchen and bathroom, light and bright living room dining room, amole closet

Ben Weinberg Oxford Realty

40-42 Jane St, Bridgeport, CT 06608
/40
$2,395,000
- 6 Beds
- 5.5 Baths
- 7,000 Sq Ft
3010 Redding Rd, Fairfield, CT 06824

Perched at the end of a private, tree-lined drive, this grand 5/6 bedroom, 5 full and 1 half bathroom, Georgian-style home seamlessly blends form and function. Designed to highlight the property's exquisite natural beauty, each room looks out onto lush, professionally landscaped lawns, gardens, & mature trees. Sunrises and sunsets are stunning. In every room, out every window are the most

Terry Keegan Fairfield County Real Estate

3010 Redding Rd, Fairfield, CT 06824
/40
$2,995,000
- 6 Beds
- 4 Baths
- 4,614 Sq Ft
9 Bobwhite Dr, Westport, CT 06880

Prepare to fall in love with this extraordinary home, crafted with love by a talented architect for his own family. The charming shingle-style residence at 9 Bobwhite Drive is nestled on a picturesque, level acre amidst other fine homes in a peaceful cul-de-sac setting, offering plenty of space for fun and entertainment. You'll find joy around every corner with its custom woodwork, innovative

Laurie Morris Compass Connecticut, LLC

9 Bobwhite Dr, Westport, CT 06880
/40
$7,695,000
- 7 Beds
- 8.5 Baths
- 10,039 Sq Ft
1227 Ponus Ridge, New Canaan, CT 06840

Stylish, sophisticated and fun, this stunning 10,000 SF westside country estate borders two acres of land trust for total privacy, and is conveniently located close to town and schools. Extensive and impeccable renovations in 2023 with exquisite details and millwork, superior quality craftsmanship, luxurious amenities, smart home technology, designer light fixtures, new mechanicals, new cedar

Mary Higgins Brown Harris Stevens

1227 Ponus Ridge, New Canaan, CT 06840
/32
$1,450,000
- 5 Beds
- 3 Baths
- 5,984 Sq Ft
53 Pinnacle Rock Rd, Stamford, CT 06903

Elegant 5 bedroom, 3 bathroom expansive residence set on 1.22 serene acres with stunning renovations throughout. A gracious foyer leads to a spacious eat-in gourmet kitchen with island and breakfast area. Recent renovations include new granite counters, induction cooktop, and stainless steel hood/appliances. The formal dining room and grand living room with fireplace as well as updated Azek

Joy Kim Metalios Houlihan Lawrence

53 Pinnacle Rock Rd, Stamford, CT 06903
/44
$7,450,000
- 5 Beds
- 9 Baths
- 9,974 Sq Ft
386 North St, Greenwich, CT 06830

This stunning 9,974 sq. ft. estate showcases exceptional craftsmanship and luxurious interiors. The striking oversized brick exterior with a wood-shingle roof sets the tone for this impressive home, nestled on 2.3 acres of park-like grounds within a 1-acre zone. The expansive ground-floor primary suite offers a serene sitting room and direct access to a private office. Three additional spacious

Stephen Archino Sotheby's International Realty

386 North St, Greenwich, CT 06830
/33
$2,595,000
- 5 Beds
- 6 Baths
- 5,271 Sq Ft
129 Long Close Rd, Stamford, CT 06902

Introducing 129 Long Close Rd - a 5,300 sq ft architectural masterpiece nestled on 5 acres in the highly desirable Westover neighborhood, just minutes from the Greenwich border and downtown Stamford. Thoughtfully redesigned by Eric Baker Architects - a renowned architect - for his own family, every element of this exceptional home reflects a passion for quality, craftsmanship, & timeless design.

Jen Turano Compass Connecticut, LLC

129 Long Close Rd, Stamford, CT 06902
/38
$1,099,000
- 5 Beds
- 3 Baths
- 1,954 Sq Ft
2715 Post Rd, Darien, CT 06820

Darien CT!!! Location, Location, Location! Super Spacious 4+ Bedroom, 3+ Bath Home in Prime Darien-Stamford Location! Welcome to this light-filled, beautifully aportioned home offering the best of both worlds-highly sought-after Darien schools with the vibrant lifestyle of Stamford, CT! Enjoy easy access to Cove Island Park, Stamford dining and entertainment, and the Darien YMCA with pool and

Fiona Porter Keller Williams Realty

2715 Post Rd, Darien, CT 06820
/40
$549,900
- 5 Beds
- 2.5 Baths
- 1,989 Sq Ft
1852 Madison Ave, Bridgeport, CT 06606

Spacious and elegant North End Brick Colonial ready for a small or large family. As you drive up the driveway you will immediately feel at home with the beautifully mature planting, pristine green lawn leading to your 2 car garage and additional parking for 3+ paved spots. Upon entering the front door you'll notice the bright hardwood floors. There is a living room to your right with wood burning

Carlos Perez RE/MAX Right Choice

1852 Madison Ave, Bridgeport, CT 06606

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