5-Bedroom Homes for Sale in Fairfield County CT

/40
$1,125,000
- 7 Beds
- 4 Baths
- 3,167 Sq Ft
29 Priscilla Rd, Norwalk, CT 06850

Location, Location!! Beautiful big house in the heart of Norwalk, 7-Beds, 4-Baths, 2 spacious garages. Don't miss the opportunity to live just 40min from NYC. Close to MCC. Vacancy subject to owner finding a suitable home within the next 60 days

Miguel Jaraba Marquez

Whitestone Real Estate Group

(203) 769-9354

29 Priscilla Rd, Norwalk, CT 06850
/40
$2,250,000 Open Sun 1PM - 4PM
- 5 Beds
- 4 Baths
- 2,452 Sq Ft
32 Beeholm Rd, Redding, CT 06896

Your exceptional 24+ acre private oasis awaits. This significant piece of Redding's natural beauty offers more than just a home; it includes two charming rustic cottages, adding an impressive 1,023 sq. ft. (#A) and 982 sq. ft. (#B) of versatile living space. Each cottage features 1 bedroom and 1 bath, providing ideal accommodations for guests, extended family, caretakers, or a steady revenue

Ellen Garcia

Brown Harris Stevens

(475) 291-4216

32 Beeholm Rd, Redding, CT 06896
/40
$1,750,000 Open Sun 1PM - 3PM
- 6 Beds
- 5 Baths
- 3,461 Sq Ft
47 Hollow Tree Ridge Rd, Darien, CT 06820

PRICE ADJUSTMENT. A Rare Darien Gem and opportunity to own this historic Federal Colonial 2-family home, one of Darien's few multi-family properties. Spanning over 3,460 SF on .47 acres, this turn-key furnished residence blends timeless elegance with modern versatility, ideal for investors, families, multi-generational households, or those seeking rental income. Historic Charm, Modern Comfort: *

Karen Finn

Gatehouse Realty Inc

(475) 325-5924

47 Hollow Tree Ridge Rd, Darien, CT 06820
/36
$5,100,000
- 6 Beds
- 8 Baths
- 7,930 Sq Ft
20 Sherwood Farm Ln, Greenwich, CT 06831

Step into luxury with this newly staged custom built home in one of Greenwich's prestigious associations. Perfectly situated near downtown, this elegant property offers a blend of sophistication and convenience- now at an improved price! A stunning custom built white Georgian Colonial in the coveted mid country Sherwood Farm Association is sited on a picturesque level acre lot. This six bedroom

Richard Higgins

Higgins Group Bedford Square

(203) 433-0559

20 Sherwood Farm Ln, Greenwich, CT 06831
/40
$1,950,000
- 7 Beds
- 7 Baths
- 4,806 Sq Ft
803 N Salem Rd, Ridgefield, CT 06877

Historic Ridgefield Estate - Where Legacy Meets Modern Luxury. Originally built in 1911 as the Ridgefield School for Boys, this unique estate once anchored a vast 115-acre campus and featured more than 100 rooms, including classrooms, dormitories, and offices. When the school closed, the property was purchased by Francis D. Martin, who gave it a bold architectural overhaul by removing the top

Shaylene Neumann

Houlihan Lawrence

(475) 252-9158

803 N Salem Rd, Ridgefield, CT 06877
/33
$550,000
- 8 Beds
- 3 Baths
- 3,178 Sq Ft
657 Park St Unit 659, Bridgeport, CT 06608

Location, Location, Location!!! Great Opportunity to own a Two-Family House with a potential to convert it into a Three-Family. You can also buy it as a Package with the house next door making it a 4-Family house with a potential to convert it into a Six-Family House. Each house can generate $84,000.00 a year or $168,000.00 combined. Make this your next investment property. It is also a great

Santiago Jaraba

Whitestone Real Estate Group

(203) 457-6539

657 Park St Unit 659, Bridgeport, CT 06608
/39
$550,000
- 8 Beds
- 3 Baths
- 3,178 Sq Ft
661 Park St, Bridgeport, CT 06608

Location, Location, Location!!! Great Opportunity to own a Two-Family House with a potential to convert it into a Three-Family. You can also buy it as a Package with the house next door making it a 4-Family house with a potential to convert it into a Six-Family House. Each house can generate $84,000.00 a year or $168,000.00 combined. Make this your next investment property. It is also a great

Santiago Jaraba

Whitestone Real Estate Group

(203) 599-7216

661 Park St, Bridgeport, CT 06608
/34
$1,695,000
- 6 Beds
- 6 Baths
- 2,960 Sq Ft
1 Marker Rd, Danbury, CT 06811

Lakefront Investment Paradise - 100 Feet of Direct Waterfront! Live the lake life while generating serious income with this rare opportunity on the water. Set on a private stretch of shoreline, this income-producing property features six individual cottages and three docks with six boat slips - perfect for short-term rentals or seasonal tenants. Each cottage offers a private wood deck, scenic

Edmundo DaSilva

eXp Realty

(203) 872-0911

1 Marker Rd, Danbury, CT 06811
/4
$725,000
- 8 Beds
- 3 Baths
- 2,615 Sq Ft
1218 Kossuth St, Bridgeport, CT 06608

**Welcome to 1218 Kossuth Street, Bridgeport!** Discover the perfect blend of modern living and convenience in this stunning new construction duplex. Featuring 4 spacious bedrooms and 2 contemporary bathrooms, this home is designed for both comfort and style. The thoughtfully laid-out upper unit boasts beautiful hardwood floors throughout, creating a warm and inviting atmosphere. The lower level

Alexander Galvez

Century 21 Galvez

(203) 442-9198

1218 Kossuth St, Bridgeport, CT 06608
/11
$5,250,000
- 5 Beds
- 8 Baths
- 9,300 Sq Ft
67 Carter St, New Canaan, CT 06840

67 Carter Street - Exceptional Modern Estate Experience unrivaled luxury at this extraordinary 2.5-acre sanctuary in New Canaan. Encompassing nearly 7,300 sq ft above grade and an additional 2,000 sq ft in the lower level with soaring 10-foot ceilings, this architectural masterpiece offers a refined and expansive living experience. A chef's gourmet kitchen anchors the home, complemented by five

Richard Breglia

Coldwell Banker Realty

(475) 241-7968

67 Carter St, New Canaan, CT 06840
/40
$12,400,000
- 12 Beds
- 16 Baths
- 18,000 Sq Ft
544 Oenoke Ridge, New Canaan, CT 06840

A rare opportunity to own a legacy estate that would command over $50 million to recreate in today's market. Orchard's End, built in 1929 designed by New York architect William B. Tubby, his outstanding designs include Waveny House in New Canaan, Dunnellen Hall in Greenwich and the William H. Childs House in Brooklyn. Beginning in 2014, the current owners retained world renowned architect Dinyar

Danielle Malloy

Serhant Connecticut, LLC

(475) 445-2580

544 Oenoke Ridge, New Canaan, CT 06840
/25
$3,999,000
- 6 Beds
- 8 Baths
- 6,000 Sq Ft
57 Evergreen Ave, Westport, CT 06880

Walk to downtown shops and restaurants from this stunning, reimagined, & rebuilt 1920 Dutch colonial home, situated on a spacious 1.17-acre in-town property.This is truly a work of art, as 2 properties have been seamlessly combined into one, creating a private oasis set way back from the road.Upon entering the home, you will be captivated by the meticulous attention to detail & the perfect blend

Hyleri Katzenberg

Compass Connecticut, LLC

(475) 253-3404

57 Evergreen Ave, Westport, CT 06880
/40
$2,995,000
- 5 Beds
- 5.5 Baths
- 5,965 Sq Ft
2015 Redding Rd, Fairfield, CT 06824

Majestically sited on 2 private acres of professionally landscaped grounds, this exceptional SMART modern farmhouse surpasses new construction standards with uncompromising attention to detail. This 5,500+ SF estate exemplifies architectural integrity with handcrafted millwork and bespoke finishes throughout. Superior craftsmanship shines in every detail-from rich white oak hardwood floors to

Susan Lieberman

The Riverside Realty Group

(475) 252-9450

2015 Redding Rd, Fairfield, CT 06824
/33
$920,000 Open Sun 1PM - 3PM
- 5 Beds
- 3 Baths
- 2,788 Sq Ft
1 Greenlea Ln, Weston, CT 06883

This charming 5-bedroom, 3-full-bath home offers 2,788 sq. ft. of beautifully designed living space, set on a generous 2-acre corner lot. Perfect for entertaining, the home boasts a convenient location with easy access to everything Weston has to offer. Main floor, eat-in Kitchen, Dining Room, Living Room with fireplace, Three Bedrooms with hall Bath and Primary Bedroom with Bath, Laundry Room,

Kevin O'Brien

O'Brien Premier Properties

(203) 632-9988

1 Greenlea Ln, Weston, CT 06883
/5
$4,895,000 New Construction
- 6 Beds
- 9 Baths
- 9,224 Sq Ft
21 Warnock Dr, Westport, CT 06880

Expected for completion Fall 2025, this striking architectural design meets refined luxury in a meticulously crafted 9,200+/- sq ft, 6-bedroom, 6 full, & 3 half bath new residence. Showcasing the collaborative excellence of AR Luxury Homes w/ interior design by Mary Beth Woods & architectural vision by Donald William Fairbanks, this exceptional property represents the pinnacle of modern

Brett Lieberman

The Riverside Realty Group

(475) 255-6647

21 Warnock Dr, Westport, CT 06880
/12
$3,499,000 New Construction
- 5 Beds
- 4.5 Baths
- 6,444 Sq Ft
20 Locust Hill Rd, Darien, CT 06820

Welcome to 20 Locust Hill Road, a stunning new construction opportunity in the heart of Darien, CT. This modern colonial/farmhouse-style home, constructed by an experienced builder renowned for high-end residential properties throughout Fairfield County, offers 5 bedrooms, 4.5 bathrooms, and an expansive 4,897 square feet of living space. Situated on a generous .50 acre in-town lot, this home

Robert Marchesi

Compass Connecticut, LLC

(475) 253-5609

20 Locust Hill Rd, Darien, CT 06820
/34
$3,450,000
- 5 Beds
- 4.5 Baths
- 3,581 Sq Ft
98 Rowayton Ave, Norwalk, CT 06853

Welcome to 98 Rowayton Ave, in the heart of Rowayton where you can walk to it all! This historic home has been thoughtfully renovated, combining luxury with advanced technology for modern living. The first floor boasts new hardwood floors, a first floor en suite bedroom with radiant heat marble bathroom floors. The gourmet kitchen features Wolf and Sub Zero appliances, heated quartzite

Elizabeth Beinfield Compass Connecticut, LLC

98 Rowayton Ave, Norwalk, CT 06853
/40
$1,095,000
- 5 Beds
- 4 Baths
- 3,652 Sq Ft
55 Mimosa Ct, Ridgefield, CT 06877

Welcome to Mimosa Estates, one of Ridgefield's most desirable neighborhoods just minutes from the vibrant town center with its shops, restaurants, cultural venues, and theaters. Residents here enjoy incredible community amenities, including a pool, tennis and basketball courts, a clubhouse, a playground, and sports fields-all just steps from home. This spacious residence is privately situated on

Chip & Heather Neumann Houlihan Lawrence

55 Mimosa Ct, Ridgefield, CT 06877
/40
$2,995,000 Open Sat 1PM - 3PM
- 5 Beds
- 5.5 Baths
- 5,916 Sq Ft
20 Old Hill Rd, Westport, CT 06880

Welcome to this beautifully maintained 1945 stone-front Cape in the heart of Old Hill. Loved by the same family for 22 years, it radiates warmth and character. With 5 bedrooms, 5.5 baths, and two flexible spaces for home offices, it offers comfort and versatility, including a first-floor suite ideal for guests or in-laws. The light-filled kitchen flows into an inviting dining area and cozy sunken

Michelle Genovesi William Raveis Real Estate

20 Old Hill Rd, Westport, CT 06880
/39
$1,800,000
- 5 Beds
- 6.5 Baths
- 6,034 Sq Ft
40 Wildwood Rd, Stamford, CT 06903

Step into timeless elegance with this newly constructed 6,034 sq. ft. Colonial masterpiece, featuring a legally finished walk-out basement with an additional 2,678 sq. ft.-where luxury meets meticulous craftsmanship. Set behind stately stone pillars, the home welcomes you with a sweeping driveway, manicured gardens, and a pool site ready for your dream oasis. Inside, a sun-drenched, two-story

Ken Wile Redfin Corporation

40 Wildwood Rd, Stamford, CT 06903
/36
$1,995,000 Open Sun 2PM - 4PM
- 5 Beds
- 5.5 Baths
- 5,705 Sq Ft
873 N Salem Rd, Ridgefield, CT 06877

Welcome Home to this beautiful estate property, sited on 7.39 private, picturesque acres just minutes from Ridgefield's vibrant village center. Built in 1970 and offering 5,705 square feet of above-grade, finished living space, this classic Colonial and the surrounding property are brimming with opportunity. The custom-built residence's main living space includes a gracious living room, formal

Chip & Heather Neumann Houlihan Lawrence

873 N Salem Rd, Ridgefield, CT 06877
/25
$849,000
- 6 Beds
- 6 Baths
- 2,928 Sq Ft
20 Maple Ave, Bethel, CT 06801

Don't miss this fantastic opportunity in the heart of Bethel! Just a stone's throw from vibrant downtown, this charming two-family offers endless potential. One unit is vacant-move right in while generating income from the other! The bright, sun-filled interiors feature an inviting open-concept living space with an eye-catching fireplace and an updated kitchen. Enjoy ample basement storage and

Jared Randall Redfin Corporation

20 Maple Ave, Bethel, CT 06801
/36
$885,000
- 5 Beds
- 3 Baths
- 2,600 Sq Ft
4 Robert Ln, Westport, CT 06880

Nestled on a secluded cul-de-sac just off Hogan Trail, this peaceful residence sits on a spacious 0.45-acre plot. Enjoy the convenience of walking distance access to the train station, downtown shopping, Saugatuck restaurants, and 5 min ride to the beach. The main level features a spacious living room, connected to the kitchen, dining area, and a deck, creating an ideal space for relaxation.

Inna Agujen Coldwell Banker Realty

4 Robert Ln, Westport, CT 06880
/40
$3,999,999
- 5 Beds
- 9 Baths
- 11,450 Sq Ft
64 Old Redding Rd, Weston, CT 06883

Discover a stunning custom-crafted luxury home, complete with a separate one-bedroom guest pool house, that stands as an architecturally significant estate designed to be cherished. Nestled on meticulously landscaped grounds with picturesque views of Pawtucket Valley Country Club, this grand colonial residence offers every amenity for a refined lifestyle. As you enter the soaring foyer, you are

Anissa Paolillo Redfin Corporation

64 Old Redding Rd, Weston, CT 06883
/7
$2,090,000
- 5 Beds
- 7 Baths
- 5,100 Sq Ft
0 Mountain Rd, Wilton, CT 06897

This proven luxury home builder wants to build your future dream home on this rarely available one of a kind private lot. Drive down a private, hidden 1000+ foot driveway to find a property totaling over 2.00+ acres of unmatched and untouched exclusivity surrounded by protected state land. Add pool and tennis too! Two amazing potential lot sites. In addition, and even a possibility of

Evan Sheftel Millstone Real Estate Corp

0 Mountain Rd, Wilton, CT 06897
/37
$1,895,000 Open Sun 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 5,474 Sq Ft
5 New England Dr, Stamford, CT 06903

Welcome to 5 New England Drive-a spacious and thoughtfully designed ranch set on a level one-acre corner lot in North Stamford, offering the rare advantage of natural gas and public water. The beautifully maintained grounds provide a true retreat with a tennis court, in-ground pool, courtyard, covered outdoor dining area with pizza oven, and a fully fenced backyard. Inside, you'll find 5,474 sq

Stephen Lasko Compass Connecticut, LLC

5 New England Dr, Stamford, CT 06903
/12
$500,000
- 6 Beds
- 3 Baths
- 3,020 Sq Ft
1906 E Main St, Bridgeport, CT 06610

The one you've been waiting for! Opportunity knocks at this spacious 3 family on Bridgeport's dynamic East Side. Convenience abounds at this centrally located cash cow with close proximity to several retail & dining options, bus line, the waterfront / Steelpointe Harbor, and so much more. A classic triple decker, each floor offers a sunny, versatile floorplan with 2 bedrooms, 1 full bath, and

Tommy Connors Redfin Corporation

1906 E Main St, Bridgeport, CT 06610
/37
$4,249,000
- 5 Beds
- 5 Baths
- 4,171 Sq Ft
179 Compo Rd S, Westport, CT 06880

Welcome to 179 Compo Road South, in the heart of Westport-super close to Longshore, Compo Beach, downtown, the train station-everything Westport has to offer. This Tudor-style gem, originally built in the 1920s, has been thoroughly renovated to honor its heritage while offering every contemporary comfort. Situated high on the hillside, sweeping property views enchant. The classic slate roof is

Judy Michaelis Coldwell Banker Realty

179 Compo Rd S, Westport, CT 06880
/40
$6,795,000
- 5 Beds
- 8 Baths
- 6,959 Sq Ft
10 Cross Rd, Darien, CT 06820

If prime location and exceptional craftsmanship are what you've been looking for, look no further than 10 Cross Road. Designed and built in 2006 by Louise Brooks & Artisan Builders, this exquisite custom built home is situated on an artistically landscaped knoll in the private Tokeneke Association. Extensive woodwork & moldings, 10 foot & cathedral ceilings, and recent exterior improvements,

Kathryn DeSalvo Compass Connecticut, LLC

10 Cross Rd, Darien, CT 06820
/30
$4,300,000 Open Sat 1PM - 4PM
- 5 Beds
- 5.5 Baths
- 5,400 Sq Ft
57 Lockwood Ave, Old Greenwich, CT 06870

This beautifully scaled five-bedroom Colonial offers refined living in one of Old Greenwich's most coveted neighborhoods, just moments from the beach, park, train, schools and dining. Set on a meticulously landscaped 1/2 acre, the 5400-square-foot sun-drenched five bedroom boasts a stone terrace, French doors, wraparound porch, butler's pantry, grand chef's kitchen with island open to the family

Noah Finz Houlihan Lawrence

57 Lockwood Ave, Old Greenwich, CT 06870
/40
$3,395,000 Open Sat 1PM - 3PM
- 5 Beds
- 6 Baths
- 7,307 Sq Ft
152 Long Lots Rd, New Canaan, CT 06840

Welcome to 152 Long Lots ~ Perfectly sited on two flat acres in the highly sought after Hoyt Farm neighborhood. This home is a rare blend of timeless design and thoughtful scale. The interior is filled with natural light and symmetry which guides you through elegant, functional spaces designed for both everyday living and entertaining. The gourmet kitchen is the heart of the home featuring a wall

William Hecker Jr Houlihan Lawrence

152 Long Lots Rd, New Canaan, CT 06840
/19
$3,995,000
- 6 Beds
- 4.5 Baths
- 3,515 Sq Ft
22 Tomac Ave, Old Greenwich, CT 06870

Terrific Old Greenwich location with easy access to south of the village with sidewalks to town, school and train. This gracious Shore Colonial is on an over-sized o.46 acre level lot (FAR in the R-12 zone could allow 6,300+ sf home), is warm and welcoming with 5 bedrooms and 3 full baths PLUS an additional studio on the main level that could be used in so many ways, as a main floor bedroom,

Jackie Hammock Coldwell Banker Realty

22 Tomac Ave, Old Greenwich, CT 06870
/49
$5,200,000
- 6 Beds
- 9 Baths
- 7,738 Sq Ft
897 Lake Ave, Greenwich, CT 06831

Peaceful, serene and private best describes this property located on a lane off Lake Avenue adjacent conservation. Meticulously renovated with both functionality and playfulness in mind. The stunning entry foyer has soaring windows inviting in an abundance of natural light. A Bilotta designed kitchen, has custom cabinetry and high-end appliances and finishes. There is a spacious primary with

Marjorie Marianacci Coldwell Banker Realty

897 Lake Ave, Greenwich, CT 06831
/40
$3,695,000 Open Thu 12PM - 2PM
- 5 Beds
- 7 Baths
- 8,061 Sq Ft
38 Fitch Ln, New Canaan, CT 06840

Nantucket-Shingle coastal-chic style home with exceptional amenities in Hoyt Farm. Nestled on a cul-de-sac within a sought after neighborhood, a custom-designed home embodies a captivating shingle style home. This meticulously updated residence offers an abundance of space and remarkable features for comfortable living and entertaining. Upon entering the double-height foyer, you are greeted by an

Hannelore Kaplan William Raveis Real Estate

38 Fitch Ln, New Canaan, CT 06840
/40
$3,275,000 Open Sun 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 4,274 Sq Ft
259 Rowayton Ave, Norwalk, CT 06853

Discover the allure of 259 Rowayton Avenue-a quintessential Victorian masterpiece that could soon be yours. This enchanting 5-bedroom, 3.5-bathroom home seamlessly marries the elegance of classic architecture with modern sophistication, offering 4,274 square feet of beautifully updated living space. The home's multiple living areas gracefully span three floors, providing abundant space for

Elizabeth Beinfield Compass Connecticut, LLC

259 Rowayton Ave, Norwalk, CT 06853
/40
$3,750,000 Open Sat 12PM - 2PM
- 6 Beds
- 9 Baths
- 7,288 Sq Ft
39 Running Brook Ln, New Canaan, CT 06840

Welcome to 39 Running Brook Lane, an exceptional custom-built home set on 2.7 acres, where timeless elegance meets everyday function. Spanning more than 7,000 square feet across three finished levels, the residence offers both scale and sophistication. Inside, freshly painted interiors highlight soaring ceilings and generously proportioned rooms. The high-end kitchen by Dean is a chef's dream,

Stacey Delikat Houlihan Lawrence

39 Running Brook Ln, New Canaan, CT 06840
/38
$4,350,000 Open Sun 1PM - 3PM
- 7 Beds
- 7.5 Baths
- 6,679 Sq Ft
102 Compo Rd S, Westport, CT 06880

THE ESTATES AT COMPO SOUTH - SIR Development presents the last of two luxury residences set back on beautiful property, each with their own distinct Modern style and pool. Officially designated by the State of CT as a Scenic Roadway, this location offers ultimate convenience to every amenity that makes Westport one of the most highly desired towns in the nation. This elevator-ready home begins

Doug Bross Coldwell Banker Realty

102 Compo Rd S, Westport, CT 06880
/40
$3,499,000
- 5 Beds
- 6 Baths
- 6,388 Sq Ft
1580 Ponus Ridge, New Canaan, CT 06840

California meets New Canaan in this William Wurster inspired transitional-style masterpiece set on 2.54 private acres on New Canaan's desirable west side that's so convenient to town. This extensively renovated home has over 100 custom windows and 16 doors bringing the outside in from every room. Amazing sun-drenched living space with wonderful views from EVERYWHERE. French doors lead to

Kelly Defrancesco William Raveis Real Estate

1580 Ponus Ridge, New Canaan, CT 06840
/40
$2,950,000
- 6 Beds
- 8 Baths
- 6,475 Sq Ft
19A Darbrook Rd, Westport, CT 06880

Tucked away on a private cul-de-sac just minutes from downtown Westport, beaches, and award-winning restaurants, this 6-bedroom, 8-bath residence combines modern architectural design with serene natural surroundings. Set on beautifully landscaped grounds, the property backs onto a gentle brook, creating a peaceful, retreat-like setting. Once home to a celebrated local artist, the interiors

Nanci Lewis Keller Williams Realty

19A Darbrook Rd, Westport, CT 06880
/37
$2,695,000
- 5 Beds
- 4.5 Baths
- 3,400 Sq Ft
46 Sunswyck Rd, Darien, CT 06820

Nestled within the highly sought-after Delafield Island Association, 46 Sunswyck Road is a distinguished brick estate set on 1.3 acres of impeccably landscaped grounds. Manicured lawns, a variety of plants, and mature trees create a serene, park-like setting that enhances the home's timeless architecture. This stately 5-bedroom residence blends classic elegance with modern upgrades. Inside, a

Nellie Snell William Raveis Real Estate

46 Sunswyck Rd, Darien, CT 06820

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