5-Bedroom Homes for Sale in Fairfield County CT

/36
$5,495,000 Open Sun 1PM - 3PM
- 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
$2,750,000
- 5 Beds
- 4 Baths
- 2,452 Sq Ft
32 Beeholm Rd, Redding, CT 06896

A Private Oasis: Discover an unparalleled opportunity at 32 Beeholm Rd, where an 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

Ellen Garcia

Brown Harris Stevens

(475) 291-4216

32 Beeholm Rd, Redding, CT 06896
/40
$1,800,000
- 6 Beds
- 5 Baths
- 3,461 Sq Ft
47 Hollow Tree Ridge Rd, Darien, CT 06820

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 young couples seeking rental income. Historic Charm, Modern Comfort: * Two

Karen Finn

Gatehouse Realty Inc

(475) 325-5924

47 Hollow Tree Ridge Rd, Darien, CT 06820
/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
/39
$1,400,000
- 5 Beds
- 4.5 Baths
- 3,594 Sq Ft
325 Rowayton Ave, Norwalk, CT 06853

A magical property reminiscent of Giverny, France or the Lakes of Litchfield County, but way better! Only an hour by train from NYC and a brief walk up the street in Rowayton, CT! Make it your year-round residence or weekend getaway. There is room for everyone. Set back from the road offering total privacy, the view captivates as you look off the deck, relax by the pool, create in the Boat House

Tammy Langalis

William Raveis Real Estate

(203) 903-9989

325 Rowayton Ave, Norwalk, CT 06853
/28
$6,995,000
- 6 Beds
- 6 Baths
- 5,190 Sq Ft
2 Bluewater Hill S, Westport, CT 06880

Discover unparalleled living at 2 Bluewater Hill South, a magnificent 5000+ SF estate on one of Westport's most prestigious street just steps from Compo Beach. This exceptional home combines sophisticated coastal elegance with resort-style amenities, offering 6 bedrooms, 6 baths, and breathtaking LI Sound views. The coveted Bluewater Hill location provides exclusive private beach access while

Susan Lieberman

The Riverside Realty Group

(203) 350-0478

2 Bluewater Hill S, Westport, CT 06880
/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
/26
$410,000
- 5 Beds
- 2.5 Baths
- 2,420 Sq Ft
1402 Boston Ave, Bridgeport, CT 06610

Nestled in the Mill Hill neighborhood of Bridgeport, 1402 Boston Avenue is a charming two-family home offering both residential comfort and investment potential. Built in 1907, this property seamlessly blends historic character with modern amenities. The main unit spans 1,712 square feet and features a spacious 4-bedroom layout, while the front unit is a cozy studio apartment, ideal for guests or

Alan Stewart Jr.

ASJ Realty Partners

(203) 875-0407

1402 Boston Ave, Bridgeport, CT 06610
/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
$569,900 Open Sun 1PM - 3PM
- 5 Beds
- 3 Baths
- 3,148 Sq Ft
170 Red Oak Rd, Bridgeport, CT 06606

Welcome to 170 Red Oak Road - where space and charm meet comfort in Bridgeport's sought-after North End! This sun-filled 5-bedroom Colonial offers 2,300+ sq ft of living space with an additional 800 sq ft of finished space in the basement. Featuring a modern kitchen, 3 fully renovated bathrooms, a Brand new HVAC System with two new condensers, and a master suite on the 3rd floor with tons of

Anthony D'Amore

Keller Williams Prestige Prop.

(203) 463-5070

170 Red Oak Rd, Bridgeport, CT 06606
/27
$6,250,000
- 6 Beds
- 8 Baths
- 7,447 Sq Ft
79 Richmond Hill Rd, Greenwich, CT 06831

Completely renovated exquisitely designed Colonial-style home, nestled on 4 park-like acres. Custom millwork, built-ins, designer lighting, and European fixtures. Light-filled family dining area featuring a 20-foot curved sliding glass wall that opens to the patio and pool. The Primary Suite boasts private balcony, large dressing room, and luxurious bath complete with radiant heated floors,

Kevin Stone

Sotheby's International Realty

(475) 255-6696

79 Richmond Hill Rd, Greenwich, CT 06831
/29
$9,950,000
- 6 Beds
- 8 Baths
- 8,896 Sq Ft
35 Club Rd, Riverside, CT 06878

Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acres with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors,

Andrew Smith

Houlihan Lawrence

(475) 265-6383

35 Club Rd, Riverside, CT 06878
/2
$4,895,000 New Construction
- 6 Beds
- 9 Baths
- 9,224 Sq Ft
21 Warnock Dr, Westport, CT 06880

Expected for completion end of summer 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
/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
$2,150,000
- 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
/39
$2,650,000 Open Sun 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 6,400 Sq Ft
433 Belden Hill Rd, Wilton, CT 06897

NEW PRICE DECREASE! 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

Alison Mark Berkshire Hathaway NE Prop.

433 Belden Hill Rd, Wilton, CT 06897
/25
$899,000
- 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
/40
$3,750,000
- 6 Beds
- 7.5 Baths
- 14,110 Sq Ft
21 Queens Grant Dr, Fairfield, CT 06824

Welcome to one of Greenfield Hill's most distinguished residences-an extraordinary 9,700+ sq. ft. Colonial estate nestled on 2 pristine acres in one of Fairfield's most prestigious enclaves. This 5-6 bedroom architectural masterpiece combines timeless elegance with modern luxury, offering an unparalleled lifestyle just moments from town. From first look, the home's unrivaled curb appeal

Michael Debiase Keller Williams Realty

21 Queens Grant Dr, Fairfield, CT 06824
/40
$2,395,000
- 6 Beds
- 6.5 Baths
- 6,219 Sq Ft
284 Ingleside Dr, Stamford, CT 06903

PRICE REDUCTION ($385/SQFT) Stunning 2022 Custom New Construction home w/sparkling waterfront views. Set back far from the road, sited on 2.20 level acres in a serene new subdivision w/a pond, this fabulous modern farmhouse features 6 bedrooms, 6.5 baths, 3 car garage & custom elevator accessing 3 levels of finished living space. Boasting 6,219 sq ft (2,239sf unfinished space in the lower-level

Gaynor Brennan BHHS Darien/New Canaan

284 Ingleside Dr, Stamford, CT 06903
/35
$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
/40
$6,980,000 New Construction
- 5 Beds
- 4.5 Baths
- 4,791 Sq Ft
22 Apple Tree Trail, Westport, CT 06880

PRICE ADJUSTED! Compo Beach living, 2 short blocks from beach on private road! Luxury construction, just completed. 5 bed, 4.5 bath modern home w/ all of the lush amenities seen in the finest resorts both inside & out. Custom Italian cabinetry by L'Ottocento in kitchen, butler's pantry, bathrooms, and mudroom. 9ft.+ ceilings, open stairs w/ glass railings & oak floors. Entry hall w/ crystal

Deborah Aulfinger Goldan Home Realty, LLC.

22 Apple Tree Trail, Westport, CT 06880
/21
$6,600,077
- 6 Beds
- 7.5 Baths
- 7,580 Sq Ft
14 5 Mile River Rd, Darien, CT 06820

World class one of a kind newly constructed modern masterpiece designed by award winning architect Vita Design with stunning unobstructed water views from every room in the house. This custom coastal build sets luxury to the highest level. The home features tall ceilings with an abundance of open space filled with natural light coming in through the floor to ceiling oversized European style

Jennifer DaSilva Mixer William Raveis Real Estate

14 5 Mile River Rd, Darien, CT 06820
/40
$3,995,000
- 8 Beds
- 9 Baths
- 12,853 Sq Ft
27 Country Club Rd, Ridgefield, CT 06877

"HOMEWOOD" - This remarkable country compound is one of the precious few 18th/19th century shingle style colonial revival estates remaining in Fairfield Cty. Dating back to 1750, the original pre-revolutionary war home captivated the attention of prominent NYC banker, George Haven, who purchased the home in 1890 & expanded it significantly including a glorious 50' ballroom designed by Elsie de

Laura Ancona William Pitt Sotheby's Int'l

27 Country Club Rd, Ridgefield, CT 06877
/37
$3,495,000
- 6 Beds
- 5.5 Baths
- 8,000 Sq Ft
52 Garibaldi Ln, New Canaan, CT 06840

Just completed stunning new construction in the heart of New Canaan. Local designer creates 1 project per year, every detail is curated with quality materials & high end finishes. This is not the typical spec house. Designed for a modern lifestyle with a warm classic touch. The show-stopping kitchen includes an oversized seating island, built-in breakfast nook, top-of-the-line stainless

Hannelore Kaplan William Raveis Real Estate

52 Garibaldi Ln, New Canaan, CT 06840
/39
$6,200,000
- 6 Beds
- 6 Baths
- 5,577 Sq Ft
21 Ridge St, Greenwich, CT 06830

Situated on a quiet St. in the heart of Greenwich, this cedar/stone house is beautifully designed with the style and comfort to meet the needs in today's living. Taken down to the studs, expanded, and professionally designed by the owners. A welcoming front porch opens to the two-story, dramatically lit entry hall w/ repetitive archways passing by a gracious LR, into the light, bright

Dorothy Salisbury Coldwell Banker Realty

21 Ridge St, Greenwich, CT 06830
/30
$6,550,000
- 7 Beds
- 9 Baths
- 10,723 Sq Ft
28 Thunder Mountain Rd, Greenwich, CT 06831

Elegance and luxury define this light-filled modern stone and clapboard home on 2 stunning acres near town and top schools. Designed by Rich Granoff, this 7-bedroom, 7.2-bath residence offers exceptional indoor/outdoor living with pool, spa, covered terrace with fireplace + firepit—all on a quiet cul-de-sac. Built in 2005 and recently redesigned, the open floor plan and soaring ceilings create a

B.K. Bates Houlihan Lawrence

28 Thunder Mountain Rd, Greenwich, CT 06831
/40
$2,995,000
- 6 Beds
- 6.5 Baths
- 6,500 Sq Ft
28 Pin Oak Ct, Westport, CT 06880

Stunning brand new construction just minutes from downtown!! - Fantastic 6 bedroom, 6.1 bath colonial boasts 6,500+ sq/ft of living space! - Open floor plan with 9' ceilings and tons of natural light! - Gorgeous kitchen features Thermador appliances, white shaker-style cabinetry, quartz counters, tile backsplash, custom step-in wine locker, and large walk-in pantry! - Great flow for entertaining

Todd Turcotte Milligan Realty.com

28 Pin Oak Ct, Westport, CT 06880
/39
$3,195,000
- 5 Beds
- 3.5 Baths
- 4,100 Sq Ft
36 Hendrie Ave, Riverside, CT 06878

Totally updated and renovated, this charming 1920's Shore Colonial mixes timeless turn of the century charm with today's contemporary design and technology. A great neighborhood near schools, playground and shopping has easy access to I95 and Metro North. The welcoming front porch introduces a spacious main level with living room with new gas fireplace/ shiplap and hearth and opens into the newly

Megan Epand Houlihan Lawrence

36 Hendrie Ave, Riverside, CT 06878
/40
$3,095,000
- 6 Beds
- 6 Baths
- 4,848 Sq Ft
9 Point o Woods Rd S, Darien, CT 06820

Charming Cape with Guest Cottage & Pool in Coveted Ox Ridge District Tucked away on a peaceful cul-de-sac in the highly sought-after Ox Ridge School district, this enchanting 4-bedroom Cape style home offers timeless charm, exceptional privacy, and flexible living options. A breezeway connects the main residence to a delightful 2-bedroom cottage-perfect for guests, in-laws, or a private home

Margot Klingman Houlihan Lawrence

9 Point o Woods Rd S, Darien, CT 06820
/40
$5,995,000
- 5 Beds
- 8 Baths
- 7,505 Sq Ft
354 South Ave, New Canaan, CT 06840

Experience extraordinary living in this sophisticated, estate-style majestic brick townhouse with slate roof - a truly unique custom-built home showcasing timeless elegance & impeccable architectural detail across 4 expansive levels. A gracious gated entrance opens to a charming cobblestone courtyard, setting the stage for an unmatched living experience. Inside, you'll find beautifully appointed

Jaime Sneddon William Pitt Sotheby's Int'l

354 South Ave, New Canaan, CT 06840
/40
$4,899,000
- 6 Beds
- 8 Baths
- 7,663 Sq Ft
129 Long Lots Rd, Westport, CT 06880

One of the most impressive and distinctive offerings to become available in Westport, the historic "John Hyde V House" combines the magnificently restored original home with more recent additions and new updates. Accessed off Peabody Lane and set on nearly 2.5 tranquil acres of spectacular, landscaped property with a new swimming pool & waterfall spa, tennis court, enclosed garden, dining

Alex Chingas Coldwell Banker Realty

129 Long Lots Rd, Westport, CT 06880
/28
$3,495,000
- 6 Beds
- 8 Baths
- 5,613 Sq Ft
4 Mountain Laurel Dr, Greenwich, CT 06831

Stately Georgian brick on a private cul-de-sac w/2 landscaped acres, stunning pool & spa. Approach via wrought iron gates to a circular driveway. Elegant, beautifully decorated home boasts 5,613 SF (add. 1000+/- sf in finished part of garden level), high ceilings, hardwood & stone floors & 5 fireplaces. Spacious entry foyer leads to gourmet kitchen w/Sub Zero, Viking & Bosch appliances, adj.

Barbara Wells Houlihan Lawrence

4 Mountain Laurel Dr, Greenwich, CT 06831
/35
$3,795,000
- 5 Beds
- 5 Baths
- 5,662 Sq Ft
27 Cognewaugh Rd, Cos Cob, CT 06807

Beautiful light filled Shingle Style Home set high above the Mianus River Valley in Greenwich; views of open sky, tree tops + the River. Five bedrooms; primary suite with sitting room, luxury bath. Screened in porch with hanging bed, three double bedrooms and one single with Jack + Jill baths. Open floor plan with eat-in gourmet kitchen open to dining room, family room with French doors to deck

Rebecca Karson Houlihan Lawrence

27 Cognewaugh Rd, Cos Cob, CT 06807
/35
$3,275,000
- 5 Beds
- 3 Baths
- 3,670 Sq Ft
14 Highview Ave, Old Greenwich, CT 06870

RARE OPPORTUNITY AND ENDLESS POSSIBILITIES ON OVERSIZED LOT IN THE HEART OF OLD GREENWICH! Charming, lived in and loved, this 1918 Colonial sits on one of OG's most desirable streets in The Village. The 3,670sf home blends timeless architecture with a welcoming layout and high ceilings. Additional FAR available for expansion. A wide wraparound front porch opens to well-proportioned entry hall,

Christine McKelvey Corcoran Centric Realty LLC

14 Highview Ave, Old Greenwich, CT 06870
/40
$2,950,000
- 6 Beds
- 6 Baths
- 6,280 Sq Ft
882 Silvermine Rd, New Canaan, CT 06840

A rare opportunity to own a truly turn-key, updated Colonial in one of the most charming & coveted neighborhoods in New Canaan. This 6br, 4.2ba home offers over 6,280sf of updated living space, blending timeless architecture with modern amenities for today's lifestyle. From the moment you arrive, you'll be captivated by the home's serene setting, fully fenced front & back yards, & its inviting

Molly Fewster Houlihan Lawrence

882 Silvermine Rd, New Canaan, CT 06840
/40
$3,300,000 Open Sun 1PM - 4PM
- 5 Beds
- 8 Baths
- 6,414 Sq Ft
750 Burr St, Fairfield, CT 06824

Lions Gate: No need to move to the south of France as this extraordinary residence is right here in coveted Fairfield. Enter through grand gates into a world of privacy where character, convenience, security & serenity magically meet. Magazine-worthy grounds are the soul of the estate-lush, expansive, & exquisitely curated. With a shimmering pool, spectacular California Redwood Pool House with

Julie Vanderblue Higgins Group Real Estate

750 Burr St, Fairfield, CT 06824

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