Homes for Sale in Fairfield County CT with 5-Bedrooms

/46
$6,895,000
- 6 Beds
- 8 Baths
- 6,117 Sq Ft
Unlisted Address

Sensational resort-style amenities enhance this architecturally stunning six-bedroom Colonial on 2.29 level acres with pool, pool house, outdoor Kalamazoo kitchen, screened-in porch with heaters, sandbox and garden near schools, shops and trains. Built in 2014, the luxurious interior features wood floors, high coffered ceilings and four fireplaces. Three finished levels reveal chef's kitchen

Spencer Sodokoff

Houlihan Lawrence

(475) 244-6867

Unlisted Address
/40
$2,995,000
- 6 Beds
- 7 Baths
- 9,664 Sq Ft
91 Algonquin Rd, Fairfield, CT 06825

Iconic Georgian Manor. A rare offering of architectural significance, this distinguished 1922 Georgian Colonial is set on 1.88 acres of level, park-like grounds in a desirable Fairfield enclave. Encompassing over 10,000 square feet, this 6-bedroom estate seamlessly blends historic grandeur with elevated, modern living. A stately presence is immediately felt through classic Georgian symmetry,

Danielle Malloy

Serhant Connecticut, LLC

(475) 271-2961

91 Algonquin Rd, Fairfield, CT 06825
/40
$2,595,000 Coming Soon
- 5 Beds
- 5.5 Baths
- 6,100 Sq Ft
32 Steep Hill Rd, Weston, CT 06883

This restored, 6,100sf, expanded 18th century farmhouse commands a view of its 1.24 acre, brook-fed lake, expansive lawn, raised beds and 400 ft. bleached stone driveway. Those features read: Big Tented Celebration, Fabulous Local Tomatoes. The former NYC chef's kitchen is open to the entertaining areas' 5 rooms that circle around the heartbeat that makes a home feel and taste just right. A

Mark Gilrain

Brown Harris Stevens

(475) 348-7574

32 Steep Hill Rd, Weston, CT 06883
/29
$6,000,000 Coming Soon
- 6 Beds
- 8 Baths
- 6,998 Sq Ft
9 Frost Rd, Greenwich, CT 06830

Exquisitely renovated Cotswold-style manor on a private road, blending timeless charm with modern elegance. Set on two serene, landscaped acres overlooking Horseneck Brook, this home offers tranquility and understated sophistication. A gourmet kitchen anchors the home with high-end finishes and seamless flow for everyday living and entertaining. French doors from the living, dining, and kitchen

Linna Yuen

Coldwell Banker Realty

(475) 252-8941

9 Frost Rd, Greenwich, CT 06830
/34
$869,900 Open Sat 12PM - 2PM
- 9 Beds
- 3 Baths
- 2,922 Sq Ft
219 Orland St Unit 221, Bridgeport, CT 06605

Exceptional opportunity to own a well-maintained 3-family home in the highly sought-after Black Rock section of Bridgeport. Situated on a rare double lot, this property offers abundant outdoor space along with ample off-street parking-an uncommon and valuable feature in the area. Roof, siding, windows and all 3 high efficiency Navien boilers were replaced 2 years ago. All apartments were recently

Jorge Cintron

Vylla Home (CT) LLC

(475) 473-8158

219 Orland St Unit 221, Bridgeport, CT 06605
/34
$3,550,000 Open Sat 1PM - 3PM
- 5 Beds
- 4.5 Baths
- 4,602 Sq Ft
10 Winding Ln, Westport, CT 06880

Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an

Susan Lieberman

The Riverside Realty Group

(475) 255-2758

10 Winding Ln, Westport, CT 06880
/16
$629,000
- 5 Beds
- 3 Baths
- 2,684 Sq Ft
264 Clover St, Stratford, CT 06614

Excellent opportunity to own a three-family property in desirable Fairfield County with strong income potential. Each unit features separate utilities, and with current rents well below market value, there is significant upside for increased cash flow. With a little elbow grease, this property offers the chance to add value and maximize its full potential. Ideally located just over a mile from

Marc Seigel & Lauren Seigel-Gross

RE/MAX RISE

(475) 264-6752

264 Clover St, Stratford, CT 06614
/28
$1,425,000
- 14 Beds
- 6 Baths
- 6,578 Sq Ft
1389 Pembroke St, Bridge Port, CT 06608

Well-maintained 6-family investment property offering a strong opportunity for both immediate cash flow and long-term upside. The building features a mix of spacious 2- and 3-bedroom units, all with generous layouts that appeal to quality tenants. Units have been updated/renovated, and the property is currently occupied with good-paying tenants, making this a turnkey addition to any portfolio.

Lisa Nussbaum

Top Tier Realty Group, LLC

(475) 473-9406

1389 Pembroke St, Bridge Port, CT 06608
/26
$450,000
- 5 Beds
- 1.5 Baths
- 2,205 Sq Ft
500 Park St, Bridgeport, CT 06608

Spacious three-story residential property located in Bridgeport's East Side neighborhood offering over 2,200 square feet of living space. Built in 1905, this home features five bedrooms, multiple bathrooms, and approximately ten total rooms, providing ample space for comfortable living. The property sits on a 3,920-square-foot lot and includes a detached two-car garage along with additional

Alexander Galvez

Century 21 Galvez

(475) 255-3953

500 Park St, Bridgeport, CT 06608
/19
$659,000
- 6 Beds
- 3 Baths
- 2,618 Sq Ft
384 Thompson St, Stratford, CT 06615

Excellent opportunity to own a three-family property in desirable Fairfield County with strong income potential. Each unit features separate utilities, and with current rents well below market value, there is significant upside for increased cash flow. With a little elbow grease, this property offers the chance to add value and maximize its full potential. Ideally located just over a mile from

Marc Seigel & Lauren Seigel-Gross

RE/MAX RISE

(475) 255-3866

384 Thompson St, Stratford, CT 06615
/31
$8,880,000
- 6 Beds
- 8 Baths
- 7,718 Sq Ft
15 Vineyard Ln, Greenwich, CT 06831

Location, location, location! This stunning stone colonial sits on 2 park like acres just minutes from downtown Greenwich. With over 9,000 sq ft of beautiful living space, this 6-bedroom, 6.5-bath home offers graciously scaled rooms and an exceptional floor plan. The luxurious primary suite features a fireplace, dual bathrooms, and walk-in closets. Enjoy the spacious playroom over the garage, a

Megan Sullivan

Douglas Elliman of Connecticut

(475) 265-6175

15 Vineyard Ln, Greenwich, CT 06831
/6
$5,500,000
- 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

(203) 349-8841

67 Carter St, New Canaan, CT 06840
/40
$8,600,000
- 7 Beds
- 6.5 Baths
- 9,420 Sq Ft
63 Turney Rd, Redding, CT 06896

Another Day in Paradise! Timeless grandeur, architectural mastery, and opportunity define this exceptional plantation-style colonial set on 39.23 acres bordered by 100+ acres of protected forestland-a rare opportunity for stately country living in a singular setting.For the sportsman, pristine woodlands and abundant wildlife offer boundless opportunities for hunting, hiking, and connecting with

Roni Agress

William Pitt Sotheby's Int'l

(203) 717-5061

63 Turney Rd, Redding, CT 06896
/2
$4,200,000
- 6 Beds
- 7.5 Baths
- 7,450 Sq Ft
760 Valley Rd, New Canaan, CT 06840

A Historic Masterpiece, Reimagined for Modern Living Originally crafted in 1931 by renowned architect Frazier Forman Peters, this iconic stone residence has been completely reinvented-expanded, redesigned, and redefined for today's luxury lifestyle. The newly completed home now offers over 9,000 square feet of exquisite living space with 6 bedrooms, 7.5 baths, and every modern comfort imaginable,

Richard Breglia

Coldwell Banker Realty

(203) 721-7670

760 Valley Rd, New Canaan, CT 06840
/40
$6,595,000
- 6 Beds
- 9 Baths
- 16,126 Sq Ft
62 Summersweet Ln, New Canaan, CT 06840

Welcome to a truly exceptional New Canaan architectural masterpiece built in 2004, nestled on a majestic private lane occupied by only 6 estates, enveloped by serene forests and 48 acres of reservoir conservancy. This picturesque estate offers a tranquil escape and sense of openness with intricate millwork and wainscoting adorning every corner, 9 to 12-foot ceilings on every level and

Danielle Malloy

Serhant Connecticut, LLC

(475) 241-0980

62 Summersweet Ln, New Canaan, CT 06840
/24
$499,900
- 5 Beds
- 3.5 Baths
- 1,740 Sq Ft
242 Pearl Harbor St, Bridgeport, CT 06610

Charming side- by- side brick ranch duplex, nestled on a quiet cul-de-sac. Hardwood floors throughout and a newer roof are among many updates. One unit offers 3 bedrooms, 1.5 baths. Second unit 2beds, 1 bath. Both units are very well kept and turn key. Enjoy the durability and low maintenance of brick exterior. Both units have a nice private, fenced in yard. It offers a fantastic opportunity for

Jorge Cintron

Vylla Home (CT) LLC

(475) 473-8165

242 Pearl Harbor St, Bridgeport, CT 06610
/40
$12,000,000
- 7 Beds
- 6.5 Baths
- 8,119 Sq Ft
260 Willow St, Southport, CT 06890

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

Libby Tritschler

William Raveis Real Estate

(203) 350-0943

260 Willow St, Southport, CT 06890
/40
$4,495,000 New Construction
- 6 Beds
- 9 Baths
- 9,700 Sq Ft
21 Warnock Dr, Westport, CT 06880

This striking architectural design meets refined luxury in a meticulously crafted 9,700+/- 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 sophistication w/ premium finishes,

Brett Lieberman

The Riverside Realty Group

(203) 717-5836

21 Warnock Dr, Westport, CT 06880
/38
$6,195,000 New Construction
- 5 Beds
- 4.5 Baths
- 4,550 Sq Ft
22 Apple Tree Trail, Westport, CT 06880

Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak

Deborah Aulfinger Gold & Home Realty

22 Apple Tree Trail, Westport, CT 06880
/39
$1,675,000
- 5 Beds
- 6.5 Baths
- 6,034 Sq Ft
40 Wildwood Rd, Stamford, CT 06903

Step into timeless elegance with this 6,034 sq. ft. Colonial masterpiece, featuring a legally finished 2638 square foot walk-out basement over lower level. 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 marble foyer sets the stage for stunning architectural details

Ken Wile Redfin Corporation

40 Wildwood Rd, Stamford, CT 06903
/40
$2,438,000
- 5 Beds
- 5 Baths
- 6,199 Sq Ft
16 Robin Hood Ln, Easton, CT 06612

This stately Colonial tucked away at the end of a cul de sac in Easton, blends classic architecture with resort style living. From the moment you arrive, the brick facade and grand scale set the tone. Stepping inside, the impressive two story foyer with gleaming marble floors and Palladian windows creates a true magazine worthy first impression. Crown molding flows throughout the home along with

Bogdan Stefanide KW Legacy Partners

16 Robin Hood Ln, Easton, CT 06612
/40
$5,495,000
- 5 Beds
- 8 Baths
- 8,502 Sq Ft
7 Buttonwood Ln, Darien, CT 06820

Spectacular quintessential New England home in Darien has it all! Step into a world of refined elegance with this stately 8,000+SF Colonial masterpiece. Set back on nearly two acres of manicured grounds, boasting a custom 2021 Gunite pool, outdoor kitchen, new patio, huge backyard and firepit, this treasured residence is the ultimate venue for indoor & outdoor living and entertaining. The main

Gaynor Brennan BHHS Darien/New Canaan

7 Buttonwood Ln, Darien, CT 06820
/40
$4,650,000
- 5 Beds
- 7 Baths
- 8,550 Sq Ft
49 Hillspoint Rd, Westport, CT 06880

Tucked away in the heart of Westport, Hillspoint offers the perfect blend of luxury, lifestyle and location. Minutes to Longshore Club Park, Compo Beach, town and train, it delivers rare privacy with exceptional convenience. Inside, soaring ceilings and sun-filled spaces create a light, airy flow enhanced by high-end finishes throughout. Designed for everyday living and effortless entertaining,

Michelle Genovesi William Raveis Real Estate

49 Hillspoint Rd, Westport, CT 06880
/40
$1,299,000
- 5 Beds
- 3.5 Baths
- 5,512 Sq Ft
41 Ridge Line Rd, Easton, CT 06612

Tucked away at the end of a quiet cul de sac colonial gorgeous home. It's Blend modern luxury with thoughtful design and quality throughout . Be wowed by the timeless curb appeal as you approach this elegant 5 Bedroom home. Step into the welcoming foyer and be struck by tons of natural light. The adjacent office and recreation room offers a multifunctional space that can be used for both work and

Eli Carneiro William Raveis Real Estate

41 Ridge Line Rd, Easton, CT 06612
/40
$1,699,900
- 6 Beds
- 5 Baths
- 4,033 Sq Ft
12 Werf Dr, Redding, CT 06896

Welcome to this expansive and beautifully updated six-bedroom Colonial, offering three full and two half baths and thoughtfully positioned on a sprawling 2.42-acre lot that provides both privacy and presence. A grand wraparound driveway creates a striking approach to the home, offering ample parking in addition to a two-car attached garage ideal for guests, entertaining, and everyday convenience.

Jonathan Gineo Silver and Oak Realty

12 Werf Dr, Redding, CT 06896
/40
$2,899,900
- 6 Beds
- 7 Baths
- 9,454 Sq Ft
25 Hermit Ln, Westport, CT 06880

NEW PRICE!! Discover the epitome of luxury in this beautifully furnished Colonial estate located in Westport's prestigious Red Coat neighborhood. Offering over 7,000 square feet of elegant living space plus an additional 2,400 square feet in the finished lower level, this 6-bedroom, 5.2-bath home is designed for both everyday comfort and grand entertaining. The gourmet kitchen is outfitted with

Jolanta Rojek eXp Realty

25 Hermit Ln, Westport, CT 06880
/8
$900,000
- 8 Beds
- 3 Baths
- 2,520 Sq Ft
51 Lincoln Ave, Stamford, CT 06902

Great opportunity in the heart of Stamford! This spacious multi-family property at 51 Lincoln Ave features two 3-bedroom, 1-bath units, plus a finished basement with 2 bedrooms and 1 bath-offering flexibility for a variety of uses. The large driveway provides ample parking, and the prime location near Downtown, shopping, and dining adds to its appeal. Perfect for investors seeking strong cash

Abdul Kader Guy Bocicaut Real Estate

51 Lincoln Ave, Stamford, CT 06902
/22
$499,000
- 6 Beds
- 2 Baths
- 3,108 Sq Ft
185 Grandview Ave, Bridgeport, CT 06606

Welcome home to this spacious and beautifully maintained single-family colonial located in the North End of Bridgeport. This home features six bedrooms and two full bathrooms with an updated Kitchen newer stainless steal appliance's and tons of storage. With its expansive layout, this property offers endless possibilities to make it your own. You'll find a detached two-car garage providing

Carolyn Colon-Ortega Century 21 Scala Group

185 Grandview Ave, Bridgeport, CT 06606
/26
$5,800,000
- 5 Beds
- 3.5 Baths
- 4,324 Sq Ft
8 Indian Point Ln, Riverside, CT 06878

Tucked within the secluded Indian Point Association, this 1.55-acre waterfront sanctuary in coveted Riverside invites you to imagine the lifestyle that you have always wanted. From its sweeping southwestern vantage point, the property opens to mesmerizing views of Long Island Sound-a living canvas that shifts with every season, every tide, every change of light. A charming 1949 built house sits

Patte Nusbaum Sotheby's International Realty

8 Indian Point Ln, Riverside, CT 06878
/31
$699,000
- 9 Beds
- 3 Baths
- 3,236 Sq Ft
43 Elmwood Ave Unit 45, Bridgeport, CT 06605

Solid three-family home featuring three bedrooms in each unit. This well-maintained property has been owned and cared for by the same owner for over 25 years. Recent upgrades within the last five years include a new asphalt shingle roof, updated exterior siding, and upgraded mechanicals, including gas furnaces and hot water heaters. All three units have been freshly painted, with updated kitchens

Jennifer Capozziello Coldwell Banker Realty

43 Elmwood Ave Unit 45, Bridgeport, CT 06605
/27
$2,100,000
- 5 Beds
- 4 Baths
- 2,612 Sq Ft
29 Coventry Ln, Riverside, CT 06878

Located in one of Riverside's most desirable neighborhoods, this home offers both privacy and convenience. Sun-filled and with hardwood floors throughout, the house provides space and flow, featuring a living room with fireplace, dining room, and updated kitchen with granite countertops and stainless steel appliances. The primary bedroom with en-suite bathroom and multiple closets, along with

Teresa Silvani BHHS New England Properties

29 Coventry Ln, Riverside, CT 06878
/33
$959,000
- 7 Beds
- 2 Baths
- 3,797 Sq Ft
35 Ramapoo Rd, Ridgefield, CT 06877

Flexible home in the heart of Ridgefield featuring a separate living space for an in-law unit or potential extra income. Just steps from downtown Ridgefield amenities and schools, this well-maintained home offers a front unit and rear unit with separate entrance, full kitchens, baths, and laundry. The rooms are large, easily updated and great for family gatherings. Front unit includes: 3BRs

Tim Dent Coldwell Banker Realty

35 Ramapoo Rd, Ridgefield, CT 06877
/18
$2,295,000 Open Sat 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 3,023 Sq Ft
35 Deep Gorge Rd, Greenwich, CT 06831

Close to delightful downtown Greenwich, this jewel, located on a cul-de-sac, has had a gut renovation and restoration that brings today's conveniences and expected finishes into yesteryear's gracious character. Unerring attention to detail shows in every room. Bathed in Natural light, the gourmet kitchen flows easily to the large living room with a fireplace and the rear blue stone patio. When

Barbara Zaccagnini Coldwell Banker Realty

35 Deep Gorge Rd, Greenwich, CT 06831
/34
$5,500,000
- 7 Beds
- 8 Baths
- 8,194 Sq Ft
757 Oenoke Ridge, New Canaan, CT 06840

The "Legacy Estate" An Oenoke Ridge Masterpiece: The main brick residence captures the essence of Gilded Age elegance with 10-12 ft ceilings, eight fireplaces, a classic wrap-around-porch, and a porte-cochere. Spanning four finished levels, the main residence seamlessly blends original character with a significant three-story addition completed in 2012. The newer wing features a spacious

Hannelore Kaplan William Raveis Real Estate

757 Oenoke Ridge, New Canaan, CT 06840
/37
$1,099,000 Open Sat 11AM - 2PM
- 5 Beds
- 3 Baths
- 3,109 Sq Ft
87 Fulling Mill Ln, Ridgefield, CT 06877

Your Next Chapter Starts Here. Stop scrolling - this is the one. This stunning 5-bed, 3-bath colonial delivers the space, style, and flexibility today's lifestyle demands, all wrapped in a character-filled home that actually has room to grow. Work from home? There's a dedicated office *and* flex space for it. Love to entertain? The open-flow chef's kitchen (granite counters, newer stainless

Karen Sheftell William Pitt Sotheby's Int'l

87 Fulling Mill Ln, Ridgefield, CT 06877
/26
$580,000
- 6 Beds
- 2 Baths
- 2,924 Sq Ft
57 Milne St Unit 59, Bridgeport, CT 06604

Two-family property with extensive renovations completed, offering excellent income potential or a solid owner-occupant opportunity. Recent improvements include new hardwood flooring, new roof, new windows, new doors, and fresh interior paint, creating a move-in-ready feel while still allowing room for future value-add. First-floor unit features 3 bedrooms, a newer eat-in kitchen with new

Stephanie Ferreira BHGRE Gaetano Marra Homes

57 Milne St Unit 59, Bridgeport, CT 06604
/40
$2,950,000 Open Sat 2PM - 4PM
- 5 Beds
- 4.5 Baths
- 4,865 Sq Ft
89 Raymond St, Darien, CT 06820

Few homes in Darien offer this combination: five bedrooms, five indoor entertainment spaces, a private elevator, gunite pool, hot tub, and pool cabana with wet bar-all on a private .70-acre lot in the Tokeneke School district. Fully updated 2021-2026 and just a walk to Metro-North and downtown. Spanning three fully finished floors, the main floor is built for living and entertaining: a formal

Anika Charron William Raveis Real Estate

89 Raymond St, Darien, CT 06820
/39
$2,225,000 Open Sat 12PM - 3PM
- 5 Beds
- 6 Baths
- 5,143 Sq Ft
151 Skunk Ln, Wilton, CT 06897

Set on 1.1 acres of beautifully landscaped grounds, this charming country home offers a rare balance of history, scale, and everyday livability. With over 5,000 square feet, five bedrooms, and six baths, the property unfolds in a way that feels both expansive and comfortable, shaped over time with care and intention. The home's origins date to the late 1800's. Each addition has been thoughtfully

Laura Kottler Compass Connecticut, LLC

151 Skunk Ln, Wilton, CT 06897
/40
$2,850,000 Open Sat 1PM - 3PM
- 5 Beds
- 5 Baths
- 4,922 Sq Ft
55 Center St, Westport, CT 06880

Located in Westport's coveted Greens Farms neighborhood, this light-filled home is perfectly sited high and dry on a private park-like acre with room for a pool and pool house. A renovated kitchen with top-of-the-line appliances and sunny breakfast nook opens to a spacious great room with stone fireplace and expansive deck overlooking the property, ideal for indoor-outdoor living. The flexible

Mary Ann Lindwall The Riverside Realty Group

55 Center St, Westport, CT 06880
/40
$4,595,000 Open Sat 1PM - 3PM
- 7 Beds
- 10 Baths
- 10,258 Sq Ft
1421 Oenoke Ridge, New Canaan, CT 06840

Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush

Jaime Sneddon William Pitt Sotheby's Int'l

1421 Oenoke Ridge, New Canaan, CT 06840

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