5-Bedroom Homes for Sale in Fairfield County CT with Private Pool

/39
$915,000
- 5 Beds
- 3.5 Baths
- 2,883 Sq Ft
81 Plymouth Ave, Trumbull, CT 06611

Welcome to a true hidden gem in Trumbull, CT! This expansive custom-built Ranch offers more than 3200 sq.ft. of single-level living, including 5 bedrooms and 3.5 bathrooms. At the heart of the home, the kitchen is both stylish and functional, with quartz countertops, stainless steel appliances, and a breakfast area that invites casual dining. The kitchen opens to an inviting family room, where

Danielle McCain BHGRE Gaetano Marra Homes

81 Plymouth Ave, Trumbull, CT 06611
/40
$1,800,000
- 6 Beds
- 7 Baths
- 7,071 Sq Ft
132 Merrimac Dr, Trumbull, CT 06611

Welcome to this one-of-a-kind property in Trumbull, offering over 7,000 sf of living space across two separate ranch-style units-perfect for multi-generational living, extended family, or flexible use. With a total of 17 rooms, 6 bedrooms, 5 full & 2 half baths, these two residences blend spaciousness, comfort, and luxury in a breathtaking setting. Upper level has a private entrance. Each unit

Carl Surrusco William Raveis Real Estate

132 Merrimac Dr, Trumbull, CT 06611
/40
$1,175,000
- 6 Beds
- 6 Baths
- 6,764 Sq Ft
21 Fuller Rd, Trumbull, CT 06611

Steeped in history and lovingly preserved, the Elijah Mallett House dates back to 1798 and stands today as a cornerstone of Trumbull's past. Once a simple colonial homestead, it has grown through generations into a nearly 6,000 sq. ft. family estate-carefully expanded while honoring its origins. Inside, the home carries the spirit of New England craftsmanship: wide-plank floors worn smooth with

Matthew Nuzie RE/MAX Right Choice

21 Fuller Rd, Trumbull, CT 06611
/39
$11,750,000
- 7 Beds
- 10 Baths
- 9,992 Sq Ft
10 Copper Beech Rd, Greenwich, CT 06830

Nestled privately, and surrounded by matured trees, on 1.82 bucolic mid-country acres, sits this seven bedroom, seven full and three half bath, gorgeous estate! Extraordinary stone & shingle construction, built by Aberdeen Properties, and gardens magnificently designed by Rutherford & Associates. Dramatic front to back, double height entry, exquisite millwork throughout, 10' ceilings, and a

Roberta Jurik Berkshire Hathaway NE Prop.

10 Copper Beech Rd, Greenwich, CT 06830
/35
$1,325,000
- 6 Beds
- 5.5 Baths
- 4,778 Sq Ft
60 Redmont Rd, Stamford, CT 06903

Live your best life at 60 Redmont Road, situated on the North side of Stamford, offering over an acre of land with complete privacy. This six-bedroom home features five full baths and an additional half bath. The inground heated pool, located just outside the kitchen area, creates an ideal spot for barbecues and an outdoor kitchen, offering endless summer fun and serving as a perfect retreat.

Ashley Hamedi Compass Connecticut, LLC

60 Redmont Rd, Stamford, CT 06903
/40
$2,249,000
- 5 Beds
- 3.5 Baths
- 4,343 Sq Ft
545 Shrub Oak Ln, Fairfield, CT 06824

Welcome to 545 Shrub Oak Lane, an expanded Colonial on 2 private acres in Greenfield Hill. This home sits on a beautifully flat front yard that enhances its curb appeal. Fully renovated in 2012, the family room and oversized kitchen is the heart of the home. The custom designed kitchen has an 10 foot mahogany island with granite countertops, walk-in panty, and mahogany wood framed glass doors

Christine Howard William Raveis Real Estate

545 Shrub Oak Ln, Fairfield, CT 06824
/40
$799,000
- 5 Beds
- 3.5 Baths
- 3,714 Sq Ft
11 Emerald Ridge Ct, Shelton, CT 06484

Located on a quiet cul de sac, this 4 bedroom 2.5 bath colonial with a large in-law awaits its new owner. This home was custom built with hardwood floors throughout the first floor. Formal living room opens to family room and a large eat in kitchen. The formal dining room with crown molding completes the main floor. 2nd floor offers a primary suite with extra closets, 3 bedrooms, walk up attic

Lisa Valenti Century 21 AllPoints Realty

11 Emerald Ridge Ct, Shelton, CT 06484
/29
$450,000
- 5 Beds
- 1.5 Baths
- 2,507 Sq Ft
47 Lenox Ave, Bridgeport, CT 06605

Welcome to 47 Lenox Avenue, a generously sized Colonial full of charm and character. This home offers 5 bedrooms, with the flexibility to use the 5th as a private office or den. The first floor features a living room with a classic fireplace, a kitchen, a half bath, and a dining room currently being used as a bedroom-but easily converted back for traditional dining. Upstairs, you'll find four

Lucy Billini-Artis BHGRE Gaetano Marra Homes

47 Lenox Ave, Bridgeport, CT 06605
/40
$3,499,000
- 5 Beds
- 7 Baths
- 8,110 Sq Ft
4 Jennings Ct, Westport, CT 06880

Tucked away on a sought-after Westport cul-de-sac, this elegant 5-bedroom home offers the perfect blend of luxury, comfort, and convenience. Set on over an acre of beautifully landscaped property, enjoy resort-style living with a stunning gunite pool, private patio, and lush lawn-ideal for summer entertaining or peaceful relaxation. The spacious first-floor primary suite is a true retreat,

Linda Skolnick Coldwell Banker Realty

4 Jennings Ct, Westport, CT 06880
/40
$2,249,000
- 6 Beds
- 7.5 Baths
- 6,560 Sq Ft
85 Spring Valley Rd, Ridgefield, CT 06877

Tucked away on 6 gorgeous acres of privacy & possibility, 85 Spring Valley Rd isn't just a home - it's an experience. Whether you're hosting a crowd, escaping the city, or saddling up for a morning ride, this 6,560sf retreat was designed to live large, breathe easy & entertain beautifully. Inside, 6 en-suite BRs and 7.5 baths offer plenty of space for family & guests, each with its own private

Tim Dent Coldwell Banker Realty

85 Spring Valley Rd, Ridgefield, CT 06877
/38
$9,500,000
- 8 Beds
- 9 Baths
- 10,328 Sq Ft
31 Sawmill Ln, Greenwich, CT 06830

Extraordinary 3+acre Greenwich mid country estate in a bucolic & private setting, situated within close proximity to downtown Greenwich. Available exclusively as furnished rental as well. This recently renovated & elegantly furnished stone Georgian Colonial blends timeless character with modern aesthetics. This substantial home features gracious & luxurious living spaces, ideal for entertaining

Kevin Sneddon Compass Connecticut, LLC

31 Sawmill Ln, Greenwich, CT 06830
/7
$8,750,000
- 6 Beds
- 7.5 Baths
- 10,400 Sq Ft
11 Winterset Rd, Greenwich, CT 06830

Mid Country New Construction smart home on 2.16 exquisite level acres will be completed by early fall, 2025. 10K+ SF of finished space on 4 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th en-suite bedroom on 3rd floor. Custom kitchen with Subzero/Wolf Appliances, island and breakfast area. Spectacular indoor / outdoor living is designed

Amanda Bates Houlihan Lawrence Inc.

11 Winterset Rd, Greenwich, CT 06830
/40
$1,475,000
- 6 Beds
- 8 Baths
- 5,797 Sq Ft
20 Fieldstone Dr, Easton, CT 06612

D. FAIRCHILD WHEELER ESTATE - Built in 1949 for the well-known philanthropist, this stately home sits majestically atop a sweeping front lawn w/ breathtaking views. This 5+ acre estate includes the 6-bedroom home w/ adjacent 2-bedroom in-law apartment/legal rental, a gunite pool & spa tub, multiple outbuildings & scenic views in every direction. The main house is brimming w/ old world charm

Gayle Worthington William Raveis Real Estate

20 Fieldstone Dr, Easton, CT 06612
/40
$1,750,000 Open Sat 11:30AM - 1PM
- 5 Beds
- 4 Baths
- 4,056 Sq Ft
31 Riverfield Dr, Weston, CT 06883

The Ultimate Trifecta: Riverfront, Poolside, and Court with Exceptional Touches This extraordinary estate is a masterpiece that marries nature's splendor with expert craftsmanship. A rare and private oasis, it offers a serene retreat where the river's gentle flow dictates the rhythm of life. Picture waking up to the soothing sounds of water, stepping out to witness the river's beauty unfold

Betty Stroll William Raveis Real Estate

31 Riverfield Dr, Weston, CT 06883
/40
$1,400,000
- 5 Beds
- 4.5 Baths
- 3,817 Sq Ft
7 Topping Ln, Norwalk, CT 06854

Tucked away at the end of a private road in Norwalk's Brookside neighborhood, 7 Topping Lane offers rare privacy and space on 2.39 acres. This 5-bedroom 4.5-bath Tudor-style home combines timeless charm with modern updates. The open-concept main level features dramatic 17-foot cathedral ceilings, a striking wood-burning stone fireplace, and exposed beams. The updated kitchen boasts quartz

Brandy Hall Higgins Group Real Estate

7 Topping Ln, Norwalk, CT 06854
/21
$6,600,077 Open Sun 1PM - 3PM
- 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
$1,139,000 Open Sun 12PM - 2PM
- 5 Beds
- 3 Baths
- 4,359 Sq Ft
4 Whippoorwill Ln, Weston, CT 06883

Discover exceptional living at this distinguished 5-bedroom, 3-bathroom ranch home spanning over 5,000 square feet on prestigious Whippoorwill Lane in coveted Weston. Built in 1955 and situated on a magnificent 1.72-acre lot, this timeless residence offers the perfect blend of classic New England charm and modern potential in one of the most sought-after communities. Ready for a new homeowners

Christine Oleynick Keller Williams Realty

4 Whippoorwill Ln, Weston, CT 06883
/40
$1,299,000
- 5 Beds
- 3.5 Baths
- 3,611 Sq Ft
101 Golden Hill St, Trumbull, CT 06611

"A Premier Waterfront Sanctuary"! Please view the fabulous virtual tour of this property at (101goldenhill.com) for spectacular drone imaging here on tranquil "Dogwood Lake", (spring fed) in historic "Nichols" & the award winning "Booth Hill School District". Resort styled living inside & out w/established perennial & raised bed vegetable gardens, level lawn spaces, (irrigated) stretching out to

Kenneth Martin William Raveis Real Estate

101 Golden Hill St, Trumbull, CT 06611
/38
$1,199,999
- 5 Beds
- 4.5 Baths
- 3,751 Sq Ft
137 Rockwell Rd, Bethel, CT 06801

If These Walls Could Talk...Welcome to a remarkable piece of Bethel's history. Built in 1760, this enchanting antique Colonial is far more than a home, it's a living story. Once the original homestead of the Dibble family, one of Bethel's earliest settlers, the property carries the legacy of generations past. Years later, this storied home became the residence of Mort Lewis, iconic music manager

Nicole Costantino Keller Williams Realty

137 Rockwell Rd, Bethel, CT 06801
/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

Elizabeth Tritschler William Raveis Real Estate

260 Willow St, Southport, CT 06890
/40
$25,500,000
- 9 Beds
- 14 Baths
- 14,266 Sq Ft
104 Dans Hwy, New Canaan, CT 06840

Clark House, a legacy property with extraordinary provenance, was re-imagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge and built like a fortress from steel and concrete in 1937, the property was purchased as a country residence by copper heiress Huguette Clark, and remained unoccupied and untouched until a

Leslie Razook William Pitt Sotheby's Int'l

104 Dans Hwy, New Canaan, CT 06840
/28
$2,500,000
- 5 Beds
- 4 Baths
- 3,772 Sq Ft
43 Buckfield Ln, Greenwich, CT 06831

Nestled at the end of a quiet street in one of the most prestigious towns in the country, this rare 8.5-acre estate in Greenwich, offers an exceptional opportunity for those seeking space, privacy, and potential. Built in 1936, this stately residence features 5 bedrooms, 4 full bathrooms, and over 3,700 square feet of living space, all set on a sprawling flat parcel rarely found in the area. The

Jolanta Rojek eXp Realty

43 Buckfield Ln, Greenwich, CT 06831
/40
$10,750,000
- 7 Beds
- 6.5 Baths
- 9,420 Sq Ft
63 Turney Rd, Redding, CT 06896

39 PRIVATE ACRES Setting! Convenient! Secluded & bordered by over 200 ACRES of protected open space is a Hunters paradise with over 20 deer stands in this property's wooded area just the beginning of the Major Benefits of this bespoke 9,400+ sq. ft. CUSTOM Georgian Colonial with it's 97ft. Covered front Veranda. Two luxurious staircases frame the breath-taking Grand Foyer 's Soaring Domed

John Cavaliere William Raveis Real Estate

63 Turney Rd, Redding, CT 06896
/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
/37
$2,099,000
- 6 Beds
- 5.5 Baths
- 7,804 Sq Ft
47 Tubbs Spring Dr, Weston, CT 06883

This modern farmhouse offers year-round comfort and effortless entertaining! Set behind powered gates at the end of a quiet cul-de-sac, the 7,760 sq ft home borders the 37 acres of trails of the Grace Robinson Nature Sanctuary - yet is just minutes to Weston's award-winning schools and village center. Inside, the home is light-filled and inviting, featuring a flexible layout and spacious rooms. A

Cyd Hamer William Pitt Sotheby's Int'l

47 Tubbs Spring Dr, Weston, CT 06883
/40
$15,000,000
- 7 Beds
- 10 Baths
- 9,129 Sq Ft
4800 Congress St, Fairfield, CT 06824

Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the

Leslie Razook William Pitt Sotheby's Int'l

4800 Congress St, Fairfield, CT 06824
/40
$3,300,000
- 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
/31
$13,400,000
- 6 Beds
- 9 Baths
- 11,157 Sq Ft
31 Meadow Ln, Greenwich, CT 06831

Exceptional Tanner White ultra-luxurious six-bedroom modern residence in the estate area of Greenwich. The open floor plan with 12+ foot ceilings is filled with natural light and allows for versatile use of the dramatic formal and casual rooms, all leading to a captivating outdoor living space complete with a fireplace overlooking the serene pool with spa and verdant lawn. The interior design and

Leslie McElwreath Sotheby's International Realty

31 Meadow Ln, Greenwich, CT 06831
/38
$6,495,000
- 6 Beds
- 9 Baths
- 8,392 Sq Ft
474 Ponus Ridge, New Canaan, CT 06840

Discover elegance at this custom stone and shingle French Colonial on 4.9 bucolic acres on New Canaan's coveted west side. Bordering an 11-acre land trust, this 8,332 SF home, plus 2,300 SF finished lower level, offers privacy and proximity to downtown New Canaan and NYC commutes. The exquisite gardens, Inspired by Villa d'Este, create a resort-like setting with spectacular views from every

Melissa Engel Douglas Elliman of Connecticut

474 Ponus Ridge, New Canaan, CT 06840
/23
$22,000,000
- 8 Beds
- 12 Baths
- 14,071 Sq Ft
8 Fox Run Ln, Greenwich, CT 06831

Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls

James Hoffman Houlihan Lawrence

8 Fox Run Ln, Greenwich, CT 06831
/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
$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
/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
$2,100,000
- 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
/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
/33
$4,750,000
- 5 Beds
- 6.5 Baths
- 8,886 Sq Ft
61 High Ridge Ave, Ridgefield, CT 06877

61 High Ridge Ave, a regal estate nestled in the heart of Ridgefield, CT's Historic District, with walking distance to downtown. Custom built in 1997, this exceptional property is anchored by a distinguished Stone Manor-a showcase of timeless elegance, expert craftsmanship, and dedication to quality. Spanning over 8,000 sq ft across 3 levels, the main residence features a stone facade, slate

Brian Milton Compass Connecticut, LLC

61 High Ridge Ave, Ridgefield, CT 06877
/40
$1,325,000
- 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
/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
/31
$1,850,000
- 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
/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

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