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

/29
$6,950,000
- 5 Beds
- 6 Baths
- 4,202 Sq Ft
18 Shoal Point Ln, Greenwich, CT 06878

Amazing 5-bedroom Riverside waterfront home, not in the flood zone, with mesmerizing views, a private dock & heated pool. Built in 2004 but renovated in 2024, w/ 3 fully finished levels, high ceilings, & easy access to outdoor patios & gardens for a coveted indoor/outdoor lifestyle. Beautiful & generous rooms for waterfront entertaining. Oversized kitchen w/ island & separate breakfast room

Amanda Miller Houlihan Lawrence

18 Shoal Point Ln, Greenwich, CT 06878
/36
$7,500,000
- 7 Beds
- 9 Baths
- 14,066 Sq Ft
4 Cowdray Park Dr, Greenwich, CT 06831

Nestled within the confines of Conyers Farm, this French Normandy chateau epitomizes exclusivity and grandeur. Blending exquisite architecture with lavish comforts and resort amenities that elevate luxury living to new heights. Showcasing impeccable materials, palatial entertaining spaces, a luxurious kitchen, family room, paneled library, and a sprawling terrace overlooking the pool. Seven

Joan Marks Christie's International Real Estate

4 Cowdray Park Dr, Greenwich, CT 06831
/39
$4,200,000
- 6 Beds
- 10 Baths
- 12,071 Sq Ft
637 Valley Rd, New Canaan, CT 06840

Showcasing the unparalleled 637 Valley Road estate, a majestic stone Georgian Colonial that offers an enchanting lifestyle along the tranquil banks of the Silvermine River. Spanning over 7.04 acres of idyllic park-like grounds, this 12,000 square foot masterpiece with a charming guest cottage is a treasure not to be missed. The estate boasts an expansive chef's kitchen, a stately home library,

JoAnne Fisher William Pitt Sotheby's Int'l

637 Valley Rd, New Canaan, CT 06840
/49
$7,695,000
- 7 Beds
- 8 Baths
- 8,068 Sq Ft
2 Winding Ln, Greenwich, CT 06831

LOCATION, LOCATION LOCATION Set back on 2 private acres very close to town & landscaped to perfection, this exquisite property with over sized salt water pool, tennis court, children's playground, exquisite gardens & entertaining terraces offer today's buyers the perfect lifestyle. 8000+sq.ft. brick residence w/ new slate composite roof features 6 bdrms/6 bths, private office., lg light filled

Helene Barre Sotheby's International Realty

2 Winding Ln, Greenwich, CT 06831
/29
$2,899,000
- 5 Beds
- 6.5 Baths
- 6,070 Sq Ft
23 Benedict Hill Rd, New Canaan, CT 06840

Welcome to this exquisite stone and shingle home, an extraordinary masterpiece built in the timeless English Cotswold tradition. Updated in 1999 and again in the early 2000's, this impeccably designed home showcases unparalleled craftsmanship, and captivates with its attention to every detail, offering a truly custom living experience. As you step inside, you'll be greeted by the allure of

Melissa Engel Douglas Elliman of Connecticut

23 Benedict Hill Rd, New Canaan, CT 06840
/38
$35,000,000
- 6 Beds
- 7.5 Baths
- 8,684 Sq Ft
0 Hay Island Unit 24078034, Darien, CT 06820

HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom,

Leslie McElwreath Sotheby's International Realty

0 Hay Island Unit 24078034, Darien, CT 06820
/35
$16,990,000
- 6 Beds
- 8 Baths
- 8,111 Sq Ft
6 Windrose Way, Greenwich, CT 06830

Newly updated, stunning waterfront home with heated pool in the exclusive Mead Point Association. Sited on 2 beautiful acres with 230ft of frontage, the property has been recently landscaped to maximize the water views. West-facing rooftop terraces and decks act as a seamless extension of the modern, glass-walled interiors overlooking Indian Harbor. This custom-built home with 6 bedrooms and

Joseph Barbieri Sotheby's International Realty

6 Windrose Way, Greenwich, CT 06830
/41
$35,000,000
- 6 Beds
- 8 Baths
- 8,684 Sq Ft
157 Long Neck Point Rd, Darien, CT 06820

HAY ISLAND: Breathtaking, unobstructed views of the Long Island Sound stretch from this private island at the end of a gated causeway on Darien's cherished waterfront coast. Held by one family for over a century, this waterfront sanctuary features a meticulously crafted 8,684 SF New England colonial built in 2010. Positioned high above the water, with sweeping southeasterly views the six-bedroom,

Leslie McElwreath Sotheby's International Realty

157 Long Neck Point Rd, Darien, CT 06820
/38
$1,695,000
- 7 Beds
- 6.5 Baths
- 8,445 Sq Ft
35 Grace View Dr, Easton, CT 06612

Experience luxury living in this exquisite and stately Federal style colonial tucked at the end of a cul-de-sac in Easton! Sited beautifully with breathtaking views on over 3 acres with an in-ground pool. The main level features a formal dining and living room and a family room with fireplace. The chef's kitchen has 2 islands, both with prep sinks - one with granite counters, one with butcher

Kelly Higgins Coldwell Banker Realty

35 Grace View Dr, Easton, CT 06612
/40
$7,000,000
- 6 Beds
- 7 Baths
- 7,541 Sq Ft
384 West Ln, Ridgefield, CT 06877

Welcome to 384 West Lane, an exquisite estate that embodies timeless luxury across 13 spectacular acres in a park-like setting. This magical country compound offers unparalleled privacy, nestled just an hour away from NYC. At the heart of this estate is a classic Georgian Manor, a testament to architectural excellence with 7,500 sqft of extraordinary custom details. Revel in the outstanding

Karla Murtaugh Compass Connecticut, LLC

384 West Ln, Ridgefield, CT 06877
/39
$2,750,000
- 5 Beds
- 6 Baths
- 6,378 Sq Ft
170 Branchville Rd, Ridgefield, CT 06877

Welcome home to this stunning Nantucket style residence on 2.33 lush acres. Beautiful landscaping surround this residence enhanced by a stunning heated gunite pool and spa. Enter the two story marble foyer with columns leading to the living room with fireplace, one of four fireplaces in this home.,hardwood floors and french door to terrace. The open floor plan extends to the formal dining room

Carol Hanlon Coldwell Banker Realty

170 Branchville Rd, Ridgefield, CT 06877
/40
$14,900,000
- 6 Beds
- 10 Baths
- 10,579 Sq Ft
Unlisted Address

Home by the Sea is set majestically behind stone pillars and gates on one of the largest Long Neck Point parcels, affording its residents 3.2 landscaped acres of privacy. As you enter, the peaceful setting of the secluded cove takes your breath away. There are wrap-around decks, velvet lawns, flowering gardens and water views for miles. Nature lovers will be in Heaven. The acclaimed architect

Candace Blackwood BHHS Darien/New Canaan

Unlisted Address
/41
$3,250,000
- 6 Beds
- 8 Baths
- 6,635 Sq Ft
8 Tinker Ln, Greenwich, CT 06830

Located just 8 min. from downtown GR & tucked away at the end of a quiet cul-de-sac off of Lake Ave, this exceptional property offers privacy and space. Spanning 2.07 acres of beautiful grounds with a circular driveway, this timeless home offers 6,636SF of living space designed for both comfort and grand-scale entertaining. With 6 bedrooms, 5 full baths and 3 half baths, every detail of this

Joan Suter BHHS New England Properties

8 Tinker Ln, Greenwich, CT 06830
/46
$19,500,000
- 5 Beds
- 7 Baths
58 Quaker Ln, Greenwich, CT 06831

Unparalleled equestrian estate on 16.23 private acres on three separate lots of exceptional land with pastures, paddocks, orchards, gardens, stables and an aviary. Scenic drive through historic iron gates leads to three residential structures. Exquisite newly renovated main residence #58 is a five bedroom, 5.2 bathroom shingle style house set on 5 acres. French Country kitchen with intricately

Danielle Claroni Sotheby's International Realty

58 Quaker Ln, Greenwich, CT 06831
/39
$2,450,000
- 5 Beds
- 7.5 Baths
- 9,440 Sq Ft
25 Cogswell Ln, Stamford, CT 06902

This stunning 5-bedroom, 7.5 bath brick contemporary blends timeless elegance with modern sophistication. From the grand foyer, showcasing skylights and a limestone feature wall, to the living room with a quartzite fireplace and cathedral ceiling, every space in this home is designed for both beauty and function. The formal dining room, features a large bay window, offering picturesque views. The

Jim Caldarone William Pitt Sotheby's Int'l

25 Cogswell Ln, Stamford, CT 06902
/37
$4,595,000
- 5 Beds
- 8 Baths
- 6,725 Sq Ft
490 North St, Greenwich, CT 06830

Rare opportunity to own a 200 year old Barn on one mid-country acre, designed in the 70's by renowned architect Charles Gwathmey. Owners updated it to add additional bedrooms and seamlessly connect indoor and outdoor spaces offering year-round entertainment. Main entrance opens to an expansive 30 X 35' Great room filled with natural light, original beams, and impressive fireplace. A generous

Spencer Sodokoff Houlihan Lawrence

490 North St, Greenwich, CT 06830
/39
$1,385,000
- 5 Beds
- 5 Baths
- 5,204 Sq Ft
10 Robin Hood Ln, Easton, CT 06612

Your outdoor oasis awaits! Sited on a coveted double cul-de-sac, when you step in to 10 Robin Hood Lane and you will know it's "the one". This 2000 built colonial has everything you are looking for and more. The gracious entry foyer is both impressive and welcoming. Through arched French doors you will find the perfect home office with built-ins. The dining room has in-laid hardwood flooring and

Kelly Higgins Coldwell Banker Realty

10 Robin Hood Ln, Easton, CT 06612
/39
$9,500,000
- 8 Beds
- 10 Baths
- 13,349 Sq Ft
262 Brushy Ridge Rd, New Canaan, CT 06840

Welcome to Pemberly Hill, a truly exceptional home of unparalleled grandeur and sophistication. Boasting 8 bedrooms on 4 acres of pristine grounds on desirable Brushy Ridge, this magnificent property is a true masterpiece. This classic home has been thoughtfully designed to the highest standards, seamlessly blending its rich history with modern luxury. The result is an extraordinary residence

Michele Murray-Sloan Houlihan Lawrence

262 Brushy Ridge Rd, New Canaan, CT 06840
/38
$1,499,000
- 6 Beds
- 5.5 Baths
- 4,825 Sq Ft
99 Cross Hwy, Redding, CT 06896

Gorgeous fall afternoons on the patio; cozy winter nights by a fireplace; spring days uncovering flora & fauna of the property; delightful summers lounging at the pool-this country enclave is ideal in all seasons. Originally built in 1880 as a colonial cottage with two-sided central fireplace, this farmhouse has been reimagined through the years and is set for today's lifestyle. The professional

Karen Hagen Compass Connecticut, LLC

99 Cross Hwy, Redding, CT 06896
/40
$11,800,000
- 5 Beds
- 8 Baths
- 10,800 Sq Ft
260 Hillspoint Rd, Westport, CT 06880

Experience the unparalleled luxury of this exquisite Compo Beach seaside home,a masterpiece of design and craftsmanship, designed by renowned architect Peter Cadoux. Just steps from a private beach, this architectural gem is bathed in natural light and boasts breathtaking panoramic water views from nearly every room.The full chef's kitchen opens to a radiant sunroom with a glass ceiling, perfect

Elizabeth Steffen Higgins Group Bedford Square

260 Hillspoint Rd, Westport, CT 06880
/39
$2,490,000
- 9 Beds
- 6.5 Baths
- 6,363 Sq Ft
1209 Westover Rd, Stamford, CT 06902

Welcome to 1209 Westover Rd, the ideal estate package with two strategically placed properties w/ 8 Bedrooms 6.5 baths a total of 6,863 sq ft on its prime, sought after location on 1.93 park-like acres straddling the Greenwich /Stamford townline. The Main House is a stately Georgian with superior craftsmanship incorporating the finest materials with a steel frame, oak-hardwood floors interspersed

Demetrios Frazis William Pitt Sotheby's Int'l

1209 Westover Rd, Stamford, CT 06902
/34
$2,725,000
- 5 Beds
- 5 Baths
- 3,975 Sq Ft
979 Lake Ave, Greenwich, CT 06831

Serene Country Retreat. Recently renovated, this home features a flexible first-floor plan with dramatic views through a large picture window. New eat-in kitchen. Heated inground pool & spa with automatic cover & outdoor shower & heated 620 sq. ft. custom deck perfect for entertaining. The primary suite includes a stunning bath & walk-in closet. The second floor has 3 additional bedrooms sharing

Danielle Claroni Sotheby's International Realty

979 Lake Ave, Greenwich, CT 06831
/40
$4,500,000
- 5 Beds
- 4.5 Baths
- 6,013 Sq Ft
29 Covelee Dr, Norwalk, CT 06855

Welcome to Saugatuck Shores, an exceptional waterfront enclave offering unparalleled luxury and privacy.A boater's dream come true w/ a deep water dock and direct access to LI Sound.This hidden gem neighborhood has a labyrinth of quiet,walkable streets, culminating in a cul-de-sac.Private Covlee Assn membership w/ sandy beach & social gatherings.The 5 bedroom high-end masterpiece w/ elevator was

Julie Vanderblue Higgins Group Real Estate

29 Covelee Dr, Norwalk, CT 06855
/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
/40
$4,495,000
- 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
/41
$10,950,000
- 6 Beds
- 8 Baths
- 9,258 Sq Ft
142 Cedar Cliff Rd, Riverside, CT 06878

Exquisite 2016 French Normandy manor designed by premier architect, Douglas VanderHorn blends classic elegance with 3 levels of stunning modern aesthetics in coveted Riverside association with Shoreline pool and neighborhood private beach. Sophisticated, custom crafted interior with Italian marble mantels framing four fireplaces, quarter-sawn white oak flooring, 10 ft. ceilings, French doors to

Alison Farn-Leigh BHHS New England Properties

142 Cedar Cliff Rd, Riverside, CT 06878
/39
$24,950,000
- 10 Beds
- 19 Baths
- 17,878 Sq Ft
97 Pecksland Rd, Greenwich, CT 06831

Truly unique 19 Acre estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the

Robert Johnson Brown Harris Stevens CT, LLC

97 Pecksland Rd, Greenwich, CT 06831
/37
$3,900,000
- 5 Beds
- 9 Baths
- 8,639 Sq Ft
249 Sturges Hwy, Westport, CT 06880

Relaxed, entertaining luxury with all the bells and whistles....Privacy, serenity and convenience featuring Entertaining at it's finest - step into 249 Sturges Highway greeted by welcoming floor plan from living room, dining room, open concept kitchen which highlights gorgeous quartzite counters, a Subzero refrigerator, Bosch dishwasher, and a 60" Viking Dual Fuel range flowing into the great

Lainie Floyd William Pitt Sotheby's Int'l

249 Sturges Hwy, Westport, CT 06880
/40
$15,000,000
- 5 Beds
- 7 Baths
- 3,955 Sq Ft
50 Compo Mill Cove, Westport, CT 06880

A TRUE PIECE of ART. Tranquil Hamptons alternative at a great price point and views of Long Island Sound. A short walk across the Wooden Footbridge w/ Sherwood Mill Pond on your left and LI Sound on your right leads to the gated private Island of Compo Mill Cove & a handful of unique waterfront homes. The property itself has been customized from top to bottom w/ exceptional thought & detail. Only

Robert Perriello Century 21 AllPoints Realty

50 Compo Mill Cove, Westport, CT 06880
/42
$9,450,000
- 10 Beds
- 9 Baths
- 9,483 Sq Ft
14 Meadow Dr, Greenwich, CT 06831

DISCOVER BREEZEMORE https://www.breezemoregreenwich.com/ Experience the rare opportunity to own a piece of history with the stunning Breezemore estate located in Greenwich, Connecticut. Built in 1909, this magnificent property offers 10,000 square feet of architectural splendor, old-world charm, and modern conveniences. Set high on 3.2 private, park-like acres within close distance of downtown

Ryan Hoffman Houlihan Lawrence

14 Meadow Dr, Greenwich, CT 06831
/39
$3,850,000
- 5 Beds
- 8 Baths
- 9,084 Sq Ft
39 Keelers Ridge Rd, Wilton, CT 06897

Luxurious Keelers Ridge Estate: A Serene Sanctuary of Sophistication and Comfort Nestled on a private cul-de-sac in the prestigious Keelers Ridge neighborhood, this executive property is a testament to luxury, tranquility, and meticulous upkeep. Spanning over 2 acres of meticulously curated gardens and specimen plantings, this oasis promises an ambiance of refined elegance and natural beauty. As

Aileen Mastey William Pitt Sotheby's Int'l

39 Keelers Ridge Rd, Wilton, CT 06897
/20
$6,670,000
- 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
/35
$4,300,000
- 7 Beds
- 5 Baths
- 6,000 Sq Ft
378 Penfield Rd, Fairfield, CT 06824

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

378 Penfield Rd, Fairfield, CT 06824
/37
$4,300,000
- 7 Beds
- 5.5 Baths
- 6,000 Sq Ft
394 Penfield Rd, Fairfield, CT 06824

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

394 Penfield Rd, Fairfield, CT 06824
/38
$1,200,000
- 5 Beds
- 5 Baths
- 5,079 Sq Ft
235 W Haviland Ln, Stamford, CT 06903

Welcome to your new retreat in this highly desirable N Stamford neighborhood! This expanded colonial is designed w/space & comfort for everyone. From the moment you step inside, you'll be welcomed by an inviting, open floor plan on the main level that seamlessly connects each room. Beautiful hardwood floors add warmth & elegance to the space. The chef-friendly kitchen is well-equipped & the

Catherine Richardson William Pitt Sotheby's Int'l

235 W Haviland Ln, Stamford, CT 06903
/50
$11,300,000
- 12 Beds
- 16 Baths
- 16,487 Sq Ft
724 North St, Greenwich, CT 06831

Eight private, gated acres showcase a sprawling back-country home with stone terraces, secluded backyard, fountain and resort-style amenities including tennis court, indoor pool, spa, steam room and separate office. Thoughtful floor plan accommodates both grand scale entertaining as well as comfortable everyday living with elegant formal rooms, fireplaces in living, family rooms and library;

Julie Church Houlihan Lawrence

724 North St, Greenwich, CT 06831
/33
$2,800,000
- 7 Beds
- 6 Baths
- 7,843 Sq Ft
125 Brett Ln, Fairfield, CT 06824

Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Go into the elegant formal living and dining rooms, both warmed by inviting FPs, setting the stage for memorable moments. The custom gourmet kitchen, designed for living, opens

Linna Yuen Coldwell Banker Realty

125 Brett Ln, Fairfield, CT 06824
/32
$8,950,000
- 6 Beds
- 10 Baths
- 8,146 Sq Ft
26 Andrews Farm Rd, Greenwich, CT 06831

Classic brick Georgian updated for today's lifestyle. Just renovated, the residence features high ceilings, oversized windows, hardwood flooring, tasteful stone and tile throughout three levels, a splendid backdrop for both formal and casual entertaining. One of a kind first-floor primary suite with two stunning bathrooms and two dressing rooms. Elegant formal rooms open to a west-facing brick

Leslie McElwreath Sotheby's International Realty

26 Andrews Farm Rd, Greenwich, CT 06831
/40
$25,500,000
- 9 Beds
- 14 Baths
- 14,266 Sq Ft
104 Dans Hwy, New Canaan, CT 06840

Welcome to Le Beau Chateau, a grand French-style manor house originally built in 1937 on a 52 acre property restored and reimagined by Reed & Delphine Krakoff to perfection. Boasting pedigree, provenance and stunning design, this timeless and priceless estate (formerly owned by copper heiress Huguette Clark) has been magically transformed with a deep respect for its history, and a seamless

Robert Johnson Brown Harris Stevens CT, LLC

104 Dans Hwy, New Canaan, CT 06840
/39
$8,688,000
- 6 Beds
- 10 Baths
- 16,255 Sq Ft
119 Proprietors Crossing, New Canaan, CT 06840

119 Proprietors Crossing is a breathtaking estate by architect James E. Gearity. Set on four acres, this fully restored six-bedroom home blends timeless elegance with modern function. A private drive and grand fountain lead you in to a soaring foyer with a sweeping staircase beneath a dramatic Baccarat chandelier. The parlor, with one of seven fireplaces, flows to a serene terrace. The Blue Room

Ashlei De Souza Serhant Connecticut, LLC

119 Proprietors Crossing, New Canaan, CT 06840

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

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

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