Fairfield County CT Houses for Sale with Private Pool

/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
/39
$894,900
- 4 Beds
- 3.5 Baths
- 3,722 Sq Ft
17 Kathleen Dr, Stratford, CT 06614

Welcome to this extraordinary reproduction Colonial with top-of-the-line modern updates throughout, creating an incredible home well worth touring! Perfectly situated at the end of a peaceful cul-de-sac on a private, level 1.02-acre lot in Stratford's desirable North End, this beautifully updated 3,722 sq. ft., 12+ room, 3.5 bath home blends timeless New England charm with outstanding

Fredda Takacs

Coldwell Banker Realty

(203) 902-4713

17 Kathleen Dr, Stratford, CT 06614
/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
/23
$480,000
- 3 Beds
- 1.5 Baths
- 1,312 Sq Ft
10 Almar Dr, Bethel, CT 06801

Bethel cul-de-sac Ranch with 3 bedrooms, 1 1/2 baths, a large deck, and a detached 2-car garage. This home is less than a mile from Downtown Bethel and all it has to offer, including shopping, dining, and the Metro North train station. The large eat-in kitchen leads to the living room and dining room combination. Hardwood floors throughout. It is on a nice level lot and has natural gas heat. Come

Edmundo DaSilva

eXp Realty

(475) 338-3718

10 Almar Dr, Bethel, CT 06801
/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
$800,000 Open Sun 1PM - 3PM
- 2 Beds
- 3 Baths
- 1,723 Sq Ft
2 Old Kings Hwy, Norwalk, CT 06850

Located in the heart of the Silvermine Historic District, this enchanting home offers classic New England charm and a prime location just a short stroll to the acclaimed GrayBarns Inn & Tavern and the Silvermine Arts Center. This location blends heritage, culture, and natural beauty in one of Norwalk's most coveted enclaves. A light and bright spacious foyer greets you as you enter the home.

Pam Toner

Berkshire Hathaway NE Prop.

(475) 263-4644

2 Old Kings Hwy, Norwalk, CT 06850
/40
$749,000
- 3 Beds
- 2 Baths
- 2,612 Sq Ft
102 Hanover Rd, Newtown, CT 06470

Three Bedrooms and Two full Baths Contemporary Cape. With an open floor plan, a large Family Room with a Wood stove, a Sun Room, and a screened-in Hot Tub room. The kitchen has granite countertops and stainless steel appliances. The main level has a split A/C heating unit and skylights throughout. Outside with an above-ground pool and abundant Nature. An oversized deck that steps down to a patio

Edmundo DaSilva

eXp Realty

(203) 590-9796

102 Hanover Rd, Newtown, CT 06470
/53
$4,995,000
- 4 Beds
- 6 Baths
- 5,244 Sq Ft
34 Edgewood Dr, Greenwich, CT 06831

Tucked discreetly at the end of a long, private drive in coveted mid-country Greenwich, masterfully renovated in 2025 this Colonial offers a harmonious blend of heritage architecture and sophisticated modernity. Designed to accommodate both grand-scale entertaining and intimate daily living, the residence unfolds across three levels and over 7,000 square feet of meticulously curated

Danielle Malloy

Serhant Connecticut LLC

(203) 769-9185

34 Edgewood Dr, Greenwich, CT 06831
/40
$4,750,000
- 3 Beds
- 3 Baths
- 2,650 Sq Ft
34 Shorehaven Rd, Norwalk, CT 06855

Exclusive Waterfront Retreat in Gated Island Community - Just One Hour from NYC. Welcome to a rare opportunity to own one of only twelve homes on a secluded private island on the Long Island Sound. This 3-bedroom, 3-bathroom waterfront home offers the perfect escape from city life while remaining effortlessly connected to the best of Fairfield County. Perched between the sparkling waters of Long

Toni Mickiewicz

William Pitt Sotheby's Int'l

(475) 405-1946

34 Shorehaven Rd, Norwalk, CT 06855
/27
$6,250,000 Open Sun 11AM - 12PM
- 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
/34
$853,000
- 3 Beds
- 3.5 Baths
- 4,433 Sq Ft
53 W Hill Cir, Stamford, CT 06902

** Highest and Best by Monday, July 28, 2025 at 12:00 PM (Noon) ** Lovingly owned by one family for 63 years, this expansive custom-built Westover ranch offers incredible space, versatility, and untapped potential! With over 3,000 SF on the main level and an additional ~1,423 SF in the walk-out lower level, this home is ideal for multigenerational living, entertaining, or future in-law/guest

Linda Lang-Bankowski The Real Estate Boutique, LLC

53 W Hill Cir, Stamford, CT 06902
/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
$2,995,000
- 4 Beds
- 4.5 Baths
- 5,629 Sq Ft
166 Long Lots Rd, Westport, CT 06880

Your private oasis awaits! This beautifully renovated home offers an ideal location with easy access to town, shopping, and the beach. Designed with comfort and style in mind, the home features inviting living spaces including a two-story family room with an open staircase. The gourmet eat-in kitchen is open to a sitting area with a corner fireplace. Two family bedrooms with en-suite baths

Michelle Genovesi William Raveis Real Estate

166 Long Lots Rd, Westport, CT 06880
/30
$2,490,000
- 3 Beds
- 3.5 Baths
- 6,900 Sq Ft
88 Green Ln, Ridgefield, CT 06877

Mid-Century Modern Inspired Turnkey Contemporary - influenced by the works of Frank Lloyd Wright and Philip Johnson: Including spacious indoor/outdoor living, more than 100 picture windows, skylights, and the delight of a brook that runs beneath the great room which sports 22-foot-high ceilings above -- and a see-through glass table next to the two-sided fireplace -- below. The sounds and sights

Karen Heller Coldwell Banker Realty

88 Green Ln, Ridgefield, CT 06877
/34
$3,450,000
- 4 Beds
- 6 Baths
- 8,912 Sq Ft
266 Great Plain Rd, Danbury, CT 06811

Welcome Home to this incredible lakefront oasis! Exclusive access to Candlewood Lake awaits you at this pristine, elegant masterpiece. Spectacular views abound from every room of the spacious, yet relaxed home. The open-concept main level includes a vaulted living room, resplendent dining room, comfortable great room with floor-to-ceiling stone fireplace, stunning office with built-ins and

Chip & Heather Neumann Houlihan Lawrence

266 Great Plain Rd, Danbury, CT 06811
/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
/24
$1,599,000 Open Fri 12PM - 2PM
- 4 Beds
- 5 Baths
- 5,098 Sq Ft
9 Long Meadow Ln, Redding, CT 06896

Live your best life in this Quintessential 4 Bedroom Center Hall Colonial home located on one of Redding's most desirable streets. Long Meadow Lane is a quiet cul-de-sac in the sought after Redding Ridge neighborhood, close to schools & Redding Centre. Enjoy the last of the warm months by the pool & play Bacci with family in the private yard abutting a land trust that can't be developed. The home

Jessica Brookbanks Coldwell Banker Realty

9 Long Meadow Ln, Redding, CT 06896
/39
$3,250,000
- 4 Beds
- 4.5 Baths
- 5,092 Sq Ft
36 Bonnie Brook Rd, Westport, CT 06880

Welcome to your dream home in one of Westport's most desirable and charming neighborhoods. This beautifully crafted residence includes a sparkling pool and is perfectly nestled in a peaceful, walkable community-for bike rides and evening strolls. This home seamlessly blends modern design with a fresh take on the timeless Modern Farmhouse, offering both style and function. A spacious front porch

Michael Ferraro Compass Connecticut, LLC

36 Bonnie Brook Rd, Westport, CT 06880
/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
$3,499,000
- 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
/38
$3,375,000
- 5 Beds
- 6 Baths
- 4,668 Sq Ft
91 Turkey Hill Rd S, Westport, CT 06880

Welcome to a home that lives as beautifully as it looks. In the heart of Greens Farms, this timeless 5 bedroom, 6 bath Colonial is where classic elegance meets modern ease, designed for how you live, work, and entertain today. A circular drive, stone walls, and a charming front porch create an inviting first impression. Inside, a sun-filled double-height entry sets the tone for open, gracious

Chrissie Rodriguez Higgins Group Real Estate

91 Turkey Hill Rd S, Westport, CT 06880
/40
$4,300,000
- 8 Beds
- 9 Baths
- 9,208 Sq Ft
88 Main St, Ridgefield, CT 06877

Welcome to one of Ridgefield's most iconic estates-a true Crown Jewel-nestled in the heart of the town's historic village and Connecticut's first designated Cultural District. Framed by stunning stone walls at the entrance, this grand estate is a masterclass in timeless elegance and modern luxury. Impeccably restored and thoughtfully reimagined, this home offers refined living space across four

Julie Setterlund William Pitt Sotheby's Int'l

88 Main St, Ridgefield, CT 06877
/40
$4,695,000
- 6 Beds
- 9 Baths
- 7,376 Sq Ft
174 Branchville Rd, Ridgefield, CT 06877

Welcome to Stonewall Manor-a spectacular mini-estate on 2.76 level manicured acres just minutes to town. A gated entry and circular drive lead to this custom residence that blends timeless elegance with high-end design. Inside, a 2-story foyer introduces exquisite millwork, coffered ceilings, arched doorways and grand-scale rooms. Formal living and dining rooms flank the entry, while the

John Pellegrino William Raveis Real Estate

174 Branchville Rd, Ridgefield, CT 06877
/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
$6,950,000
- 5 Beds
- 7.5 Baths
- 14,038 Sq Ft
11 Beachside Common, Westport, CT 06880

A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive homes on the Connecticut coast-known to anyone who's ever strolled Burying Hill Beach. Set on 2.6 waterfront acres, the property offers sweeping southern views over Sherwood Island and Long Island Sound, with sunsets that rival the Low Country and birdlife that fills the surrounding marsh with movement and

Wendy Ryan Brown Harris Stevens

11 Beachside Common, Westport, CT 06880
/40
$2,650,000
- 5 Beds
- 4.5 Baths
- 3,703 Sq Ft
2821 Congress St, Fairfield, CT 06824

Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A

Andrew Whiteley Brown Harris Stevens

2821 Congress St, Fairfield, CT 06824
/39
$2,545,000
- 5 Beds
- 4.5 Baths
- 3,510 Sq Ft
81 Birch Rd, Fairfield, CT 06824

Live the ultimate coastal lifestyle in this sensational 5-6 bedroom, 4.5 bathroom Nantucket-style Colonial w/brand new Gunite pool. Set on an oversized, wide lot, this home was recently reimagined by one of Fairfield County's most acclaimed interior designers. Sun-flooded w/9' ceilings & a breezy beach-inspired layout, every detail feels custom & elevated: coffered ceilings, transom doorways,

Kate Cacciatore William Raveis Real Estate

81 Birch Rd, Fairfield, CT 06824
/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
$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
/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
/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
/40
$2,495,000
- 4 Beds
- 5 Baths
- 7,046 Sq Ft
96 Norrans Ridge Dr, Ridgefield, CT 06877

Be in before school starts! Timeless Elegance Minutes from Downtown Ridgefield. As you enter the property, you're immediately welcomed by refined elegance and serene privacy, just minutes from the heart of Ridgefield's vibrant downtown. This meticulously maintained residence is a true showcase of luxury, craftsmanship, and thoughtful design. As you enter the grand foyer the newly refinished

Jay Contessa William Pitt Sotheby's Int'l

96 Norrans Ridge Dr, Ridgefield, CT 06877
/39
$2,749,000
- 5 Beds
- 3 Baths
- 4,250 Sq Ft
181 Highland Ave, Norwalk, CT 06853

This architect-designed home offers approximately 4,250 square feet of living space with five bedrooms and three bathrooms. It is situated on over a half acre of flat property including a refreshing in-ground pool, an expansive patio, mature plantings and cedar fence. The first floor features a private bedroom suite with separate outdoor access, a state-of-the-art kitchen, living room with

Mary Petro Noonan Coldwell Banker Realty

181 Highland Ave, Norwalk, CT 06853
/40
$2,649,000
- 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
$2,999,000
- 4 Beds
- 7 Baths
- 6,766 Sq Ft
226 Nod Hill Rd, Wilton, CT 06897

A waterfront Shangri-La! Situated on Popes/Streets Pond in picturesque Nod Hill, this detail rich colonial is one of few waterfront homes in all of Wilton. Immerse yourself in nature and privacy as if you're in VT or NH while residing just 50 miles from midtown NYC! Situated on 2.43 acres, this residence offers every feature/amenity one could ask for & w/high-style! Prominent views can be enjoyed

Jon Magnotta Outlook Realty

226 Nod Hill Rd, Wilton, CT 06897
/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

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