Fairfield County CT Homes for Sale with Pool

/13
$4,350,000
- 5 Beds
- 4.5 Baths
- 3,858 Sq Ft
121 Round Hill Rd, Greenwich, CT 06831

This home was built with great bones and is now ready for a full renovation. OR, take it down and build new - see photos. Gorgeous 2.3 acres combine with a premier Round Hill Rd. address! The topography of 121 Round Hill Road offers uncommon long vistas from all floors with a unique blend of openness and privacy. Irrigated, manicured lawns, plantings, old stonewalls, and natural areas provide a

Sabine Schoenberg Primesites, Inc.

121 Round Hill Rd, Greenwich, CT 06831
/36
$1,999,000
- 5 Beds
- 5 Baths
- 7,014 Sq Ft
13 Cove Rd, Brookfield, CT 06804

WATERFRONT OASIS... HUGE PRICE IMPROVEMENT!!! Welcome to this stunning custom-built contemporary home, nestled on over 300 feet of waterfront along Lake Lillinonah in the Barkwood Falls subdivision of Brookfield. This one-owner estate on over 2 acres offers breathtaking views and unparalleled privacy! The grand two-story foyer is adorned with Carrera marble, setting the tone for the elegance that

Jennifer Carbone Howard Hanna Rand Realty

13 Cove Rd, Brookfield, CT 06804
/38
$2,750,000
- 6 Beds
- 4.5 Baths
- 4,702 Sq Ft
85 Cutler Rd, Greenwich, CT 06831

This New England-style center hall colonial sits majestically atop a long private drive in idyllic back country Greenwich. The combination of outdoor spaces, set on 4 acres, make this home ideal for relaxation & entertaining...an in-ground pool, pool house, tennis court, and a versatile heated barn for creative pursuits. The interior features truly create an inviting atmosphere. Custom moldings,

Jodi Gutierrez Alliance R.E. Consultants

85 Cutler Rd, Greenwich, CT 06831
/40
$2,599,000
- 11 Beds
- 10 Baths
- 15,118 Sq Ft
124 Old Battery Rd, Bridgeport, CT 06605

A very special Fairfield County Connecticut Gold Coast mansion at St. Mary's-by-the-Sea and Long Island Sound. Experience The Chimneys, an architectural gem designed by Charles Wellington Walker in 1928. This Georgian Revival home won America's Finest Home Award in 2015. The 54-foot Grand Hall features a sweeping staircase with hand-wrought iron balustrades. Eleven artful fireplaces add warmth

Gail Robinson William Raveis Real Estate

124 Old Battery Rd, Bridgeport, CT 06605
/23
$4,350,000
- 6 Beds
- 4.5 Baths
- 4,958 Sq Ft
121 Round Hill Rd, Greenwich, CT 06831

Rare find - property on one of Greenwich' estate roads, Round Hill Rd. Oversized, private property, pool, stable, with a perfect blend of tranquil, manicured and natural landscapes. Enjoy your morning coffee gazing across beautiful east-facing rear vistas.Move right into this 5 bedroom 4 1/2 bath home, featuring upgrades like generator, irrigation, and largely new windows. Create your

Sabine Schoenberg PrimeSites, Inc.

121 Round Hill Rd, Greenwich, CT 06831
/2
$10,995,000
- 5 Beds
- 7 Baths
- 6,025 Sq Ft
14 Owenoke Park, Westport, CT 06880

Bluewater Home presents another beach property in the sought after Compo location. Construction has started on this 6100+sqft modern designed home with private yard, pool with spa, water views of the pond and walking distance to Compo Beach. Enjoy new construction living in the heart of Westport while peacefully tucked away on a private cul-de-sac

Deirdre Andreoli Compass Connecticut, LLC

14 Owenoke Park, Westport, CT 06880
/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
/49
$6,395,000
- 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
/38
$29,500,000
- 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
/41
$29,500,000
- 6 Beds
- 7.5 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
$1,450,000
- 5 Beds
- 3.5 Baths
- 5,044 Sq Ft
20 Blanket Meadow Rd, Monroe, CT 06468

Welcome to 20 Blanket Meadow Rd. This stunning custom-built Colonial sits on nearly 2.5 flat acres in one of Monroe's most desirable neighborhoods, offering over 5,000 sq.ft. across three levels. The main level features an expansive open-concept kitchen with solid wood cabinetry, granite countertops, a gas range, and double ovens, seamlessly flowing into the family room where you'll be welcomed

Terri Tournas Coldwell Banker Realty

20 Blanket Meadow Rd, Monroe, CT 06468
/37
$5,600,000
- 6 Beds
- 10 Baths
- 7,438 Sq Ft
27 Stiles Ln, Greenwich, CT 06831

Grand Greenwich Estate | Luxurious Living on 4.3 AcresTucked at the end of a quiet cul-de-sac, 27 Stiles Lane is a magnificent brick manor set on 4.3 acres of private, manicured grounds. With 7,438 sq. ft. of refined living space, this estate offers six ensuite bedrooms for ultimate privacy. The home features two fireplaces and a beautiful library with custom millwork. The resort-style

Fatou Niang William Pitt Sotheby's Int'l

27 Stiles Ln, Greenwich, CT 06831
/39
$10,250,000
- 6 Beds
- 9 Baths
- 5,920 Sq Ft
828 Sasco Hill Rd, Fairfield, CT 06824

"Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of

Wendy Ryan Brown Harris Stevens

828 Sasco Hill Rd, Fairfield, CT 06824
/41
$3,100,000
- 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
/40
$2,200,000
- 5 Beds
- 7.5 Baths
- 6,354 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
$4,275,000
- 5 Beds
- 7.5 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
/40
$5,850,000
- 6 Beds
- 5.5 Baths
- 6,588 Sq Ft
17 River Ln, Westport, CT 06880

This remarkable stone mansion, built in 1929, stands as one of the most historically and culturally significant residences in Westport and Fairfield County, celebrated as an exceptional trophy property. Meticulously restored and in impeccable, move-in ready condition, this home is poised for immediate enjoyment. Crafted in the esteemed tradition of Europe's grand Manor Houses, it boasts

Alex Chingas Coldwell Banker Realty

17 River Ln, Westport, CT 06880
/40
$8,600,000
- 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
/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
/63
$2,595,000
- 5 Beds
- 4.5 Baths
- 3,975 Sq Ft
979 Lake Ave, Greenwich, CT 06831

Welcome to 979 Lake. Conveniently located only minutes from shopping in Greenwich, Armonk or Bedford, this modern home was renovated in 2022. Picture yourself on your expansive, heated ipe deck enjoying family & friends while getting serenaded by birds in spring & summer or take in the dramatic views through large picture windows throughout the house all year long. Frolic in the new heated

Danielle Claroni Sotheby's International Realty

979 Lake Ave, Greenwich, CT 06831
/33
$485,000
- 2 Beds
- 2.5 Baths
- 1,863 Sq Ft
15 Bristol Terrace Unit 15, Danbury, CT 06810

Welcome to Timber Oaks, a desirable townhome community in Danbury. This well-maintained home offers a comfortable and stylish living space with gleaming hardwood floors on the main and upper levels. The inviting eat-in kitchen boasts granite countertops and stainless steel appliances. The open-concept living and dining areas provide a welcoming atmosphere, with a cozy gas fireplace in the living

Marilyn Profit Coldwell Banker Realty

15 Bristol Terrace Unit 15, Danbury, CT 06810
/40
$4,995,000
- 5 Beds
- 5.5 Baths
- 4,286 Sq Ft
29 Lockwood Dr, Old Greenwich, CT 06870

Stylish five-bedroom Contemporary provides a modern oasis with stunning pool, Ipe wood decks and secluded backyard on a quiet drive south of the village near shops, trains, school and beach. Striking architectural details ranging from maple wood floors, glass stair railings on three levels, high ceilings, expansive windows, sliding doors and skylights enhance 4,286 sq. ft. interior. Boasts sleek

Julie Lowe Houlihan Lawrence

29 Lockwood Dr, Old Greenwich, CT 06870
/33
$4,995,000
- 5 Beds
- 5.5 Baths
- 4,286 Sq Ft
29 Lockwood Dr, Old Greenwich, CT 06870

Stylish five-bedroom Contemporary provides a modern oasis with stunning pool, Ipe wood decks and secluded backyard on a quiet drive south of the village near shops, trains, school and beach. Striking architectural details ranging from maple wood floors, glass stair railings on three levels, high ceilings, expansive windows, sliding doors and skylights enhance 4,286 sq. ft. interior. Boasts sleek

Julie Lowe Houlihan Lawrence

29 Lockwood Dr, Old Greenwich, CT 06870
/18
$299,090
- 1 Bed
- 1 Bath
- 654 Sq Ft
29 Van Buren Ave Unit H2, Norwalk, CT 06850

This Highview East Condo is a delightful first floor 1-bedroom end unit with an updated kitchen and flooring, offering spacious living areas and an in-unit washer and dryer. It provides access to a summer pool and is conveniently located near a mall, medical facilities, and highway access. It's a great opportunity for ownership instead of renting.

Leigh Ann Lengyel Clarke Cappello Realty

29 Van Buren Ave Unit H2, Norwalk, CT 06850
/7
$7,995,000
- 8 Beds
- 11.5 Baths
- 10,646 Sq Ft
68 Dearfield Dr, Greenwich, CT 06831

Perched high on a hill in downtown Greenwich, 66 Dearfield is unparalleled in its grandeur with over 10,000 square feet of luxury living spanning 4 floors. Close to Greenwich Library, Greenwich Avenue, the train and all downtown amenities. This exquisite colonial boasts stone chimneys with extra height ceilings on each floor. Upon entry, the 2 story foyer nestled between the living room and

Nina Frandson BHHS New England Properties

68 Dearfield Dr, Greenwich, CT 06831
/22
$425,000
- 2 Beds
- 1.5 Baths
- 1,100 Sq Ft
160 Fairfield Woods Rd Unit 2, Fairfield, CT 06825

Nestled in a sought-after community, this charming townhouse offers the perfect blend of convenience and comfort. Ideally located near two universities, grocery stores, shopping, restaurants, town beaches, and with easy access to major highways, this home is perfect for those looking for both accessibility and a peaceful setting. The first floor features a well-appointed kitchen that flows into a

Katerina Hendrickson Coldwell Banker Realty

160 Fairfield Woods Rd Unit 2, Fairfield, CT 06825
/41
$10,950,000
- 6 Beds
- 7.5 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
$4,999,000
- 4 Beds
- 4.5 Baths
- 5,885 Sq Ft
10 Surf Rd, Westport, CT 06880

Offered for the first time in over 50 years, this cherished, custom-built waterfront retreat on Bermuda Lagoon is an extraordinary find. Lovingly maintained and never flooded, 100 feet of private beach, a deepwater dock, and breathtaking views of Long Island Sound and Bermuda Lagoon. Designed for year-round enjoyment, the home's soaring ceilings and expansive windows perfectly frame the stunning

Inna Agujen Coldwell Banker Realty

10 Surf Rd, Westport, CT 06880
/42
$8,950,000
- 10 Beds
- 9 Baths
- 9,483 Sq Ft
14 Meadow Dr, Greenwich, CT 06831

DISCOVER BREEZEMORE 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 Greenwich, this property stands

Ryan Hoffman Houlihan Lawrence

14 Meadow Dr, Greenwich, CT 06831
/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
/5
$891,000
- 4 Beds
- 2.5 Baths
- 2,933 Sq Ft
61 Maler Ave, Shelton, CT 06484

Opportunity awaits with this expansive and inviting home, perfectly situated in the heart of Shelton. Featuring a large, open layout and modern finishes, this property is designed for both comfort and style. The cozy backyard offers a private oasis, ideal for relaxation or entertaining friends and family. Located in a highly sought-after neighborhood, this home provides unparalleled convenience,

Jonathan Gineo Silver and Oak Realty

61 Maler Ave, Shelton, CT 06484
/51
$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
/40
$4,600,000
- 4 Beds
- 3.5 Baths
- 4,636 Sq Ft
87 Red Coat Rd, Westport, CT 06880

MOST UNIQUE HOUSE IN WESTPORT LARGE LOG HOME ON THE RIVER THAT IS STOCKED WITH TROUT. INGROUND GUNITE POOL BEAUTIFUL GROUNDS VERY PRIVATE ONE FLOOR LIVING. 4 BEDROOMS 3.5 BATHS. 1 HOUR TO NYC BEACH ACCESS. WONDERFUL RARE OPPORTUNITY TO OWN THE HOME YOU HAVE ALWAYS WONDERED ABOUT. THE BEAUTIFUL TRANQUIL RIVERVIEW LODGE LOG HOME THAT SITS ON THE MAJESTIC SAUGATUCK RIVER. WITH OVER 500+ FEET OF

Rebecca Ellsley Higgins Group Bedford Square

87 Red Coat Rd, Westport, CT 06880
/33
$2,595,000
- 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
/24
$1,375,000
- 2 Beds
- 2 Baths
- 1,265 Sq Ft
41 Richmondville Ave Unit 109, Westport, CT 06880

The Mill Westport offers high-end luxury living with all the amenities of a fine custom home in the heart of downtown Westport. With a concierge on-site and approximately 10,000 square feet of spectacular interior and exterior amenity spaces such as The Great Room & Cafe, Pool, Health & Wellness Center, Patio & Rooftop Deck, residents will enjoy carefree, 5-star living. The 31 residences feature

Doug Bross Coldwell Banker Realty

41 Richmondville Ave Unit 109, Westport, CT 06880
/39
$7,999,999
- 6 Beds
- 10 Baths
- 15,399 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
/35
$44,600,000
- 6 Beds
- 8 Baths
- 12,492 Sq Ft
545 Indian Field Rd, Greenwich, CT 06830

An idyllic coastal resort, this regal stone Georgian features 450 feet of direct waterfront acreage with expansive water views of the Long Island Sound to the NYC skyline, inside the exclusive Mead Point Association with 24hr guard-gated security. Masterfully designed and meticulously constructed in 2014 with inspiration from the original 1928 stone manor, this sophisticated residence offers

Leslie McElwreath Sotheby's International Realty

545 Indian Field Rd, Greenwich, CT 06830

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