Fairfield County CT Homes for Sale with Pool

• 

  

  

  /41

  $800,000

  • 4 Beds
  • 2.5 Baths
  • 3,277 Sq Ft

  754 Milltown Rd, Brewster, NY 10509

  The Crown Jewel of Milltown Road! Enter through stone pillars accented by a beautiful white picket fence! Set on three private, level, landscaped acres along the Brewster/Danbury border, this custom-built Colonial offers a rare blend of seclusion, convenience, and long-term value—enhanced by the advantage of Danbury taxes. Meticulously built and maintained by its current owners, this home is

  Filiz Dalo Coldwell Banker Realty

  754 Milltown Rd, Brewster, NY 10509
• 

  

  

  /39

  $2,995,000

  $355K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,789 Sq Ft

  221 Greens Farms Rd, Westport, CT 06880

  The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and

  Patricia Shea Coldwell Banker Realty

  221 Greens Farms Rd, Westport, CT 06880
• 

  

  

  /18

  $585,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,138 Sq Ft

  2 Ken Oaks Dr, Danbury, CT 06810

  Extremely well cared for home - Shows like a new home! really does! hardwood flrs throughout- corner double lot, with finished lower level ready to move in - Very close to I84 and RT 7...Danbury Mall and Danbury Airport- this home will not disappoint!

  Jorge Sousa Clearview Realty LLC

  2 Ken Oaks Dr, Danbury, CT 06810
• 

  

  

  /39

  $1,899,000

  • 4 Beds
  • 5 Baths
  • 3,921 Sq Ft

  2177 Cross Hwy, Fairfield, CT 06824

  2177 Cross Hwy welcomes you home. This extensively renovated iconic contemporary awaits your personal touches. The blending of dramatic architecture with everyday comfort, offering nearly 4,000 sq ft of functional living space designed for gathering, relaxing and entertaining. Soaring 22' ceilings, oversized windows and park-like views fill the main living area with light, while a striking

  JaKeith Action Jackson ASJ Realty Partners

  2177 Cross Hwy, Fairfield, CT 06824
• 

  

  

  /40

  $679,000

  • 2 Beds
  • 2.5 Baths
  • 1,719 Sq Ft

  2435 Bedford St Unit 17B, Stamford, CT 06905

  Quiet oasis with Mid-City convenience! Welcome to this spacious, airy 2-bedroom, 2.5-bath townhome in the coveted, gated Chesterfield II community-where comfort, convenience, and lifestyle meet seamlessly. Designed for everyday living and entertaining, the open-concept layout features a dining room and living room with a cozy fireplace and sliders to a private deck surrounded by mature trees -

  Geri Guzinski William Pitt Sotheby's Int'l

  2435 Bedford St Unit 17B, Stamford, CT 06905
• 

  

  /38

  $897,000

  • 4 Beds
  • 1.5 Baths
  • 1,771 Sq Ft

  5 Caddy Rd, Norwalk, CT 06851

  Nestled on a level, park-like half-acre in the desirable Cranbury neighborhood, this beautifully updated contemporary ranch offers 4 bedrooms, 1.5 baths, and the perfect blend of modern updates, warmth, and exceptional indoor-outdoor living. Filled with natural light from skylights in the living room, dining room, and primary bedroom, the home features open living and dining spaces with

  Ninfa Valella Coldwell Banker Realty

  5 Caddy Rd, Norwalk, CT 06851
• 

  /2

  $5,980,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 10,521 Sq Ft

  21 Sturges Commons, Westport, CT 06880

  NEW CONSTRUCTION TO BE BUILT IN THE COVETED HUNT CLUB NEIGHBORHOOD - Renowned, luxury builder Mattera Construction is well-known for architecturally significant & stunning modern homes filled with elegance, timeless beauty, custom interiors with state-of-the-art amenities. Now offering a perfectly designed 6 bedroom home finished on 4 levels filled with elegant finishes, well sited on a quiet

  Patricia Shea Coldwell Banker Realty

  21 Sturges Commons, Westport, CT 06880
• 

  

  /45

  $1,295,000

  • 2 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  51 Forest Ave Unit 172, Old Greenwich, CT 06870

  Experience sophisticated one-level living in this exceptional top-floor end unit in the heart of Old Greenwich. A dramatic living room with fireplace and soaring ceilings flows into a spacious dining area and inviting den space with sliders to a private deck--ideal for both elegant entertaining and everyday comfort. The sun-filled eat-in kitchen overlooks beautifully landscaped grounds, while the

  Patricia Cameron BHHS New England Properties

  51 Forest Ave Unit 172, Old Greenwich, CT 06870
• 

  

  /36

  $680,000

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft

  19 Junction Rd, Brookfield, CT 06804

  Discover exceptional country living in this updated vintage colonial set on a sprawling 2.5 acre private lot. This charming home is the perfect blend of classic architecture with modern amenities. Enjoy expansive outdoor space with a stunning stone heated pool and wonderful covered patio great for relaxation or entertaining. Inside the home boasts spacious living areas enhanced by large bay

  Laurie Levitt William Pitt Sotheby's Int'l

  19 Junction Rd, Brookfield, CT 06804
• 

  /2

  $6,999,999

  New Construction

  • 6 Beds
  • 9 Baths
  • 10,521 Sq Ft

  32 Narrow Rocks Rd, Westport, CT 06880

  NEW CONSTRUCTION BY RENOWNED LUXURY BUILDER MATTERA CONSTRUCTION - STEPS TO COMPO BEACH! A rare opportunity to own a brand-new, architecturally refined home in one of Westport's most coveted coastal locations-just steps to Compo Beach, Longshore Club, downtown Westport, the train, and schools. Currently under construction, this impeccably designed 6-bedroom residence spans four finished levels

  Judy Michaelis Coldwell Banker Realty

  32 Narrow Rocks Rd, Westport, CT 06880
• 

  

  /36

  $1,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,308 Sq Ft

  145 Pine Hill Rd, New Fairfield, CT 06812

  Welcome to 145 Pine Hill Rd. A renovated Organic Modern home mixing both modern amenities and rustic charm. Adorned with random plank flooring, hand-hewn beams and massive field stone fireplace. The 12ft sliders in the Living Room allow for access onto the spacious deck. The culinary space is a chef's haven, equipped with state-of-the-art appliances & premium finishes that inspire culinary

  Cheryl Finley Coldwell Banker Realty

  145 Pine Hill Rd, New Fairfield, CT 06812
• 

  

  /36

  $85,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft

  32 Greenlawn Dr, Danbury, CT 06810

  Enjoy easy living and one-level living in this affordably priced mobile home, located in a desirable 55+community. It offers an open floor plan and a wonderfully bright eat-in-kitchen. Relax outdoors on the covered patio or deck, no matter rain or shine. The community features a pool and clubhouse. It's located on the shores of Danbury's Lake Kenosia and is minutes from dining, shopping and

  Julie Thompson Coldwell Banker Realty

  32 Greenlawn Dr, Danbury, CT 06810
• 

  

  /40

  $5,650,000

  New Construction

  • 7 Beds
  • 9 Baths
  • 8,762 Sq Ft

  8 Pleasant Valley Ln, Westport, CT 06880

  Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft

  Doug Bross Coldwell Banker Realty

  8 Pleasant Valley Ln, Westport, CT 06880
• 

  

  /34

  $7,495,000

  • 6 Beds
  • 11 Baths
  • 7,528 Sq Ft

  229 Umpawaug Rd, Redding, CT 06896

  Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor plan, formal and informal rooms, embracing the incredibly private 6.5 acres of hand-stacked walls, privacy gates and

  Stacy Young William Raveis Real Estate

  229 Umpawaug Rd, Redding, CT 06896
• 

  

  /40

  $4,750,000

  • 6 Beds
  • 6.5 Baths
  • 6,829 Sq Ft

  234 Brookside Rd, Darien, CT 06820

  Set along a picturesque stretch in one of Darien's most sought-after neighborhoods, 234 Brookside Road offers a rare blend of timeless architecture, privacy, and modern comfort. Surrounded by mature trees and beautifully landscaped grounds, this exceptional property provides a serene, retreat-like setting just minutes from town, top-rated schools, and the coastline. This HOBI award-winning

  Kristin Nemec William Pitt Sotheby's Int'l

  234 Brookside Rd, Darien, CT 06820
• 

  

  /40

  $699,000

  • 4 Beds
  • 5 Baths
  • 4,360 Sq Ft

  31 Pole Bridge Rd, Sandy Hook, CT 06482

  Stunningly Updated Ranch close to Treadwell Park and the Award-Winning Aquila's Nest Vineyards! This beautiful 4 BEDROOM, 5 FULL BATH home boasts soaring ceilings and bright open spaces. You'll love the gorgeous "Chef's" kitchen with high-end stainless appliances, white quartz counters, expansive dining area, and a cozy sitting area looking through oversize windows to the wide open backyard! The

  Robert Morey RE/MAX Right Choice

  31 Pole Bridge Rd, Sandy Hook, CT 06482
• 

  

  /15

  $6,995,826

  New Construction

  • 6 Beds
  • 10 Baths
  • 8,417 Sq Ft

  24 Edgemarth Hill Rd, Westport, CT 06880

  This Beauty will be ready Summer 2026! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted

  Jaclyn Picarillo Higgins Group Bedford Square

  24 Edgemarth Hill Rd, Westport, CT 06880
• 

  

  /7

  $10,650,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,100 Sq Ft

  11 Dogwood Ln, Westport, CT 06880

  Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

  Jen Kass Higgins Group Bedford Square

  11 Dogwood Ln, Westport, CT 06880
• 

  

  /69

  $7,450,000

  • 6 Beds
  • 7 Baths
  • 6,972 Sq Ft

  736 Lake Ave, Greenwich, CT 06830

  Timeless 1925 Colonial reimagined for modern living. Set on oversized, stunning 3.43 private acres in a coveted Mid-Country Greenwich location, this exceptional estate offers over 7,000 square feet of beautifully updated living space. Thoughtfully transformed, the home seamlessly blends the architectural character and craftsmanship of a bygone era with sleek contemporary design and today's most

  Stephen Archino Sotheby's International Realty

  736 Lake Ave, Greenwich, CT 06830
• 

  

  /38

  $1,598,000

  • 5 Beds
  • 3.5 Baths
  • 3,264 Sq Ft

  91 Lockwood Rd, Fairfield, CT 06825

  Welcome to 91 Lockwood Road, where modern farmhouse charm meets elevated design. Nestled in one of the area's most desirable neighborhoods, this beautifully reimagined home offers the perfect blend of style, comfort, and functionality. Designed for today's lifestyle, this home offers 5-6 bedrooms, 3 full baths, and 1 half bath, along with an open-concept floor plan that seamlessly connects the

  Susan Bento Distinct Realty

  91 Lockwood Rd, Fairfield, CT 06825
• 

  

  /36

  $525,000

  Open Sun 12PM - 2:30PM $14K PRICE DROP

  • 1 Bed
  • 2.5 Baths
  • 1,633 Sq Ft

  638 Onondaga Ln, Stratford, CT 06614

  Step into the possibilities of this beautifully updated, ideally located Emerson-style condo in the lively 55+ community of Oronoque Village. Thoughtfully renovated, the home features gleaming hardwood floors, a brand-new kitchen, and stylishly updated baths. Designed for easy single-level living, the main floor welcomes you with a bright, open-concept living and dining space, highlighted by a

  Sailoz Sikka William Raveis Real Estate

  638 Onondaga Ln, Stratford, CT 06614
• 

  

  /29

  $750,000

  Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 4,323 Sq Ft

  26 Mountain Laurel Ln, Sandy Hook, CT 06482

  Welcome to this beautifully updated Colonial situated on a private, lightly wooded lot in Sandy Hook. Thoughtfully maintained and move-in ready, this home offers the perfect blend of comfort, style, and convenience. The updated kitchen features quartz countertops, modern cabinetry, and newer stainless-steel appliances, creating an ideal space for everyday living and entertaining. Spacious living

  Christopher Glahn William Pitt Sotheby's Int'l

  26 Mountain Laurel Ln, Sandy Hook, CT 06482
• 

  

  /47

  $13,100,000

  • 6 Beds
  • 8 Baths
  • 10,286 Sq Ft

  7 Parsonage Rd, Greenwich, CT 06830

  SUMMER FUN BEGINS HERE! An extraordinary newly constructed residence in the heart of Greenwich,7 Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously

  Leslie McElwreath Sotheby's International Realty

  7 Parsonage Rd, Greenwich, CT 06830
• 

  

  /36

  $765,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,046 Sq Ft

  148 Osborn Ln, Monroe, CT 06468

  Price Improved! Discover one of Monroe's most versatile properties, offering a rare opportunity to own a spacious single-family home with a fully permitted accessory apartment-all under one roof and eligible for conventional single-family financing. The heart of the main home is a stunning open-concept living space featuring a show-stopping kitchen with a large center island, vaulted ceilings

  Julie Avellino Connecticut Realty Studios LLC

  148 Osborn Ln, Monroe, CT 06468
• 

  

  /38

  $3,575,000

  • 4 Beds
  • 7 Baths
  • 5,958 Sq Ft

  610 Cheese Spring Rd, New Canaan, CT 06840

  Welcome to this stunning custom shingle-style residence set amid sweeping lawns, mature flowering trees, and beautiful natural surroundings in one of New Canaan's most picturesque settings.This exceptional 4/5-bedroom residence blends timeless New England architecture with modern living and refined architectural detail throughout. The cathedral-ceiling living room with fireplace, walls of

  Bettina Hegel Brown Harris Stevens

  610 Cheese Spring Rd, New Canaan, CT 06840
• 

  

  /40

  $5,199,000

  New Construction Open Sun 12PM - 4PM

  • 6 Beds
  • 8 Baths
  • 8,935 Sq Ft

  4 Sycamore Dr, Westport, CT 06880

  Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is this new construction home built by CCO Habitats. Three levels of finished living space with ten foot ceilings on the first floor give an amazing sense of openness, as well as better functionality than four level homes. Think about it. Who really wants to walk up to the third floor every day? That's

  Maryann Levanti Higgins Group Bedford Square

  4 Sycamore Dr, Westport, CT 06880
• 

  

  /36

  $650,000

  • 3 Beds
  • 3.5 Baths
  • 1,900 Sq Ft

  29 Greystone, Shelton, CT 06484

  ***Seller will entertain offers between $610K - $650K*** Welcome to this wonderful 1900 sq foot ranch-style unit at Greystone on the Lake complex in the Huntington area; Shelton's highly desired and sought-after community. It is conveniently located in a wooded private setting yet just a few minutes to shopping, dog park, walking trails, library, golf course, Merritt Pkwy, Route 8 - and just

  Anthony Parenti Berkshire Hathaway NE Prop.

  29 Greystone, Shelton, CT 06484
• 

  

  /17

  $5,997,000

  • 6 Beds
  • 8.5 Baths
  • 6,860 Sq Ft

  14 5 Mile River Rd, Darien, CT 06820

  Designed by custom home builder Vita Design, this exciting newly constructed modern residence is a refined architectural statement that balances scale and light, capturing direct 5 Mile River views and a connection to its natural surroundings. Finished across four levels, the home features dramatic 10- and 16-foot ceilings and a main level wrapped in floor-to-ceiling European-style windows

  Jennifer DaSilva Mixer William Raveis Real Estate

  14 5 Mile River Rd, Darien, CT 06820
• 

  

  /15

  $225,000

  $70K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 939 Sq Ft

  50 Glenbrook Rd Unit 1F, Stamford, CT 06902

  Welcome to 50 Glenbrook Road #1F, a move-in ready 1-bedroom condominium in a convenient Stamford location. This bright and inviting unit offers a spacious layout with generously sized rooms, an updated feel, and abundant natural light throughout. The well-appointed kitchen provides ample cabinet space and opens to a comfortable dining area, while the living space is perfect for everyday living

  Adam Wagner Keller Williams Prestige Prop.

  50 Glenbrook Rd Unit 1F, Stamford, CT 06902
• 

  

  /25

  $349,000

  • 1 Bed
  • 2 Baths
  • 1,279 Sq Ft

  211 Windgate Cir Unit B, Monroe, CT 06468

  Welcome to The Hills of Monroe! This spacious and versatile one-level ranch-style condo offers the ease of low-maintenance living in one of Monroe's most desirable condominium communities. Featuring 1 bedroom plus a potential second bedroom, home office, or den, and 2 full bathrooms, this home provides flexibility to fit your lifestyle. The inviting living room is the heart of the home, complete

  Liz Moretti BHGRE Gaetano Marra Homes

  211 Windgate Cir Unit B, Monroe, CT 06468
• 

  

  /31

  $1,290,000

  • 5 Beds
  • 4.5 Baths
  • 5,169 Sq Ft

  29 Alpine Rd, Monroe, CT 06468

  Tucked away in one of Fairfield County's most desirable suburban settings, this exceptional property offers over 4,000 square feet of beautifully designed living space including an in-law apartment. The main house includes 4 bedrooms and 2.5 bathrooms, with an incredible combination of comfort, flexibility, and outdoor living. From the moment you arrive, the impressive 4-car garage, expansive

  Michael Dziedzic Precision Realty LLC

  29 Alpine Rd, Monroe, CT 06468
• 

  

  /39

  $1,250,000

  • 5 Beds
  • 6 Baths
  • 4,703 Sq Ft

  9 Damia Dr, Danbury, CT 06811

  Set within a private gated community, this thoughtfully designed residence is defined by its sense of space, flexibility and a layout that feels both open and intentional. With five bedrooms, four full baths and two half baths, the layout includes a two primary suites with ensuite bathrooms, providing versatile living arrangements suited for a variety of needs. On the main level, the layout

  Lisa McDonald The Brokerage of New England

  9 Damia Dr, Danbury, CT 06811
• 

  

  /38

  $1,699,000

  $139K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 5,385 Sq Ft

  7 Long Meadow Ln, Redding, CT 06896

  Sweeping meadow views, privacy & sunsets from an elevated setting 7 Long Meadow Lane is a distinctive property defined by its scale, setting, and versatile layout, offering generous proportions and an architectural presence that supports a wide range of lifestyles. Sited on an elevated, scenic 4.39 acres with exceptional privacy and open meadow outlooks, the home enjoys a peaceful setting

  Linda Sweeny William Raveis Real Estate

  7 Long Meadow Ln, Redding, CT 06896
• 

  

  /40

  $1,300,000

  • 2 Beds
  • 3.5 Baths
  • 2,088 Sq Ft

  88 Southfield Ave Unit P6, Stamford, CT 06902

  Welcome to 88 Southfield Avenue, a spectacular two level penthouse offering 2,088 square feet of luxury living with breathtaking views of Stamford Harbor. This 2 bedroom, 3.1 bath residence is an entertainer's dream, featuring expansive balconies on both levels, stunning harbor views throughout, and soaring 14-foot ceilings on the upper level. The eat-in kitchen offers a comfortable dining area

  Kristen Studwell Compass Connecticut, LLC

  88 Southfield Ave Unit P6, Stamford, CT 06902
• 

  

  /21

  $899,000

  • 4 Beds
  • 2 Baths
  • 1,737 Sq Ft

  73 High Clear Dr, Stamford, CT 06905

  Charming and beautifully maintained 1956 Cape Cod offering timeless character with thoughtful updates throughout. This inviting 4-bedroom, 2-bath home features an updated kitchen, warm and comfortable living that creates exceptional curb appeal. Enjoy outdoor entertaining or quiet relaxation on the private patio surrounded by established landscaping. A perfect blend of classic charm and modern

  James Capparelle Coldwell Banker Realty

  73 High Clear Dr, Stamford, CT 06905
• 

  

  /25

  $800,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,788 Sq Ft

  95 Wildwood Dr, Stratford, CT 06614

  Welcome home to 95 Wildwood Drive! This meticulously maintained Colonial offers 2,388 sq ft above grade plus an additional 1,400 sq ft of finished lower-level space, all just minutes from Rt. 8 and Rt. 15, as well as nearby restaurants, Jones Family Farms, and Two Roads Brewery. The home features 4 bedrooms, 2.5 bathrooms, flexible options for dedicated home offices, a formal dining room, and a

  Matthew Boateng Coldwell Banker Realty

  95 Wildwood Dr, Stratford, CT 06614
• 

  

  /7

  $245,000

  • 1 Bed
  • 1 Bath
  • 703 Sq Ft

  30 Rollingwood Dr, Brookfield, CT 06804

  Beautifully kept and updated. Directly off federal rd Brookfield.

  Cody Ruschmeyer New England Realty

  30 Rollingwood Dr, Brookfield, CT 06804

Showing Results 481 - 517, Page 13 of 13