Fairfield County Real Estate

Welcome to Fairfield County, located in the picturesque state of Connecticut! Known for its charming towns, beautiful coastline, and rich history, Fairfield County offers a unique blend of suburban tranquility and urban sophistication.

With its proximity to New York City, Fairfield County is a popular choice for those seeking a peaceful retreat while still having easy access to the bustling city life. The county is home to a variety of communities, each with its own distinct character and amenities.

From the historic streets of Greenwich to the vibrant cultural scene in Stamford, Fairfield County has something to offer everyone. Outdoor enthusiasts will appreciate the county's numerous parks, beaches, and hiking trails, while foodies will delight in the diverse culinary options available throughout the area.

In addition to its natural beauty and recreational opportunities, Fairfield County boasts top-rated schools, making it an ideal location for families looking to settle down. Whether you're searching for a waterfront property, a historic home, or a modern condo, Fairfield County has a range of real estate options to suit your lifestyle.

Come discover all that Fairfield County has to offer - from its charming neighborhoods to its vibrant downtowns, this region truly has something for everyone. Experience the best of both worlds in Fairfield County, where small-town charm meets big-city convenience.

Newest Listings in Fairfield County

$460,000

2 Beds ⋅ 3 Baths ⋅ 24195198 MLS ⋅ Northbrook Of Monroe BLDG.

Welcome to Northbrook, one of Monroe's most desirable condominium communities. This exceptionally well-maintained, move-in ready townhouse offers a spacious open floor plan with vaulted ceilings, beautiful hardwood floors, and an updated kitchen. The inviting living room features a cozy fireplace and nearly floor-to-ceiling windows that showcase peaceful views of the pond and stream beyond. The adjacent screened porch provides another comfortable space to relax while enjoying the same scenic setting. The main-level primary bedroom suite offers convenience and privacy with a full bath, while the upper level features a second bedroom suite with its own full bathroom, making it ideal for guests or additional living space. The partially finished lower level provides flexible space for recreation, a home office, fitness area, or hobbies, along with a spacious storage room, utility room, and an attached one-car garage. Northbrook offers a park-like setting with beautifully maintained grounds, walking paths, gazebos, two in-ground swimming pools, tennis courts, and a clubhouse. Conveniently located near shopping, restaurants, parks, and major commuting routes, this home also benefits from Monroe's highly regarded public school system. A wonderful opportunity to enjoy low-maintenance living in a scenic community.

12 Wrabel Cir Unit 12, Monroe

$275,000

2 Beds ⋅ 1 Baths ⋅ 24195211 MLS ⋅ Heather Ridge BLDG.

Move right into this beautifully renovated 2-Bedroom, 1-Bath Ranch-style condo offering effortless one-level living with no stairs. Ideally situated on the main level, this turnkey home has been thoughtfully updated from top to bottom with today's most desirable finishes. The stunning new Kitchen features all-new appliances, including a stainless steel range and dishwasher, while the completely remodeled Bathroom showcases stylish tile-work, a double vanity, and a tub/shower combination. Fresh paint, elegant crown molding, new carpeting, premium luxury vinyl flooring and a new hot water heater complete the extensive list of upgrades. The bright and inviting Living Room is filled with natural light and opens through sliding glass doors to your own private patio-an ideal spot to enjoy morning coffee or unwind at the end of the day. The functional floor plan offers comfortable, low-maintenance living that's perfect for first-time buyers, down-sizers, or anyone seeking convenience without compromise. Just a short stroll to the fenced-in community in-ground pool, this home also offers ample parking and an unbeatable location close to shopping, restaurants, major highways, Metro-North Railroad and everything Shelton has to offer. Whether you're looking for a carefree lifestyle or a move-in ready home in a peaceful community, this exceptional condo checks every box.

49 Heather Rdg, Shelton

$2,195,000

5 Beds ⋅ 5 Baths ⋅ 24193848 MLS

An extraordinarily rare opportunity in Fairfield's coveted Winton Park Association. Offered for the first time in over 4 decades, this timeless 5-bedroom, 4.5-bath Colonial is set on nearly 2 breathtaking, park-like acres, offering estate-like privacy w/an unparalleled walk-to-town lifestyle. A gracious foyer welcomes you inside, where a magnificent staircase, wide-plank hardwood floors & exquisite millwork define the home's enduring character. Oversized windows & beautifully scaled rooms reflect craftsmanship rarely found today. The step-down living room showcases elegant paneling, custom built-ins & a wood-burning fireplace, while the formal dining room opens through French doors to a private patio for effortless indoor/outdoor entertaining. The spacious eat-in kitchen overlooks spectacular grounds & opens to a sun-filled family room w/custom built-ins, 2nd fireplace & French doors to an enchanting brick patio w/tranquil waterfall. Upstairs offers 4 spacious bedrooms & 3 full baths including a gracious primary suite w/abundant closet space & ensuite bath. Private guest suite w/separate entrance, vaulted ceilings, fireplace, 5th bedroom & full bath. Expansive, level grounds offer endless possibilities for a pool, pool house, ADU or future expansion in a setting rarely found just moments from downtown, Metro-North, award-winning schools & beaches. Complete w/natural gas, public sewer, irrigation & attached 3-car garage. A legacy property ready for its next chapter.

50 Brookbend Rd, Fairfield

$559,000

4 Beds ⋅ 3 Baths ⋅ 24195196 MLS

Welcome to 87 Jockey Hollow Road, a wonderful opportunity to own a charming home in one of Monroe's most desirable neighborhoods. Lovingly cared for over the years, this home reflects true pride of ownership and offers the perfect canvas for its next owner to make it their own. While some cosmetic updates and TLC will enhance its full potential, the home features a functional layout, generous living spaces, and a warm, welcoming atmosphere that has been enjoyed for years. Set on a beautiful property with plenty of outdoor space, the yard offers endless possibilities for gardening, entertaining, or simply relaxing in a peaceful setting. As a member of the sought-after Lake Estate Association, you'll enjoy access to the lake and the unique lifestyle it offers, including swimming, kayaking, fishing, and enjoying the natural beauty of the community. Located in the award-winning Monroe school district and just minutes from shopping, restaurants, parks, and major commuter routes, this home combines everyday convenience with the tranquility of suburban living. Whether you're looking to personalize your forever home or invest in a property with tremendous potential, this is an exceptional opportunity to build equity in a highly desirable location. Don't miss your chance to bring your vision and make this special property your own. Property SOLD AS-IS. Professional photos coming soon!

87 Jockey Hollow Rd, Monroe

$2,299,000

4 Beds ⋅ 6 Baths ⋅ 24187328 MLS

UNDER CONSTRUCTION - Photos are architectural renderings and are intended to illustrate the home's anticipated finished appearance. Actual finishes, materials, features, and landscaping may vary. Be the first to own this exceptional new luxury home in one of Weston's most desirable locations. Situated on approximately 2 private acres, this custom-designed 5,600 SF residence offers 4 bedrooms, 4 full bathrooms, 1 half bath, and a 3-car garage. Designed with luxury and comfort in mind, the home features soaring cathedral ceilings, an open-concept floor plan, a fireplace, a gourmet kitchen with premium appliances, a finished lower level, heat pump with central air, private well and septic, and a spectacular in-ground pool for exceptional indoor-outdoor living. There may be an opportunity to add select personal touches depending on the stage of construction. Don't miss this rare opportunity to own a brand-new luxury home in Weston. Specifications, dimensions, features, finishes, pricing, and completion timeline are subject to change without notice.

15 Cannondale Rd, Weston

$749,900

3 Beds ⋅ 3 Baths ⋅ 24194382 MLS ⋅ 442 BLDG.

Extremely spacious end unit with four floors of usable and move-in ready living space! Freshly painted, this unit is available for immediate occupancy. Special and custom features include a private side entrance with ramp for easy and/or handicap access to the unit and an elevator from the Entry Level to the Main Living Level where a light/bright and "dine-in" kitchen with stunning black granite countertops and stainless appliances, as well as a center island, is located. Also on this floor is the generous sized living/dining area with deck access. The Second Floor bedroom level has a full-size laundry adjacent to the primary bedroom which has a vaulted ceiling, bay window and en suite bath with heated floor, jetted tub and separate shower. The second/guest bedroom is also en suite. The Third Floor features a loft style 3rd bedroom with wall-to-wall carpeting, high ceilings and a Juliet balcony accessed through lovely French doors. The oversized and attached garage provides additional storage and an alternate entry to the unit. This entry level floor provides excellent space for a den/office arrangement or perhaps a home gym... Other plus features include central vac and hook-ups for a second laundry, plus full size bath. 442 is well-located with easy access to the RT 7 Connector, Merritt Pkwy and I-95, the recently updated and expanded MetroNorth RR station, as well as shopping and dining.

442 Main Ave Unit 8, Norwalk

$609,000

5 Beds ⋅ 2 Baths ⋅ 24195182 MLS

5 Bedroom / 2 Bath Multi-Family Rare opportunity to own a well-maintained two-family home, perfectly situated in the highly sought-after Paradise Green neighborhood! Enjoy a vibrant, walkable lifestyle just steps from local restaurants, the historic Green, weekly farmers markets, and lively seasonal concerts. This prime location offers unmatched convenience, with easy access to schools nearby. Commuters will appreciate being just a 2-minute walk to the Metro-North train station and 5 minutes to I-95, offering exceptional access rarely found with this much space and privacy. Each unit spans a generous 1,200 square feet, making this one of the larger multi-family offerings in the area. The first-floor unit features three spacious bedrooms and showcases brand new hardwood floors throughout, giving the space a fresh, move-in ready feel. The property sits on a very large lot, offering plenty of outdoor space for entertaining, recreation, or future possibilities. A standout feature is the oversized two-bay garage, complete with space ideal for a home office, studio, or additional storage. Property also features a new roof adding long term value and peace of mind. Whether you're seeking an investment property a multi-generational living arrangement, or an owner-occupied home with rental income potential, this property offers strong value in a sought-after, walkable location with unbeatable commuter access!

530 King St, Stratford

$1,949,000

4 Beds ⋅ 4 Baths ⋅ 24195155 MLS

Inspired by today's most sought-after Organic Modern homes, this custom residence blends clean architectural lines, warm natural materials, and highly functional living spaces to create a home that is as beautiful as it is livable. This newly constructed 4-bedroom, 3.5-bath custom home offers approximately 4,500 square feet of refined living on a private, level lot, showcasing exceptional quality, craftsmanship, and attention to detail throughout. The heart of the home is a designer kitchen featuring Thermador appliances, custom cabinetry, an oversized island, a dedicated bar area, and a fully equipped walk-in pantry with an additional sink, creating exceptional space for entertaining and everyday living. White oak flooring flows throughout, while 9-foot ceilings create an open, airy feel. The spacious living room is anchored by a gas fireplace and a dramatic 10-foot bifold door that opens to a covered porch and private, fully fenced level backyard. Upstairs, vaulted ceilings in the expansive primary suite and Jack-and-Jill bedrooms add architectural character and a sense of volume. Every bedroom features an ensuite bath and custom walk-in closet. The finished lower level provides exceptional flexibility for recreation, fitness, work, or guests. Set on a quiet neighborhood street just moments from Lake Mohegan with walkable access to local parks, close proximity to shopping and the Merrit this home offers a rare blend of thoughtful design, and everyday functionality.

125 Coleman Rd, Fairfield

$640,000

1 Beds ⋅ 3 Baths ⋅ 24195116 MLS ⋅ Oronoque Village BLDG.

Rare Golf Course Gem with Modern Open-Concept Living! Welcome home to 585 Pequot in Stratford's premier resort-style 55+ active adult community, Oronoque Village. Situated directly on the golf course, this sought-after Whittier model has been beautifully reimagined for today's active lifestyle with top-tier finishes from top to bottom. Step inside to discover a stunning, fully renovated Open-Concept Kitchen, a rare find in the Village, featuring sleek custom cabinetry, premium countertops, stainless steel appliances, and a seamless flow directly into the expansive living and dining areas. Bathed in natural light, the main living space boasts high vaulted ceilings, a cozy fireplace, and newer glass sliding doors that open to your private oversized deck with sweeping, unobstructed rare dual views of the 10th and 11th golf course holes. The main level designed for effortless single-level living offers a dedicated home office behind a stylish glass barn door, along with an updated full guest bath tastefully finished in marble that includes a convenient all-in-one washer/dryer for quick everyday loads. The primary suite serves as a peaceful retreat, complete with a custom closet system and an exquisitely updated private bath.

585 Pequot Ln Unit B, Stratford

$699,000

3 Beds ⋅ 2 Baths ⋅ 24194942 MLS

Move right in to this beautiful 3 bed/2 full bath Colonial in Norwalk's desirable Wolfpit neighborhood! Thoughtfully improved throughout, this home features a beautifully renovated eat-in kitchen, new roof with solar panels, new high-efficiency heating and central air system, new energy-efficient windows, upgraded electrical, and new hardwood floors installed throughout for timeless style and easy maintenance. Step inside to a warm and inviting living room featuring custom built-ins and a charming stone fireplace. The versatile family room/dining room provides the perfect space for entertaining and flows seamlessly into the updated eat-in kitchen, complete with sliding doors leading to the deck-ideal for indoor-outdoor living. A full bath completes the main level. Upstairs, you'll find generously sized bedrooms, including a spacious primary suite with vaulted ceilings and walk-in closet. Plus a bonus room in the basement for music, play or exercise. Conveniently located just minutes from shopping, restaurants, parks, major commuting routes, and the train, this move-in-ready home seamlessly blends classic charm with today's most desirable amenities.

53 Wolfpit Ave, Norwalk

$518,000

2 Beds ⋅ 2 Baths ⋅ 24195142 MLS ⋅ Rivington Landing (Pending Verification) BLDG.

The Taft New England blends timeless style with everyday comfort in a thoughtfully designed open-concept layout. An inviting foyer welcomes you into a beautifully appointed gourmet kitchen that seamlessly flows into the casual dining area and spacious great room, creating the perfect setting for entertaining or relaxing at home. The kitchen features generous counter space, a large center island with breakfast bar seating, and a pantry for added storage. Extend your living space outdoors with a large covered patio, ideal for morning coffee or evening gatherings. The private primary suite offers a spacious walk-in closet and a spa-inspired bath with dual vanities and a luxurious walk-in shower. A well-appointed secondary bedroom with ample closet space and a full bath provides comfort and privacy for guests or family members.

123 Woodland Rd Unit 1023, Danbury

$5,900,000

7 Beds ⋅ 8 Baths ⋅ 24194285 MLS

Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Thoughtfully conceived with elegant architecture, exceptional proportions, soaring 10-foot ceilings on the main level, 9-foot ceilings on the second floor and finished lower level, and light-filled interiors, the home blends sophisticated style with effortless everyday living. A stunning custom kitchen appointed with premium Thermador appliances anchors the home, flowing seamlessly into beautifully designed living and entertaining spaces. Superior materials, custom millwork, and bespoke finishes define every room, while 6 ensuite bedrooms in the main residence provide exceptional comfort. Elevator-ready! Walk-up attic offers added possibilities. Outdoors, beautifully landscaped grounds create a private resort setting featuring a spectacular saltwater pool and spa. A separate 550-square-foot guest/pool house/ADU offers ideal accommodations for guests, wellness, or entertaining, while the expansive property provides ample room for a future tennis or sport court. A rare offering in one of Westport's most coveted and prestigious locations, it's just minutes from Westport's bustling downtown, sunny beaches, and award-winning schools. This remarkable estate combines thoughtful design and an unparalleled lifestyle defined by privacy, bespoke design and high-end amenities. Still time to customize. Floor plans available

22 Cavalry Rd, Westport

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.