Fairfield Homes with Roger Ludlowe Middle school

Welcome to Fairfield, Connecticut, a picturesque town nestled along the stunning coastline of Long Island Sound. Known for its charming neighborhoods, vibrant community, and rich history, Fairfield is the perfect place to call home. With a blend of suburban tranquility and urban convenience, this town offers an exceptional quality of life for families, young professionals, and retirees alike.

One of the standout features of Fairfield is its commitment to education, particularly with the highly regarded Roger Ludlowe Middle School. Families seeking homes in this area can rest assured that their children will receive a top-notch education in a nurturing environment. The school is not just a place of learning; it’s a community hub where students thrive academically and socially, fostering a sense of belonging and camaraderie.

The real estate market in Fairfield boasts a diverse range of homes, from charming historic houses to modern builds, ensuring that there’s something for everyone. Whether you’re looking for a cozy cottage or a spacious family home, you’ll find properties that cater to your needs and lifestyle. The tree-lined streets and welcoming atmosphere make it an ideal setting for raising children, with plenty of parks, recreational facilities, and family-friendly events throughout the year.

Living in Fairfield means enjoying the best of both worlds—easy access to the bustling cities of New York and New Haven, while still being able to retreat to a peaceful home environment. With its excellent schools, beautiful landscapes, and strong sense of community, Fairfield truly offers an unparalleled living experience. Come explore this charming town and discover your dream home near Roger Ludlowe Middle School today!

Newest Fairfield Homes with Roger Ludlowe Middle school

$3,975,000

5 Beds ⋅ 5 Baths ⋅ COMING SOON Status ⋅ 24206348 MLS

Over an acre to yourself. The best of Fairfield within reach. In the heart of downtown Fairfield and the beach area, 415 Old Post Road offers something almost impossible to find: land and privacy to create a generational estate, with the life of a coastal town just beyond your gate. Only a handful of properties in the Sherman School district offer this. Fewer still could tell this story. The family who built this Italianate Victorian stayed for more than a century. Stand beneath its soaring ceilings, admire the craftsmanship, then step onto the screened-in porch. You begin to understand. Trees surround you. Church bells carry through the air. It feels like your own park. Yet the beach, schools, restaurants, shops and train are all within walking distance. For the current owners, that has meant children walking home from school with friends. Thanksgiving dinners for twenty. Additional bedroom options for overnight guests. Winter evenings around the parlor fire. A front porch filled with friends as the Memorial Day parade passes by. There is room here for the life you have imagined. Explore the possibilities for a pool, tennis court and gardens. Create a place where everyone gathers now-and where the next generation will want to return. Historic architecture. Meticulously maintained, thoughtfully updated and in pristine condition. A once-in-a-lifetime opportunity. Come discover what makes this place so hard to leave-and imagine what the next 50 years could look like.

415 Old Post Rd, Fairfield

$1,925,000

4 Beds ⋅ 4 Baths ⋅ COMING SOON Status ⋅ 24206227 MLS

Tucked at the end of a quiet Greenfield Hill cul-de-sac, 550 Wellington Drive feels like a true retreat-private, peaceful and designed for the way you actually want to live. Set on 2.47 secluded acres, this 4-bed, 4,776sqft home offers an exceptional amount of space to gather, entertain and spread out, with a floor plan that gives everyone a place of their own. The 1st floor is especially expansive, with a gracious living room, dramatic vaulted family room, oversized playroom, sunroom and sophisticated wood-paneled office-spaces that easily adapt for entertaining, working from home, play or simply finding a quiet corner to unwind. The kitchen sits at the heart of the home, creating an easy connection between everyday living and the many gathering spaces. Upstairs, four bedrooms provide a comfortable separation from the main living areas, complemented by recently updated bathrooms. Outside is where 550 Wellington truly becomes an escape. Surrounded by mature landscaping and complete privacy, the backyard resembles a private resort with pool, expansive deck, screened-in porch and abundant space for outdoor dining, entertaining and long summer days at home. A three-car garage completes the offering. Spacious yet inviting, private yet close to everything Greenfield Hill has to offer, 550 Wellington Drive is a homemade for gathering, entertaining and getting away-without ever having to leave home.

550 Wellington Dr, Fairfield

$1,495,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205674 MLS

SOUTHPORT CHARM, WALK TO EVERYTHING.... Ideally situated in the coveted town of Southport, this custom designer residence offers an exceptional opportunity to enjoy the very best that Southport has to offer. Thoughtfully designed for today's lifestyle to maximize both space, functionality and style, the home features an open-concept main level with seamless living offering gas fireplace, in-ceiling speakers, foyer w/glass staircase, Marvin floor to ceiling windows and KLAR steel doors. The bespoke kitchen features Aurea Stone island & floating display shelf, stainless Bosch appliances, induction range & wine cooler. The second floor is anchored by a fabulous primary suite featuring a custom walk-in closet and a beautifully appointed spa-worthy bathroom with soaking tub. An additional guest bedroom with ensuite bath and a light filled office complete the 2nd level. The 3rd floor loft space offers library/study space with custom built-in bookcases and bedroom with built-in bed. A fabulous light filled home with 6" white oak character hardwood flooring throughout. Work from home or work out at home with the temperature controlled detached office, gym or studio. Plentiful storage and large cedar closet in the finished lower level. Lovely outdoor entertaining space with evergreen privacy hedges, bluestone patio and outdoor speakers and wifi. An enviable location, timeless appeal, and the ease of having everything within reach make this a truly special offering.

624 Center St, Fairfield

$2,499,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24205683 MLS

Secluded Southport mini-estate built with character and attention to detail. Rarely do you find a home that needs nothing. Well loved and enhanced by the current owners including an upper level addition and expanded and renovated kitchen - the home and property have been improved and updated throughout their stewardship. Set on a gentle knoll at the end of a gated drive, enjoy sprawling lawns, professional landscaping and lighting, an inviting heated Gunite pool and enviable privacy. The exterior is further enhanced with a detached barn/garage, a treehouse featured in magazines and a sport court. Fall in love and watch the seasons change on your wraparound front porch. The recently renovated kitchen will delight every home chef. The kitchen and dining is open to a very spacious family room with fireplace, making entertaining a pleasure. Upstairs the romantic and secluded primary suite includes a full bath, plus a separate sitting room/study that is well suited for use as a home office, nursery or dressing room. There are now 3 additional family bedrooms plus two additional full baths. The finished lower level provides great play space and additional living area to enjoy. Gracious, tasteful finishes throughout with meticulous attention to maintenance and quality materials. This is an opportunity to truly have it all.

245 Cedar Rd, Fairfield

$2,690,000

5 Beds ⋅ 5 Baths ⋅ COMING SOON Status ⋅ 24205145 MLS

A rare Greenfield Hill find, 1074 Sturges Highway pairs the presence of a classic Colonial with a sleek, thoroughly modern point of view. Thoughtfully reimagined, the home retains its original craftsmanship while introducing clean-lined updates and a minimalist sensibility that feels chic, current and effortless. Inside, the balance between old and new is masterfully struck. Original millwork and architectural details are paired with elegantly edited finishes, creating spaces that feel sophisticated without ever tipping into formal. The layout flows naturally for everyday living, with room to gather, entertain and simply enjoy the house. Set on over 2 acres of impeccably manicured and extremely private grounds, the property offers a rare sense of seclusion. A gorgeous patio with fireplace extends the living space outdoors, setting the scene for summer dinners, cocktails and fireside evenings. A newly constructed garage with loft above adds flexibility for a home office, studio, gym or creative retreat. Where classic architecture meets a fully modern point of view, 1074 Sturges Highway is a masterclass in understated sophistication - Greenfield Hill living, reimagined. Fairfield Schools: Dwight, Ludlow, Ludlow.

1074 Sturges Hwy, Fairfield

$1,699,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205064 MLS

Welcome to 160 Cedar Road, a truly special farmhouse in Southport that has been thoughtfully renovated and reimagined. Filled with warmth, character, and modern updates, this unique property beautifully blends timeless charm with contemporary comfort. Privately set and abutting Aspetuck Land Trust property, the 2-bedroom, possible 3-bedroom, 1.5-bath home enjoys a beautiful natural setting on 4.45 acres while being conveniently close to all that Southport and Fairfield have to offer, including beaches, shopping, restaurants, I95 and the train. The property features a saltwater inground pool, pool cabana, tanning deck, and outdoor shower-creating an exceptional setting for relaxing and entertaining. Three barns, a fenced paddock, and riding ring, along with additional outbuildings and a partially fenced yard, offer tremendous versatility. Rarely does a property combine this much character, thoughtful renovation, privacy, and natural beauty with such a convenient location. 160 Cedar Road is a truly unique property offering a lifestyle unlike any other. Please no driving down driveway without a confirmed appointment- trespassers will be fed to the pigs!

160 Cedar Rd, Fairfield

$2,395,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24203568 MLS

This beautifully crafted 4,600 sq. ft. Colonial, built by renowned builder Frank Dooley, combines exceptional craftsmanship with thoughtful design. Located on a welcoming cul-de-sac in lower Greenfield Hill, the home features spacious rooms with clear sightlines that create a comfortable flow. At the center of the home, a generous kitchen seamlessly connects to the dining area and one of two large stone patios, ideal for both everyday living and entertaining. The expansive family room and elegant front-to-back living room each feature a fireplace, while a charming sunporch offers a cozy retreat. A finished bonus room above the garage provides flexible space for 5th bed, media room. Upstairs, four spacious bedrooms include a well-appointed primary suite with 2 full baths, an ensuite bedroom, and two additional bedrooms sharing an updated hall bath. Abundant custom built-in storage throughout and a finished third floor office enhances the home's versatility. The level, fenced, and beautifully landscaped 2+acres, designed by Oliver's Nursery, features irrigation and outdoor lighting. A 11'-23' room accessible from the yard and garage offers extra storage with finishing potential. Enjoy the convenience of walking to local shops and the farmers market, with easy access to downtown Fairfield, Merritt Pkwy, and I-95. This home offers effortless living in a prime location where everyday life feels relaxed and refined.

128 Cobblers Hill Rd, Fairfield

$849,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24203937 MLS

Tucked on a tree-lined side street in the desirable University neighborhood, this charming and spacious home is beautifully maintained and updated throughout! The inviting exterior features bluestone steps, stone accents, updated siding, garage doors and windows. Inside, hardwood floors flow throughout the main level with an open-concept layout ideal for everyday living and entertaining. The spacious living room features built-ins and a wood-burning fireplace with an insert that provides an additional heat source in winter. The dining room opens to the kitchen, featuring white shaker cabinetry, granite countertops, butcher block island, pantry, glass tile backsplash and access to the back deck and yard. A private office and updated powder room complete the main level. Upstairs are three generously sized bedrooms with large closets and an updated full bath. The finished lower level offers a family room, additional office or guest space with barn doors, built-in desk or dry bar area and laundry room with storage. An attached 2-car garage provides abundant space. Additional updates include the boiler, electrical panel, gutters, roof, interior doors and more! Ideally located in the heart of town, just 7 minutes to downtown and the train!

87 Oxbow Rd, Fairfield

$2,095,000

6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24202996 MLS

Just a few blocks from the Greenfield Hill Green, an extraordinary opportunity awaits: a beloved estate, held by the same owners for more than 20 years, now reimagined for its next chapter. Taken virtually to the studs and thoughtfully rebuilt, much of the transformative work has already been done - creating the rare opportunity to step in at an exciting moment and complete a nearly 9,000-square-foot home entirely to your own vision. A new roof, siding, insulation, Marvin windows and doors, subflooring, extensive plumbing rough-ins and mechanical systems are among the significant improvements already in place, along with an exceptional newly built four-car garage. What remains is the rewarding part: the finishes, details and personal choices that will make it yours. Set on one of Greenfield Hill's picturesque properties, the home's generous, light-filled floor plan was designed for both everyday living and effortless entertaining. The main level flows between expansive living and family rooms, an eat-in kitchen, office, mudroom and potential first-floor en-suite bedroom. Upstairs, beautifully proportioned en-suite bedrooms offer privacy and flexibility, while the space above the four-car garage presents the potential for a private two-bedroom, two-bath guest or in-law suite with its own entrance.

201 Whites Hill Ln, Fairfield

$995,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24203183 MLS ⋅ Sherman Court BLDG.

Simply move in and enjoy...it's all been done for you! This beautifully renovated condo offers an easy, turnkey lifestyle in a private enclave tucked at the end of a cul-de-sac just steps from the heart of vibrant downtown Fairfield. WALK to everything! Enjoy restaurants, shopping, coffee shops, live music, theaters, town green, farmer's market, public Library, & Metro-North train station just 3 blocks away. Inside, the open-concept layout is designed for comfortable everyday living & effortless entertaining. The Living Room w/ fireplace & Dining Room flow seamlessly into the beautifully updated Kitchen featuring granite countertops, soft-close cabinetry & abundant custom storage. Stainless steel appliances include a beverage fridge & warming drawer. The vaulted Family Room offers wonderful flexibility & can easily serve as a 3rd Bedroom, guest suite or home office, complete with walk-in closet & direct access to full Bathroom. Upstairs, the Primary Bedroom features a vaulted ceiling & great closet space. An additional Bedroom, laundry area & renovated full Bathroom with jetted tub, double vanity & heated towel bar complete the upper level. Recent improvements include new stairwell carpeting, HVAC, dishwasher, fridge, 2nd level flooring, washer & dryer. A rare opportunity to enjoy the very best of IN-TOWN living without sacrificing privacy and tranquility. Leave the car at home, stroll into town or catch the train to NYC...WELCOME home to your own peaceful retreat.

146 Sherman Ct, Fairfield

$1,299,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201368 MLS

A coveted combination of coastal privacy, walkable convenience and exceptional outdoor living, this exquisitely updated Cape in Fairfield's coveted Beach neighborhood offers an enviable lifestyle just minutes from the shoreline, Southport Village, Metro North train, Par 3 golf, and local favorites. Recent updates include a brand-new HVAC system and updating to natural gas, adding comfort & efficiency and the installation of a full fenced yard adding peace of mind and privacy. A major renovation and addition completed in 2018 added a dormer, roof, windows, mudroom, fireplace, bathroom, and other thoughtful improvements. Filled with natural light and timeless character, the home features an inviting living room with a striking stone fireplace and a spacious kitchen with white shaker cabinetry, leathered granite countertops, stainless steel appliances, and a generous island making meal prep a cinch. An open dining area is perfect for entertaining, while the mudroom offers everyday functionality and direct access to the deck. Outdoor living truly shines with an oversized Trex deck and bluestone patio overlooking peaceful marsh views and the private, fully fenced yard. Enjoy morning coffee, summer dinners, or evenings gathered around the fire pit. With its stylish updates, new HVAC, private fenced grounds, and coveted Beach location, this home offers a refined Fairfield lifestyle where coastal charm meets modern comfort and everyday ease.

877 S Pine Creek Rd, Fairfield

$899,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24203108 MLS

A ranch in Fairfield's Beach neighborhood offering easy one-level living. The home features 2 bedrooms, 1 full bath, hardwood floors throughout and a kitchen with inset cherry cabinetry, granite countertops and stainless steel appliances. Living room with fireplace and built-in shelving. Full unfinished basement provides additional storage. Attached one-car garage, paved driveway and level yard. Located in the Roger Sherman Elementary, Roger Ludlowe Middle School and Fairfield Ludlowe High School district. Convenient to Fairfield beaches, downtown, train station, shopping and restaurants.

73 Alden St, Fairfield

Start Your Search

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.