Refine Search
Sort by
$629,000
4 Beds 2 Baths 24196770 MLS
Traditional on the outside and surprisingly spacious on the inside, this University cape is freshly updated and is ready for its next owners. A sun-filled living room welcomes guests a it features a bay window and gleaming hardwood floors which extend throughout bedrooms on the main and upper levels. A total of four bedrooms ( two on the main level and two upper) feature potential dining and home office use. Refreshed kitchen with stainless steel appliances, subway backsplash, two full bathrooms are in move-in ready condition. A breezeway, mud room links the attached garage for all weather coverage. A full walk-out basement leads to a private patio and peaceful back yard. The generous sized lower level also includes a washer/dryer, extra refrigerator, workshop and space for a possible home gym and additional storage. Ideally located minutes from town, medical facilities, two train stations, schools, shopping, Merritt and I-95.

438 High St, Fairfield

$869,000
3 Beds 2 Baths 24205513 MLS
One of the best side street locations in Fairfield's University neighborhood! This updated single family home is so close to all town amenities: the train, center of town, highways and Black Rock Turnpike! Beyond location, this home has newly refinished hardwood flooring and fresh paint throughout offering bright living spaces, lots of storage and a gorgeous fully-fenced in backyard! Just off Mill Plain Rd, this home is on a dead-end side street with open space across the street, a perfect combo offering privacy within a neighborhood setting! Featuring 3 bedrooms, 1.5 bathrooms and many newer features for high efficiency living like new central air in 2025, updated furnace, 200 amp electric, windows, and an updated kitchen with pantry! The main floor has an open floor plan with a large living room, dining room, kitchen and family room. All 3 bedrooms are upstairs along with a full bathroom and large linen closet. The spacious bonus room is a walk-out featuring a half bathroom with laundry and full-size windows for lots of light. Other features include an attached 1 car garage and large deck and pea-stone patio overlooking the flat yard. This home is stunning with a great property, close to everything. What a charming place to call home!

65 Cynthia Dr, Fairfield

$1,399,000
4 Beds 4 Baths 24205035 MLS
Step into a storybook setting of Fairfield's "CT Cotswolds." This 1931 custom-built Cape Colonial is a masterclass in timeless elegance, where old-world character seamlessly blends w/high-end modern comforts. From the moment you cross the flagstone-covered front porch & enter the foyer, the home's heritage shines through the graceful curved staircase & rich wide-board flooring. The main level is designed for both sophisticated entertaining & quiet relaxation. The impressive LR anchors the home w/its wood-burning FP & beamed ceilings, while the formal DR delights w/artisan details like classic corner cabinetry. For those seeking a quiet retreat, the sun-drenched den serves as the perfect library or bright home office. At the heart of the home, the gourmet chef's kitchen is a showstopper. Vaulted, beamed ceiling & expansive windows frame views of the lush grounds, while Viking appliances, granite countertops, & clever storage solutions cater to the most ambitious culinary pursuits. The 1st flr Primary suite is a sprawling sanctuary featuring b/i closets, bath w/dbl shower, & private sitting room for peaceful mornings. Upstairs, 3 add'l bright BRs & FBA. The fin LL is the ultimate destination for game days, complete w/wet bar, b/ins, 1/2 bath, office space. Outside, the property transforms into a private oasis. Exquisite perennial gardens wrap the home in color, providing a stunning backdrop for alfresco dining. It's more than just a house; it's a retreat that feels like HOME.

394 Wakeman Rd, Fairfield

$1,499,000
4 Beds 3 Baths 24204891 MLS
Welcome to 50 University Dr, where character, craftsmanship, and comfort come together effortlessly. Tucked into one of the most coveted enclaves near Fairfield University, this colonial-style home was custom built from the foundation up in 2021 with refined finishes and carefully selected upgrades. Outside: cedar shake siding, Azek pergola and trim, Trex decking, oversized Nicolock patio, horseshoe driveway, Marvin windows and doors, and a full-house generator. The landscaped grounds include a "dog proof" fully fenced backyard. Inside, 8" white oak floors run throughout, with high ceilings, modern trim, neutral paint, and brass and aged brass hardware. The kitchen connects to the garage and sits between the family and dining rooms for effortless entertaining. A walk-in pantry doubles as "kitchen overflow" to hide clutter. It's finished with custom cabinetry, Bosch SS appliances, quartz counters, and a large island with hidden storage and seating for 3. The 1st floor also offers a formal living room with custom marble-surround gas fireplace, a full bath, and a bedroom that works as an office or guest room. Upstairs, the primary suite features a tray ceiling, large walk-in closet, and spa-like bath with heated tile floor, double vanity, and glass-door tiled shower with heated seat. 2 more bdrms have vaulted ceilings, ceiling fans, and closet systems, served by a 3rd full bath. Timeless character and lasting quality, ready from day one.

50 University Dr, Fairfield

$849,000
3 Beds 2 Baths 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

$1,225,000
3 Beds 3 Baths 24203250 MLS
Walk to Town, Train, Fairfield U, University Area Location. 2/3 acre. Ample Living Space. Character. A stand out in its price range w/ NEW ROOF! Rarely does one find a quintessential center hall colonial w/ abundant architectural details, charm, condition & updates, all in the heart of Fairfield! Travel down the long private drive to the secluded garden & up the charming porch. Inside, the Formal Dining Room & Living Room each flow effortlessly to the Great Room & Kitchen. The LR impresses with original wide plank flooring, space, fireplace and french doors to the Great Room. There, walls of windows overlook a sunny & delightful view of the expansive rear property. Wainscot accents, sliders, dining area and red brick floor beneath it all complete the space. Columns lead to an open kitchen where the home's vintage flair truly comes to life. Solid wood cabinetry, copper sink, even a rotary dial wall phone! Beyond, the hall leads to a tasteful powder room w/ pocket door, laundry, pantry, and steps down to a traditional family room w/vaulted ceiling & beams. Here, cozy up to a second fireplace. More sliders lead to the rear brick patio, while additional entries allow access to the front garden and garage. Upstairs features a primary suite w/ modern bath, vaulted ceilings & beams, two guest bedrooms, one w/door to 2nd fl. deck, modern hall bath, and hardwood throughout. Roof '26, Washer/Dryer '26, Front Door '25, Deck '23, Furnace '21, Siding '17, MBTH '15, Addition '04.

130 Elm St, Fairfield

$1,900,000
5 Beds 6 Baths 24199415 MLS
MOVE IN READY. Nestled on a rare one-acre lot, this stunning home offers 4,180 sq ft of above-grade living space. Situated in the highly desirable University area of Fairfield, it features 5 beds/5.5 baths. The heart of the home is a culinary masterpiece with GE Monogram appliances, shaker style cabinets, premium quartz countertops and a large kitchen island. The kitchen opens to a sunlit breakfast area, and to an open-concept dining and family room with a dry bar, gas fireplace and a spacious deck overlooking a secluded serene backyard. A coveted fully self-sufficient ground-floor suite for multi-generational living or guests is included with its own dedicated vented laundry, a rare premium offering! The primary suite serves as a private, spa-inspired sanctuary with cathedral ceilings, a sprawling floor-mounted custom walk-in closet and a luxurious bath with high end fittings. A private balcony off the bedroom offers an intimate retreat to unwind. Enjoy total privacy with a protected rear buffer ensuring no future development, professionally landscaped lawn and garden path-way and a custom built firepit. Amenities include a home office, walk-in pantry, two covered parking spaces & a two car attached garage. The home is close to beaches, schools and downtown. A commuters dream with close access to Metro North stations for a seamless commute to NYC. 1 year AllShield Home Protection incld. Original 1400 sq' built 1919-Complete renovation/New Construction 2026. Owner/Agent.

1964 N Benson Rd, Fairfield

$1,499,900
4 Beds 4 Baths 24199290 MLS
Exceptional opportunity to own what is essentially a brand-new home in Fairfield University area. Expanded with a full second-story addition and reconstructed from the original foundation up, this remarkable residence offers 3,290 square feet of beautifully finished living space with virtually every major component newly built. Designed for today's lifestyle, the open-concept floor plan features 4 bedrooms, 4 full baths, and flexible living space across three levels. The heart of the home is a stunning chef's kitchen with Thermador appliances, quartz countertops, abundant cabinetry, and a large island, opening to a dining room with coffered ceilings, and seamless flow into the living room, creating an ideal setting for both everyday living and entertaining. A first-floor bedroom and full bath provide flexibility for guests, a home office, or multigenerational living. The second floor features a spacious primary suite with a walk-in closet and beautifully appointed primary bath, along with two additional bedrooms, another full bath, and a conveniently located laundry room. The finished third floor offers a spacious office with glass French doors, valuable bonus space perfect for a playroom, media room, or guest retreat, along with a full bath. Beyond the attractive finishes, conveniently located near Fairfield's beaches, train stations, shopping, dining, parks, and top-rated schools, 694 Jennings Road offers a rare combination of modern design, turnkey living.

694 Jennings Rd, Fairfield

$1,549,000
5 Beds 4 Baths 24198508 MLS
Featured in Fairfield Magazine, this beautifully restored 1834 Cape Cod farmhouse blends nearly 200 years of history, character & modern luxury in the sought-after Osborn Hill School District. Thoughtfully expanded over 30 years by its owners, including an accomplished NYC designer, this 5BR home retains exposed beams, wide-plank floors, handcrafted millwork & multiple fireplaces. A welcoming front porch leads to a charming parlor w/FP & French doors, 1st-floor office w/built-ins, formal DR w/exposed barnwood & FP, plus a 1st-floor BR w/FP. The chef's kitchen features custom cabinetry, granite counters, oversized island, 6-burner range, wine fridge & premium appliances, opening to a sun-filled family room w/wood-paneled ceiling. 1.5 updated baths & a spacious laundry room complete the main level. Upstairs, the primary suite offers exposed beams, built-ins, WIC & spa bath w/heated floors, soaking tub, dual vanities & oversized shower, plus 2 BRs w/Juliet balconies. The attached barn is an entertainers dream w/soaring ceilings, bamboo floors, barnwood bar & stone gas FP, plus an ensuite guest BR, 2nd office & fitness/flex space. The oversized garage includes an art/craft studio w/cedar closet. Outside, the private landscaped yard invites garden parties & quiet evenings alike, w/stone patio, outdoor LR w/stone FP, dining area, bar, hot tub, outdoor shower & firepit. Minutes to downtown, beaches, Black Rock, Metro-North, shopping & dining. Very special, once-in-a-lifetime home!

2580 N Benson Rd, Fairfield

$649,000
3 Beds 2 Baths 24196297 MLS
Welcome to this beautiful home at 681 Jennings Rd, Fairfield, CT! This well-maintained property offers a flexible and functional layout with 3 bedrooms and 2 full bathrooms. The second floor features two spacious bedrooms, a full bathroom, and beautiful hardwood floors. The main level includes an additional bedroom, a bright living room and dining room with hardwood flooring, a beautifully remodeled kitchen, and a full bathroom for added convenience. A partial finished basement. Ideally close to shopping, restaurants, schools, parks, Fairfield's beautiful beaches, the train station, and major highways, this home offers both comfort and convenience. Whether you're looking for your first home, downsizing, or seeking a great investment opportunity, this property is ready for you to move in and enjoy.

681 Jennings Rd, Fairfield

$2,699,000
5 Beds 6 Baths 24195451 MLS
There's a certain kind of iconic home that settles over you the moment you step inside, because the craftsmanship was never meant to be temporary. Nine-foot ceilings in the living & dining rooms, 3 wood-burning fireplaces, solid proportions & large windows & glass doors that still frame the light the way they were designed to nearly a century ago. The kind of quiet authority that newer construction spends a fortune trying to approximate. The current owners understood the assignment. They preserved what mattered & refined the rest without ever losing the house's original voice. The original 1929 paneled den with a hidden wet bar. A family room built for actual gathering, complete with Sub-Zero, beverage fridge & kegerator. The gourmet kitchen opens directly onto an oversized patio so the line between inside & outside nearly disappears. 5/6 beds, 5.5 stunning baths, two staircases, a first-floor office, & a walk-out lower level with its own entrance & full bath give the house a flexibility that feels intentional. Outside, 1+ acres sit quietly behind stone walls - already equipped with a grilling station, a built-in fire pit, irrigation, & the soft structure of mature plantings, privacy & play space. You can walk to Fairfield's vibrant downtown, the Metro-North station to NYC, & schools. You border lovely Winton Park. Natural gas, city water, town sewer. Some homes you tour. This one stays with you. A spectacular house with a soul.

1123 Round Hill Rd, Fairfield

$1,399,000
4 Beds 4 Baths 24194703 MLS
This brand-new construction showcases an elite architectural design that prioritizes complete autonomy. The two separate units share absolutely no living space walls-the only common point is the garage wall,ensuring the noise control and privacy of a fully detached single-family home. NO HOA Each residence features its own distinct, privately sectioned, and fully fenced yard, creating a personal space for your outdoor activities. Step inside to a dramatic airy open concept layout. Custom cabinets in a earthy taupe shade, waterfall quartz countertops adorn the large island with plenty of space for company. Open floor plan with a banquet area for dining table. Sweeping throughout the home is natural 4in white oak flooring. Sun drenched rooms create a warm inviting atmosphere. Flexible luxury living offering 4 bedrooms or 3 Bedrooms with a 3rd floor complete with modern full bath, optional 4th bdr, office etc. The lower level is also finished with luxury plank flooring heat/Ac ...gym or media room? Each bathroom impeccably styled with clean lines and modern finishes, the primary suite bath is truly a lavish retreat with spa shower, soaking tub and highlighted by a sleek floating double vanity. Location is key and this address delivers a lifestyle of ultimate convenience: Schools, a mere stones throw from top rated holland hill, currently ludlowe school district and 3 min to FFld University. The Coast: 1.3 miles to 5 miles of sandy shores, bike routes and marina.

30 Country Rd, Fairfield

$589,000
3 Beds 2 Baths 24191581 MLS
An amazing opportunity to own in a highly desirable University neighborhood - Welcome home to 245 Oakwood Drive. Distinguishable features include a picture perfect move in ready home, hardwood floors, an updated kitchen with granite countertops, freshly painted cabinetry and natural sunlight that brightens daily living. The main level presents beautifully with a bright and inviting living room, connected to the eat-in kitchen. With a split level layout, an additional large family room on the lower level, and bedrooms on the upper level are all steps away. Upstairs, three well-appointed bedrooms offer flexibility for family, guests, or work. The finished lower level adds living space with a comfortable family room and half bath. Ideal for movie nights, a playroom, home office, or workout area. For convenience, the storage room in the lower level walks out to the back yard. Set on a level .14-acre corner lot in one of the neighborhood's quieter streets, this picturesque home combines a peaceful setting with an exceptional location. With quick access to I95 and the Merrit Pkwy, nearby shopping, restaurants, award winning schools, and parks, you will spend most of your time just minutes from your own home. Few locations offer the balance of neighborhood charm and everyday convenience. This home offers so much and holds great value. A beautiful home awaits!

245 Oakwood Dr, Fairfield

$625,000
3 Beds 1 Baths 24186541 MLS
SELLER OFFERING $12,000 TO BUYER @ CLOSING!! Ideally situated in a highly convenient location, this home offers easy access to shopping, dining, schools, parks, transportation and everyday essentials within easy reach. Enjoy the ideal balance of comfort and accessibility, with everything you need just moments from your front door. This home has an open floor plan that connects the kitchen to the dining area with an easy entrance from the back of the home. The main level also has a generous size living room and a bedroom with a full bath. Upstairs, you will find two beautifully appointed bedrooms that are filled with natural light, creating bright and inviting retreats to unwind at the end of the day. The spacious lower level offers exceptional flexibility for today's lifestyle. Featuring two separate finished rooms on opposite sides of this level providing the perfect opportunity to create distinct living spaces. One room can serve as a family room or media room for movie nights, while the other is ideal for a recreation room, music studio, gym or playroom. With ample room to spread out, this versatile lower level adapts easily to your needs. Step outside to a generous sized back yard and two car detached garage. With its spacious layout, flexible living areas and a location close to everything, you will be impressed with the value that 439 Stillson Road provides

439 Stillson Rd, Fairfield

$1,790,000
5 Beds 6 Baths 24146666 MLS
Set on a cul-de-sac in Fairfield's sought-after University area, this custom-built 5-bedroom, 6-bath residence was originally designed as the developer's own home, with a focus on natural light, architectural detail, and elevated everyday living. The primary suite features soaring 18-foot cathedral ceilings, a custom white oak ceiling treatment, an 11-foot picture window, and a spa-inspired bath. A 300-square-foot covered balcony with 18-foot ceilings extends the living experience outdoors and serves as one of the home's defining spaces. Designed for both entertaining and everyday living, the home includes a gourmet kitchen with Sub-Zero refrigeration, quartzite countertops, custom cabinetry, an oversized island, and a fully outfitted butler's pantry with additional refrigeration, wine storage, a dishwasher, and prep space. Three additional bedrooms offer en-suite baths, while the finished third level provides flexible space for a home office, recreation room, guest suite, or studio. The walk-out lower level offers versatility, with a full bath and ample space for a home gym, recreation room, extended living arrangement, or potential in-law suite. Outside, a flat backyard, mature maple tree, and fire pit create a welcoming setting for entertaining. Combining custom craftsmanship, thoughtful design, and refined finishes throughout, 309 Hunyadi Avenue presents a rare opportunity to own a newly constructed residence in one of Connecticut's most desirable towns.

309 Hunyadi Ave, Fairfield

$1,199,000
3 Beds 3 Baths 24166766 MLS
Turnkey, beautifully renovated & expanded...this home feels like NEW! This University home tucked away in one of the sweetest neighborhoods...so convenient to downtown, restaurants, train, beaches, shopping and walk to elementary, park, ballfield & pickleball. Featuring a flexible floor plan w/over 2,100 sq.ft. including 3 spacious bedrooms (main level option or office), 3 full designer bathrooms, gorgeous chef's kitchen w/center island, quartz counters, Thermador appl's, walk-in pantry, mudroom w/deck access, large open great room, eating area, dining room with fireplace and gorgeous full bathroom. The second floor includes a stunning primary suite with a luxury bathroom, heated floor & sleek tile and walk-in closets, an additional large bedroom, full hall bathroom and laundry closet on large landing. The finished lower level offers additional sq.ft...playroom, yoga, etc. and conveniently located one car attached garage. Enjoy the expansive yard with room for a pool and large driveway. See attached list for special features/upgrades.

27 Brookdale Rd, Fairfield

$2,199,999
6 Beds 7 Baths 24160360 MLS
Exceptional new construction in the desirable University area, scheduled for completion in Fall 2026. Built by an experienced local builder known for quality craftsmanship and thoughtful design, this impressive home offers 4,709 square feet across four levels, including a walk-out lower level. Designed for modern living, the home features 6 bedrooms and 5.5 baths, providing flexibility for guests, home offices, or multi-generational living. The open and functional layout includes a beautifully designed kitchen with a generous walk-in pantry conveniently located between the kitchen and dining room, perfect for entertaining and everyday living. Enjoy seamless indoor-outdoor living with a deck off the kitchen and a patio from the walk-out lower level, offering multiple spaces to relax or entertain. The primary suite is a true retreat, featuring two walk-in closets and a spa-like bath. Additional highlights include a two-car attached garage, impeccable design throughout, and high-end finishes that reflect the builder's commitment to quality. Ideally situated on a quiet street with easy access to downtown, beaches, schools, and shopping, this home offers the perfect combination of luxury, space, and convenience.

280 Tuckahoe Ln, Fairfield

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.