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195 Rock Major Rd, Fairfield
$900,000
3 Beds ⋅ 2 Baths ⋅ 24215095 MLS
Tucked along one of the University Area's peaceful, tree-lined streets, 195 Rock Major Road presents a rare opportunity to call one of Fairfield's most coveted neighborhoods home. Properties offering this combination of location, generous land, and character seldom come to market, making this three-bedroom ranch an exciting find. Set on over half an acre, the home offers privacy, space, and possibility. An expansive kitchen with ample room to cook, gather, and entertain opens directly onto a south-facing deck. Oak hardwood floors, timeless built-ins, and wood-burning fireplaces bring warmth and character, setting the scene for leisurely mornings, shared meals, fireside evenings, and cherished moments with family and friends. Outdoors, the generous grounds invite a spirited game of catch, gardening, or simply savoring the tranquility of the surrounding landscape. An attached two car garage adds to the ease of living. With its enduring charm, versatile living spaces, and the exceptional potential to make it your own, this special Fairfield property offers a compelling opportunity for you to create a truly memorable home for years to come.

195 Rock Major Rd, Fairfield

125 University Dr, Fairfield
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 24215209 MLS
Set on 0.24 acres in one of the most sought-after pockets of the University Area, this expanded cape/colonial is ready for its next owner. The backyard is one of the home's best features: sunny, private, and fully fenced, with plenty of room to play. Summer evenings are made for dinner on the deck, watching the sun go down. Inside, the home balances casual, open living with quieter formal spaces. The updated kitchen, with new cabinetry, quartz countertops, and stainless appliances, is the natural gathering spot. It opens to a flexible space that works as a den or a larger informal dining area. A sunny breakfast nook leads through French doors onto the deck. A family room with a wood-burning stove offers a cozy retreat on cooler nights, and a charming dining room also opens to the deck, making indoor-outdoor dining effortless. Upstairs are three bedrooms and two full baths. The primary suite steals the show, with soaring ceilings, a generous walk-in closet, and a bath with double vanities and a jetted soaking tub. A second oversized bedroom offers plenty of space, and the third bedroom is perfect as a home office or guest room. The lower level adds a partially finished space ready for a gym, playroom, or media room, plus an unfinished area for storage. Great location, flexible space, and room to grow. This is the one you've been waiting for.

125 University Dr, Fairfield

45 Dogwood Ln, Fairfield
$1,185,000
4 Beds ⋅ 3 Baths ⋅ 24213952 MLS
Picturesque University Colonial, beautifully set in one of Fairfield's most sought-after neighborhoods! Welcome to 45 Dogwood Lane, a home filled w/ warmth, character & an ideal design for everyday living. Step inside & instantly feel at home! There is so much to love about this special property & home & so much the current homeowner will truly miss, from the welcoming neighborhood & its beloved block parties to the 2 wood burning fireplaces that bring warmth & coziness + the privacy & of the backyard & the list goes on! The main level features a sun-filled living room w/ hardwood floors & wood burning fireplace, flowing into a delightful sun porch, the perfect spot to relax. The dining room is ideal for hosting, while the eat-in kitchen offers Quartz countertops & stainless-steel appliances. The expansive family room is truly this home's gathering spot, featuring a 2nd wood burning fireplace, hardwood floors, custom built-ins & sliders leading to your private backyard & a expansive deck - perfect for outdoor dining, Summer gatherings & making memories in your new home. Upstairs 4 large bedrooms await, all featuring hardwood floors. The primary bedroom suite offers a walk-in closet & skylight, creating a nice retreat. Beyond its wonderful living spaces, this home offers the lifestyle buyers are looking for. Ideally located minutes from downtown Fairfield, top-rated schools, beautiful beaches, restaurants & shopping. 45 Dogwood Lane is a special place to call home!

45 Dogwood Ln, Fairfield

35 Highlawn Rd, Fairfield
$739,900
2 Beds ⋅ 2 Baths ⋅ 24214956 MLS
Welcome to 35 High Lawn Road in Fairfield! This beautifully maintained, move-in-ready ranch offers comfortable one-level living, inviting outdoor spaces, and a wonderful setting for everyday enjoyment. Featuring 2 bedrooms, 2 full baths, central air with heat pump and a finished lower level providing additional versatile living space, this home is exceptionally clean and ready for its next owner. Step outside to enjoy the beautiful, level lot with a fenced-in backyard and inviting in-ground pool, perfect for relaxing, entertaining, and making the most of the warmer months. Additional amenities include central vacuum and an irrigation system. Ideally situated for convenience, with easy access to shopping, downtown Fairfield, Metro-North, I-95, and the Merritt Parkway. A wonderful opportunity to enjoy easy one-level living, a private outdoor retreat, and an excellent location. Come see all that this special home has to offer!

35 Highlawn Rd, Fairfield

9 Millspaugh Dr, Fairfield
$899,000
3 Beds ⋅ 2 Baths ⋅ 24212765 MLS
Welcome to this charming Cape nestled on a desirable, well-established street in the sought-after University area. Full of warmth and character, this inviting home features beautiful hardwood floors throughout the main living level areas, an updated kitchen and a refreshed downstairs bathroom. The home offers 3 bedrooms with the upstairs rooms providing additional flexibility for bedrooms, a home office or a nursery. The finished lower level adds valuable living space with comfortable bonus rooms perfect for a family room, office, playroom, gym or guest space along with additional storage. Outside enjoy a nicely sized yard, a fully fenced backyard offers privacy and plenty of room for entertaining. It also offers a perfect blend of convenience and lifestyle. Enjoy easy access to both I-95 and the Merritt Parkway, as well as the Metro-North Train station. Fairfield's vibrant downtown and beautiful beaches make this an ideal location. Make this charming home the setting for your next Thanksgiving gathering and many wonderful memories to follow.

9 Millspaugh Dr, Fairfield

280 Brookbend Rd, Fairfield
$1,549,000
4 Beds ⋅ 3 Baths ⋅ 24212214 MLS
AN EXTRAORDINARY HOME. AN EXCEPTIONAL LIVING EXPERIENCE IN WINTON PARK. Welcome to one of the most exciting homes to hit the market! Rarely does a home offer such an experience at every turn. From the moment you enter, you are greeted by soaring ceilings, dramatic architectural details, and incredible expanses of glass letting the outside in. This is a home where nature becomes part of your everyday living. Beautifully maintained and thoughtfully updated, this remarkable residence has a fabulously designed kitchen - one you'd love spending time in. An inviting dining room highlighted by a stunning exposed brick accent wall, sets the stage for memorable gatherings and a dining experience that is anything but ordinary. And everyone loves a sunroom! Two separate living spaces each with a stunning architecturally designed fireplace, four generously sized bedrooms including a beautiful en suite primary retreat. And then there is the yard - truly magical! Set on nearly an acre of lush, rolling and level grounds, with a collection of charming outdoor vignettes creates distinct spaces for entertaining, relaxing and gathering with friends. The custom-enclosed garden with water source is a gardeners dream. Every turn there is something to discover, something to appreciate. This is not simply a home to see, it is a home to experience and an experience you won't soon forget.

280 Brookbend Rd, Fairfield

72 Old Barn Rd, Fairfield
$2,399,000
4 Beds ⋅ 4 Baths ⋅ 24212223 MLS
Winton Park is the type of address that people in Fairfield already know by name. Incorporated by special act in 1937, it is a private association spanning an est. 70 acres on just a few tree-lined streets w/stone pillars at the entrances, one-acre zoning, mature plantings, & the quiet authority of an established, walkable neighborhood. People call it "downtown's Greenfield Hill" for a reason. You get the soft structure & privacy of the Hill, & you are still inside the life of town. Introducing 72 Old Barn Road. This classic colonial has front & back staircases, a covered front entry, wood-burning fireplace, a screened porch & a private backyard w patio & built-in firepit. Hardwood floors run through the house, with charming design details & generous closets throughout.The large front-to-back chef's kitchen has top-of-the-line appliances and a large center island that seats six. Upstairs are 4/5 bedrooms & 3 full baths, including an oversized primary suite w/ a vaulted ceiling & large, walk-in closet. Beside it, a private second-floor office w/custom built-ins overlooks the backyard. A finished lower level offers room for a playroom & gym, den or game room. Winton Park is a neighborhood that cannot be replicated. Downtown Fairfield, shops, restaurants, theaters & Main Library, & Fairfield University are all right there. Ludlowe Middle School, Fairfield Ludlowe High School & the Metro North Station are a short walk or an easy bike ride away, along quiet side roads.

72 Old Barn Rd, Fairfield

38 Milandale Rd, Fairfield
$865,000
4 Beds ⋅ 2 Baths ⋅ 24212800 MLS
Set on a tranquil street in a convenient Fairfield location, this Colonial offers a versatile floor plan with plenty of room to live, relax, and entertain. Situated on a level quarter acre property within walking distance of the elementary school, the home features generous indoor and outdoor living spaces, freshly painted interiors, and beautifully refinished hardwood floors. The inviting living room features a classic brick fireplace framed by rich mahogany trim, adding warmth and character. At the back of the home, a sun drenched family room welcomes an abundance of natural light, with sliding doors opening to a wraparound deck overlooking the expansive, level backyard. The main level also features three bedrooms and a full bath, offering flexibility for guests, a home office, or everyday living. Upstairs, a spacious bonus room provides additional living space, while the primary suite features cathedral ceilings, a generous walk-in closet, and a private bath with a stall shower. A two-car garage adds everyday convenience and additional storage. Just five minutes from Metro North and Fairfield's vibrant downtown, with shopping, restaurants, parks, and schools nearby, this home offers an appealing combination of convenience, comfortable living spaces, and a flexible layout to accommodate a variety of lifestyles.

38 Milandale Rd, Fairfield

295 Reid St, Fairfield
$749,900
3 Beds ⋅ 2 Baths ⋅ 24212796 MLS
Step into a home where decades of memories have been made-and where the potential for its next chapter is truly exciting. Tucked away at 295 Reid St, this quintessential 3 bedroom, 2 bathroom Cape Cod is a hidden gem, offering classic charm, solid bones, & an incredible opportunity to create something uniquely your own. Lovingly cared for over the years, this home is functional & ready to enjoy from day one. The traditional interior provides a wonderful foundation for those looking to add their own personal style. With thoughtful updates & a little vision, this home has the potential to shine while offering the opportunity to build meaningful equity just minutes from Fairfield University in one of the town's most desirable locations. The main level features a comfortable, easy-flowing layout with a convenient bedroom & full bathroom. Upstairs, 2 additional spacious bedrooms showcase the timeless character & charm of a classic Cape. Need more space? The unfinished lower level opens the door to endless possibilities-a future recreation room, home gym, office, workshop, or creative studio. Then there's the location. Enjoy all that Fairfield has to offer while staying perfectly positioned for commuters, convenient access to the train station & major highways, getting to NYC, surrounding communities, & throughout the tri-state area is remarkably easy. Opportunities to find a well-loved home with this much potential in such a sought-after location don't come around often.

295 Reid St, Fairfield

41 Reynolds Dr, Fairfield
$1,399,000
4 Beds ⋅ 3 Baths ⋅ 24212212 MLS
Nestled on a quiet cul-de-sac in Fairfield's sought-after University neighborhood, this timeless Colonial combines the feel of new construction with exceptional character & craftsmanship. Completed in late 2022, this nearly 3,400 SF, 4-bed, 2.5-bath home is filled with natural light & elevated by custom millwork, shiplap, steel railings & thoughtful architectural details. The open first floor features 9' ceilings and a gourmet kitchen w/ custom cabinetry, quartz countertops and high-end appliances, flowing seamlessly to the family room anchored by a gas fireplace. Sliding French doors open to an AZEK deck and manicured, level lawn, creating an ideal setting for indoor/outdoor entertaining & everyday living. A generous dining room, w/ custom built accent wall, is perfect for holidays or casual gatherings, while the spacious, thoughtfully designed mudroom connects directly to the attached 2-car garage. Upstairs, the impressive Primary Suite features 2 walk-in closets, including a custom dressing closet, and spa-like bath w/ soaking tub & glass shower. 3 add'l bedrooms, all w/ walk-in closets, plus a 4-piece hall bath & dedicated laundry complete the 2nd floor. The beautifully finished lower level offers a private home office and flexible recreation/bonus room. An incredibly convenient location ideal for commuters. Walkable to Fairfield Metro, Whole Foods, Jennings Beach, shops and restaurants. Incredible storage, functionality, efficiency and design detail sets this home apart.

41 Reynolds Dr, Fairfield

28 Country Road Unit 28, Fairfield
$1,199,000
4 Beds ⋅ 4 Baths ⋅ 24153694 MLS
A lifestyle you can truly enjoy at an unbeatable price for new construction in Fairfield's university area. Perfect blend of luxury, select finishes and custom cabinetry create a warm and inviting home. White oak flooring grounds you while natural light spills in through large windows. The kitchen blends seamlessly with the open floor plan, the large island is the main focal point which provides plenty of seating with glamorous waterfall-style quartz countertops. You can customize your dining nook or keep the dining area centered. Cozy up on a chilly night and relax by the fireplace. A modern half bath and mudroom area complete the main level. The primary suite is located on the 2nd floor and features a sophisticated luxurious shower, large soaking tub and wood-fluted double vanity. Walk in closet with custom features. The 2nd and 3rd bedrooms are in tandem with a full bathroom, private bath/shower and elegant double vanity. 3rd floor features private quarters with yet another full bath. Currently set up as an office, this space is versatile. A closet and storage room finish this level. Bonus finished space in Lower level THERE ARE NO HOA FEES HERE! Mere stone's throw from Holland Hill School. 5 miles of sandy shores. 1 mile to Fairfield University. Effortless access to community and culture in vibrant downtown Fairfield. Dining and shopping all within close proximity. Easy commute to NYC. Quality craftsmanship and low maintenance. Private fenced yard. City sewer & water.

28 Country Road Unit 28, Fairfield

270 Andrassy Ave, Fairfield
$1,299,000
4 Beds ⋅ 4 Baths ⋅ 24211703 MLS
Agent/Owner - Essentially a brand-new home in Fairfield's sought-after University area, reconstructed from the original foundation up and thoughtfully designed for modern living. This impressive 4-bedroom, 3.5-bath home offers a fresh, elevated feel throughout, beginning with 9ft ceiling open main level anchored by a beautifully designed Fabuwood kitchen, spacious living and dining areas, and a flexible main-floor bedroom or private office. Upstairs, the primary suite features a spa-inspired wet room, while the additional bedrooms are served by a spacious Jack-and-Jill bath and convenient second-floor laundry. The third floor adds a huge family room with its own full bath-ideal for guests, movie nights, a playroom or private retreat. A finished basement provides even more space for recreation, fitness or everyday living. Just minutes from Fairfield University, downtown Fairfield, Metro-North, beaches, shopping, dining and commuter routes. A welcoming covered front porch and rear deck extend the living space outdoors, while the home's thoughtful layout, generous room sizes and multiple living areas offer the flexibility today's buyers are looking for. From the main-level office/bedroom to the upper-level family room and finished lower level, there is space here to live, work, gather and unwind. A rare opportunity to own a nearly new home in one of Fairfield's most convenient neighborhoods.

270 Andrassy Ave, Fairfield

280 Tuckahoe Ln, Fairfield
$2,199,999
6 Beds ⋅ 7 Baths ⋅ 24211148 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, 5 full and 2 half baths. This offers 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

38 Reynolds Dr, Fairfield
$845,000
3 Beds ⋅ 3 Baths ⋅ 24210126 MLS
From the moment you pull into the cul-de-sac at 38 Reynolds Drive, this charming colonial greets you with a genuine sense of home. It is a picture perfect setting where light filled spaces and an effortless room to room flow immediately make you want to stay a while. A welcoming front living room provides an inviting initial space for relaxed conversation. At the heart of the residence is an expansive family room featuring soaring vaulted ceilings, a wood burning fireplace, custom built ins, and walls of windows that bring in incredible natural light. French doors open to a wraparound deck and a private, fenced yard framed by mature landscaping. The kitchen serves as a central highlight, crafted with custom cabinetry, sleek granite surfaces, under cabinet lighting, and stainless steel appliances. Adjacent to the kitchen is a versatile formal dining space, currently outfitted as a dedicated home office, offering the flexibility to suit your lifestyle needs. Upstairs, the primary bedroom offers a newly renovated en-suite bath featuring a gorgeous tiled shower with glass doors and stylish new tile flooring. Completing the upper level are 2 well appointed bedrooms and a shared full bath. A full walk up attic for storage and offers potential to finish space as your needs evolve. Every detail has been curated for comfort, plus a prime location just minutes from local parks, top rated schools, shopping and the train, perfectly pairing peaceful serenity with Fairfield convenience.

38 Reynolds Dr, Fairfield

20 Glen Arden Dr S, Fairfield
$899,000
3 Beds ⋅ 3 Baths ⋅ 24208763 MLS
Slow mornings, lively gatherings and room to unwind-welcome to life at 20 Glen Arden Drive South. Set on nearly half an acre in Fairfield's University neighborhood, this 3-bedroom, 3-bath Colonial offers inviting spaces for every pace of the day. Gather around the kitchen island for coffee and conversation, host dinner in the dining room, then mix a favorite drink at the wet bar and settle in beside the fire. Two fireplaces bring warmth to evenings at home, while hardwood floors lend classic character throughout. Outside, the professionally landscaped grounds set the stage for everything from backyard games to leisurely afternoons. Serve dinner on the patio, linger with friends by the cabana or slip away to the balcony for a quiet moment. There's space here to entertain a crowd and enjoy a little solitude. Main-level laundry and a two-car garage keep daily routines easy, while nearby shopping, dining, beaches and parks put the best of Fairfield within easy reach. Thoughtful improvements include a new roof, exterior painting and carpentry completed in 2025, plus kitchen updates featuring an induction cooktop, center island with microwave, counters and pantry. Attic spray foam insulation, a newer water heater and refinished hardwoods further enhance this inviting home.

20 Glen Arden Dr S, Fairfield

78 Greenbriar Rd, Fairfield
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 24207389 MLS
Set in the desirable University area, this expanded ranch offers inviting spaces, beautiful architectural details and a backyard that feels like a private oasis. Custom craftsman touches incl crown molding and custom paneling create a warm sense of character throughout. The chef's kitchen, with generous island,is perfect for morning coffee, and casual meals.The dining room is ideally situated for inspired entertaining. The heart of the home is the stunning family room, where a soaring cathedral ceiling and fireplace create a comfortable place to gather. French doors open to an extraordinary outdoor retreat designed for long summer days and unforgettable evenings. Swim in the heated gunite pool, relax in the spa, enjoy dinner on the patio, and gather for drinks at the tiki bar. An outdoor shower and lush grounds complete this vacation-at-home setting.Upstairs, the thoughtfully added bonus space offers room to adapt as life changes; whether used as a home office,playroom, 4th bedroom, or creative studio. A finished space in the bsmt plus plenty of storage add to the home's functionality. The ease of ranch-style living with flexible additional space and exceptional indoor-outdoor entertaining, this is a home meant to be enjoyed in every season. All situated on a culdesac road just minutes from Fairfield Center dining, shopping, MetroNorth and 5 LI Sound beaches. Walk to Osborn Hill School.Easy NYC commute by highway, Merritt Parkway or train.

78 Greenbriar Rd, Fairfield

250 Szost Dr, Fairfield
$1,489,999
5 Beds ⋅ 5 Baths ⋅ 24205742 MLS
FALL in love with this new home sitting proudly on a beautiful tree-lined circular street in the exceptional Fairfield University area. A covered Front porch greets you, with a sleek metal roof providing not only curb appeal but durability. Plenty of room to sit, sip, and enjoy the neighborhood. Upon entering this 5 Bedroom home, you instantly are comforted by the neutral tones and natural light that spills in. The comfortable living room flows seamlessly into the kitchen, natural hardwood flooring throughout and a gas fireplace offers a cozy spot on a chilly evening At the heart is the custom Kitchen designed for serious cooking and effortless entertaining. The kitchen features Thermador appliances an oversized island topped with gleaming white quartz and a walk in pantry. The adjoining dining area includes a dry bar and beverage cooler with sliders that lead to expansive deck overlooking the fenced in private yard. An optional first floor bedroom and full bath are located off the dining area, a laundry room competes this main level. Upstairs the primary suite is a true retreat with spa inspired bath, soaking tub and generous walk in closet. Two more spacious bedrooms with full bath complete this level. The third floor Bonus room is yours to design..Rec room, music, office? A Full bathroom and Fifth bedroom live on this 3rd level. Just in case you need more space, the entire lower level is finished with half a bath. Efficient mechanicals provide for lower cost utility costs

250 Szost Dr, Fairfield

438 High St, Fairfield
$599,000
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. Agent is related to owner.

438 High St, Fairfield

309 Hunyadi Ave, 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

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