Fairfield Homes with Osborn Hill Elementary school

Welcome to Fairfield, Connecticut—a picturesque town that seamlessly blends suburban charm with vibrant community life. Nestled in Fairfield County, this delightful locale is renowned for its stunning coastal views, rich history, and a strong sense of community. With its convenient access to major highways and the Metro-North train, commuting to New York City is a breeze, making Fairfield an ideal choice for both professionals and families alike.

One of the standout features of Fairfield is its commitment to education, particularly evident in the highly regarded Osborn Hill Elementary School. Families seeking homes within this district will find a warm and nurturing environment that prioritizes academic excellence and personal growth. The school is celebrated for its dedicated staff, innovative programs, and a strong emphasis on community involvement, providing children with a solid foundation for lifelong learning.

In addition to its exceptional educational offerings, the real estate market in Fairfield boasts a diverse array of homes, from charming historic houses to modern new builds. Many properties are nestled in serene neighborhoods, surrounded by parks, nature trails, and recreational facilities, making it easy for families to enjoy an active lifestyle.

Living in Fairfield means embracing a lifestyle filled with rich cultural experiences, outdoor adventures, and a close-knit community atmosphere. Whether you’re strolling along the beautiful beaches, exploring local shops and restaurants, or attending community events, you’ll quickly discover why so many families are proud to call this town home. Experience the perfect blend of quality education, family-friendly living, and coastal beauty in Fairfield, CT!

Newest Fairfield Homes with Osborn Hill Elementary school

$599,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24191813 MLS

Welcome to 41 Stillson Place, a classic three-bedroom Cape brimming with character and poised for its next chapter. Tucked away on a beautiful lot in one of Fairfield's most coveted pockets, this home offers a timeless silhouette and a warm, inviting energy that you feel the moment you pull into the drive. Inside, the layout is remarkably functional, featuring a cozy living and dining area, eat-in kitchen and three well-proportioned bedrooms that offer plenty of versatility. While the interior serves as a charming throwback to an earlier era, it is exceptionally well-maintained-the perfect "blank canvas" for someone with a vision. Whether you're dreaming of a modern farmhouse kitchen or an open-concept flow, the solid bones of this residence provide the ideal foundation for a custom transformation. The exterior is just as promising, with a generous yard that offers ample space for summer gatherings, vibrant gardens, or outdoor living space. The detached one-car garage has space for cars and storage. It's a rare opportunity to secure a home with this much heart and potential in such a prime Fairfield location. This is your chance to settle into a wonderful community and tailor every detail of your home to perfectly suit your lifestyle. 41 Stillson Place isn't just a house-it's the perfect place to call home.

41 Stillson Pl, Fairfield

$1,199,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194385 MLS

Completely renovated from top to bottom, this stunning 4-bedroom, 2-bath home blends modern luxury with timeless charm in Fairfield's desirable University area. Offering 1,814 sq ft of finished living space plus an 884 sq ft unfinished basement, this move-in-ready home delivers style, comfort, and future potential. The open-concept layout centers on a designer kitchen with custom cabinetry, an oversized waterfall island, quartz countertops, a sleek vent hood, and brand-new stainless steel appliances. Sun-filled living spaces feature recessed lighting, wide-plank flooring, and modern finishes throughout. Retreat to the beautifully designed primary suite or unwind in one of the fully updated, spa-inspired bathrooms. Generous bedrooms and thoughtfully redesigned interiors complete a floor plan built for everyday living and entertaining. Outside, contemporary updates and architectural details create standout curb appeal, while the oversized deck and spacious backyard set the stage for outdoor gatherings. A 2-car attached garage, updated mechanicals, premium finishes, and a large unfinished basement - ideal for storage or expansion - round out the offering. Ideally located near Fairfield University, downtown Fairfield, Metro-North, shopping, dining, beaches, and parks, with easy access to major commuting routes. A rare opportunity to own a fully renovated home in one of Fairfield's most sought-after neighborhoods.

1646 Jennings Rd, Fairfield

$839,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24153624 MLS

Located in Fairfield's highly sought-after University area, this classic Cape Cod-style home offers curb appeal, charm and character. Featuring hardwood floors throughout the main living areas and bedrooms, the home boasts a recently installed white kitchen with quartz countertops, farmhouse sink, center island, stainless-steel appliances and small butler's pantry with wine refrigerator. The large formal dining room is ideal for entertaining, and the inviting living room with fireplace has French doors which open to a spacious deck, bluestone patio and private backyard. An adjacent sunroom/den has a vaulted ceiling and provides additional flexible living space. The upper level includes a primary bedroom with generous closet space and attic storage, along with two additional bedrooms and a beautiful full bath featuring stylish tile finishes. A partially finished lower level offers additional living space, along with a laundry area, utility room, and ample storage. Outside, enjoy a level yard enhanced by mature landscaping, lovely plantings, a garden shed, a wood deck and bluestone patio, ideal for outdoor entertaining. The breezeway entry leads to an attached one-car garage. This home presents an exceptional opportunity in one of Fairfield's most desirable neighborhoods. While some finishing touches remain, the property offers outstanding value and recent updates like the recent kitchen, baths and roof. Close to Fairfield University, train stations,

31 Smedley Rd, Fairfield

$829,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24190167 MLS

Welcome to 163 Windsor Road, a beautifully updated home set on a double cul-de-sac in Fairfield's desirable University Area. A welcoming foyer opens to a bright main living space with vaulted ceilings, exposed beams, recessed lighting, hardwood floors, and a warm sense of character throughout. The open-concept living room, dining area, and renovated kitchen create an easy flow for everyday living and entertaining. The kitchen features white cabinetry, quartz countertops, a center island, coffee bar, with modern finishes. Just beyond the main living area, the cozy den offers a rare expansion of the floor plan and opens directly to the deck, creating an easy connection outdoors for barbecues and al fresco dining. The second floor is home to three bedrooms and a full bathroom. From there, the lower level extends across two additional floors, adding flexibility with a mudroom that provides access to the attached garage, an office or potential fourth bedroom, laundry, and a spacious room ideal for a playroom, media room, or gym. Set on a fenced corner lot in a friendly neighborhood setting, the property offers the ease of being able to walk to Osborn Hill Elementary and nearby Black Rock Turnpike eateries, with parks, shopping, commuter routes, downtown Fairfield, train, beaches, and the best of the University Area lifestyle just a short drive away. Move-in ready with modern updates, natural gas, future expansion potential, and true neighborhood appeal.

163 Windsor Rd, Fairfield

$949,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24189655 MLS

This approximately 1500 square foot house features 4 bedrooms and 2 full bathrooms. The property includes a new patio and a new portico, as well as window boxes, bright kitchen cabinets, and a new backsplash. The home also boasts a built-in pool with a new liner and an irrigation system, along with a whole-house generator as well as a spacious fenced in backyard. The primary bedroom offers ample space and privacy, while the three additional bedrooms provide versatility for a variety of uses. The two bathrooms are well appointed and accessible from the main living areas. The kitchen showcases a modern, bright aesthetic with white cabinets and a new backsplash, complementing the overall style of the home. The new patio and portico provide outdoor living spaces for enjoying the surrounding environment. List agent related to owner.

58 Millspaugh Dr, Fairfield

$625,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24186541 MLS

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. Thoughtfully positioned for privacy and comfort, these airy spaces offer a warm and welcoming atmosphere that you will love coming home to. 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

$1,875,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24183302 MLS

Nestled on a sprawling one-acre lot, this stunning home offers 4180 sq ft of above-grade living space. Situated in the highly desirable University area of Fairfield, it features 5 bedrooms/5.5 bathrooms. The heart of the home is a culinary masterpiece with GE Monogram appliances, classic shaker-style cabinetry, quartz countertops and a large kitchen island. The kitchen flows into 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 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 in the Fairfield area. The primary suite serves as a private, spa-inspired sanctuary with soaring cathedral ceilings, a sprawling floor-mounted custom walk-in closet, and a luxurious bath with high-end fixtures. A private balcony off the bedroom offers an intimate retreat to unwind. Enjoy total privacy with a protected rear buffer ensuring no future development, with professionally landscaped lawn and bespoke patio. Amenities include a private home office, walk-in pantry, two covered parking spaces & two-car attached garage. The home is close to beaches, schools & downtown. A commuters dream with close access to MetroNorth stations. 1-year AllShield Home Protection plan incl. Original 1400 sq' built 1919-Complete Renovation/New Construction 2026. Planned finish July 2026. Owner/Agent

1964 N Benson Rd, Fairfield

$939,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24177465 MLS

Welcome home to this beautifully maintained 3-bedroom Cape, ideally situated on a quiet cul-de-sac. Filled with natural light and surrounded by mature plantings and professionally landscaped grounds, this home offers the perfect blend of comfort, convenience, and lifestyle. Just minutes from the Merritt Parkway, I-95, Metro North, vibrant downtown Fairfield, exceptional restaurants, shopping, and five miles of beautiful Long Island Sound beaches. Designed for both everyday living and entertaining, the open-concept first floor creates seamless flow from room to room and effortlessly extends outdoors. The oversized deck, located just off the chef's kitchen, will become the heart of every summer barbecue, holiday gathering, and special celebration. Looking to unwind? Curl up with a good book or enjoy a glass of wine beside the warm wood-burning fireplace in the inviting living room, while the separate family room offers the perfect spot for movie nights or cheering on your favorite team. The true jewel of the home is the stunning second-floor primary suite featuring vaulted ceiling, walk-in closet, and a spa-inspired bath complete with an air-jet soaking tub, double sinks, and a separate stall shower. Additional flexible second-floor space offers endless possibilities for a home office, nursery, fitness area, or private retreat to suit every stage of life. A rare opportunity to enjoy space, style, and an exceptional location - this is one you won't want to miss.

43 Green Knolls Ln, Fairfield

$2,199,999

6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 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

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