Old Hill Homes for Sale

Welcome to Old Hill, one of Westport, Connecticut's most charming and sought-after neighborhoods. Nestled in the heart of Fairfield County, Old Hill boasts a unique blend of suburban tranquility and vibrant community life. Known for its picturesque tree-lined streets and beautifully maintained homes, this neighborhood is perfect for families, professionals, and anyone looking to enjoy the best of what Westport has to offer.

Old Hill is characterized by its diverse architectural styles, from classic New England colonials to modern contemporary designs, ensuring that there's a home for every taste. Many properties feature spacious yards, perfect for outdoor gatherings and children’s play, while others may offer stunning views of the nearby Saugatuck River. With homes for sale in Old Hill, prospective buyers will find a variety of options that cater to different lifestyles and budgets.

The neighborhood is conveniently located just a short drive from Westport’s vibrant downtown area, where residents can enjoy an array of shops, restaurants, and cultural attractions. For those who appreciate the outdoors, Old Hill is close to several parks and recreational facilities, including the beautiful Compo Beach, which is just a stone's throw away.

Families will appreciate the excellent schools in the area, known for their commitment to academic excellence and community involvement. Whether you’re looking for a peaceful retreat or a lively community atmosphere, Old Hill offers the perfect blend of both. Explore the homes for sale in this delightful neighborhood and discover your dream home in Old Hill today!

Newest Old Hill Homes for Sale

$4,050,000

5 Beds ⋅ 6 Baths ⋅ 24211806 MLS

Privately set in Westport's coveted Old Hill neighborhood, this like-new sophisticated residence designed by famed architect Peter Wormser pairs striking architecture with timeless, understated elegance. Soaring ceilings, beautifully curated spaces and abundant natural light define the stylish interiors, creating a home that is at once impressive and inviting. 4 finished levels provide exceptional space for everyday living, entertaining, work and guests. The primary suite stuns with its 20-foot ceilings, fireplace, 2 walk-in closets and spa bath. 4 additional bedrooms each feature walk-in closets, while 2 private offices offer dedicated work-from-home space. A 3rd-floor recreation room with full bath adds more flexibility, while the beautifully finished lower level has a home theater, gym, space for play, plus storage. Outdoors, the magical setting unfolds through multiple entertaining spaces, from inviting covered porches to an expansive stone patio with a fully-equipped outdoor kitchen, built-in grill and Big Green Egg, offering an exceptional backdrop for gatherings large and small. Lush, established landscaping creates a remarkable sense of privacy, yet the home is just over a mile to Westport's vibrant downtown. Whole-house generator, solar and level 2 EV charger! The NYC-bound train is just 9 minutes away. Distinctive, sophisticated and effortlessly livable, this exceptional Old Hill residence is a rare offering of inspired architecture, privacy and a prime location.

11 Woodside Ln, Westport

$4,550,000

5 Beds ⋅ 7 Baths ⋅ 24204438 MLS

A fresh take on Modern Luxury awaits at this new construction home set on stunning property in the Old Hill area of Westport. Now complete and ready for immediate enjoyment, this dynamic residence is perfectly located for convenience to commuting, the train station, schools, shopping and more. Exhilarating architecture will awaken your senses as you approach this customquality home. Walls of glass blend the natural setting with stunning interiors, and bring sunlight deep into the spectacular rooms. The chef's kitchen is a showpiece, featuring bespoke oak cabinetry, premium finishes, and a substantial walkin pantry. Dual mainlevel offices support today's lifestyle. 5 spacious bedrooms and 7 refined baths create a harmonious balance of comfort and sophistication. The primary suite is a serene retreat with three fitted closets and a spalevel ambiance. Additional bedrooms offer generous scale and thoughtful design. A sunlit upstairs lounge and a finished thirdfloor space provide flexible areas for work, play, or creativity. The finished lower level offers exceptional spaces for fitness, media, or entertaining. Outside, an expansive patio overlooks 1.68 acres of private grounds, ideal for gatherings or quiet reflection. A 3car garage (with a separate bay for a trophy vehicle or storage) and sleek modern detailing complete this remarkable offering. An inspired blend of architecture, setting, and convenience await in a prime location. Pool permit in place.

1 Twin Oaks Ln, Westport

$2,595,000

5 Beds ⋅ 4 Baths ⋅ 24203288 MLS

Privately nestled in Westport's coveted Old Hill neighborhood, this distinctive five-bedroom New England residence blends timeless character with thoughtful modern updates. Sun-filled interiors, beautifully scaled rooms, and original architectural details create warmth and authenticity throughout. The chef's kitchen is designed for both everyday living and entertaining, while the stunning, light-filled family room with fireplace offers a welcoming gathering space overlooking the beautifully landscaped grounds. A true standout is the inviting pub room with its original wood bar - an exceptional setting for entertaining, celebrations, or relaxed evenings at home. The versatile third level offers endless possibilities as a private guest retreat, second primary suite, home office or gym. Outside, mature specimen trees, flowering gardens, rolling lawns, and elegant stone terraces create a private retreat that evolves beautifully with the seasons. A charming barn with electricity, water, cable, and convenient parking adds exceptional flexibility as a studio, workshop, recreation space, or future vision. Just minutes from downtown Westport, award-winning schools, beaches, shopping, dining, and the train, 4 Crawford Road offers a rare opportunity to own a home with genuine character, exceptional privacy, and a wonderful sense of place. A truly special Westport residence that brings together character, comfort, and an exceptional setting.

4 Crawford Rd, Westport

$5,199,000

5 Beds ⋅ 8 Baths ⋅ 24201547 MLS

From the moment you enter the gates of this Old Hill estate, you know you've arrived- a rare sanctuary built with a level of custom stonework and craftsmanship impossible to replicate today. This stunning 5 bedroom, 6.2 bath home offers an extraordinary blend of elegance, privacy, and nature. Set in a mature landscape that takes generations to establish, the setting delivers unmatched wildlife views-from herons and owls to ducks and otters along picturesque Stony Brook. Resort-style amenities feature a heated saltwater pool/spa, a private pond with a fountain, and deeded access to nearby Nash's Pond for kayaking and fishing. Inside, a dramatic wall of glass captures sweeping water views, creating a seamless connection to the outdoors. The main level includes a gourmet kitchen, family room with fireplace, dining room with wet bar, living room with fireplace and lounge, stone entry foyer, mudroom and two powder rooms. Upstairs, the primary suite boasts two terraces, dual walk-in closets, and a spa bath. Four additional bedrooms each with its own bathroom, a sprawling home office/6th bedroom with fireplace, a large playroom with a full bath, a third floor family room, and a mirrored gym/yoga studio with a ballet barre offer exceptional living options. Moments from Earthplace nature trails, key features include a heated 3-car garage, Crestron lighting, full-house generator, and a built-in poolside gas grill. A rare opportunity to own a sanctuary where design and nature converge.

31 Stonybrook Rd, Westport

$1,695,000

4 Beds ⋅ 4 Baths ⋅ 24199886 MLS

Located in the highly sought after Old Hill Neighborhood - set back from the street on a one acre lot. This is a 4 bedroom colonial with a spacious first floor lay out including a formal living room with a lovely mantled fireplace, formal dining room, with French doors to the sunroom, library or office with bookcases, eat-in kitchen with an island and a relaxed family room featuring a fireplace, vintage wooden ceiling beams and a bow window. The entry foyer and adjacent powder room designed with reclaimed antique marble. Four spacious bedrooms on the second floor. The primary bedroom has a walk in closet and its own full bath, plus access to unfinished attic space with a walk in cedar closet. The property needs some TLC.

40 Pequot Trl, Westport

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Old Hill Homes for Sale

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