Old Hill Homes for Sale

Welcome to Old Hill, one of Westport, Connecticut’s most enchanting neighborhoods! Nestled in the heart of Fairfield County, Old Hill is a charming community that seamlessly blends suburban tranquility with vibrant local culture. This picturesque area is known for its tree-lined streets, beautifully maintained homes, and a welcoming atmosphere that makes it a perfect place for families, professionals, and retirees alike.

Old Hill boasts an array of architectural styles, from classic New England colonials to modern contemporary designs, catering to diverse tastes and preferences. Whether you’re searching for a cozy starter home or a luxurious estate, you’ll find a selection of homes for sale that reflect the unique character of this delightful neighborhood. Many properties feature spacious gardens, inviting patios, and stunning views, providing an ideal backdrop for outdoor gatherings and family activities.

Residents of Old Hill enjoy a strong sense of community, with friendly neighbors and a variety of local events throughout the year. The neighborhood is conveniently located near top-rated schools, upscale shopping, and delectable dining options, ensuring that everything you need is just a stone’s throw away. Additionally, the nearby beaches and parks offer ample opportunities for outdoor recreation, making it easy to embrace the beautiful Connecticut seasons.

Explore the homes for sale in Old Hill and discover the perfect blend of comfort, convenience, and charm. Your dream home awaits in this idyllic neighborhood, where every day feels like a retreat!

Newest Old Hill Homes for Sale

$999,000

3 Beds ⋅ 3 Baths ⋅ 24196339 MLS

SHOWINGS BEGIN MONDAY SEPTEMBER 14. An incredible opportunity has become available in a prime Westport, CT location. Set off the road on a quiet turnoff at the corner of the Overlook cul-de-sac, this expanded Cape on 0.52+/- acre of enchanting property is ready for your creative vision. This is the only 3 bedroom, 3 full bathroom home available in Westport below $1,649,000 - making this a spectacular chance to add value by updating, remodeling, expanding, or building new construction within moments of downtown, train, the Merritt Parkway, I-95, the Y, & schools. This quintessential New England Cape Cod-style home begins with a larger than expected foyer/center hall. The large LR has the first fpl, built-ins, and French doors leading to the distinctive family room with a custom-patterned hardwood floor, stone fpl & bookshelves. Formal dining room for entertaining. The kitchen was remodeled w/quality cabinetry and beautiful granite counters, top appliances including Sub Zero, and leads to the vltd ceiling breakfast room with skylights & glass doors facing both front & back. Private office/bonus room/playrm w/built-ins. The 1st of the 3 BRs is on the main level, w/built-ins & an adjacent full bath. Upstairs, the 2nd BR has its own full bath and the primary suite is an incredible surprise, with king-size BR, oversized lux-scale bathroom & walk-in clst. Partially fin LL. Patios & charming garden paths add to the character. This home requires work and is being sold-as is.

183 Wilton Rd, Westport

$4,750,000

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

$5,349,000

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

$905,000

3 Beds ⋅ 2 Baths ⋅ 24201989 MLS

Quite possibly the best renovation opportunity this year! This 3-4 bedroom, 2 full bath 1940's cape awaits your vision to polish this home to perfection. Sited beautifully at the end of a most desirable Old Hill cul de sac; enjoy privacy and build equity in a convenient neighborhood of high end homes. The flat, fenced .32 acre property offers room to play and space to entertain outdoors. The antique barn is not only an oversized two-car garage, but the vaulted room above can serve any need you have for additional living space. Served by public water - Natural gas and public sewers are in the street - amenities on every buyers "must have" list. The property is located in a designated "limited historic district", and the sale is subject to Probate Court approval.

15 Hyatt Ln, 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

$1,150,000

2 Beds ⋅ 2 Baths ⋅ 24187676 MLS

Build your dream house on this beautiful property close to town in the Old Hill section of Westport. This .87 acre lot in a AA zone has views of town and river through the trees. There is a small single-family home that was converted into two apartments in the 1930s by its then-owners. This can be a perfect ADU opportunity as part of a new house to be built. Have an office on one level and an in-law suite on the other. The land is rolling, elevated, and ideally positioned high off Kings Highway North. This is a rare and exciting opportunity for the next owner who can create something truly special. Each level in the house has a separate entrance and features a living room, one-bedroom, one-bath and eat-in kitchen. A truly unique offering with potential for flexible living opportunities. House is being sold AS IS. Please perform diligence with the town for required building regulations. Sewer hookup available on Kings Highway and that assessment has been paid in full.

119 Kings Hwy N, Westport

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