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

$2,799,000

5 Beds ⋅ 4 Baths ⋅ 24189715 MLS

Privately nestled in Westport's coveted Old Hill neighborhood, this extraordinary five-bedroom New England residence offers a rare opportunity to own a home where timeless character & modern comfort come together beautifully. Thoughtfully updated while preserving its remarkable architectural details, the residence features sun-filled interiors, beautifully scaled rooms, & an inviting warmth throughout. Original elements reflect the home's storied past, while carefully integrated updates provide exceptional comfort for today's lifestyle. A standout feature is the distinctive pub room with its original wood bar - an unforgettable setting for intimate gatherings, celebrations, or quiet evenings at home. The versatile third level offers endless possibilities as a private guest retreat, second primary suite, or home office. Outside, mature specimen trees, flowering gardens, rolling lawns, and elegant stone terraces create a private retreat that evolves beautifully with the seasons. Completing the property is a charming barn with electricity, water, cable, & convenient parking, offering exceptional flexibility as a studio, workshop, recreation space, or a future vision uniquely tailored to the next owner. Just minutes from downtown Westport, award-winning schools, shopping, restaurants, beaches, & the train, this exceptional property presents a rare opportunity to become the next steward of one of Westport's most treasured homes. A truly special place to call home!

4 Crawford Rd, 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

$5,750,000

5 Beds ⋅ 8 Baths ⋅ 24178699 MLS

Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an expansive, light-filled layout is ideal both for grand entertaining and quiet retreat. A dramatic wall of windows captures sweeping views of the brook, creating a seamless connection between indoor comfort and the surrounding landscape. The ground floor consists of a gourmet kitchen, large family room with fireplace, dining room with wet bar, living room with fireplace + lounge area with water views, a large entry foyer with stone floors and two powder rooms. Upstairs, a primary bedroom suite with two balconies overlooking the pond and brook, two walk in closets & beautifully appointed bathroom, 4 additional bedrooms each with its own bathroom, a large home office/6th bedroom with fireplace and brook & pond views, a large playroom with full bathroom, windowed home gym, and another family room on the 3rd floor, offering multiple options for relaxation and entertainment. Fully fenced for privacy with automated driveway gates, it has a heated 3 car garage, Crestron lighting system, full house generator, mature landscaping, and a gas grill seamlessly built into the stonework by the pool.

31 Stonybrook Rd, Westport

$4,100,000

6 Beds ⋅ 6 Baths ⋅ 24164137 MLS

A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and well-proportioned spaces create an environment that feels both elevated and effortlessly comfortable. At the center of the home, a beautifully designed kitchen opens to expansive living and dining areas, creating a seamless flow for both everyday living and entertaining. The layout flows easily with ample room for work-from-home, multi-generational living, and evolving lifestyle needs. A main-level suite with a full bath provides privacy and versatility-ideal for guests, a dedicated office, or an extended family. Every detail accentuates comfort, function, and understated luxury. A back yard patio with pool abutting a nature preserve offers privacy with open space and the ease of in-town living. Positioned near Nash Pond and close to local nature trails and amenities, the home also offers exceptional convenience-walkable to the Post Road and just minutes to downtown Westport, shopping, dining, and Metro-North train service to New York City. Luxury new construction in Old Hill, Westport, CT-where location, design, and lifestyle align in one of the town's most desirable settings.

48 Woodside Ave, Westport

$5,500,000

5 Beds ⋅ 6 Baths ⋅ 24171432 MLS

Discover exceptional modern living in this stunning new construction home set on 1.68 acres of private, serene property in Westport, CT. Designed with both luxury and functionality in mind, this residence offers 5 spacious bedrooms and 7 beautifully appointed bathrooms. The primary suite is a true sanctuary, featuring three generous closets and a spa-inspired feel. Each additional bedroom is thoughtfully designed with ample space and comfort. Upstairs, a bright and inviting sitting area creates the perfect retreat, while a fully finished attic provides an ideal space for a playroom or creative zone. The heart of the home is a chef's kitchen, showcasing elegant oak cabinetry, high-end finishes, and a large walk-in pantry-perfect for everyday living and entertaining alike. A dedicated home office on the main level adds convenience for today's lifestyle. The fully finished basement offers incredible versatility, ideal for a home gym, bar, or entertainment space. Step outside to a beautiful, expansive patio overlooking the private grounds-perfect for gatherings or quiet relaxation. Completing this remarkable home is a 3-car garage and a sleek, modern design throughout. This is a rare opportunity to own a truly special property that combines sophistication, space, and privacy in one of Westport's most desirable locations.

1 Twin Oaks Ln, Westport

$1,599,876

5 Beds ⋅ 4 Baths ⋅ 24170706 MLS

Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The front to back living room with marble fireplace offers peaceful views through expansive windows. The formal dining room with picture window is adjacent to a generous country kitchen featuring a bay window, granite countertops, a gas cooktop and double ovens. The oversized family room boasts a vaulted ceiling and access to main level laundry area. The rear of the house features a 58 ft long deck overlooking private acreage. The home contains 5 bedrooms and 4 full bathrooms. The primary suite includes a full bathroom, dressing area, linen closet and a walk in closet with built-in armoire. This home has fabulous closet space with each bedroom offering a minimum of 2 closets. The walk out lower level hosts a private den / office with wet bar and sliders to a stone patio. There is an additional laundry area and storage space that leads to an oversized 2 bay garage. Central air conditioning will keep you comfortable during summer months while five zone heating, Thermopane windows and extra insulation keep this home energy efficient all year long. Westport's luxury shops, fine restaurants, relaxing beaches and award winning school system combine to make this an irresistible value!

30 Pequot Trl, Westport

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