Old Hill Real Estate

Welcome to Old Hill, a picturesque neighborhood nestled in the heart of Westport, Connecticut. Known for its charming blend of suburban tranquility and vibrant community spirit, Old Hill offers a unique lifestyle that appeals to families, professionals, and retirees alike.

As you stroll through the tree-lined streets of Old Hill, you’ll be captivated by the stunning architecture that ranges from classic New England homes to modern masterpieces. The neighborhood is characterized by its spacious lots and lush greenery, providing residents with a serene environment to unwind and enjoy nature.

Old Hill is not just about beautiful homes; it boasts a strong sense of community, with friendly neighbors who take pride in their surroundings. The area is well-served by top-rated schools, making it an ideal location for families. Children can thrive in the educational opportunities provided by the Westport school district, known for its commitment to excellence.

For those who enjoy an active lifestyle, Old Hill is conveniently located near several parks and recreational facilities. Whether you prefer hiking, biking, or simply enjoying a picnic in the park, there’s something for everyone. Additionally, the neighborhood is just a short drive away from Westport’s vibrant downtown area, which features an array of boutique shops, gourmet restaurants, and cultural attractions.

With its perfect blend of suburban charm and modern amenities, Old Hill is a hidden gem in Fairfield County. Come discover why so many choose to call this enchanting neighborhood home, where every day feels like a retreat from the hustle and bustle of city life.

Newest Listings in Old Hill

$999,000

3 Beds ⋅ 3 Baths ⋅ 24196339 MLS

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 living room has the first fireplace, built-ins, and French doors leading to the distinctive family room with a custom-patterned hardwood floor, stone fireplace and 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/playroom lined with built-ins. The first of the 3 BRs is on the main level, with built-ins and 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

$1,500,000

24199468 MLS

Lee's Pond Retreat | 1.13 Acres of Opportunity A rare opportunity to create your dream home on 1.13 acres along the shores of Lee's Pond in Westport. This residentially zoned property offers a unique combination of privacy, natural beauty, and exceptional potential. Currently home to an existing tennis court, the property is ready for a developer or end user to bring their vision to life and create a truly special residence in one of Westport's most desirable settings. Build new and take advantage of the tranquil pond setting, generous acreage, and the opportunity to design a home tailored entirely to your lifestyle. A remarkable canvas for those seeking a one-of-a-kind Westport property.

River Lane, 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

$1,150,000

24187682 MLS

Don't miss this great opportunity close to town. The .87Acre lot is elevated ,rolling and ideally positioned off Kings Highway. There are distance views of the river and town through the trees. There is an older small 1400 sq ft. single family home that has been a rental for many years. The previous owners in the 30's made each floor into apartments. Each level with its own entrance features a living room , one bedroom, kitchen and full bath. This small house offers a unique opportunity to be a ADU or separate office as part of a new home that can be built.There is a sewer hook up for the new house has been paid in full. Please refer to town hall for required building regulations. This is a rare opportunity for the next owner to create something special close to town. Need permission to walk property and see house.

119 Kings Highway North Road, Westport

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