Old Hill Real Estate

Welcome to Old Hill, one of Westport's most charming and desirable neighborhoods nestled in the heart of Fairfield County, Connecticut. Known for its picturesque landscapes and tight-knit community, Old Hill offers a perfect blend of suburban tranquility and vibrant local culture.

As you stroll through the tree-lined streets, you'll be captivated by the stunning architecture of the homes, ranging from classic New England styles to modern designs. Each property is set against a backdrop of lush greenery, creating an inviting atmosphere that feels like a retreat from the hustle and bustle of city life. The spacious lots provide ample room for outdoor activities, making it an ideal place for families and nature enthusiasts alike.

Old Hill is not just about beautiful homes; it’s also about a lifestyle. Residents enjoy easy access to Westport’s top-notch schools, parks, and recreational facilities. The nearby Compo Beach offers a perfect spot for summer fun, while the vibrant downtown area boasts an array of shops, restaurants, and cultural attractions. Whether you’re indulging in a gourmet meal or exploring local art galleries, there’s always something to discover.

For those who commute, Old Hill's location is incredibly convenient, with quick access to major highways and the Metro-North train station, making trips to New York City a breeze.

In Old Hill, you’re not just buying a home; you’re investing in a lifestyle enriched with community spirit, natural beauty, and endless opportunities for exploration. Come and experience the charm of Old Hill, where your dream home awaits!

Newest Listings in Old Hill

$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

$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

$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

$1,475,000

24151295 MLS

ATTENTION BUYERS : FLAT DRY, ONE -OF-A-KIND LAND OPPORTUNITY NOW HUGELY IMPROVED WITH WELL DEFINED SITE PLAN. Do you hope for new custom construction no bigger than "about" 4500sf, yet continue to see 7000sf and larger get the edge? Stop wishing for it and take action! Bring your architect or builder to consider a new home that meets your dream to be practically-sized for every life stage. No other land offers this package in sought-after Westport: -Prestigious Old Hill location convenient to the town hub. -Minutes to trains both in Westport and Norwalk, Interstate-95 and Merrit Parkway. -Deed Restrictions that prevent an ordinary spec-construction. -Pristine, dry flat 1+ acre without wetlands or noise pollution of highways and trains. -Connection to Town history. This park-like acre is is behind the stone walls and just inside the original gates to the 1928 Arthur Whiteside Estate at 50 Sylvan North, and was once the welcoming gateway into the 25-acre estate owned by the business titan . He founded the Dun & Bradstreet commercial credit rating system that responded to client requests with a business's accurate credit rating report within an astonishing 2 minutes of a call. :) Whiteside's original 1920's Tudor home remains visible in the distance on Lot #2 where the Sellers of Lot #1 will continue in residence as your next-door neighbor. New England's reputation for understated elegance leaves a wide palette for the creative mind.

50 Sylvan Rd N, Westport

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.