Long Lots Real Estate

Welcome to Long Lots, a charming and vibrant neighborhood nestled in the heart of Westport, Connecticut. Known for its picturesque tree-lined streets and friendly ambiance, Long Lots offers a unique blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike.

One of the standout features of Long Lots is its prime location. Residents enjoy easy access to the bustling downtown Westport, where a variety of boutique shops, gourmet restaurants, and cultural attractions await. Whether you’re indulging in a leisurely afternoon at the Westport Country Playhouse or savoring a delicious meal at one of the local eateries, there’s always something to explore just moments from your doorstep.

Nature enthusiasts will appreciate the nearby parks and recreational facilities, including Long Lots Park, which features playgrounds, sports fields, and walking trails. The neighborhood is also conveniently located near the stunning beaches of Long Island Sound, perfect for weekend getaways or a relaxing day under the sun.

Long Lots is known for its excellent schools, making it a popular choice for families seeking quality education for their children. The community is tight-knit, with numerous events and activities that foster a sense of belonging among residents. From seasonal festivals to neighborhood gatherings, there’s always an opportunity to connect with neighbors and make lasting memories.

With its perfect blend of convenience, community spirit, and natural beauty, Long Lots is not just a place to live—it's a place to thrive. Discover the charm of this delightful neighborhood and see why so many have chosen to call Long Lots home!

Newest Listings in Long Lots

$1,649,000

4 Beds ⋅ 3 Baths ⋅ 24201214 MLS

Set on a private flat half acre and thoughtfully expanded and beautifully maintained, this move-in-ready 4 bedroom home offers a flexible floor plan designed for today's lifestyle, with exceptional space for work, entertaining, and relaxation. Enter to a wonderful sun filled living room with fireplace, a new renovated kitchen with large island and stainless steel appliances and separate dining area. Adjacent to the kitchen is a sun filled great room with vaulted ceilings that opens to a generous stone patio-perfect for endless entertaining inside and out. Finished across four levels, the home offers a wonderful blend of comfort and privacy. The spacious primary suite occupies its own private floor and features vaulted ceilings, a walk-in closet, and a luxurious bath. An adjacent oversized room provides the perfect retreat for a home office, gym, or additional living space. 3 additional bedrooms share another large bath. The finished lower level offers even more versatility, with a separate entrance, mudroom/laundry room, full bath, and a flexible playroom, family room, or second home office. Outside, the level, fully fenced yard provides plenty of room for play, pets, gardening, and entertaining. With its exceptional location, thoughtfully designed spaces, and inviting indoor-outdoor living, 104 Old Road is a wonderful opportunity to enjoy all that Westport has to offer-close to town, schools, shopping, & just minutes from the Greens Farms train station.

104 Old Rd, Westport

$4,600,000

6 Beds ⋅ 8 Baths ⋅ 24204809 MLS

Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

2 Windy Hill Rd, Westport

$2,350,000

5 Beds ⋅ 5 Baths ⋅ 24203971 MLS

Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens Farms train. This special home captures the soul of historic Westport while delivering the comfort of today's lifestyle. Thoughtfully renovated, it blends original character, architectural detail, warmth, and six fireplaces with the amenities today's buyers expect. Set on a flat property with room for a potential pool, the home offers inviting indoor and outdoor spaces ideal for entertaining and everyday living. At the center is a chef's kitchen with a Sub-Zero refrigerator, a Wolf range, custom cabinetry, and generous prep space, opening to a sun-filled family room. Formal rooms, antique details, and multiple fireplaces create a space that feels both elegant and welcoming. The primary suite offers an oversized dressing room with abundant closet space, and a spa-like bath with a soaking tub and steam shower. The finished lower level includes a game room, wine cellar, and flexible recreation space. Outside, the expansive lawn offers space for sports, gatherings, gardens, or a future pool. Ideally located with one light to Greens Farms train, and minutes to Long Lots Elementary, Post Road shopping, and Main Street dining. A rare blend of antique charm and modern living.

28 Bulkley Ave N, Westport

$2,250,000

4 Beds ⋅ 3 Baths ⋅ 24201502 MLS

25 Bauer Place Ext, Walk to long lots School. 4 minutes to beach. Close to restaurants and shopping. A charming house located in the picturesque town of Westport, CT. This inviting residence accords a unique opportunity to enjoy the best of suburban living. Nestled in a tranquil setting, this property boasts a blend of traditional architecture and modern comforts. The exterior features a classic design that fits seamlessly into the beautiful surroundings. As you approach the house, you'll appreciate the well-maintained landscaping that enhances the curb appeal. While specific interior details are not provided, the house presents a canvas for personalization and the creation of a home that suits your tastes and needs. Whether you're looking for a peaceful retreat or a place to host gatherings, this property provides the foundation for a comfortable lifestyle. Explore the potential of this home and envision the possibilities that await at 25 Bauer Place Ext in Westport.

25 Bauer Pl Ext, Westport

$2,850,000

5 Beds ⋅ 6 Baths ⋅ 24195597 MLS

Still hoping to move before school starts? This exceptional new construction home is ready for immediate occupancy! Built by SIR Development, Westport's premier luxury builder with 30+ years of experience and 300+ homes built, this hidden gem sits at the end of a cul-de-sac in a welcoming neighborhood within walking distance to Long Lots Elementary School. The open layout spans 4 beautifully finished levels and showcases SIR Signature Home craftsmanship and designer finishes throughout. The custom eat-in kitchen with butler's pantry features sleek white cabinetry with warm oak accents, quartz countertops, handmade ceramic tile backsplash and premium Thermador appliances, opening seamlessly to the inviting family room with fireplace. The main level also offers a private study with custom oak shelving, formal dining room, mudroom and powder room. The luxurious primary suite features vaulted ceilings, a spa-inspired bath and two walk-in closets. The finished 3rd floor includes a 5th bedroom and full bath. The walk-out lower level offers custom built-ins, recreation room, gym and half bath. Outside, enjoy a level backyard, spacious granite patio with room for a pool, professionally landscaped grounds and fencing for privacy. Connected to city water and sewer with propane gas, this move-in-ready home offers the perfect blend of luxury, comfort and style.

27 Bauer Pl Ext, Westport

$6,495,000

6 Beds ⋅ 8 Baths ⋅ 24194674 MLS

Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped outdoor kitchen. There's still space to add a full sized Tennis Court and ADU to create a luxury compound! Built by award-winning Westport Family Homes, this thoughtfully designed 6 bed/8 bath home spans 9,062 square feet on 4 finished floors, showcasing exceptional craftsmanship and attention to detail. Soaring ceilings and an abundance of natural light. Main Level: Gracious Foyer, 2 Powder Rms, Formal Liv/Din Rms, private Office, Designer Kitchen w/Scullery for entertaining. Kitchen opens to large Great Rm w/FP and Outdoor Liv Rm. Second Level: Primary Ste w/FP, 2 walk in closets, spa inspired Bathrm and 4 other Bedrms. Third Level: Playroom w/Bathrm. Lower Level: Walk out to Pool w/ 6th Bedrm, full Bathroom, Family Rm w/Bar, Play/Media Room and large Gym. Full-house generator, oversized 3 car garage w/EV charging capability and room for 3 car lifts. The home is elevator-ready, enhancing convenience and long-term livability. Great for multi generational living. City Water, Natural Gas. This masterfully crafted home has a timeless floor plan and modern design.

5 Baldwin Pl, Westport

$1,999,000

5 Beds ⋅ 4 Baths ⋅ 24191704 MLS

Experience modern luxury in this beautifully reimagined home, set on 1.57 scenic, park-like acres. Thoughtfully renovated, this 2,864 sq ft residence offers open-concept living spaces filled with natural light and sophisticated finishes throughout. The designer kitchen features a stunning island and premium cabinetry, flowing seamlessly into the dining and living areas with a dramatic linear fireplace. The spacious family room opens to a sun-soaked bluestone patio overlooking an expansive backyard extending to the pond-an idyllic setting for entertaining and everyday enjoyment. The fabulous primary suite is a private retreat with a cozy fireplace, incredible walk-in closet, and beautifully appointed modern bath. Two additional bedrooms complete the second level, while a private 4th-bedroom ensuite is ideal for guests or flexible living space. A main-level office/5th bedroom, powder room, and mudroom with custom built-ins leading to the 2-car garage add versatility and convenience. Ideally located within walking distance of Staples High School and Bedford Middle School, and minutes from Westport's beaches, vibrant downtown, shopping, dining, and train station.

110 Cross Hwy, Westport

$8,450,000

6 Beds ⋅ 8 Baths ⋅ 24190641 MLS

Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling details & European windows that flood the interiors w/ natural light.The Chef's Kitchen is highlighted by natural stone countertops,a dramatic stone backsplash & custom stone hood, premium appliances with column refrigerator & freezer all set flush to the cabinets. Luxurious living and entertaining spaces flow seamlessly to the outdoor oasis featuring a sparkling pool, spa, & private 1.6 property w/an irrigation system Belgium block trimmed driveway The magnificent primary suite is a private retreat, complete w/ a custom rift oak cathedral ceiling & a covered balcony w/ glass & wood railings overlooking the property.The 2nd level features 5 BRs w/ensuite baths. The 6th BR Suite is privately in the LL where there is a large FR & Gym.Additional amenities include natural gas, city water, Visual Comfort luxury lighting throughout, integrated recessed lighting, & countless custom features that elevate every room.This is a rare opportunity to own a newly built, architecturally stunning estate where exceptional design and refined living come together beautifully. Ready for move in Summer 2026

10 Beltas Farm Ln, Westport

$4,995,700

4 Beds ⋅ 5 Baths ⋅ 24176377 MLS

Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage and specs can vary, but the standard of excellence does not. Coastal Luxury Homes is the premier Fairfield County bespoke builder.

22 Dawn Dr, Westport

$5,650,000

7 Beds ⋅ 9 Baths ⋅ 24172635 MLS

Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft ceilings, custom paneling, character grade oak floors, refined millwork, and expansive windows. Sun-filled living and dining rooms complement the great room with a sleek 60inch fireplace and reclaimed beams. The chef's kitchen includes full size SubZero refrigerator and freezer, Wolf cooktop and double ovens, quartzite waterfall island, custom cabinetry, and walk-in pantry. A private office with built ins enhances work from home convenience. Outdoor living shines with a covered porch, granite patio, outdoor kitchen, and direct access to the 20x40 saltwater pool. The luxurious primary suite offers vaulted ceilings with antique beams, oversized walk ins, and a spa bath with custom vanities and textured tile. All five second floor bedrooms are ensuite. The finished third floor adds a full bath, office/craft room, and playroom. The walkout lower level includes a bedroom and bath, gym, wet bar, media room with raised platform, and large recreation area.

8 Pleasant Valley Ln, Westport

$5,990,000

6 Beds ⋅ 7 Baths ⋅ 24147970 MLS

New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with generous room sizes, flexible living areas, and seamless indoor-outdoor flow. Additional highlights include a three-car garage and thoughtful design throughout. Conveniently located close to Westport schools, train, beaches, and town amenities, this is a rare opportunity to own a custom home in a coveted setting.

10 Mary Jane Ln, Westport

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