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22 Evergreen Ave, Westport

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

5 Beds ⋅ 5 Baths ⋅ 24172211 MLS

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

22 Evergreen Ave, Westport

6 Janson Dr, Westport

Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed kitchen equipped with premium appliances including Wolf and Sub-Zero, expansive island, and seamless flow to the family room with fireplace. Three fireplaces throughout the home add warmth and architectural interest. White oak flooring, custom millwork, and high-end finishes elevate every space. The upper levels offer a luxurious primary suite with spa-like bath and custom closet, along with well-appointed secondary bedrooms. A fully finished lower level with walkout access provides flexible space for recreation, fitness, or additional living. Set on a level .50-acre property, the outdoor experience is complete with a 15' x 30' heated gunite pool, bluestone patio, and professionally planned landscaping-perfect for enjoyment and relaxation. Additional features include city water and sewer, propane gas, 400-amp electrical service, 24 KW generator, and wiring for audio, security, and smart home systems. A rare opportunity to own a new construction home with exceptional scale, quality, and amenities. Still time to customize finishes.

6 Beds ⋅ 9 Baths ⋅ 24165540 MLS

Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed kitchen equipped with premium appliances including Wolf and Sub-Zero, expansive island, and seamless flow to the family room with fireplace. Three fireplaces throughout the home add warmth and architectural interest. White oak flooring, custom millwork, and high-end finishes elevate every space. The upper levels offer a luxurious primary suite with spa-like bath and custom closet, along with well-appointed secondary bedrooms. A fully finished lower level with walkout access provides flexible space for recreation, fitness, or additional living. Set on a level .50-acre property, the outdoor experience is complete with a 15' x 30' heated gunite pool, bluestone patio, and professionally planned landscaping-perfect for enjoyment and relaxation. Additional features include city water and sewer, propane gas, 400-amp electrical service, 24 KW generator, and wiring for audio, security, and smart home systems. A rare opportunity to own a new construction home with exceptional scale, quality, and amenities. Still time to customize finishes.

6 Janson Dr, Westport

6 Willowbrook Dr, Westport

Tucked away on a private lane just minutes from downtown, Compo Beach, and Metro-North, this beautifully updated 4-bedroom, 3-bath expanded Cape offers turnkey living in one of Westport's most desirable locations. Renovated in 2015 with all-new electrical and plumbing, the home has been meticulously maintained with significant recent improvements, including a new roof, furnace, A/C condenser, water heater, and irrigation system. The sun-filled open-concept living, dining, and kitchen spaces are designed for effortless everyday living and entertaining, featuring a wood-burning fireplace, expansive picture windows, and seamless access to a professionally landscaped backyard retreat centered around a charming flagstone patio. The beautifully appointed kitchen offers a large center island, stainless steel appliances, farmhouse sink, instant hot water dispenser, and chimney-style vent hood. A flexible formal dining room with custom built-in bar cabinetry, guest bedroom or home office, and full bath complete the main level. Upstairs, the primary suite features custom California Closets and a spa-inspired bath with marble finishes, soaking tub, double vanity, and glass-enclosed shower. Two additional bedrooms, an updated hall bath, and second-floor laundry complete the upper level. The finished lower level provides versatile living space, while refinished hardwood floors, privacy fencing, and an oversized one-car garage complete this exceptional home!

4 Beds ⋅ 3 Baths ⋅ 24189022 MLS

Tucked away on a private lane just minutes from downtown, Compo Beach, and Metro-North, this beautifully updated 4-bedroom, 3-bath expanded Cape offers turnkey living in one of Westport's most desirable locations. Renovated in 2015 with all-new electrical and plumbing, the home has been meticulously maintained with significant recent improvements, including a new roof, furnace, A/C condenser, water heater, and irrigation system. The sun-filled open-concept living, dining, and kitchen spaces are designed for effortless everyday living and entertaining, featuring a wood-burning fireplace, expansive picture windows, and seamless access to a professionally landscaped backyard retreat centered around a charming flagstone patio. The beautifully appointed kitchen offers a large center island, stainless steel appliances, farmhouse sink, instant hot water dispenser, and chimney-style vent hood. A flexible formal dining room with custom built-in bar cabinetry, guest bedroom or home office, and full bath complete the main level. Upstairs, the primary suite features custom California Closets and a spa-inspired bath with marble finishes, soaking tub, double vanity, and glass-enclosed shower. Two additional bedrooms, an updated hall bath, and second-floor laundry complete the upper level. The finished lower level provides versatile living space, while refinished hardwood floors, privacy fencing, and an oversized one-car garage complete this exceptional home!

6 Willowbrook Dr, Westport

4 Woods Grove Rd, Westport

HUGE OPPORTUNITY. PROPERTY TO BE SOLD AS-IS, WHERE IS WITH NO REPRESENTATIONS AS TO CONDITION. PERFECT FOR BUILDER/DEVELOPER TO BUILD ON .41 PARKLIKE ACRES AT IN-TOWN LOCATION. SALE SUBJECT TO PROBATE.

4 Beds ⋅ 3 Baths ⋅ 24142924 MLS

HUGE OPPORTUNITY. PROPERTY TO BE SOLD AS-IS, WHERE IS WITH NO REPRESENTATIONS AS TO CONDITION. PERFECT FOR BUILDER/DEVELOPER TO BUILD ON .41 PARKLIKE ACRES AT IN-TOWN LOCATION. SALE SUBJECT TO PROBATE.

4 Woods Grove Rd, Westport

383 Main St, Westport

Great opportunity for Investors, Builders or First Time Home Buyers to renovate or Tear Down and Build a New House in Westport. 3-4 Bedrooms & 2 Bath Cape in need of Rehab. House has Spacious Living Room, Kitchen, Dining area Full bath on the first Floor, Master Bedroom, Full bath & Family Room on 2nd floor. Family Room can be converted into 4th Bedroom. House is Close to Downtown, Shopping, Dining, Recreation and Bus Line. Sold AS IS. Cash Offers and Quick Closing Preferred. Agent/Partner

3 Beds ⋅ 2 Baths ⋅ 24199434 MLS

Great opportunity for Investors, Builders or First Time Home Buyers to renovate or Tear Down and Build a New House in Westport. 3-4 Bedrooms & 2 Bath Cape in need of Rehab. House has Spacious Living Room, Kitchen, Dining area Full bath on the first Floor, Master Bedroom, Full bath & Family Room on 2nd floor. Family Room can be converted into 4th Bedroom. House is Close to Downtown, Shopping, Dining, Recreation and Bus Line. Sold AS IS. Cash Offers and Quick Closing Preferred. Agent/Partner

383 Main St, Westport

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.

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