4 Exceptional Luxury Homes Offering Waterfront and Estate Living in Sag Harbor and Connecticut

Discover the epitome of luxury living with four exceptional homes offering waterfront and estate elegance in Sag Harbor, NY, and Connecticut. From Sag Harbor’s stunning Bay Point vistas to Westport’s timeless Colonial estates, each property is a masterpiece of design, privacy, and modern amenities. Explore these breathtaking residences that redefine sophistication and comfort in every detail.

Waterfront New | $4,995,000

60 Harbor Dr, Sag Harbor, NY 11963
Listing agent: Simon Harrison

New in Sag Harbor’s Bay Point; Wow views over 120’ frontage; Published, well-considered rebuild, dock with Viking, Sub-Zero Chefs kitchen.

 

Size: 3,000 sf

 

Price: $4,995,000

 

Listing details:

 

Contact: Simon Harrison, Simon Harrison Real Estate, +1 917.822.6652

Westport, Connecticut | $4,995,000

1 Sturges Hwy, Westport, CT 06880
Listing agent: Annie Klyver

Timeless Colonial Estate: This exquisite five-bedroom, four full and two half-bath Colonial is a testament to charm and grace, set on a sprawling 5.7-acre property complete with a pool and a pool house. Situated just a stone’s throw from the prestigious Hunt Club polo fields, this family compound offers the rare blend of ultimate privacy with the convenience of proximity to town, train, and shops.

 

Size: 5,790 sf

 

Price: $4,995,000

 

Listing details: As you pass through the private gates, you’ll be greeted by a picturesque view that reflects the estate’s storied past and timeless elegance. Built in 1955 in the style of renowned architect Cameron Clark, this Colonial showcases classic architectural beauty with its distinctive French doors opening to a magnificent backyard. Here, specimen trees, age-old patios, and gracefully aged stone walls and landscaping create a serene environment only time can bestow. This estate is more than just a home; it’s a legacy of luxury and refinement, waiting to be cherished by its next owner. Don’t miss this rare opportunity to own a piece of history and enjoy unparalleled privacy and sophistication. Listing Agent is related to the Seller.

 

Contact: Annie Klyver, Higgins Group Real Estate, +1 203.520.9913

49 Indian Mill Rd | $4,695,000

49 Indian Mill Rd, Cos Cob, CT 06807
Listing agent: Graham Gyesky

Gorgeous midcountry property, recently custom built located at the end of a private cul-de-sac with its own private entrance to the Mianus River trails. This 5 bedroom home sits on over 2 private acres with a possible pool site. The glass entry opens to a formal dining and living room with wine closet and gas fireplace.

 

Size: 7,500  sf

 

Price: $4,695,000

 

Listing details: Stunning modern gourmet kitchen with breakfast area flows seamlessly into a large family room with vaulted ceiling and fireplace. Office, mudroom, powder and large pantry complete the first floor. Spacious primary suite with sitting room, spa like bathroom and two luxurious closets greet you on the second floor. Three additional bedrooms with walk in closets plus a nursery and laundry room. Go up to the third level with an additional bedroom, bath and open space. Finished walk out lower level boasts a large bar/entertaining area, office and gym with sauna. This smart, efficient home has heat pumps, solar panels (with powerwall backups), tankless water heaters and European triple pane windows throughout.

 

Contact: Graham Gyesky, Greenwich Realty Group LLC, +1 203.516.0694

249 Sturges Hwy | Contact for pricing

249 Sturges Hwy, Westport, CT 06880
Listing agent: LM Homes Team

Relaxed, entertaining luxury with all the bells and whistles….Privacy, serenity and convenience featuring Entertaining at it’s finest – step into 249 Sturges Highway greeted by welcoming floor plan from living room, dining room, open concept kitchen which highlights gorgeous quartzite counters, a Subzero refrigerator, Bosch dishwasher, and a 60″ Viking Dual Fuel range flowing into the great room accented with a stunning stone fireplace. French doors lead you outside to be greeted by an 18×40′ Heated Gunite Pool and Spa, a large patio with an an awning perfect for relaxing while listening to the waterfall. You are steps away from the pool room with a wet bar.

 

Size: 8,639 sf

 

Price: Contact for pricing

 

Listing details: The Primary Bedroom Suite has been thoughtfully laid out for enjoying a night cap in the sitting area with wet bar, two glass fronted wine refrigerators. No stone was left unturned with your primary new bathroom showcasing double sinks, radiant heat flooring, large rainfall shower, high-end lighting, free-standing soaking tub, a private balcony for morning coffee overlooking the luschious landscaping completes this masterpiece. 3 generous Ensuite bedrooms finish the second floor – The 3rd floor offers a fifth bedroom and full bath, as well as a bonus room for Movies, Gaming and will accommodate a Golf Simulator. The finished lower level has a wine cellar, gym and access to the 3 car garage. New mechanical systems including a new furnace, new Roth oil tank and 80 gallon hot water tank along with a Full House Generator ensure the home is in top condition. With over 8,000 square feet of space, this home truly has all the bells and whistles.

 

Contact: LM Homes Team, William Pitt Sotheby’s Int’l, +1 917.903.6275, 203.644.6172