Real Estate Agent in Connecticut and Western Massachusetts

2 Windy Hill Road
Westport, Connecticut

Single Family For Sale

6

Bedrooms

6 (full) / 2 (half)

Bathrooms

8,185

Sq Ft

$ 4,795,000

Price

2 Windy Hill Road
Westport, Connecticut

Westport, Connecticut

Description:

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.

Listing Courtesy of Keller Williams Prestige Prop.

Meet Our Team

Our team consists of dedicated real estate professionals passionate about helping our clients achieve their goals. Every client receives personalized attention, expert guidance, and unparalleled service. Meet our team:

Alison Malkin
Alison Malkin

Broker/Owner

860-214-8008

Email
Alison Malkin
Nicole Malkin James

Broker/Owner

843-614-7222

Email
Alison Malkin
Luis Torres

Associate Broker

860-383-5211

Email
Alison Malkin
Debra Pliego

Realtor®

860-919-7376

Email
Alison Malkin
Madison Wells

Realtor®

860-538-7567

Email
Alison Malkin
Lori Sierpinski

Realtor®

860-222-4692

Email
Alison Malkin
Jim Murkette

Realtor®

860-539-5009

Email
Alison Malkin
Leah Pliego

Realtor®

860-681-7373

Email

Acres : 1
Appliances Included : Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Attic : Pull-Down Stairs
Basement : Full, Heated, Fully Finished
Full Baths : 6
Half Baths : 2
Baths Total : 8
Beds Total : 6
City : Westport
Cooling : Central Air, Zoned
County : Fairfield
Elementary School : Long Lots
Fireplaces : 2
Foundation : Concrete
Garage Parking : Attached Garage
Garage Slots : 3
Description : Fence - Partial, Level Lot, On Cul-De-Sac, Professionally Landscaped
Middle School : Bedford
Amenities : Commuter Bus, Golf Course, Health Club, Library, Playground/Tot Lot, Public Rec Facilities, Shopping/Mall
Neighborhood : Long Lots
Parcel : 411794
Pool Description : Gunite, Heated, In Ground Pool
Postal Code : 06880
Roof : Metal
Additional Room Information : Bonus Room, Foyer, Gym, Laundry Room
Sewage System : Public Sewer Connected
SgFt Description : New Construction
Total SqFt : 8185
Tax Year : July 2025-June 2026
Total Rooms : 14
Watersource : Public Water Connected
weeb : RPR, IDX Sites, Realtor.com

Phone

860-384-7624

Address

20 Hopmeadow St, Unit 821, Weatogue, CT 06089


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