Bedrooms
Bathrooms
Sq Ft
Price
Fairfield, Connecticut
Welcome to 99 Old Academy Road, a distinguished Cape originally reimagined by local architect Richard Swann and thoughtfully expanded in 2019 by Alex Esposito. Arched-top dormers elevate the architecture, blending tradition with luxury. This residence offers 6 bedrooms plus a private two-level guest suite, 7 full / 3 half baths, all set on 2+ acres in lower Greenfield Hill. At the heart of the home, the kitchen offers an open layout with a spacious dining area, custom cabinetry, a floor-to-ceiling glass wine display, and walk-in pantry. The kitchen flows seamlessly onto a bluestone patio with a double-sided fireplace, perfect for indoor-outdoor living. The kitchen leads to the lower level, featuring a stone bar in the game room, a 10-seat cinema, and ample storage. The family room, with its built-ins, poolside views, and gas fireplace, offers an inviting year-round retreat, the main level also includes a private office. Upstairs, every bedroom is paired with its own private bath, each with a unique design. The custom mahogany library serves as a passage to the East Wing, where the main level offers a gym, poolside lounge, & outdoor shower, while the upper-level features three additional en-suite bedrooms and a second laundry room. Outdoors, enjoy wrap-a-round mahogany decks, multiple bluestone patios, a heated pool, volleyball court, pergola gardens, and fruit trees. 99 Old Academy Road isn't just a home, it's a lifestyle of elegance, comfort, and unforgettable spaces.
Listing Courtesy of William Raveis Real Estate
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:
Broker/Owner
860-214-8008
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Broker/Owner
843-614-7222
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Associate Broker
860-383-5211
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Realtor®
860-919-7376
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Realtor®
860-538-7567
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Realtor®
860-222-4692
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Realtor®
860-539-5009
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Realtor®
860-681-7373
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Realtor®
860-249-1641
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Acres : 2.17
Appliances Included : Gas Range, Microwave, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Attic : Crawl Space, Storage Space, Pull-Down Stairs
Basement : Partial, Partially Finished
Full Baths : 7
Half Baths : 1
Baths Total : 8
Beds Total : 6
City : Fairfield
Cooling : Ceiling Fans, Central Air, Zoned
County : Fairfield
Elementary School : Burr
Fireplaces : 3
Foundation : Block, Concrete
Garage Parking : Attached Garage
Garage Slots : 3
Description : Level Lot, Cleared, Professionally Landscaped
Middle School : Tomlinson
Amenities : Golf Course, Health Club, Library, Paddle Tennis, Private School(s), Shopping/Mall
Neighborhood : Greenfield Hill
Parcel : 129507
Pool Description : Pool House, Vinyl, In Ground Pool
Postal Code : 06824
Roof : Wood Shingle
Additional Room Information : Bonus Room, Foyer, Greenhouse, Gym, Laundry Room, Mud Room, Sitting Room
Sewage System : Septic
Total SqFt : 7062
Tax Year : July 2025-June 2026
Total Rooms : 10
Watersource : Public Water Connected
weeb : RPR, IDX Sites, Realtor.com
Phone
860-384-7624
Address
20 Hopmeadow St, Unit 821, Weatogue, CT 06089