99 Old Academy Rd, Fairfield, CT 06824

$3,292,000
6
BD
8
BA
7,062
SqFt

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Sold Price
$3,292,000
List Price
$2,999,000
Status
CLOSED
Days on Market
74
Closing Date
Dec 15, 2025
MLS#
24130154
Subtype
Single Family For Sale
Style
Cape Cod
Year Built
1937
Bedrooms
6
Bathrooms
8
Full Baths
7
Half Baths
1
Living Area
7,062
Lot Size
94,525
Acres
2.17
Neighborhood
Greenfield Hill

Property Description

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.

Additional Information

Interior Features
Wired Audio, Cable Available, Open Floor Plan, Security System
Exterior Features
Breezeway, Deck, Hot Tub, Patio, Fruit Trees, Gazebo, Garden
Taxes
$37,341
Property Description
Cape Cod
Zoning
AAA
Appliances
Gas Range, Microwave, Refrigerator, Freezer, Ice Maker, Dishwasher, Washer, Dryer
Heating
Hot Air
Air Conditioning
Ceiling Fan(s), Central Air, Zoned
Foundation
Block, Concrete
Pool
Yes
Parking Features
Attached
Garage Spaces
3
Elementary School
Burr
Middle School
Tomlinson
High School
Fairfield Warde

Listing courtesy of Christine Howard from William Raveis Real Estate. (646) 239-5676 (203) 255-6841

Selling Office: Compass Connecticut, LLC.

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