Connecticut
Fairfield
99 Old Academy Road

$2,999,000

99 Old Academy Road, Fairfield, CT 06824

6 beds |
8 baths |
7,062 sqft

Single-Family Home
Built in 1937
2.17acre lot
3 car garage
$425/sqft
Listed 4 days ago

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.

Listing Status:: Active
Date Added:: October 2, 2025 at 11:09AM
Listing Office:: William Raveis Real Estate : (203) 255-6841
Listing Agent:: Christine Howard : (646) 239-5676
MLS ID:: 24130154

General: Audio SystemAuto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System
Rooms: Bonus RoomFoyerGreenhouseGymLaundry RoomMud RoomSitting Room
Appliances: Gas RangeMicrowaveRefrigeratorFreezerIcemakerDishwasherWasherDryerWine Chiller
Laundry: Main LevelUpper Level
Basement: PartialPartially Finished
A/C: Ceiling FansCentral AirZoned
Heating: Hot AirNatural Gas
Fireplace: Fireplaces: 3

General: BreezewayWrap Around DeckGuttersHot TubFrench DoorsPatioFruit TreesGazeboGarden Area
Style: Cape Cod
Pool: Pool HouseVinylIn Ground Pool

Roofing: Wood Shingle

County: Fairfield

Zoning: AAA129507

Water: Public Water Connected
Sewer: Septic

Exclusions: Gas Grill

This listing courtesy of Christine Howard, William Raveis Real Estate

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Burr Elementary School

1960 Burr St, Fairfield, CT, 06824

Grades KG-5

1.18 miles away

Tomlinson Middle School

200 Unquowa Rd, Fairfield, CT, 06824

Grades 6-8

2.85 miles away

Fairfield Warde High School

755 Melville Ave, Fairfield, CT, 06825

Grades 9-12

2.32 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.