USACTFairfieldGreenfield Hill99 Old Academy Rd
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99 Old Academy Rd, Fairfield, CT

House

Sold

Listed price in listed location currency (USD).
$3,292,000
$2,999,000

680

MLS® 24130154

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 7062 sqft
Garage Yes
Taxes $37,341
Lot Size 2.17 acres
Approx. Age 1937
Avg. Price Per Sqft $424
MLS® Number 24130154

Property Address: 99 Old Academy Rd, Fairfield, CT, 06824-7141

Average square foot calculated using Size range provided by listing agent.

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.
MLS® Number24130154
Laundry LevelMain Level, Upper Level
Central VacNo
FireplaceNo
Acreage2.17
Exterior
GarageYes
Approx. Age1937
BasementPartial, Partially Finished
DrivewayAttached Garage
Garage Spaces3
Heat
A/C
Heating Fuel

Extras

Rooms

Change to metres

Bedroom 2:Upper Level13 × 19 ft
Bedroom 1:Upper Level20 × 15 ft
Bedroom 2:Upper Level20 × 15 ft
Bedroom 4:Upper Level13 × 16 ft
Bedroom 3:Upper Level14 × 17 ft
Bedroom 5:Upper Level13 × 24 ft
Office:Main Floor12 × 13 ft
Other:Main Floor15 × 22 ft
Media Room:Lower Level15 × 29 ft
Bedroom 4:Upper Level13 × 16 ft
Family Room:Main Floor15 × 29 ft
Bedroom 3:Upper Level14 × 17 ft
Bedroom 1:Upper Level13 × 19 ft
Bedroom 2:Upper Level20 × 15 ft
Other:Upper Level15 × 29 ft
Bedroom 5:Upper Level13 × 24 ft
Dining Room:Main Floor17 × 18 ft
Other:Upper Level20 × 21 ft
Kitchen:Main Floor29 × 29 ft
Other:Lower Level17 × 29 ft
Bedroom 3:Upper Level13 × 19 ft
Bedroom 1:Upper Level20 × 15 ft
Bedroom 4:Upper Level13 × 24 ft
Bedroom 5:Upper Level13 × 16 ft

Similar Listings

Price History

Oct 8, 2025End Date
$3,292,000Sold Price

Sold

Oct 2, 2025List Date
$2,999,000List Price
  • Commute

Commute

Starting Address
Destination Address
99 Old Academy Rd, Fairfield, CT

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