99 Old Academy Road
Fairfield, CT, 06824 $ 2,999,000
Bedrooms6 Baths7.1 Sq 7,062 Monthly Estimate*
$ 18,710
for $2,999,000 with 6 bedrooms and 7 full baths, 1 half bath. This 7,062 square foot home was built in 1937 on a lot size of 2.17.
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.
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FeaturesGeneralZoning AAA
Neighborhood Greenfield Hill
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract
Acres 2.17
Directions Burr to Old Academy Road
High School Fairfield Warde
City Fairfield
Elementary School Burr
Sq Ft Total 7062
DOM 6
Year Built 1937
Exclusions Gas Grill
Style Cape Cod
Year Built Source Public Records
Pool Description Pool House Vinyl In Ground Pool
Energy Features Fireplace Insert Generator Programmable Thermostat Thermopane Windows
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InteriorCooling System Ceiling Fans Central Air Zoned
Total Rooms 10
Basement Description Partial Partially Finished
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ExteriorWater Source Public Water Connected
Lot Description Level Lot Cleared Professionally Landscaped
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* Excluded FeaturesList ByChristine HowardListing Agent
William Raveis Real EstateBroker
christine.howard@raveis.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $18,710
- Monthly Property Taxes
- $3,112
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Fairfield, CT
Average List Price $2,123,016
Percent of Sale Price 29%
About Fairfield, CT 60,257 Population
5% Since 2002
$ 123,531 Median Income
41.47 Median Age
37% Households with Children
Trends Information provided by ATTOM Data Solutions.
3042648 Elementary School
1968319 Middle School
Fairfield Warde High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/2/2025 | $2,999,000 | | Listed Price |