99 Old Academy Road Fairfield, CT $ 2,999,000
99 Old Academy Road
$ 2,999,000
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99 Old Academy Road

Fairfield, CT, 06824
$ 2,999,000
Bedrooms6 Baths7.1 Sq 7,062

Monthly Estimate*

$ 18,710

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Single Family Home for sale in Fairfield, CT

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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Single Family Contingent

Price

$ 2,999,000

Bedrooms

6

Full Bath

7

Half Bath

1

Property Type

Single Family

Taxes

$ 37,341

Style

Lot Size

2.17

Year Built

1937

Town/City

Fairfield

MLS | Web ID

24130154

Features
General
Zoning 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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Interior
Cooling System Ceiling Fans Central Air Zoned
Total Rooms 10
Basement Description Partial Partially Finished
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Exterior
Water Source Public Water Connected
Lot Description Level Lot Cleared Professionally Landscaped
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* Excluded Features
List By
Christine Howard

Listing Agent

William Raveis Real Estate

Broker

christine.howard@raveis.com

Email

Affordability Calculator

$21,822
Per Month
86%
14%
0%
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.
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Nearby
3042648 Elementary School
1968319 Middle School
Fairfield Warde High School High School
Pricing History
DatePricePrice ChangeDescription
10/2/2025$2,999,000 Listed Price

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99 Old Academy Road, Fairfield, CT, 06824 is a Single Family Home for sale at $2,999,000 with 7,062 sqft and a lot size of 2.17. 99 Old Academy Road has 6 bedrooms, 7.1 baths, and was built in 1937. The property's zip code is 06824 which is in Fairfield, CT