About 99 Old Academy Road
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.
Features of 99 Old Academy Road
| MLS® # | 24130154 |
|---|---|
| Price | $2,999,000 |
| Bedrooms | 6 |
| Bathrooms | 8.00 |
| Full Baths | 7 |
| Half Baths | 1 |
| Square Footage | 7,062 |
| Acres | 2.17 |
| Type | Single Family For Sale |
| Style | Cape Cod |
| Status | Under Contract |
Community Information
| Address | 99 Old Academy Road |
|---|---|
| Area | Greenfield Hill |
| City | Fairfield |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06824 |
Amenities
| Features | Fireplace Insert, Generator, Programmable Thermostat, Thermopane Windows |
|---|---|
| Parking | Attached Garage |
| # of Garages | 3 |
| Is Waterfront | No |
| Waterfront | Not Applicable |
| Has Pool | Yes |
| Pool | Pool House, Vinyl, In Ground Pool |
Interior
| Interior Features | Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System |
|---|---|
| Appliances | Gas Range, Microwave, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller |
| Heating | Hot Air, Natural Gas |
| Cooling | Ceiling Fans, Central Air, Zoned |
| Fireplace | Yes |
| # of Fireplaces | 3 |
| Has Basement | Yes |
| Basement | Partial, Partially Finished |
Exterior
| Exterior | Clapboard |
|---|---|
| Exterior Features | Breezeway, Wrap Around Deck, Gutters, Hot Tub, French Doors, Patio, Fruit Trees, Gazebo, Garden Area |
| Lot Description | Level Lot, Cleared, Professionally Landscaped |
| Roof | Wood Shingle |
| Foundation | Block, Concrete |
School Information
| Elementary | Burr |
|---|---|
| Middle | Tomlinson |
| High | Fairfield Warde |
Additional Information
| Date Listed | October 2nd, 2025 |
|---|---|
| Days on Market | 6 |
| Zoning | AAA |
| RE / Bank Owned | No |
Listing Details
| Office | William Raveis Real Estate |
|---|