This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
$3,292,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
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.
Full Property Details
Full Property Details for 99 Old Academy Rd
General
- Sold For: $3,292,000
- Taxes: (July 2025-June 2026)
- Status: Closed
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24130154
- Added to Site: 142 day(s) ago
Interior
- Number of Rooms: 10
- Rooms/Areas: Bonus Room, Foyer, Greenhouse, Gym, Laundry Room, Mud Room, Sitting Room
- Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
- Fireplace: Yes
- Number of Fireplaces: 3
- Appliances: Gas Range, Microwave, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Rooms
Bathrooms
- Total Bathrooms: 8
- Full Bathrooms: 7
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 6
- Primary Suite: Dressing Room, Full Bath, Walk-In Closet, Hardwood Fl, 29 x 15, Upper
- Bedroom 1: Bedroom - Palladian Window(s), Vaulted Ceiling, Full Bath, Walk-In Closet, Hardwood Floor, 15 x 20, Upper
- Bedroom 2: Bedroom - Palladian Window(s), 9 ft+ Ceilings, Ceiling Fan, Full Bath, Walk-In Closet, 16 x 13, Upper
- Bedroom 3: Bedroom - Palladian Window(s), Full Bath, Hardwood Floor, 17 x 14, Upper
- Bedroom 4: Bedroom - Palladian Window(s), Vaulted Ceiling, Full Bath, Walk-In Closet, Hardwood Floor, 19 x 13, Upper
- Bedroom 5: Bedroom - Palladian Window(s), Book Shelves, Full Bath, Hardwood Floor, 24 x 13, Upper
Other Rooms
- Family Room: Family Room - Built-Ins, Gas Log Fireplace, French Doors, Patio/Terrace, Hardwood Floor, 29 x 15, Main
- Kitchen: Kitchen - Quartz Counters, Dining Area, Wet Bar, French Doors, Island, Pantry, 29 x 29, Main
- Dining Room: Dining Room - Fireplace, French Doors, Hardwood Floor, 18 x 17, Main
- Office: Office - Built-Ins, Hardwood Floor, 13 x 12, Main
- Game room: Yes
- Game Room: Rec/Play Room - Dry Bar, Laminate Floor, 29 x 17, Lower
- Rec Room: Dry Bar, Laminate Floor, 29 x 17, Lower
- Theater/Media: Media Room - Wall/Wall Carpet, 29 x 15, Lower
- Laundry: Main Level, Upper Level
- Other Room 1: Other - Palladian Window(s), Bedroom Suite, Dressing Room, French Doors, Full Bath, Hardwood Floor, 21 x 20, Upper
Additional Information
- Pool: Yes
- Pool Description: Pool House, Vinyl, In Ground Pool
Exterior
- Exterior Features: Breezeway, Wrap Around Deck, Gutters, Hot Tub, French Doors, Patio, Fruit Trees, Gazebo, Garden Area
- Color: White
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Parking: Attached Garage
Location
- County: Fairfield
- Neighborhood: Greenfield Hill
- Driving Directions: Burr to Old Academy Road
School Information
- Elementary School: Burr
- Middle School: Tomlinson
- High School: Fairfield Warde
Community
- Community Name: Greenfield Hill
Heating & Cooling
- Cooling Type: Ceiling Fans, Central Air, Zoned
- Heating Type: Hot Air, Natural Gas
- Heating Fuel: Natural Gas
- Water Heater: Natural Gas, Tankless Hotwater
Utilities
- Sewer: Septic
- Water: Public Water Connected
Structural Information
- Architectural Style: Cape Cod
- Construction Status: No/Resale
- Exterior Const.: Clapboard
- Basement Desc.: Partial, Partially Finished
- Roof: Wood Shingle
- Attic: Yes
- Square Feet: 7,062
- Above Ground: 7,062 Sq. Ft.
- Year Built: 1937
Lot Features
- Lot Size (Acres): 2.17
- Zoning: AAA
- Lot Description: Level Lot, Cleared, Professionally Landscaped
Green Features
- Energy Features: Fireplace Insert, Generator, Programmable Thermostat, Thermopane Windows
Financial Considerations
- Assessment Amount: $1,315,300
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Exclusions: Gas Grill,
- Property ID: 129507
Listed by William Raveis Real Estate, Christine Howard
Sold by Compass Connecticut, LLC, Veronica Monahan
Get Pre-Approved Today
Schools
Schools serving 99 Old Academy Rd
School District:Fairfield School District
| Name | Grades | Distance |
|---|---|---|
Burr Elementary School 1960 Burr Street, Fairfield, CT 06824 | PK-5 | 1.2 mi |
Tomlinson Middle School 200 Unquowa Road, Fairfield, CT 06824 | 6-8 | 2.9 mi |
Fairfield Warde High School 755 Melville Avenue, Fairfield, CT 06825 | 9-12 | 2.3 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 99 Old Academy Rd
Date
Details
Price
Change
Source
12/15/2025
Sold
$3,292,000
9.77%
MLS
10/02/2025
Listed
$2,999,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
99 Old Academy Road, Fairfield, CT 06824 (MLS# 24130154) is a Single Family property that was sold at $3,292,000 on December 15, 2025. Want to learn more about 99 Old Academy Road? Do you have questions about finding other Single Family real estate for sale in Fairfield? You can browse all Fairfield real estate or contact a Coldwell Banker agent to request more information.

