99 Old Academy Rd Fairfield, CT 06824
Greenfield Hill NeighborhoodEstimated payment $18,841/month
Highlights
- Greenhouse
- Pool House
- Cape Cod Architecture
- Burr Elementary School Rated A
- Open Floorplan
- Fruit Trees
About This Home
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.
Listing Agent
William Raveis Real Estate Brokerage Phone: (646) 239-5676 License #RES.0798049 Listed on: 10/02/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $37,341
Year Built
- Built in 1937
Lot Details
- 2.17 Acre Lot
- Fruit Trees
- Garden
- Property is zoned AAA
Home Design
- Cape Cod Architecture
- Concrete Foundation
- Block Foundation
- Frame Construction
- Wood Shingle Roof
- Clap Board Siding
Interior Spaces
- 7,062 Sq Ft Home
- Open Floorplan
- Sound System
- Ceiling Fan
- 3 Fireplaces
- Self Contained Fireplace Unit Or Insert
- Thermal Windows
- French Doors
- Mud Room
- Entrance Foyer
- Sitting Room
- Bonus Room
- Home Gym
Kitchen
- Walk-In Pantry
- Gas Range
- Microwave
- Ice Maker
- Dishwasher
- Wine Cooler
Bedrooms and Bathrooms
- 6 Bedrooms
Laundry
- Laundry Room
- Laundry on main level
- Dryer
- Washer
Attic
- Storage In Attic
- Pull Down Stairs to Attic
- Attic or Crawl Hatchway Insulated
Partially Finished Basement
- Partial Basement
- Crawl Space
Home Security
- Home Security System
- Smart Lights or Controls
- Smart Thermostat
Parking
- 3 Car Garage
- Automatic Garage Door Opener
Eco-Friendly Details
- Energy-Efficient Lighting
Pool
- Pool House
- In Ground Pool
- Spa
- Vinyl Pool
Outdoor Features
- Wrap Around Balcony
- Patio
- Greenhouse
- Gazebo
- Breezeway
- Rain Gutters
Location
- Property is near shops
- Property is near a golf course
Schools
- Burr Elementary School
- Tomlinson Middle School
- Fairfield Warde High School
Utilities
- Zoned Heating and Cooling
- Heating System Uses Natural Gas
- Programmable Thermostat
- Power Generator
- Tankless Water Heater
- Cable TV Available
Listing and Financial Details
- Exclusions: Gas Grill,
- Assessor Parcel Number 129507
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $37,341 | $1,315,300 | $374,430 | $940,870 |
| 2024 | $36,697 | $1,315,300 | $374,430 | $940,870 |
| 2023 | $36,184 | $1,315,300 | $374,430 | $940,870 |
| 2022 | $35,829 | $1,315,300 | $374,430 | $940,870 |
| 2021 | $35,487 | $1,315,300 | $374,430 | $940,870 |
| 2020 | $25,845 | $964,740 | $454,860 | $509,880 |
| 2019 | $25,845 | $964,740 | $454,860 | $509,880 |
| 2018 | $25,431 | $964,740 | $454,860 | $509,880 |
| 2017 | $24,910 | $964,740 | $454,860 | $509,880 |
| 2016 | $24,553 | $964,740 | $454,860 | $509,880 |
| 2015 | $24,077 | $971,250 | $512,890 | $458,360 |
| 2014 | $23,699 | $971,250 | $512,890 | $458,360 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 10/09/2025 10/09/25 | Pending | -- | -- | -- | |
| 10/02/2025 10/02/25 | For Sale | $2,999,000 | +85.1% | $425 / Sq Ft | |
| 07/26/2019 07/26/19 | Sold | $1,620,000 | -4.4% | $303 / Sq Ft | View Prior Sale |
| 06/25/2019 06/25/19 | Pending | -- | -- | -- | |
| 05/01/2019 05/01/19 | For Sale | $1,695,000 | -3.1% | $317 / Sq Ft | |
| 05/09/2016 05/09/16 | Sold | $1,750,000 | 0.0% | $317 / Sq Ft | View Prior Sale |
| 04/09/2016 04/09/16 | Pending | -- | -- | -- | |
| 02/16/2016 02/16/16 | For Sale | $1,750,000 | -- | $317 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $1,620,000 | -- | |
| Warranty Deed | $1,620,000 | -- | |
| Warranty Deed | $1,750,000 | -- | |
| Warranty Deed | $1,750,000 | -- | |
| Warranty Deed | $645,000 | -- | |
| Warranty Deed | $645,000 | -- | |
| Warranty Deed | $1,525,000 | -- | |
| Warranty Deed | $1,525,000 | -- | |
| Warranty Deed | $645,000 | -- | |
| Warranty Deed | $645,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $225,000 | Purchase Money Mortgage |
Source: SmartMLS
MLS Number: 24130154
APN: FAIR-000150-000000-000025
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