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.
Sold for $3,292,000
$3,292,000
99 Old Academy Road, Fairfield, CT 06824
6beds
7,062sqft
Single Family Residence
Built in 1937
2.17 Acres Lot
$3,332,700 Zestimate®
$466/sqft
$7,694 Estimated rent
Home value
$3,332,700
$3.00M - $3.70M
$7,694/mo
Zestimate® history
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List your homeWhat's special
Zillow last checked: 8 hours ago
Listing updated: December 16, 2025 at 09:21am
Listed by:
Christine Howard (646)239-5676,
William Raveis Real Estate 203-255-6841
Bought with:
Veronica A. Monahan, RES.0776529
Compass Connecticut, LLC
Source: Smart MLS,MLS#: 24130154
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 8
- Full bathrooms: 7
- 1/2 bathrooms: 1
Primary bedroom
- Features: Dressing Room, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 435 Square Feet
- Dimensions: 15 x 29
Bedroom
- Features: Palladian Window(s), Bookcases, Full Bath, Hardwood Floor
- Level: Upper
- Area: 312 Square Feet
- Dimensions: 13 x 24
Bedroom
- Features: Palladian Window(s), Full Bath, Hardwood Floor
- Level: Upper
- Area: 238 Square Feet
- Dimensions: 14 x 17
Bedroom
- Features: Palladian Window(s), High Ceilings, Ceiling Fan(s), Full Bath, Walk-In Closet(s)
- Level: Upper
- Area: 208 Square Feet
- Dimensions: 13 x 16
Bedroom
- Features: Palladian Window(s), Vaulted Ceiling(s), Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 247 Square Feet
- Dimensions: 13 x 19
Bedroom
- Features: Palladian Window(s), Vaulted Ceiling(s), Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 300 Square Feet
- Dimensions: 20 x 15
Dining room
- Features: Fireplace, French Doors, Hardwood Floor
- Level: Main
- Area: 306 Square Feet
- Dimensions: 17 x 18
Family room
- Features: Built-in Features, Gas Log Fireplace, French Doors, Patio/Terrace, Hardwood Floor
- Level: Main
- Area: 435 Square Feet
- Dimensions: 15 x 29
Kitchen
- Features: Quartz Counters, Dining Area, Wet Bar, French Doors, Kitchen Island, Pantry
- Level: Main
- Area: 841 Square Feet
- Dimensions: 29 x 29
Media room
- Features: Wall/Wall Carpet
- Level: Lower
- Area: 435 Square Feet
- Dimensions: 15 x 29
Office
- Features: Built-in Features, Hardwood Floor
- Level: Main
- Area: 156 Square Feet
- Dimensions: 12 x 13
Other
- Features: Palladian Window(s), Bedroom Suite, Dressing Room, French Doors, Full Bath, Hardwood Floor
- Level: Upper
- Area: 420 Square Feet
- Dimensions: 20 x 21
Rec play room
- Features: Palladian Window(s), Built-in Features, Hardwood Floor
- Level: Upper
- Area: 560 Square Feet
- Dimensions: 20 x 28
Rec play room
- Features: Dry Bar, Laminate Floor
- Level: Lower
- Area: 493 Square Feet
- Dimensions: 17 x 29
Sun room
- Features: Built-in Features, Wet Bar, French Doors, Engineered Wood Floor
- Level: Main
- Area: 330 Square Feet
- Dimensions: 15 x 22
Heating
- Forced Air, Natural Gas
Cooling
- Ceiling Fan(s), Central Air, Zoned
Appliances
- Included: Gas Range, Microwave, Refrigerator, Freezer, Ice Maker, Dishwasher, Washer, Dryer, Wine Cooler, Gas Water Heater, Tankless Water Heater
- Laundry: Main Level, Upper Level, Mud Room
Features
- Sound System, Open Floorplan, Entrance Foyer, Smart Thermostat
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Partial,Partially Finished
- Attic: Crawl Space,Storage,Pull Down Stairs
- Number of fireplaces: 3
- Fireplace features: Insert
Interior area
- Total structure area: 7,062
- Total interior livable area: 7,062 sqft
- Finished area above ground: 7,062
Property
Parking
- Total spaces: 3
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 3
Features
- Patio & porch: Wrap Around, Patio
- Exterior features: Breezeway, Rain Gutters, Fruit Trees, Garden
- Has private pool: Yes
- Pool features: Vinyl, In Ground
- Spa features: Heated
Lot
- Size: 2.17 Acres
- Features: Level, Cleared, Landscaped
Details
- Additional structures: Gazebo, Greenhouse, Pool House
- Parcel number: 129507
- Zoning: AAA
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Block, Concrete Perimeter
- Roof: Wood
Condition
- New construction: No
- Year built: 1937
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available
Green energy
- Energy efficient items: Thermostat, Windows
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Golf, Health Club, Library, Paddle Tennis, Private School(s), Shopping/Mall
Location
- Region: Fairfield
- Subdivision: Greenfield Hill
Price history
| Date | Event | Price |
|---|---|---|
| 12/15/2025 | Sold | $3,292,000+9.8%$466/sqft |
Source:  Smart MLS #24130154 Report a problem | ||
| 10/9/2025 | Pending sale | $2,999,000$425/sqft |
Source: Smart MLS #24130154 Report a problem | ||
| 10/2/2025 | Listed for sale | $2,999,000+85.1%$425/sqft |
Source: Smart MLS #24130154 Report a problem | ||
| 7/26/2019 | Sold | $1,620,000-4.4%$229/sqft |
Source: Smart MLS #170167310 Report a problem | ||
| 5/1/2019 | Listed for sale | $1,695,000-3.1%$240/sqft |
Source: William Raveis Real Estate #170167310 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $37,341 +1.8% | $1,315,300 |
| 2024 | $36,697 +1.4% | $1,315,300 |
| 2023 | $36,184 +1% | $1,315,300 |
Find assessor info on the county website
Neighborhood: 06824
Nearby schools
GreatSchools rating
- 8/10Burr Elementary SchoolGrades: K-5Distance: 1.2 mi
- 7/10Tomlinson Middle SchoolGrades: 6-8Distance: 2.9 mi
- 9/10Fairfield Warde High SchoolGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Burr
- Middle: Tomlinson
- High: Fairfield Warde
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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$3,332,700
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- Connecticut
- Fairfield County
- Fairfield
- 06824
- 99 Old Academy Road