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
$3,478,700 Zestimate®
$466/sqft
$7,694 Estimated rent
Home value
$3,478,700
$3.13M - $3.86M
$7,694/mo
Zestimate® history
Owner options
List your home for rent
$7,694/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$7,694/mo
Rent Zestimate®
Refinance and save
$18,554/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$18,554/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Heated poolGas fireplaceDouble-sided fireplaceWrap-a-round mahogany decksArched-top dormersCustom mahogany libraryBluestone patio
Zillow last checked:
Listing updated:
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
Rooms
- Room types: Bonus Room, Gym, Laundry, Sitting Room
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 & HOA
Community
- Features: Golf, Health Club, Library, Paddle Tennis, Private School(s), Shopping/Mall
- Security: Security System
- Subdivision: Greenfield Hill
HOA
- Has HOA: No
Location
- Region: Fairfield
Financial & listing details
- Price per square foot: $466/sqft
- Tax assessed value: $1,315,300
- Annual tax amount: $37,341
- Date on market: 10/2/2025
- Exclusions: Gas Grill,
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 | ||
| 5/9/2016 | Sold | $1,750,000$248/sqft |
Source: Smart MLS #99134585 Report a problem | ||
| 3/2/2016 | Pending sale | $1,750,000$248/sqft |
Source: Higgins Group Real Estate #99134585 Report a problem | ||
| 2/25/2016 | Listed for sale | $1,750,000+171.3%$248/sqft |
Source: Higgins Group Real Estate #99134585 Report a problem | ||
| 7/10/2013 | Sold | $645,000-57.7%$91/sqft |
Source: Public Record Report a problem | ||
| 2/10/2003 | Sold | $1,525,000+136.4%$216/sqft |
Source: Public Record Report a problem | ||
| 1/31/1997 | Sold | $645,000$91/sqft |
Source: Public Record 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 |
| 2022 | $35,829 +1% | $1,315,300 |
| 2021 | $35,487 +37.3% | $1,315,300 +36.3% |
| 2020 | $25,845 | $964,740 |
| 2019 | $25,845 +1.6% | $964,740 |
| 2018 | $25,431 +2.1% | $964,740 |
| 2017 | $24,910 +3.5% | $964,740 -0.7% |
| 2015 | $24,077 +1.6% | $971,250 |
| 2014 | $23,699 +2% | $971,250 |
| 2013 | $23,242 +6.5% | $971,250 |
| 2011 | $21,824 +11.3% | $971,250 -4.5% |
| 2010 | $19,606 +2% | $1,017,450 |
| 2009 | $19,230 +1.7% | $1,017,450 |
| 2008 | $18,904 +6.7% | $1,017,450 |
| 2007 | $17,714 +4.4% | $1,017,450 |
| 2006 | $16,961 -7.8% | $1,017,450 +37.2% |
| 2005 | $18,391 +19.5% | $741,580 +12.8% |
| 2004 | $15,389 +15.3% | $657,650 +5.9% |
| 2003 | $13,346 +60.3% | $620,760 +117.7% |
| 2001 | $8,327 +106.4% | $285,180 +11.4% |
| 2000 | $4,034 -41% | $255,990 |
| 1999 | $6,835 | $255,990 |
Find assessor info on the county website
Neighborhood: 06824
Nearby homes
- $2,185,6005 bd4 ba4.1k sqft33 Old Academy Rd, Fairfield, CT 06824Off Market
- $1,545,0005 bd3 ba4k sqft36 Old Academy Rd, Fairfield, CT 06824Off Market
- $874,650-- bd-- ba-- sqft90 Lancelot Rd, Fairfield, CT 06824Off Market
- $1,915,4005 bd4 ba4.1k sqft33 Old Academy Rd, Fairfield, CT 06430Off Market
- $1,846,9005 bd4 ba4k sqft60 Old Academy Rd, Fairfield, CT 06824Off Market
- $2,288,2004 bd4 ba5k sqft101 Old Academy Rd, Fairfield, CT 06824Off Market
- $2,421,0004 bd2 ba3.5k sqft100 Lancelot Rd, Fairfield, CT 06824Off Market
- $2,958,1005 bd6 ba7.9k sqft667 Burr St, Fairfield, CT 06824Off Market
Nearby schools
GreatSchools rating
- 8/10Burr Elementary SchoolGrades: K-5Distance: 1.2 mi
- 8/10Tomlinson 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.
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$3,478,700
2% more
+$69,574
With Zillow Showcase(estimated)
$3,548,274
- Connecticut
- Fairfield County
- Fairfield
- 06824
- 99 Old Academy Road
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Fairfield Topics
