Highest/Best 2/16 by 5 PM. Applewood is a rare and charming 2-acre petite estate that seamlessly blends historic character with exceptional potential. Originally a barn, nestled within the remnants of a picturesque apple tree farm, this unique home offers an incredible opportunity to renovate, reimagine, or build anew while taking advantage of the existing 2-BEDROOM GUEST COTTAGE, INGROUND POOL and lovingly curated gardens planted over the last 2 decades. The main residence is filled with vintage appeal including wood-burning fireplace, custom built-ins and hardwood floors. Notable features include a private guest wing with full bath, the inviting screened porch, primary bedroom with bath en suite in a second wing and the finished walk-out level. This lower level presents a flexible bonus room/BR with full bath and fireplace with wood-burning stove. MAIN RESIDENCE: SF is 1815 + 209 screened porch + 480 Fin LL = 2504 SF with 4BR, 4 full baths. A versatile GUEST HOUSE offers endless possibilities, whether for guests, a home office, or rental income. The cozy living room features a wood-burning fireplace and built-ins open to kitchen, while 2 bedrooms share 1 full bath. SF = 930 SF. An IN-GROUND POOL provides a refreshing escape embraced by a perimeter of mature trees. An idyllic setting adorned with stone walls, creeping ivy and stone fireplace. Walk along the period homes, shady lanes and meandering stone walls to Greenfield Hill's center, farmer's market and parks. The location of Applewood is highly sought-after, just a short stroll from the Greenfield Hill town green with its annual Dogwood festival and surrounding homes include multi-million $$ gentleman farms and estates. Close to private and public schools, private clubs and Greenfield Hill's charming center for coffee, dinner, farmer's market or shopping. Sited in lower Greenfield Hill, the location is notable for its convenience to train, Southport, Westport + Fairfield town centers.
Sold for $1,600,000
$1,600,000
1242 Old Academy Road, Fairfield, CT 06824
3beds
3,225sqft
Single Family Residence
Built in 1946
2.02 Acres Lot
$1,719,300 Zestimate®
$496/sqft
$7,560 Estimated rent
Home value
$1,719,300
$1.53M - $1.93M
$7,560/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
The Denise Walsh Team,
Denise Walsh 203-650-1583,
William Raveis Real Estate 203-255-6841
Bought with:
Matthew D. Hyde, RES.0802189
William Raveis Real Estate
Source: Smart MLS,MLS#: 24071518
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 4
- Full bathrooms: 4
Primary bedroom
- Features: Full Bath, Hardwood Floor, Tile Floor
- Level: Main
- Area: 210 Square Feet
- Dimensions: 14 x 15
Bedroom
- Features: Built-in Features, Hardwood Floor
- Level: Main
- Area: 156 Square Feet
- Dimensions: 13 x 12
Bedroom
- Features: Full Bath, Wall/Wall Carpet
- Level: Main
- Area: 120 Square Feet
- Dimensions: 10 x 12
Bathroom
- Features: Stall Shower, Tile Floor
- Level: Main
- Area: 24 Square Feet
- Dimensions: 8 x 3
Bathroom
- Features: Hydro-Tub, Stall Shower, Tile Floor
- Level: Main
- Area: 84 Square Feet
- Dimensions: 7 x 12
Bathroom
- Features: Tub w/Shower, Tile Floor
- Level: Main
- Area: 35 Square Feet
- Dimensions: 7 x 5
Bathroom
- Features: Stall Shower, Tile Floor
- Level: Lower
- Area: 42 Square Feet
- Dimensions: 7 x 6
Dining room
- Features: Built-in Features, Hardwood Floor
- Level: Main
- Area: 225 Square Feet
- Dimensions: 15 x 15
Family room
- Features: Bookcases, Wood Stove, French Doors, Tile Floor
- Level: Lower
- Area: 247 Square Feet
- Dimensions: 13 x 19
Kitchen
- Features: Dining Area, Kitchen Island, Pantry, Sliders, Tile Floor
- Level: Main
- Area: 270 Square Feet
- Dimensions: 18 x 15
Living room
- Features: Bay/Bow Window, Fireplace, Hardwood Floor
- Level: Main
- Area: 225 Square Feet
- Dimensions: 15 x 15
Other
- Level: Main
- Area: 198 Square Feet
- Dimensions: 18 x 11
Heating
- Forced Air, Oil
Cooling
- None
Appliances
- Included: Cooktop, Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Disposal, Washer, Dryer, Water Heater
- Laundry: Lower Level
Features
- Entrance Foyer, In-Law Floorplan
- Basement: Full,Partially Finished
- Attic: Walk-up
- Number of fireplaces: 2
Interior area
- Total structure area: 3,225
- Total interior livable area: 3,225 sqft
- Finished area above ground: 2,745
- Finished area below ground: 480
Property
Parking
- Total spaces: 6
- Parking features: Attached, Paved, Driveway, Garage Door Opener, Private
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Screened, Porch, Patio
- Exterior features: Rain Gutters, Lighting, Stone Wall
- Has private pool: Yes
- Pool features: Vinyl, In Ground
- Waterfront features: Beach Access, Water Community
Lot
- Size: 2.02 Acres
- Features: Level
Details
- Additional structures: Shed(s), Guest House
- Parcel number: 133139
- Zoning: AAA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Shingle Siding, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1946
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available
Community & HOA
Community
- Features: Golf, Health Club, Lake, Library, Playground, Public Rec Facilities, Shopping/Mall, Tennis Court(s)
- Subdivision: Greenfield Hill
HOA
- Has HOA: No
Location
- Region: Fairfield
Financial & listing details
- Price per square foot: $496/sqft
- Tax assessed value: $504,140
- Annual tax amount: $14,066
- Date on market: 1/30/2025
- Exclusions: Dining Room Chandelier, Fireplace Items, Shelving, Water Heater (RENTED), Workbench, Master Bedroom Drapes. Exterior Bird Feeders, Planters & Pots
Price history
| Date | Event | Price |
|---|---|---|
| 4/4/2025 | Sold | $1,600,000+23.2%$496/sqft |
Source:  Smart MLS #24071518 Report a problem | ||
| 2/23/2025 | Pending sale | $1,299,000$403/sqft |
Source: Smart MLS #24071518 Report a problem | ||
| 2/22/2025 | Listed for sale | $1,299,000$403/sqft |
Source:  William Raveis Real Estate, Mortgage & Insurance #24071518 Report a problem | ||
| 2/17/2025 | Pending sale | $1,299,000$403/sqft |
Source: William Raveis Real Estate, Mortgage & Insurance #24071518 Report a problem | ||
| 2/12/2025 | Listed for sale | $1,299,000$403/sqft |
Source: Smart MLS #24071518 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,313 +1.8% | $504,140 |
| 2024 | $14,066 +1.4% | $504,140 |
| 2023 | $13,869 +1% | $504,140 |
| 2022 | $13,733 +1% | $504,140 |
| 2021 | $13,602 -14.5% | $504,140 -15.1% |
| 2020 | $15,903 | $593,600 |
| 2019 | $15,903 +1.6% | $593,600 |
| 2018 | $15,647 +2.1% | $593,600 |
| 2017 | $15,327 -1.2% | $593,600 -5.1% |
| 2015 | $15,508 +1.6% | $625,590 |
| 2014 | $15,264 +2% | $625,590 |
| 2013 | $14,970 +6.5% | $625,590 |
| 2011 | $14,057 +22.5% | $625,590 +5.1% |
| 2010 | $11,474 +2% | $595,420 |
| 2009 | $11,253 +1.7% | $595,420 |
| 2008 | $11,063 +6.7% | $595,420 |
| 2007 | $10,366 +4.9% | $595,420 +0.5% |
| 2006 | $9,880 -21.7% | $592,690 +16.4% |
| 2005 | $12,626 +6% | $509,110 |
| 2004 | $11,913 +8.8% | $509,110 |
| 2003 | $10,946 | $509,110 |
Find assessor info on the county website
Neighborhood: 06824
Nearby homes
- $1,463,9004 bd2 ba2.3k sqft1200 Old Academy Rd, Fairfield, CT 06824Off Market
- $2,254,8003 bd2 ba3.3k sqft1245 Old Academy Rd, Fairfield, CT 06824Off Market
- $1,758,9003 bd2 ba4.1k sqft1296 Old Academy Rd, Fairfield, CT 06824Off Market
- $2,821,8005 bd4 ba4.7k sqft1130 Old Academy Rd, Fairfield, CT 06824Off Market
- $1,341,1003 bd2 ba2.1k sqft105 Dunham Rd, Fairfield, CT 06824Off Market
- $10,850-- bd-- ba-- sqft1 Milbank Rd, Fairfield, CT 06824Off Market
- $2,530,8004 bd4 ba3.4k sqft1291 Old Academy Rd, Fairfield, CT 06824Off Market
- $2,570,1005 bd4 ba3.7k sqft1139 Old Academy Rd, Fairfield, CT 06824Off Market
Nearby schools
GreatSchools rating
- 10/10Dwight Elementary SchoolGrades: K-5Distance: 0.6 mi
- 8/10Roger Ludlowe Middle SchoolGrades: 6-8Distance: 2.7 mi
- 9/10Fairfield Ludlowe High SchoolGrades: 9-12Distance: 2.6 mi
Schools provided by the listing agent
- Elementary: Dwight
- Middle: Roger Ludlowe
- High: Fairfield Ludlowe
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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- Connecticut
- Fairfield County
- Fairfield
- 06824
- 1242 Old Academy Road
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