Welcome to 265 Chaplin Crescent, a rare offering in the heart of South Forest Hill backing directly onto the scenic 9km Toronto Beltline Trail linear park. This spacious and well-maintained 4-bedroom, 4-bathroom detached home offers nearly 2,900 square feet of finished living space across three levels and sits on a beautifully landscaped 35ft x 120ft lot in one of Toronto's most sought-after neighbourhoods. Built in 1962 and cherished by the same family for over 50 years, the home is move-in ready while also presenting tremendous potential for updates, addition(?), customization, or a full-scale rebuild. The main floor features sun-filled formal living and dining rooms ideal for entertaining, a gas fireplace, a bright eat-in kitchen with south & east windows, and a convenient 2-piece powder room. Upstairs are four generously sized bedrooms including a primary suite with 3-piece ensuite & ample closet space, with views of the front and rear gardens. The lower level offers a large recreation room with a wood-burning fireplace, a work-from-home office space with large desk, large above-grade windows, cabinets, large cold storage room, laundry/utility room, and comfortable ceiling heights. Enjoy great natural light throughout this home from oversized double-hung windows. Exterior features include a wide covered front veranda, private driveway, built-in garage with window & shelving, and beautiful mature gardens. Located just steps from the upcoming Chaplin LRT Station and within walking distance to top public and private schools, including UCC, BSS, and Forest Hill CI, as well as parks, restaurants, and shops along Eglinton Ave. This is a unique opportunity to secure a family home or premium building lot in a prestigious, transit-connected neighbourhood with strong long-term value. Please be sure to check out our immersive Virtual Tour for a video walkthrough, floor plans, additional photos & detailed community info. **Home Inspection Report & 2015 land survey on file**
Patio, Lighting, Backs On Green Belt, Landscape Lighting
Water Heater (GAS)
Two(2) refrigerators, dishwasher, stove, deep freezer, washer, dryer, garage door opener & remote, desk w/rug in office, three(3) mirrored storage cabinets in laundry room, all electric light fixtures, all window coverings, broadloom where attached, gas fireplace remote
Water Heater (GAS)
Brick, Other
No
No
None
Park/Greenbelt, Garden
Floor
Type
Size
Other
Main
Foyer
20'2"6.15 m × 4'3"1.30 m
Large Closet, Staircase, Side Door
Main
Living Room
18'1"5.51 m × 12'11⅛"3.94 m
Gas Fireplace, Bay Window, Hardwood Floor
Main
Dining Room
13'3"4.04 m × 11'10"3.61 m
Hardwood Floor, Glass Doors, W/O To Patio
Main
Kitchen
13'3"4.04 m × 11'10"3.61 m
2 Pc Bath, Tile Floor, Large Window
Second
Other
12'4"3.76 m × 6'7"2.01 m
Linen Closet, Broadloom, Large Closet
Second
Bedroom
15'6¼"4.73 m × 12'9½"3.90 m
3 Pc Ensuite, His and Hers Closets, Large Window
Second
Bedroom 2
13'4"4.06 m × 11'6"3.51 m
Overlooks Frontyard, Double Closet, Large Window
Second
Bedroom 3
10'8"3.25 m × 9'5"2.87 m
Hardwood Floor, Large Closet, Large Window
Second
Bedroom 4
11'8"3.56 m × 10'8"3.25 m
B/I Bookcase, Large Closet, Overlooks Backyard
Basement
Recreation
20'1"6.12 m × 17'3"5.26 m
2 Pc Bath, Fireplace, Large Window
Basement
Office
12'4"3.76 m × 10'9"3.28 m
Above Grade Window, Large Window, Laminate
Basement
Laundry
10'4"3.15 m × 10'3"3.12 m
Laundry Sink, Large Window, Tile Floor
Basement
Cold Room/Cantina
17'8"5.38 m × 2'5".74 m
Above Grade Window, B/I Shelves
Floor
Ensuite
Pieces
Other
Main
No
2
4'11" x 4'3" 2 Pc Bath, Window, Overlooks Garden
Second
No
4
7'1" x 7' 4 Pc Bath, Overlooks Garden, Large Window
Data was last updated May 24, 2025 at 12:15 AM (UTC)
Area Statistics
Listings on market:
54
Avg list price:
$6,347,500
Min list price:
$1,880,000
Max list price:
$29,788,000
Avg days on market:
31
Min days on market:
2
Max days on market:
673
These statistics are generated based on the current listing's property type
and located in
Forest Hill South. Average values are
derived using median calculations.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website.
The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.