Looking for Chaplin Estates homes for sale? You’re only seeing some of the listings available here. To see them all, just click the ‘Signup’ or ‘Login’ link.
-
52 Elmsthorpe Avenue in Toronto: Forest Hill South House for sale (Toronto C03) : MLS®# C12551700
52 Elmsthorpe Avenue Toronto M5P 2L7 
$5,250,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12551700
- Bedrooms:
- 5
- Bathrooms:
- 5
Striking Contemporary Elegance In Prestigious Chaplin Estates Offering Inspired Living. A Dramatic Entry With Sleek Millwork And Designer Lighting Sets The Tone, Leading Into Sunlit Interiors With Soaring Ceilings, Skylights, And Panoramic Wall-To-Wall Windows. The Chefs Kitchen Features A Waterfall Island and Breakfast Counter Complete w/ Wolf & Miele Appliances, Seamlessly Connected To The Dining And Family Rooms With A Modern Gas Fireplace Perfect For Entertaining. The Primary Suite Overlooks The Landscaped Backyard, Complete With A Spa-Like 5-Piece Ensuite And Walk-In Closet. The Lower Level Offers A Walk-Out, Wet Bar, Recreation Room, And Flexible Bedroom/Office Ideal As A Nanny Or Guest Suite. Step Outside To A Private Backyard Sanctuary With A Saltwater Pool And Custom Waterfall. Additional Highlights Include A Heated Driveway, Integrated Home Automation, And Close Proximity To Top Private Schools, Summerhill Market, Shops, And TTC/LRT On Eglinton. More detailsListed by RE/MAX REALTRON BARRY COHEN HOMES INC.- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
308 Oriole Parkway in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12540942
308 Oriole Parkway Toronto M5P 2H5
$2,895,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12540942
- Bedrooms:
- 4
- Bathrooms:
- 3
A gracious centre hall home cherished by the same family for decades. The two storey home is perfectly positioned on the west side of Oriole Parkway on an impressive 51 x 134 foot lot in the desirable Chaplin Estates. The home features crown moulding, space, grace, flow, generous proportions and an abundance of natural light. The grand front to back living room with a wood burning fireplace, opens to a deck and the west facing garden. The dining room has a buffet nook and hardwood floors. There is a panelled den with open shelving overlooking the garden. The kitchen features a breakfast area with also a walkout to the deck and garden and a powder room complete the main floor. The second floor offers four well sized bedrooms, three piece bathroom, and the primary bedroom has two closets and a four-piece semi ensuite bathroom. The lower level with recreation room space, above grade windows, large storage room offer additional potential. There is a long private drive to a double detached garage. Chaplin Estates is one of the city's most desirable neighborhoods, known for its exceptional public and private schools close by, lush parks, pathways, community centres... Just a short stroll from the Yonge subway, and vibrant shopping areas offering a small-town vibe in the heart of the city, this location provides the perfect blend of convenience and community. This home is truly a rare find on an exceptional lot. This is ready to be reimagined for the next owners to personalize the space to suit their lifestyle and create their own special memories. More detailsListed by ROYAL LEPAGE/J & D DIVISION- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
46 Elmsthorpe Avenue in Toronto: Forest Hill South House for sale (Toronto C03) : MLS®# C12517352
46 Elmsthorpe Avenue Toronto M5P 2L7
$3,990,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12517352
- Bedrooms:
- 6
- Bathrooms:
- 6
Magnificent Custom Home In Chaplin Estates on a Premium Size Lot. Modernly designed featuring Over 4900 Sf Total Living Space (3307 sqft above ground + 1605 sqft of finished basement). Centre Hall Plan W/Contemporary Finishes & Designer Palette. Gourmet Kitchen upgraded with 6 burner Wolf stove, subzero fridge and Miele Dishwasher, Centre Island, Breakfast Bar and pantry area. Family Rm with fireplace and built in shelves, W/O To Patio & interlocked Yard. Primary bedroom features 2 large walkin closet and a 5pc ensuite overlooking the backyard. Finished basement has two extra rooms that can be used as nanny suite or guest room. Basement has a large rec room perfect for entertainment and walkup to backyard. Heated Bathroom Floors, L/L & Mudroom. Central Vac, Sec Sys, B/I Spkrs. In Walking Distance To Forest Hills Finest Schools BSS, UCC, St Mike's & In District To Forest Hill Jr & Collegiate, Parks, Shops. More detailsListed by CENTURY 21 LANDUNION REALTY INC.- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
441 Oriole Parkway in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12507112
441 Oriole Parkway Toronto M5P 2H7
$5,350,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12507112
- Bedrooms:
- 7
- Bathrooms:
- 6
Beautiful custom-built, energy-efficient home with unique personality designed by architect Paul Dowsett and interior designer Phillip Moody. This residence offers cozy, warm elegance with classical flair, designed for comfort and convenient living. Features include brick and stone exterior, bay windows, metal frame, 6+1 spacious bedrooms, 6 spa-like bathrooms, gorgeous centre hall, and an elegant Bellini eat-in kitchen with large pantry. Additional amenities include elevator access to all levels, 4 gas fireplaces, hardwood floors, energy-efficient underfloor heating throughout, third-floor winter garden/recreational room with abundant natural light and city views, walk-outs to decks on 2nd and 3rd levels, skylights, lots of storage, laundry on 3 levels, 2-car heated garage, beautiful heated driveway for 4 cars, separate entrance to finished basement w Nanny's and Entertainment rm, intercom and security reinforcement. Close to BSS, UCC, St. Clement's & York Schools. Walk to TTC, Subway & Yonge street, short drive to downtown. A forever home - a must-see! More detailsListed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
23C Lascelles Boulevard in Toronto: Yonge-St. Clair House for sale (Toronto C02) : MLS®# C12503320
23C Lascelles Boulevard Toronto M4V 2C1
$3,450,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12503320
- Bedrooms:
- 4
- Bathrooms:
- 5
Nestled In The Lushly Forested Deer Park, On The Kay Gardner Beltline, Deer Park Crossing Boasts 10 Luxury 3 Storey Townhomes, Each With A Roof Top Terrace & Pergola, Green Roof, Backyard, In Suite Elevator & The Space & Grace Of A Finely Built Custom Home. 3000 Sqft Of Gorgeous Living Space! Steps From The Shops, Cafe's, & Fine Dining Of Fab. Yonge And St. Clair. Close To Ucc, Bss Schools. In The Heart Of The City! Truly Tailored To Demands Of Upscale Living: This Is What You've Been Waiting For! Extras: See List Of Features/Finishes Attached. Inc 2 Underground Parking Spots, Flex Space For Lower Level Gym, Theatre, Games Rm., Etc. Alarm Sys (Excl. Monitoring), Inground Sprinkler Syst & More. Option For 3rd Flr Laundry. Model Suite Pictures More detailsListed by FOREST HILL REAL ESTATE INC.- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
889 Avenue Road in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12494428
889 Avenue Road Toronto M5P 2K7
$2,450,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12494428
- Bedrooms:
- 9
- Bathrooms:
- 8
Location!Location!Location!Great Rental Income! Steady Strong Cash Flow! Perfect For Investor Or End User Looking For Rental Income Supplement. Very Good Location for this beautiful 4412 sqft House. Magnificent Tudor Style Triplex Home In A Very Desireable Toronto District; W/ 2 Fireplaces, Leaded Glass Windows And Wainscoting. Hardwood & Granite Floor On Main Floor; Designer Kitchen On 2nd; Plus Stunning Basement Apartment.The Bathrooms Are Newly Renovated.Explore an Exceptional Detached Legal Three-plex With Finished Basement Apartment Strategically Positioned At One Of Toronto's Most Prestigious Intersections: Avenue Rd and Eglinton. This Rare Find Sits On An Expansive Lot Measuring 40.33x 121.46 Feet, Good Potential For Redevelopment or Continued Rental Income.The First Floor Is A 3 Bedrooms With 2 Bathrooms And 2 Living Rooms Apartment With Separate Entrance Door. The Second Floor Is A 2 Bedrooms With 2 Bathrooms And 2 Living Rooms with Separate Entrance Door, Same Large With First Floor Which Are More Then 1000 Sqft. The 3rd Floor is A Bne Bedroom Apartment With One Bathroom, One Kitchen And One Living room. The Basement Includes 3 bedrooms with 3 Seperate Bathrooms . The Property Is In A Good Condition With Inspection Report. Located Mere Steps From The New Eglinton Crosstown LRT And The Yonge-Eglinton TTC subway, This Prime Investment Property Offers Unparalleled Convenience. Enjoy Easy Access To A Vibrant Array Of Restaurants, Banks, Groceries, And Community Centers, Making It An Ideal Choice for Tenants And Future Residents A Like.Discover The Vibrant Local Scene With Shops And Dining Options Just Footsteps Away, Coupled With Proximity To Top-rated Public And Private Schools. Don't Miss This Opportunity To Capitalize On Both The Location And Potential Of This Property! **EXTRAS** 4 Washers And 4 Dryers. 3 Kitchen Appliances With More Appliances In The Basement. Please Come And See This Beautiful House Which Is Good for Big Family And Rental Potential. More detailsListed by SMART SOLD REALTY- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
85 Chaplin Crescent in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12478746
85 Chaplin Crescent Toronto M5P 1A4
$4,998,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12478746
- Bedrooms:
- 5
- Bathrooms:
- 6
An unanticipated delight awaits within this 5000+ sq.ft. architectural gem, where classic elegance meets modern refinement. Thoughtfully designed with no detail overlooked, this residence captures the essence of luxury family living in one of Toronto's most sought-after enclaves - Chaplin Estates. Step inside to discover soaring 11-foot ceilings, smoked oak chevron flooring, and a striking tiered skylight with integrated LED lighting that bathes the home in natural brilliance. Every room showcases masterful craftsmanship, from the floor-to-ceiling wainscoting to the custom built-ins and crown moulding that frame each space with timeless sophistication. The heart of the home is defined by titanium granite finishes, a chef-inspired kitchen, and expansive entertaining areas that flow seamlessly into lush treetop views of Oriole Park - a private, natural backdrop that changes with the seasons. Perfect for families seeking top-tier private schools, this home offers walkable conveniences, serene green spaces, and proximity to the city's best amenities - all wrapped in a refined, move-in-ready experience. A true statement of elegance, comfort, and enduring value - 85 Chaplin Crescent invites you to experience luxury without compromise. More detailsListed by HARVEY KALLES REAL ESTATE LTD.- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
16 Duncannon Drive in Toronto: Forest Hill South House for sale (Toronto C03) : MLS®# C12459721
16 Duncannon Drive Toronto M5P 2M1
$3,499,900Residential Freehold- Status:
- Active
- MLS® Num:
- C12459721
- Bedrooms:
- 5
- Bathrooms:
- 5
Welcome to 16 Duncannon Drive! a masterfully reimagined residence in the heart of prestigious Forest Hill. This beautifully redesigned home offers the perfect blend of timeless elegance and modern luxury, situated on a coveted street just steps from top-tier schools, parks, and vibrant local amenities. Every inch of this exceptional property has been thoughtfully renovated with high-end finishes and meticulous attention to detail. The chefs kitchen is a true showpiece, featuring a Wolf gas cooktop, double wall ovens, a fully paneled refrigerator, and sleek custom cabinetry and separate serveryideal for both everyday living and entertaining in style. The spacious living and dining areas are centered around a stunning gas fireplace, creating awarm and inviting atmosphere. Wide-plank hardwood floors, refined millwork, and expansive windows complete the sophisticated design. Upstairs, the luxurious primary suite offers a private retreat, complete with a custom dressing room and spa-inspired ensuite. Additional bedrooms are generously sized, offering comfort and versatility for family or guests. A rare find in Forest Hill, the home includes a private attached garage and a double driveway, offering ample parking in a highly walkable neighborhood. Don't miss this opportunity to own a turnkey home in one of Toronto's most sought-after locations. More detailsListed by THE AGENCY- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
137 Highbourne Road in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12433357
137 Highbourne Road Toronto M5P 2J8
$3,595,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12433357
- Bedrooms:
- 7
- Bathrooms:
- 6
Two Large Units in a Prime Location! Welcome to this stunning, fully renovated duplex in the highly sought-after Chaplin Estates. This impressive property features two spacious units: a main floor plus basement unit totaling 2,268 sq.ft. with 3+1 bedrooms and 3 bathrooms, as well as a massive 2,403 sq.ft. 3-bedroom, 3-bathroom suite spanning the second and third floors. The main floor offers ample living and dining spaces, perfect for comfortable family living. The basement features a large rec room, a 4-piece bathroom, plus a bedroom with a 2-piece ensuite, providing versatile living options. The upper two floors house an expansive suite that blends luxury and functionality. Enjoy a massive living room and formal dining area filled with natural light, along with a generous family room, private den, and separate home office. A gorgeous terrace off the family room offers a peaceful outdoor retreat in the city. This suite has been extensively renovated with premium finishes, modern fixtures, and top-tier appliances throughout, combining elegance and practicality.Located just moments from the new LRT subway station, this duplex offers unparalleled convenience for commuting, along with easy access to trendy restaurants, boutique shops, public transit, and TTC options. Chaplin Estates is renowned for its tree-lined streets, community charm, parks, and excellent public and private schools, making this property ideal as a family home or a savvy investment. Additional features include separate utilities, large windows providing abundant natural light, tasteful neutral décor, and comprehensive infrastructure upgrades that ensure comfort and safety year-round. Offering versatility, generous space, and a prime location, this duplex is perfect for living in one unit while renting the other, multigenerational families, or investors seeking a high-demand neighbourhood. Don't miss this rare opportunity to own a beautifully renovated duplex in Chaplin Estates. Welcome home! More detailsListed by ROYAL LEPAGE/J & D DIVISION- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
182 Duplex Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12423742
182 Duplex Avenue Toronto M5P 2A9
$1,998,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12423742
- Bedrooms:
- 5
- Bathrooms:
- 3
Move in immediately. Known for its excellent transit connections, thriving business cores, and a wealth of top schools, Yonge & Eg neighbourhood successfully blends historical European settlements with modern city developments. Rarely available, 182 Duplex Ave offers a tastefully renovated four(4)-bedroom turn-key home. 3 updated bathrooms, with private driveway up to Three (3) parking spots. Valuable list of refinements incl 2018 Roof, water tank (owned), Lennox Air Conditioner, Forced-air system with Coleman furnace and humidifier. Contemporary gourmet kitchen compasses premium appliances, stone countertops, central island, and spacious breakfast area. Elegant family room pleasantly accommodates a grand piano and cozy sectional sofas next to fireplace. Illuminated chandeliers & numerous pot-lights enhance a bright living. Abundant natural light generated by skylight, large windows, and glass walkout. A newer double door opens up the back, inviting scenic nature inside. Immaculate indoor outdoor transition extends to an entertainer's dream garden. Impressive backyard space boasts a generous depth of greenery, perfect for relaxation and hosting. Professional landscaping, enormous terrace, privacy fence, included garden shed, beautiful mature trees, and perennial flower beds. Exterior architecture features a stated brick facade and a separate entrance to the south yard and exclusive driveway. Area esteemed schools incl Treetop, Sanazy's, Oriole Park Junior, North Toronto CI, Havergal, Branksome Hall, BSS, St Clement's, St Michael's, York School, and Upper Canada College. Enjoy 100 walk-score. TTC subway, Crosstown LRT, upscale office towers, Yonge & Eglinton Ctr, boutique shoppings, fine dinings, trendy cafe / bars, cinemas & bookstores, trendy parks, and vibrant nightlife, are all at doorstep. Welcome to this urban sanctuary, where comfortable luxury meets perfect proximity to everything a growing family needs. More detailsListed by SOTHEBY'S INTERNATIONAL REALTY CANADA- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
-
963 Avenue Road in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12372841
963 Avenue Road Toronto M5P 2K9
$4,600,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12372841
- Bedrooms:
- 15
- Bathrooms:
- 9
Welcome to Avenue Manor. This is a legal 8 plex with one unregistered basement unit. Prime Forest Hill location - near all exclusive schools and prime shopping. 600 feet from LRT entrance. 5 suites totally renovated to condo quality. 3 one beds (400-650 sf) and 6 two beds (800-1200 sf). 4 units have gas fireplaces and 4 units have in suite laundry. All units have a dishwasher fridge and stove. Tenants above grade pay hydro and 4 of them also pay gas. 4 of the above grade units have gas fired heat pumps and the rest of the building has electric heat. Well maintained building with nicely landscaped front entrance area. The 2 top units are owner occupied and can be vacated for an owner user. Security cameras in place. More detailsListed by COMMERCIAL FOCUS REALTY INC.- OLENA FEOKTISTOVA
- 1867 Yonge Street, Suite 100, Toronto, ON M4S 1Y5
- 1 (647) 2943039
- olena@agentolena.com
Data was last updated November 22, 2025 at 11:15 PM (UTC)
powered by myRealPage.com
