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.

1-12/12
  • 889 Avenue Road in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12444804

    889 Avenue Road Yonge-Eglinton Toronto M5P 2K7
    Main Photo: 889 Avenue Road in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12444804
    $2,588,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12444804
    Bedrooms:
    9
    Bathrooms:
    8
    Location,Location,Location,Very Good And Rare 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 details
    Listed by SMART SOLD REALTY
    OLENA FEOKTISTOVA
  • 188 Duplex Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12436503

    188 Duplex Avenue Yonge-Eglinton Toronto M5P 2A9
    Main Photo: 188 Duplex Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12436503
    $3,999,888
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12436503
    Bedrooms:
    5
    Bathrooms:
    6
    Executive home Designed For Modern Family Living, Boasting Over 4,700 Square Feet Of luxury living space. Natural Light Throughout. The Main Level Is Perfect For Entertaining Guests Or Relaxing With Family And Boasts A Formal Living And Dining Room, An Eat-In Chef's Kitchen, With Top of Line Appliances and Family Room & breakfast area and an effortless walkout from floor to ceiling sliding doors to a beautifully Matured trees backyard. The third Level Has An Oversized Primary Retreat With An Impressive Dressing Room And A 5-Piece Ensuite. The Lower Level Has a Bedroom, Gym, Bathroom, theatre, and Large Recreation Room. Steps to TTC, And All The Amenities Yonge and Ellington Have To Offer. Roughed in. Snow Melting Driveway. Smart Home Control 4 Automation. Elevator, Mudroom, Dog wash, Office, Two Furnace, Two Air Conditioner, Two Laundry Room, And So Much More. More details
    Listed by HOUSESIGMA INC.
    OLENA FEOKTISTOVA
  • 45 Hillsdale Avenue W in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12438035

    45 Hillsdale Avenue W Yonge-Eglinton Toronto M5P 1E9
    Main Photo: 45 Hillsdale Avenue W in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12438035
    $1,749,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12438035
    Bedrooms:
    5
    Bathrooms:
    2
    Welcome to 45 Hillsdale Ave W, a warm and inviting 4-bedroom family home in Chaplin Estates, just steps from Yonge Street. Featuring a legal front parking pad and a desirable south-facing backyard, this move-in-ready home combines timeless character with thoughtful updates in one of Toronto's most sought-after midtown neighbourhoods. The main floor offers open-concept living and dining with hardwood floors, crown moulding, pot lights, and a gas fireplace with an elegant marble surround. A custom built-in cabinet in the dining area adds both style and storage. The kitchen includes granite counters, a built-in granite breakfast table, premium appliances including a Sub-Zero fridge, Miele gas cooktop, wall oven, and dishwasher, and generous cupboard space for storage. Walk out to a beautifully landscaped low maintenance backyard perfect for relaxing or entertaining, with a covered deck, stone patio, garden lighting and irrigation, a storage shed, and a built-in gas line for BBQ. Upstairs, you'll find 4 comfortable bedrooms and an updated 4-piece bathroom. The versatile 4th bedroom works well as a nursery or home office. The finished lower level offers an additional bedroom, 3-piece bathroom, rec room, laundry, and ample storage, with a separate rear entrance for added convenience. **RECENT UPDATES include a new sloped shingled roof and an upgraded front parking pad and mutual drive (see attachments for full list of improvements)**. Lovingly maintained and in great condition **SEE HOME INSPECTION REPORT** move in and enjoy or customize to your liking. Ideally located in Chaplin Estates, you're steps from Yonge Street's shops and restaurants, top-rated schools (Oriole Pkwy Junior Public and North Toronto Collegiate), excellent parks, and the Eglinton subway station - combining city convenience with a strong sense of community in this prime Midtown location. More details
    Listed by ROYAL LEPAGE SIGNATURE REALTY
    OLENA FEOKTISTOVA
  • 137 Highbourne Road in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12433357

    137 Highbourne Road Yonge-Eglinton Toronto M5P 2J8
    Main Photo: 137 Highbourne Road in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12433357
    $3,595,000
    Residential 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 details
    Listed by ROYAL LEPAGE/J & D DIVISION
    OLENA FEOKTISTOVA
  • 182 Duplex Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12423742

    182 Duplex Avenue Yonge-Eglinton Toronto M5P 2A9
    Main Photo: 182 Duplex Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12423742
    $1,998,000
    Residential 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 details
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
    OLENA FEOKTISTOVA
  • 53 Colin Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12404537

    53 Colin Avenue Yonge-Eglinton Toronto M5P 2B8
    Main Photo: 53 Colin Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12404537
    $3,345,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12404537
    Bedrooms:
    5
    Bathrooms:
    4
    Perfectly situated on one of the most coveted streets in Chaplin Estates, this classic centre hall home rests on a beautifully landscaped 40 x 133.5 ft lot, surrounded by mature trees and blooming perennials. Offering a rare combination of charm, space, and sophistication, this residence delivers a turnkey opportunity for refined family living in a highly sought-after community. A gracious entry hall with marble floors and a bevelled mirrored coat closet sets the tone for the homes classic elegance. The formal living room features crown moulding, high-end wool broadloom, and a wood-burning fireplace framed by a custom mantle with polished marble surround. Pocket doors with bevelled glass lead to the dining room, ideal for entertaining, with hardwood floors, wall panel detailing, pot lights, and a hidden storage closet.The heart of the home is the custom kitchen, thoughtfully designed with a large centre island, built-in bar or coffee station, high-end appliances, and a etched glass privacy door. It opens seamlessly into the spacious family room with wall-to-wall windows, floor-to-ceiling marble fireplace, concealed speakers, and a walkout to the backyard. Upstairs, the skylit landing leads to four spacious bedrooms, including a serene primary suite with dual closets and a renovated ensuite featuring heated marble floors, double vanity with Calacatta countertops, and a glass-enclosed shower. An upper-level laundry room with cabinetry, counterspace and sink adds everyday convenience. The professionally landscaped backyard offers a rare sense of privacy in the city, complete with a large interlocking stone patio, wood deck with pergola draped in flowering hydrangeas, and lush gardens framed by mature trees. A custom-built shed with electrical and built-in storage completes this outdoor oasis. Just steps to Yonge Street, the TTC subway, green spaces, and top public and private schools, this home exemplifies timeless character and an unparalleled midtown lifestyle. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
    OLENA FEOKTISTOVA
  • 441 Oriole Parkway in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12404506

    441 Oriole Parkway Yonge-Eglinton Toronto M5P 2H7
    Main Photo: 441 Oriole Parkway in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12404506
    $5,495,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12404506
    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 details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES LTD.
    OLENA FEOKTISTOVA
  • 963 Avenue Road in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12372841

    963 Avenue Road Yonge-Eglinton Toronto M5P 2K9
    Main Photo: 963 Avenue Road in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12372841
    $4,600,000
    Residential 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 details
    Listed by COMMERCIAL FOCUS REALTY INC.
    OLENA FEOKTISTOVA
  • 46 Elmsthorpe Avenue in Toronto: Forest Hill South House for sale (Toronto C03) : MLS®# C12358403

    46 Elmsthorpe Avenue Forest Hill South Toronto M5P 2L7
    Main Photo: 46 Elmsthorpe Avenue in Toronto: Forest Hill South House for sale (Toronto C03)  : MLS®# C12358403
    $4,790,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12358403
    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 details
    Listed by CENTURY 21 LANDUNION REALTY INC.
    OLENA FEOKTISTOVA
  • 16 Duncannon Drive in Toronto: Forest Hill South House for sale (Toronto C03) : MLS®# C12336896

    16 Duncannon Drive Forest Hill South Toronto M5P 2M1
    Main Photo: 16 Duncannon Drive in Toronto: Forest Hill South House for sale (Toronto C03)  : MLS®# C12336896
    $3,750,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12336896
    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 details
    Listed by THE AGENCY
    OLENA FEOKTISTOVA
  • 25 Maxwell Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12289670

    25 Maxwell Avenue Yonge-Eglinton Toronto M5P 2B4
    Main Photo: 25 Maxwell Avenue in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12289670
    $2,195,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12289670
    Bedrooms:
    6
    Bathrooms:
    3
    Welcome home to 25 Maxwell Avenue, a handsome red brick detached home located in prime Chaplin Estates featuring almost 3,500 square feet of total living space. 4+2 bedrooms, 3 bathrooms and set on a wide 32-foot frontage that includes a private driveway, this home offers wonderful potential for family living in the heart of the city. Large principal rooms include a spacious living room & dining room plus a huge family room at the rear of the home that forms part of a full 3-storey all brick addition. Upstairs, you'll find 3 well-proportioned bedrooms, a 4-piece family bathroom and a 3rd floor loft with a walkout to a rooftop terrace with city views. The lower level includes above average 8-foot ceiling height and includes a large recreation room, fifth bedroom, additional 4-piece bathroom and a sizeable laundry/utility room. With plenty of improvements throughout the home including many newer windows, recently upgraded air conditioning, 3 fireplaces and the existing addition, this home offers the perfect opportunity for a family looking for a property to renovate or those who love the neighbourhood setting and location but are not ready to renovate right away. Located steps from the hustle and bustle of Yonge & Eglinton and yet quietly tucked away in the heart of this wondeful community, this home truly offers the best that midtown has to offer including access to some of the best public and private schools, easy and walkable access to transit, shopping, dining and entertainment not to mention the community centre and park (including large playground with wading pool) that are also just a short walk away. Offers anytime. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    OLENA FEOKTISTOVA
  • 129 Imperial Street in Toronto: Yonge-Eglinton House for sale (Toronto C03) : MLS®# C12132593

    129 Imperial Street Yonge-Eglinton Toronto M5P 1C7
    Main Photo: 129 Imperial Street in Toronto: Yonge-Eglinton House for sale (Toronto C03)  : MLS®# C12132593
    $2,980,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12132593
    Bedrooms:
    4
    Bathrooms:
    3
    Sought After in Mid-town neighborhood. Walking Distance to Excellent Public and Prestigious Private Schools,Parks,Shops,and Transit Plus LRT. New Roof (2024),New Air conditioner (2024),Designer gourmet kitchen, vaulted ceiling and fireplace in the master bedroom, heated limestone spa like ensuite with turkish steam bath & body jets. More details
    Listed by REAL ONE REALTY INC.
    OLENA FEOKTISTOVA
1-12/12
Data was last updated October 9, 2025 at 12:15 AM (UTC)
powered by myRealPage.com

Make A Smart Purchase

Ready to buy a Toronto home? I’ll help you find an exceptional property in the right community to suit your family and lifestyle for years to come.