Hoggs Hollow

Hoggs Hollow is one of Toronto’s most enchanting neighbourhoods—an idyllic valley community defined by winding streets, rolling hills, and the gentle backdrop of the Don River. Its cottage-like charm blends seamlessly with luxurious custom homes, creating a rare combination of tranquility, prestige, and timeless appeal. 

Families appreciate the quiet, storybook atmosphere, complemented by top schools, including York Mills Collegiate, Loretto Abbey, and St. Andrew’s JHS. The area’s parks and green spaces are plentiful, with York Mills Valley Park, Windfields Park, and access to the Don Valley trails offering scenic walking, cycling, and seasonal family outings. 

Nearby, the shops and restaurants of Yonge and York Mills deliver upscale conveniences, while quick access to the TTC, 401, and top private schools makes daily living effortless. Hoggs Hollow is a community where luxury feels natural, and families enjoy a peaceful escape without ever leaving the city.

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1-12/16
  • 14 St Margarets Drive in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12447703

    14 St Margarets Drive Bridle Path-Sunnybrook-York Mills Toronto M4N 3E5
    Main Photo: 14 St Margarets Drive in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12447703
    $8,980,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12447703
    Bedrooms:
    7
    Bathrooms:
    10
    Welcome To 14 Saint Margarets Drive, A European-Inspired Limestone And Tyndall Stone Masterpiece Nestled On One Of The Most Picturesque And Prestigious Streets In Hoggs Hollow. This Estate Showcases A Rare Tyndall Stone Exterior Prized For Its Distinctive Rich Patterns Combining Architectural Prestige With Natural Elegance. Its Unique Textures Lend An Air Of Exclusivity And Sophistication Rarely Found In A Private Residence, Complemented By A Cedar Shake Roof. Majestically Sited On A Premium 90 By 150 Ft Lot Backing Onto The River, This Residence Offers Over 9,000 Sq.Ft. Of Luxurious Living Space Where Timeless Craftsmanship Meets Modern Comfort. A Grand Foyer With Stained Glass And Domed Ceiling Introduces Interiors Of Remarkable Scale And Craftsmanship. The Vaulted Great Room, With Vintage Beams, Soaring Windows, And A Stone Fireplace, Serves As A Dramatic Centerpiece. A Formal Dining Room With Serving Area, A Richly Panelled Office With Patio Walkout, And A Chefs Kitchen With Walk-In Pantry, Oversized Island, Butlers Pantry, And Adjoining Breakfast Area Complete The Main Level. From The Kitchen, Great Room, And Office, Walk Out To Three Patios Overlooking The River, Manicured Grounds, And Pool. The Upper Level Hosts Six Bedrooms, Each With Its Own Newly Renovated Bathroom. The Serene Primary Suite Offers A Private Balcony, Fireplace, Walk-In Closet, And Spa-Inspired Ensuite With Soaker Tub, Double Vanities, And Oversized Shower. Most Rooms Capture Sweeping River Views, While A Bright Study Nook Enhances Family Comfort. The Fully Finished Lower Level Extends The Living Space With A Recreation Lounge Featuring Fireplace And Bar, Glass-Walled Gym, Custom Wine Cellar, Nanny Suite, Walk-In Cedar Room, Media Room, And A Second Kitchen Ideal For Entertaining Or Extended Family Living. Outdoors, Enjoy A Resort-Style Retreat With Heated Pool, Outdoor Fireplace, Built-In Bbq, And Wood-Fired Pizza Oven, All Set Among Stone Terraces, Mature Trees, & Professional Landscaping. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES KATY TORABI
    Raquel Feldberg
    Alan Feldberg
  • 36 Old Yonge Street in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12438497

    36 Old Yonge Street Bridle Path-Sunnybrook-York Mills Toronto M2P 1P7
    Main Photo: 36 Old Yonge Street in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12438497
    $7,785,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12438497
    Bedrooms:
    6
    Bathrooms:
    9
    Backs Onto Ravine! Perched gracefully at the highest point of Hoggs Hollow, this French Château inspired masterpiece sits on a spectacular 239.08 x 207.81 ft ravine lot (approx. 1.14 acres). Designed by Dee Dee Taylor Hannah and built by award-winning builder Michael Rossini, this timeless stone estate offers over 10,000 sq.ft. of luxurious living space, blending European elegance with modern comfort. The homes distinctive curved and symmetrical design showcases architectural artistry rarely seen today. Featuring 4 bedrooms with ensuites, 9 washrooms, and a 3-car garage with a circular driveway accommodating up to 15 cars, all principal rooms face west, overlooking the serene ravine. A grand marble foyer, curved hallways, and custom millwork opens to elegant living and dining rooms that walk out to the ravine and garden. Two libraries on main floor, five fireplaces, built-in speakers, 10-ft ceilings, and hardwood floors throughout. The gourmet kitchen with double granite islands and an open-concept family room with motorized curtains creates a warm and inviting space for entertaining.Step out to a 700 sq.ft. patio with outdoor fireplace and panoramic ravine views. The primary suite features a lavish 9-piece ensuite, his & her walk-in closets, and heated bathroom floors. The walk-out lower level wth heated floors includes a home theatre, wine cellar, sauna, wet bar, nanny/guest ensuite, and a recreation room with fireplace opening directly to the backyard oasis.The heated concrete pool with cascading waterfall, framed by mature trees, creates a private, resort-like retreat. A rare offering combining elegance, privacy, and tranquility, just moments from the Granite Club, top private schools (Crescent, TFS, Havergal, UCC, BSS), fine dining, and Rosedale & Don Valley Golf Clubs.A true statement of taste, craftsmanship, and enduring luxury in one of Torontos most prestigious enclaves. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
    Raquel Feldberg
    Alan Feldberg
  • 27 Old Yonge Street in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12419822

    27 Old Yonge Street Bridle Path-Sunnybrook-York Mills Toronto M2P 1P6
    Main Photo: 27 Old Yonge Street in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12419822
    $5,888,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12419822
    Bedrooms:
    4
    Bathrooms:
    3
    In a city where land is scarce and one-acre parcels are unheard of, this exceptional property offers a unique opportunity to create your dream home on the upper peak of the highly sought-after Hoggs Hollow neighbourhood. Owned by the same family for many decades, it awaits the next chapter in its life. Spanning over an acre of prime land, this property is perched high on a hill, providing an unparalleled level of privacy. The surrounding ravine further enhances the secluded atmosphere, creating a tranquil oasis in the heart of the city. On a clear day, you can see the CN Tower. Ample flat table land. There is even an inground swimming pool (as is condition). The existing residence, a home of considerable scale and gracious character, presents a unique opportunity for the discerning buyer. Whether you envision restoring and renovating the current structure to its former circa 1925 glory, or if you prefer, you can create a brand-new residence tailored to your exact specifications, the possibilities are truly endless. Imagine the potential of this expansive lot, where you can design a home that perfectly reflects your lifestyle and aspirations. Build a grand estate with ample living space, incorporating modern amenities and luxurious finishes. Create a family compound with room for everyone to gather and enjoy. Or perhaps you envision a more intimate retreat, a personal sanctuary where you can escape the hustle and bustle of busy city life. Enjoy convenient access to the vibrant shops and restaurants of North Toronto along Yonge Street, just a short distance away. Commuting is a breeze with the nearby subway station and easy access to the 401 highway. Bring your architect and general contractor to your showing to explore the full potential of this incredible one-acre parcel. Envision the possibilities and begin to imagine the home of your dreams. More details
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
    Raquel Feldberg
    Alan Feldberg
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  • 32 Brookfield Road in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12513112

    32 Brookfield Road Bridle Path-Sunnybrook-York Mills Toronto M2P 1A9
    Main Photo: 32 Brookfield Road in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12513112
    $5,880,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12513112
    Bedrooms:
    4
    Bathrooms:
    5
    Welcome to Prestigious Hoggs Hollow! Gracefully nestled among lush ravines and steps from the iconic Rosedale Golf Club, this elegant residence blends timeless charm with modern sophistication. A stately steel gate and grand entry doors create a striking first impression. The sun-filled open-concept main floor showcases wall-to-wall bay windows overlooking one of the area's deepest private lots-your serene, tree-lined backyard oasis with endless potential. The living room's marble-surround fireplace adds warmth, while a mezzanine overlooking the grand foyer enhances the sense of space and luxury. The sleek chef's kitchen features top-tier appliances, a waterfall island, and an inviting breakfast area. Upstairs, the primary suite offers a private sitting room and Juliet balcony retreat. All bedrooms boast spa-like ensuite baths with in-floor heating. Attached garage and generous storage complete this exceptional home. More details
    Listed by RE/MAX ADVANCE REALTY
    Raquel Feldberg
    Alan Feldberg
  • 40 Donino Avenue in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12041767

    40 Donino Avenue Bridle Path-Sunnybrook-York Mills Toronto M4N 2W7
    Main Photo: 40 Donino Avenue in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12041767
    $5,088,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12041767
    Bedrooms:
    6
    Bathrooms:
    7
    Prime 100 x 298 Lot with 5+1 Bedrooms, 7 Washrooms, Walk-Up Basement, Inground Swimming Pool, and U-Shaped Driveway in Hoggs Hollow Ready for Your Dream Home. This lush, tree-lined property offers exceptional privacy and a rare opportunity to build your custom masterpiece, explore the potential to split the lot into two, or renovate the existing home with vintage-inspired charm into an artistic and stylish space. Surrounded by mature trees, the property provides a serene, peaceful setting with the soothing sounds of nature during the summer months. Located in the prestigious Hoggs Hollow neighbourhood, this lot offers the perfect combination of tranquility and convenience. Just steps from Yonge Street and the York Mills TTC subway station, youll enjoy easy access to top-tier schools, upscale shopping, gourmet dining, and major transportation routes. Dont miss this chance to create your ideal home in one of Torontos most sought-after communities. More details
    Listed by AIMHOME REALTY INC.
    Raquel Feldberg
    Alan Feldberg
  • 54 Plymbridge Road in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12428818

    54 Plymbridge Road Bridle Path-Sunnybrook-York Mills Toronto M2P 1A3
    OPEN HOUSE: Dec 21, 2025
    01:00 PM - 04:00 PM EST
    Open House on Sunday, December 21, 2025 1:00PM - 4:00PM
    Main Photo: 54 Plymbridge Road in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12428818
    $4,595,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12428818
    Bedrooms:
    5
    Bathrooms:
    4
    **Welcome to perfectly situated in the esteemed and scenic enclave of Hoggs Hollow, this property offers an unparalleled opportunity to all end-users(families) or investors or builders, Nestled within a private forested area, it's a haven for nature enthusiasts seeking tranquility in the city, effortlessly blends country serenity and urban convenient to yonge subway station and highways. This charm home offers a spacious over 3000 sqft of living area, 9 ft ceiling family room, recently update & upgrade elements(spent $$$$) thru-out inside/outside. The family living zone boasts a gorgeous fireplace, creating a cozy/warm atmosphere, and well situated to overlook the private backyard garden. The kitchen provides update/stainless steel appliance and update cabinet, a centre island and breakfast bar area. Upper level, 4 bedrooms are well-proportioned room size with hardwood floors and closets. The lower level offers extra space for your family needed, a separate entrance, and a direct access to the full size of 2 cars garage. The backyard offers an in-ground swimming pool, and a private ravine. 10 minutes walk to subway station, 15 minutes ride to downtown. Top ranking Armour Heights PS, York Mills CI & private schools! Most recent bank appraisal price is $5M. More details
    Listed by FOREST HILL REAL ESTATE INC.
    Raquel Feldberg
    Alan Feldberg
  • 15 York Valley Crescent in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12392609

    15 York Valley Crescent Bridle Path-Sunnybrook-York Mills Toronto M2P 1A8
    Main Photo: 15 York Valley Crescent in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12392609
    $4,250,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12392609
    Bedrooms:
    4
    Bathrooms:
    3
    Prime South West Facing Lot in Hoggs Hollow - Ready for Your Dream Home with permits already in place. Offering outstanding architectural design this custom home will be like no other. Get started right away without delay. Welcome to the epitome of luxury living in Toronto's prestigious Hoggs Hollow neighbourhood. This southwest-facing tree-lined lot presents a rare opportunity to build your custom-designed masterpiece. Situated in a tranquil and coveted location, this lot offers unparalleled privacy and serenity.Conveniently located near premier schools, upscale shopping, gourmet dining, and easy access to major transportation routes. More details
    Listed by KELLER WILLIAMS REFERRED URBAN REALTY
    Raquel Feldberg
    Alan Feldberg
  • 12 Donwoods Drive in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12551218

    12 Donwoods Drive Bridle Path-Sunnybrook-York Mills Toronto M4N 2G1
    Main Photo: 12 Donwoods Drive in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12551218
    $3,498,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12551218
    Bedrooms:
    5
    Bathrooms:
    4
    Welcome to 12 Donwoods Drive. Live in elegance in Toronto's coveted Hogg's Hollow community with this classic Georgian-style brick home, tucked away on a private laneway above Donwoods Drive. Offering over 5,000 sq.ft. of living space, this residence combines timeless architecture with thoughtful modern upgrades.Step into the bright, grand foyer that sets the tone for this sophisticated home. The spacious family room leads to a renovated gourmet eat-in kitchen with a large island and granite countertops-perfect for family gatherings. Relax by one of the four cozy fireplaces or host summer dinners on the interlocked backyard patio, surrounded by lush greenery. The large primary suite features a walk-in closet and serene views.Perfect for a family needing generous space, this well-maintained home is clean, bright, and move-in ready, with the opportunity to refresh interiors over time to suit your style.The wood-paneled office provides a quiet retreat, while the kitchen is a dream culinary space. A versatile fifth bedroom on the lower level can serve as a guest suite, gym, or nanny/granny suite.Enjoy stunning treetop vistas from the custom rooftop deck above the stone garage, complete with a modern garage door and a private, tranquil setting. The finished lower level includes a recreation room and in-law suite, ideal for extended family or guests.Location is unmatched-just a 12-minute walk to York Mills Subway, 15 minutes to downtown, and steps from Yonge Street, top-rated Armour Heights PS, York Mills CI, and elite private schools. Close to golf courses and HWY 401, this home blends elegance and serenity with everyday convenience.Experience luxury living surrounded by nature, where urban convenience meets timeless sophistication. Privately situated, this home offers exceptional charm and potential-whether you fully renovate, update, or simply move in. A rare location in one of Toronto's most coveted neighborhoods makes it highly desirable. *Virtually Staged* More details
    Listed by RE/MAX REALTRON REALTY INC.
    Raquel Feldberg
    Alan Feldberg
  • 32 Beechwood Avenue in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12551528

    32 Beechwood Avenue Bridle Path-Sunnybrook-York Mills Toronto M2L 1J1
    Main Photo: 32 Beechwood Avenue in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12551528
    $3,288,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12551528
    Bedrooms:
    7
    Bathrooms:
    4
    Rare Find fully renovated luxury home situated on an impressive 50 x 145 ft lot in 1 of the best Street of Bridle Path enclave. Every detail has been meticulously curated, from newly installed engineered hardwood floors to the striking open staircase with glass railings, refined wainscot baseboards, and the soft glow of pot lighting that enhances every space throughout .At the heart of the home, a custom-designed kitchen showcases built-in Miele appliances & brand new center island w breakfast bar & dramatic slab backsplash and countertops. O/C family room with coffered high ceilings and walkout to the garden creates a perfect flow for entertaining. Outdoors, a new composite deck, built-in station, and professionally designed lighting and irrigation systems transform the grounds into a private resort-like retreat. Among the homes most enchanting features is a secret garden suite on the main level a private bedroom accessible from the garage, with large windows the serene sanctuary feels like the lush landscaped garden is an extension of the room, offering an unparalleled sense of tranquility and privacy. The upper level is equally impressive, with a primary suite that rivals a five-star hotel. A spa-inspired ensuite and a bespoke walk-in closet set the tone for indulgence, while the additional bedrooms provide comfort and sophistication for family. Fully renovated bathrooms throughout feature exquisite vanities, sleek fixtures, and timeless design. The lower level extends the living experience ideal for rec, or guest accommodations w 2 bedroom and bath all enhanced with new flooring. Completing the transformation are upgraded exterior details including a new garage door, new front and side entrances. Situated just minutes from Toronto's finest private schools, exclusive clubs, upscale shopping, and with convenient highway access, this home offers an unparalleled lifestyle More details
    Listed by SOLTANIAN REAL ESTATE INC.
    Raquel Feldberg
    Alan Feldberg
  • 10 Campbell Crescent in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12) : MLS®# C12563514

    10 Campbell Crescent Bridle Path-Sunnybrook-York Mills Toronto M2P 1P2
    Main Photo: 10 Campbell Crescent in Toronto: Bridle Path-Sunnybrook-York Mills House for sale (Toronto C12)  : MLS®# C12563514
    $2,880,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12563514
    Bedrooms:
    3
    Bathrooms:
    2
    New price and value opportunity! Excellent large building lot, rare 60 x 151 ft west facing lot with a unique setting, backing onto Jolly Miller Park. Enjoy the sunny west exposure overlooking the park and the Don River beyond. Beautiful treelined street in coveted Hoggs Hollow, with excellent proximity to Yonge Street transit and the 401. Build your dream home in this family community close to top rated Toronto schools, both public (Armour Heights PS, York Mills CI) and private (Havergal College, Toronto French School, Crescent School). Enjoy this idyllic neighbourhood where country meets city. Wide regular shaped lot, flat, and buildable. Very private and well treed around the perimeter. Solid three bedroom bungalow currently sits on the property. More details
    Listed by ROYAL LEPAGE/J & D DIVISION
    Raquel Feldberg
    Alan Feldberg
  • 304 51 York Mills Road in Toronto: Bridle Path-Sunnybrook-York Mills Condo Townhouse for sale (Toronto C12) : MLS®# C12467633

    304 51 York Mills Road Bridle Path-Sunnybrook-York Mills Toronto M2P 1B6
    Main Photo: 304 51 York Mills Road in Toronto: Bridle Path-Sunnybrook-York Mills Condo Townhouse for sale (Toronto C12)  : MLS®# C12467633
    $1,685,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12467633
    Bedrooms:
    3
    Bathrooms:
    3
    Welcome to Estate Townhomes of Hoggs Hollow! An exclusive collection of residences in one of Toronto's most desirable neighbourhoods. Designed by one of the prominent designers, Gluckstein Design, this three-bedroom, three-bathroom executive townhome overlooks a lush courtyard and offers a thoughtful layout with high-quality finishes throughout. Offering seamless access to city amenities, it is the perfect choice for families and professionals alike seeking both convenience and comfort. The main level features an open-concept living and dining area, designed for everyday use as well as entertaining. The kitchen is fitted with custom Downsview cabinetry, updated appliances, ample storage and workspace. The 2nd floor is dedicated to a large primary suite with a built-in wall unit, a spacious 5-piece ensuite bathroom and two walk-in closets. The 3rd level offers two additional well-proportioned bedrooms that share a four-piece bathroom, creating flexibility for children, guests, a gym or a home office. A highlight of this residence is the private rooftop terrace. Updated with a new flat roof and privacy fencing in 2021, the space is well-suited for outdoor dining or relaxation. The location combines the quiet, established character of Hoggs Hollow with easy access to the rest of the city. Just minutes to Yonge Street, public transit, Highway 401, and a wide range of shops, services, and restaurants, the home provides both privacy and connectivity. Other features include two side-by-side underground parking spaces equipped with a Tesla charging station. Elfs, Window coverings. Light fixtures, Blinds, and Home security. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
    Raquel Feldberg
    Alan Feldberg
  • 309 75 York Mills Road in Toronto: Bridle Path-Sunnybrook-York Mills Condo Apartment for sale (Toronto C12) : MLS®# C12389458

    309 75 York Mills Road Bridle Path-Sunnybrook-York Mills Toronto M2P 2E7
    Main Photo: 309 75 York Mills Road in Toronto: Bridle Path-Sunnybrook-York Mills Condo Apartment for sale (Toronto C12)  : MLS®# C12389458
    $1,399,900
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12389458
    Bedrooms:
    3
    Bathrooms:
    3
    Spacious 2,268 sq. ft. double unit in a low-rise boutique building crafted by Shane Baghi offers a serene and rare south-east view of a peaceful tree-filled ravine. Located in the prime Hoggs Hollow area, this move-in gem features 3 bedrooms, 3 bathrooms, a large dining room/living room, an inviting family room with built-in cabinetry and fireplace, two balconies, three parking spaces, three lockers, elegant crown moldings, and the convenience of being within walking distance of the subway, walking park, Yonge Street shops, close to Highway 401 and much more. Dont miss the chance to be in your new home before Christmas! More details
    Listed by REAL ESTATE ADVISORS INC.
    Raquel Feldberg
    Alan Feldberg
1-12/16
Data was last updated December 21, 2025 at 04:15 AM (UTC)
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