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3325 Hollywood Court in Pickering: Rural Pickering House for sale : MLS®# E13215550
3325 Hollywood Court Pickering L1X 0A3 
$4,995,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13215550
- Bedrooms:
- 7
- Bathrooms:
- 9
Set in a quiet enclave of prestigious homes, this exceptional 11,500 sq. ft. estate (including built in garage) sits on a private 1.5-acre lot backing onto a serene forest. This elegant residence offers 7 spacious bedrooms, all with walk-in closets, including 6 with ensuite baths, and a total of 9 washrooms. The open-concept main floor features soaring 20 ft. cathedral ceilings, and dramatic floor-to-ceiling windows overlooking the expansive, private backyard. Designed for both effortless entertaining and elevated everyday living, the kitchen showcases the rare luxury of two expansive islands; a standout feature in sophisticated, open-concept homes. Thoughtfully designed to create both beauty and flow, the dual-island layout allows for dedicated culinary and social spaces, balancing function and style. The main floor primary suite spans nearly 1,000 sq. ft., offering a luxurious retreat. The second level hosts 4 generously sized bedrooms, while the finished lower level with 10 ft. ceilings includes 2 additional bedrooms and extensive additional living space all with floor to ceiling windows, perfect for extended family or guests. Two staircases seamlessly connect all three levels, enhancing both flow and functionality. A circular driveway leads to a 1,700 sf four-car garage with double height ceilings, ideal for car lifts. Additional features include 3 fireplaces, a home gym with glass wall and doors, a beautifully appointed, temperature controlled wine cellar with room for over 300 bottles tucked behind a bar and kitchen area. This is a thoughtfully designed home ideal for large families and multi-generational living. A rare offering combining scale, privacy, and refined living in an exclusive setting. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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3 Shorncliffe Avenue in Toronto: Casa Loma House for sale (Toronto C02) : MLS®# C13171166
3 Shorncliffe Avenue Toronto M4V 1S9
$3,980,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13171166
- Bedrooms:
- 6
- Bathrooms:
- 4
This elegant detached three-storey, six-bedroom family home sits on a spectacular 50 x 154 ft. pool size lot in the heart of South Forest Hill. With ample backyard space, create your own personal oasis, and never feel the need to escape the city. The original 1916 build has been completely reimagined through a meticulous back-to-the-studs renovation, seamlessly blending timeless architectural character with contemporary finishes. Offering expansive principal rooms in a 4,000 square-foot layout ideal for both family living and entertaining, this residence delivers modern pleasures and comfort. Located just steps from the shopping and dining of Forest Hill Village, and the green spaces and recreational amenities of Winston Churchill Park, this property is also walking distance from prestigious schools like Upper Canada College, Bishop Strachan School, and St. Michael's College. A unique opportunity to afford entrance into one of Toronto's most exclusive neighbourhoods, this family home is a rare offering that balances history, location, and lifestyle with attainable price. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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135 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12952628
135 Madison Avenue Toronto M5R 2S3
$3,650,000Residential Freehold- Status:
- Active
- MLS® Num:
- C12952628
- Bedrooms:
- 6
- Bathrooms:
- 5
This grand dame home sits on the iconic Madison Avenue in the prime Annex. Circa 1905, 135 Madison Avenue is just under 4,000 square feet above grade and filled with original character including 4 fireplaces, original trim, wainscoting, crown moulding, and stained glass windows. The well proportioned house features 9.5' ceilings on the main floor, a large formal living room, dining room, an oversized kitchen with a butlers pantry, and a beautiful main floor family room that leads out to the lush garden. On the second floor you will find a generous primary bedroom with a sitting area, fireplace and a three piece ensuite. There are an additional 3 large bedrooms on the second floor as well as 3 full washrooms, a dedicated laundry room, kitchen, and a large sunny deck. The third floor would make a fabulous primary suite and currently includes a spacious living room, kitchen, two additional bedrooms, one full washroom, and a large deck with skyline and treetop views. The basement is partially finished with 7 foot ceilings and features a separate side door entrance. This home flows nicely as single family, which it has been used as for many years, but has potential for other layouts and possibilities including converting the property back into multiple units. Two car private drive parking and garden suite potential. The Annex speaks for its self with easy TTC, fabulous shops, restaurants, parks and schools. Floor plans attached to listing. Offers anytime. Great opportunity for those looking for a co-ownership property! More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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2963 Dundas Street W in Toronto: Junction Area House for sale (Toronto W02) : MLS®# W12973364
2963 Dundas Street W Toronto M6P 1Z2
$3,175,000Residential Freehold- Status:
- Active
- MLS® Num:
- W12973364
- Bedrooms:
- 14
- Bathrooms:
- 6
Located in the Best block in the Junction this meticulously maintained 3 storey property is just shy of 6,000 sq. ft, and is filled with character and possibilities. Currently configured as 5 large, beautifully updated, apartments with private terraces and up to a total of 14 bedrooms, this property boasts the potential of achieving an estimated cap rate of over 6% for an investor. The building can also be offered with vacant possession allowing for many possibilities for a user including LIVE/WORK, or the 2,241 sf main floor could be converted to a commercial use with souring 14' ceilings making a perfect location for a retail, hospitality, or services business with ample auxiliary income from the floors above. Front entrance to lower level. A Green 'P' surface parking lot with electric charging stations and Bikeshare docks backs on to the property and is accessible by a rear gate. 24 hour bus at front door, walking distance to Bloor Subway, UP Express & Stockyards Mall. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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47 Pine Street S: Port Hope House for sale : MLS®# X13079808
47 Pine Street S Port Hope L1A 3E6
$2,999,000Residential Freehold- Status:
- Active
- MLS® Num:
- X13079808
- Bedrooms:
- 6
- Bathrooms:
- 8
A Keystone to the elegant Heritage of Historic Port Hope, The Meredith House, better known as Hill & Dale is incredibly captivating. Circa 1850 this stunning Estate sits hillside overlooking much of the South East portions of downtown, situated on 3+ acres of private landscaped property, natural stream, stone features, diverse trees and spacious exterior grounds. Beautifully renovated, original millwork, character details and an incredible formal layout with improvements that create a beautiful backdrop for your own personal residence, potential Bed & Breakfast, Boutique Hotel or Multi Generational living. Architectural features throughout this 6 bedroom home, a special space for entertaining, chef's kitchen, formal den/office, family room and dining room with captivating views. Wrap around covered veranda, points of entry from many locations, primary staircase centre hall plan, butlers pantry, second private staircase to expansive primary suite... The list is simply endless, you have to view to appreciate this remarkable one of a kind! Unique features, ensuite bathrooms for all bedrooms, a great set up for accommodations, lower level gym/recreational space with walk out, formal living room with stunning fireplace feature, perfect for hosting large gatherings. For those who are studious, the Main floor lounge offers that deep space, bookcases, a lovely private study. Walk to downtown and all of the beauty of Port Hope, Ganaraska River, Shops, Trinity College and all of the wonderful restaurants for dining, parks and all of the rich character of the streetscape. If you seek something simply to stand alone, this is the perfect astute property for you to establish your presence in Port Hope. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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71 Sutherland Drive in Toronto: Leaside House for sale (Toronto C11) : MLS®# C13241674
71 Sutherland Drive Toronto M4G 1H6
$2,795,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13241674
- Bedrooms:
- 4
- Bathrooms:
- 4
A rare opportunity to own one of Leaside's most admired homes. Built by Howard Henry Talbot, one of Leaside's original developers and former Mayor, this charming Cape Cod-style residence sits on an exceptional 40 x 140-foot lot, larger than most in the neighbourhood with a private double driveway. With its outstanding curb appeal and welcoming presence, this is a home that consistently draws compliments from passersby. Inside, warmth and character blend seamlessly with thoughtful family living. The main floor features separate living and dining rooms, a private study/office area, convenient laundry room, powder room, and four fireplaces that create inviting spaces throughout the home. At the heart of the house is the expansive family room with soaring cathedral ceilings, open to a well-appointed eat-in kitchen designed for both everyday family life and entertaining. A walkout leads to a spectacular private perennial garden with multiple seating and dining areas, creating a peaceful outdoor retreat. The upper level offers three bedrooms and two beautifully designed bathrooms, including a unique bedroom overlooking the family room below. The finished lower level provides exceptional additional living space with a large recreation room anchored by a gas-burning fireplace, plus an additional bedroom and bathroom ideal for guests or extended family. Rich in history, charm, and timeless appeal, this special home offers generous living space, beautiful gardens, and an exceptional setting in the heart of one of Toronto's most sought-after family communities. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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301 Keewatin Avenue in Toronto: Mount Pleasant East House for sale (Toronto C10) : MLS®# C13005066
301 Keewatin Avenue Toronto M4P 2A4
$2,399,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13005066
- Bedrooms:
- 6
- Bathrooms:
- 5
This stunning home redefines modern family life. The original 2-storey was gutted in 2000 rebuilt into a 3-storey architectural showpiece offering 3,020 SF + 1,131 SF in the LL for 4,151 SF of total living space. The architec anchored this home with a central atrium flooding the interior w/natural light creating a striking sense of openness.The main flr boasts stunning white oak wood flrs imported from Poland connecting across all levels with spiral-cured custom wood stairs and cable railings. With 5+1 spacious bdrms and 5 bathrooms, there's plenty of room. The home's thoughtful layout masterfully combines functionality w/modern style, offering bright principal rooms & custom finishes ideal for both everyday living & entertaining. The layout ensures a seamless flow across all areas of the home. The main flr's expansive 9-ft ceilings create a sense of openness thruout, with a layout designed to highlight natural light & effortless flow. The second flr's 8-ft ceilings enhance the airy feel of space. Enjoy an even more dramatic height on the third flr with 11-ft ceilings, giving the space an incredible sense of volume and grandeur which offers a flexible space where the back bdrm could serve as a bdrm or additional family rm or recreation area, especially with its cathedral ceiling, stunning window & glass door w/juliet balcony overlooking the lovely landscaped garden. The bsmt is bright, spacious, with endless possibilities with its 8.5-ft ceilings including converting it into a nanny's suite or a multi-generational home (kit roughed-in in rec rm). This home boasts so many unique features like the European church "clerestory" (stain glass window used in the nave of old churches in Europe) placed strategically in the 3rd floor alcove so that when the sun shines through it, it cascades down the atrium into the kitchen. Take a minute to read the Property Features attached to this listing. Enjoy living steps to Sherwood Park! John Fisher Jr PS. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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18 Tetbury Crescent in Toronto: Parkwoods-Donalda House for sale (Toronto C13) : MLS®# C13077210
18 Tetbury Crescent Toronto M3A 3G3
$2,349,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13077210
- Bedrooms:
- 5
- Bathrooms:
- 3
Classic Don Mills ranch bungalow set on a 90' x 125' oversized corner lot - a rare opportunity on a sought-after, quiet street only steps from Donalda Club. Built in 1959, this meticulously maintained home boasts over 3,000 square feet of thoughtfully finished living space, combining timeless charm with a flexible layout suitable for a multi-family dwelling or single-family use. The generous lot size also presents excellent potential as a future development opportunity. The main floor is anchored by a large eat-in kitchen with a walk-out to a deck overlooking the large and extremely private, landscaped backyard complete with a in-ground saltwater pool and hot tub. The fully finished lower level offers two additional bedrooms, a large recreation room with fireplace, loads of storage, and a walk-out to the private backyard patio - ideal for extended family or guests. Perfectly located for quick commutes downtown, and is surrounded by highly-rated schools, churches, parks, ravines, highways, TTC, shops, and restaurants. Home Inspection is available. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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85 Walmer Road in Toronto: Annex House for sale (Toronto C02) : MLS®# C13021728
85 Walmer Road Toronto M5R 2X6
$2,324,900Residential Freehold- Status:
- Active
- MLS® Num:
- C13021728
- Bedrooms:
- 8
- Bathrooms:
- 6
A five-unit Annex Semi Detached property with the kind of envelope and location that is not being built at today's replacement cost. Legal four-plex above grade plus a legal non-conforming lower suite across 5,225+ sq.ft. on Walmer Road, one of the most tenured income streets in central Toronto. In-place rents sit well below current Annex benchmarks. Income reflects long-tenured tenancies rather than today's market. The unit mix is differentiated - not five interchangeable bachelors. Unit 2 on the main floor is a 1,396 sq.ft. parlour-floor residence with a 21-foot living room, fireplace, oversized kitchen, and a 17-foot principal bedroom. Unit 5 on the third floor (1,171 sq.ft.) is configured with two kitchens, two four-piece baths, two primary bedrooms, an office, and a dining room - lives as one generous suite today. Unit 4 (758 sq.ft.) has a four-piece ensuite, walk-in closet, and living space. Unit 3 (710 sq.ft.) is a full one-bedroom with fireplace, kitchen, and dining. Unit 1 in the lower level (1,191 sq.ft., legal non-conforming) reads as a proper apartment: one-bedroom plus 15-foot den, full kitchen, three-piece bath, and private utility room. Three distinct buyer paths converge here. For the investor, five legal income streams on a single folio, a demand floor set by U of T, downtown professionals, and the Dupont / Spadina subway corridor. For the owner-investor - Multiple units are suitable and are amongst the most substantial owner's suites found inside a purpose-built Annex income property; live in it and let the other four units carry the debt while optionality is preserved. For the long-view buyer planning a single-family reversion - 5,225+ sq. ft. of interior envelope is a credible footprint for a top-of-market Annex restoration, and the existing plumbing stacks, kitchens, and floor plates make either path possible without starting from zero. Walking distance to Bloor Street, Casa Loma, the University of Toronto, and the Spadina subway line. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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40 Halton Street in Toronto: Trinity-Bellwoods House for sale (Toronto C01) : MLS®# C13210256
40 Halton Street Toronto M6J 1R3
$2,249,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13210256
- Bedrooms:
- 4
- Bathrooms:
- 3
Nestled in the highly sought-after Trinity Bellwoods neighbourhood, this stunning fully renovated Victorian home offers the perfect blend of timeless charm and modern luxury. Situated on a generous 20.08 x 150 ft lot and offering approximately 2,785 sq. ft. of total living space, this 3-bedroom, 3-bathroom residence has been completely gutted and meticulously renovated from top to bottom with permits, all of which have been fully closed-providing peace of mind and exceptional quality throughout. Much larger than it appears, this remarkable home features a bright and spacious open-concept main floor with soaring ceilings, elegant hardwood floors, and seamless flow between the living and dining areas. The chef-inspired kitchen is equipped with quartz countertops, stainless steel appliances, and ample storage. A full bathroom with laundry and a cozy family room addition with a striking exposed brick wall complete the space, leading out to a private, fully fenced backyard. Upstairs, you'll find three generously sized bedrooms, including one with a walkout to a private deck, as well as a beautifully designed spa-like bathroom. Thoughtfully designed access panels for plumbing have also been incorporated into both the primary and child's closets for added convenience and future accessibility. The fully finished basement has been professionally dug down and features a separate entrance.This level includes a large egress window, laminate flooring, an expansive recreation room, an additional bedroom, and a luxurious bathroom with a deep soaking tub and separate shower. Tucked behind the utility room is an enormous hidden storage area. Additional features include updated windows, a water softener, dual heating systems with a gas furnace servicing the main and basement levels, three heat pumps serving the second floor, and central air conditioning for year-round comfort. The detached garage provides parking for two small cars. Steps to shops, restaurants and TTC! More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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17 Vince Avenue in Toronto: Woodbine Corridor House for sale (Toronto E02) : MLS®# E13150782
17 Vince Avenue Toronto M4L 0A6
$1,999,999Residential Freehold- Status:
- Active Under Contract
- MLS® Num:
- E13150782
- Bedrooms:
- 3
- Bathrooms:
- 4
Step into 17 Vince Avenue and you're immediately struck by how bright, open, and effortlessly livable this 3,000+ sq. ft. space feels (3,500+ including lower level). This home is all about SPACE, SPACE and more SPACE!!! High ceilings (almost 10') and expansive windows flood the interior with beautiful natural light, creating a warm and inviting atmosphere throughout! Thoughtfully designed with an abundance of closet space and storage, every detail supports easy, organized living - a place where everything has its place!! The outdoor space is equally special. From spring through fall, enjoy your morning coffee or unwind with an evening glass of wine on the sun-filled back deck. A stunning, mature Black Walnut tree provides both beauty and privacy, creating a serene backyard retreat. As the seasons change, cozy up by the outdoor gas fireplace - or head inside to the inviting living room fireplace for the perfect winter evening. A family room + 2 bedrooms are located on the 2nd floor (both with ensuite bathrooms), and the third floor is entirely made up of the spacious primary suite with luxurious spa bathroom with HUGE shower, double sinks and "HIS/HERS" walk-in closets. A thoughtfully-designed lower level, offers endless versatility - perfect for a home gym, yoga studio, study retreat, or relaxed entertainment space. The lower level seamlessly connects to an oversized garage with ample space for a workshop and plenty of additional storage. While modern in design, this home never loses its sense of warmth and comfort. It's a space where lasting memories have been made and where your next chapter is ready to begin! The location is also fabulous! Set within a truly special community in the Bowmore and Monarch Park school district, you'll love the friendly neighbours and convenience of being just a short walk to the beach, local cafes, restaurants, numerous parks and parkettes, and everyday amenities - including the ever-popular Oxygen Yoga and Sauvignon Bistro!! More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
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7 Howard Drive in Toronto: Bayview Village House for sale (Toronto C15) : MLS®# C13175030
7 Howard Drive Toronto M2K 1K4
$1,999,000Residential Freehold- Status:
- Active
- MLS® Num:
- C13175030
- Bedrooms:
- 3
- Bathrooms:
- 3
Welcome to your private oasis in the heart of Toronto's prestigious Bayview Village neighbourhood. This exceptional 3-bedroom, 3-bathroom residence perfectly blends sophisticated indoor luxury with a spectacular resort-style backyard. The gourmet kitchen is a chef's dream, featuring granite counters, a gas stove and cozy heated flooring. The living room serves as the heart of the home, anchored by beautiful built-ins and a gas fireplace that creates an inviting atmosphere for crisp evenings. Downstairs, the comfort continues in a spacious family room, where a traditional woodburning fireplace and large windows create a bright, cozy secondary retreat. The lavish primary suite is a true sanctuary, featuring dramatic vaulted ceilings, a cedar closet, and a spa-like ensuite bathroom complete with its own heated floors, jetted shower and towel warmer for ultimate comfort. The outdoor living space is a true showstopper. Completely reimagined, the beautifully landscaped property features manicured gardens and a pristine inground pool installed in 2021. Discover multiple outdoor entertaining spots in this backyard. A premium tiered patio makes hosting effortless, fully equipped with a dedicated gas line for your BBQ and a cozy propane fire table for evening ambiance. A spacious 2-car garage provides excellent storage and convenience. Located in one of Toronto's most sought-after communities, you are steps away from the upscale boutiques and gourmet dining of Bayview Village Shopping Centre. Enjoy unparalleled convenience with nearby transit options, top-tier schools (Earl Haig School catchment), lush local parks, and quick highway access. This property is more than a home - it is a lifestyle. More detailsListed by BOSLEY REAL ESTATE LTD.- Lorraine Smith
- Bosley Real Estate Ltd., Brokerage
- 416-646-8833
- lsmith@bosleyrealestate.com
Data was last updated June 7, 2026 at 02:15 AM (UTC)
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Lorraine Smith
Bosley Real Estate Ltd., Brokerage
Location
103 Vanderhoof Ave., Toronto
45 Bruce St. S., Thornbury