Guildwood is a lakeside community near Scarborough Village east of the Bluffs. It as formerly land owned by one family, and one can see why they chose to live in this spot. Real estate in Guildwood offers stately homes and charming bungalows. There is also expansive parkland overlooking the lake. Guild Park even features various historic structures, including one of Toronto's oldest log cabins.
Welcome to Guildwood
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59 Galloway Road in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13751578
59 Galloway Road Toronto M1E 1W6 OPEN HOUSE: Sep 12, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, September 12, 2026 2:00PM - 4:00PMOPEN HOUSE: Sep 13, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, September 13, 2026 2:00PM - 4:00PM
$1,199,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13751578
- Bedrooms:
- 6
- Bathrooms:
- 4
Welcome to 59 Galloway Road, a spacious detached home set on an exceptional 45 x 208 ft lot, a rare find in Toronto offering incredible space, privacy and flexibility. Step into the backyard and it is easy to see what makes this property so special. Surrounded by mature trees and lush gardens, this expansive yard feels like a private retreat from the city. Enjoy summer barbecues under the awning, relaxing beneath the gazebo, gardening, entertaining or simply the peace and privacy of your own outdoor oasis. Inside, this spacious 5 level back-split offers 4 + 2 bedrooms, 4 bathrooms and multiple living areas, ideal for a growing family, multigenerational living, guests, home offices or potential additional income. The bright main living and dining areas offer plenty of space for everyday living and entertaining. The updated eat in kitchen features granite countertops, a distinctive brick accent wall and a walkout overlooking the spectacular backyard. The inviting family room features a gas fireplace and direct access to the backyard, gardens and gazebo. Upstairs, the spacious primary bedroom offers its own ensuite bathroom and private balcony. The finished lower levels provide even more flexibility with additional bedrooms, recreation and living areas, a second kitchen and separate entrance with walkout, ideal for extended family or a potential income generating suite. Numerous improvements include updated flooring and lighting throughout, an additional backsplit window for more natural light, 200 amp electrical service (future proofed for a hot tub or EV charger) & high efficiency Lennox A/C. An attached double garage and private driveway provide plenty of parking. Located in beautiful Guildwood, enjoy mature trees, parks, ravines, waterfront trails, Lake Ontario and convenient access to Guildwood GO Station and 20 mins to downtown Union Station. A rare extra deep lot. an incredible backyard & a spacious and flexible home... Welcome home! More detailsListed by REMAX CONNECT REALTY- JARROD ARMSTRONG
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1503 90 Dale Avenue in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13734714
1503 90 Dale Avenue Toronto M1J 3N4
$429,800Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13734714
- Bedrooms:
- 2
- Bathrooms:
- 2
WOW! THIS ONE IS A STUNNER...Welcome to Suite 1503 at 90 Dale Avenue with spectacular lake views, ideally located at the top of highly sought-after 'Guildwood Village' - Completely $$Renovated Top-to-Bottom! Offering almost 1,000 sq. ft. of beautifully finished living space, this home showcases luxurious upgrades throughout! The open living and dining area is wrapped in expansive floor-to-ceiling windows with clear panoramic south-east views, creating an airy, sun-filled space with elevated sightlines. Open $$Renovated Kitchen featuring quartz counters & 'stainless steel' appliances and a much larger expanded passthrough opening overlooking the living dining space and scenic picture window views. The suite has been thoughtfully upgraded with $Renovations to 2 generously sized bedrooms, 2 fully renovated bathrooms, and extensive custom closet space, soft neutral tones and wide-plank laminate flooring throughout enhancing the open, modern feel, new lighting and hardware, huge mirror closet doors in the entry, in-suite washer and dryer, in-suite storage, an updated heating and cooling system plus thermostat & more! All utilities are included, and the unit comes with one underground parking spot. Enjoy well-maintained amenities including an indoor pool, gym, sauna, recreation room and ample visitor parking. Exceptional location...just walking distance to the Guildwood GO Station & TTC for an easy commute to downtown Toronto, near scenic walking/biking and waterfront trails for nature lovers, shopping, schools and the local Scarborough Golf & Country Club. Stylish and spacious offering breathtaking peaceful views and lifestyle ... Completely move-in ready - don't miss this one! More detailsListed by RE/MAX ROUGE RIVER REALTY LTD.- JARROD ARMSTRONG
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PH1 20 Guildwood Parkway in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13726786
PH1 20 Guildwood Parkway Toronto M1E 5B6
$585,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13726786
- Bedrooms:
- 2
- Bathrooms:
- 2
Welcome home to the prestigious Gates of Guildwood! Resort style living in your sought after penthouse unit! Enjoy your bright and spacious home with a thoughtfully planned layout to maximize comfort, function and enjoyment. The flow from the kitchen with breakfast bar to the open concept living / dining areas makes every living space usable! Your beautiful primary bedroom offers a 4pc ensuite and walk out to the balcony. Bonus solarium room to maximize your natural light - offers fantastic "flexible space" to suit your needs (guest room / home office / additional living space). You'll love to spend every evening enjoying the colours of the sunset view! This building is a rare gem, offering a genuine opportunity for community and warmth. It has fantastic physical amenities like tennis courts, pickleball, indoor golf range, putting green, pool, sauna, gym, library, social rooms, guest suites, car wash and more. But the real unique offering of this building is all the social clubs and organized social activity calendars - from aquafit to glee club & euchre..and truly EVERYTHING in-between! Penthouse unit offers unique perks to the owner - XL storage locker & XL end spot parking. Located just minutes from highway 401, Guildwood GO station, Scarborough Bluffs, shops, restaurants, parks and more. ALL UTILITIES INCLUDED! No more juggling monthly bills - your maintenance fees keep life stress-free (heat, hydro, water, A/C..even your cable TV and internet)! If you're looking to simplify your space and upgrade your lifestyle, start packing your bags! More detailsListed by ROYAL LEPAGE SIGNATURE REALTY- JARROD ARMSTRONG
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21 Toynbee Trail in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13720656
21 Toynbee Trail Toronto M1E 1E8
$1,777,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13720656
- Bedrooms:
- 6
- Bathrooms:
- 5
A rare, high-cash-flow architectural masterpiece nestled on a private 59-foot premium lot in prime Guildwood with total tranquility and no front or rear neighbours. Offering over 2,650 sq ft of luxury living space, this extraordinary property combines an exquisitely renovated primary residence, a brand-new 1,000 sq ft semi-attached addition, and a finished lower-level bachelor suite, creating the ultimate multi-generational retreat or mortgage-crushing investment. The legal secondary 2-bedroom, 2-bathroom suite generates an impressive $4,700/month in long-term executive rental income, allowing you to live luxuriously while your investment pays for itself.Step inside the brand-new contemporary addition, showcasing a sleek stucco exterior, ultra-efficient building envelope (4-inch spray foam plus 2-inch styrofoam), and high-end modern engineering. Interior highlights include over $90,000 in custom millwork, bespoke under-stair storage, rich engineered oak veneer flooring, and dramatic glass-railed oak stairs. The chef-inspired kitchen features smart LG appliances with an air-fryer range, while spa-like bathrooms feature intelligent thermostat-controlled heated floors. Outfitted with dual Bosch heating/cooling systems, smart lighting, and hardwired Ethernet, no detail has been overlooked.The fully transformed original residence boasts designer quartz countertops with matching slab backsplash, a dedicated coffee station, integrated entertainment storage, renovated luxury baths, and two spacious bedrooms with space-saving custom Murphy beds. The fully finished basement bachelor unit features its own brand-new kitchen, perfect for an in-law, nanny suite, or guest flat.The outdoor oasis is built for entertaining, featuring a new illuminated composite deck, 68-foot retaining wall, premium stone interlocking, epoxy garage floors, brand-new asphalt driveway, and custom storage shed. An unrepeatable turnkey Guildwood showpiece. More detailsListed by RE/MAX REALTRON MARIUS MITROFAN GROUP- JARROD ARMSTRONG
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14 Fintona Avenue in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13717266
14 Fintona Avenue Toronto M1E 1V3
$849,000Residential Freehold- Status:
- Active Under Contract
- MLS® Num:
- E13717266
- Bedrooms:
- 4
- Bathrooms:
- 2
Nestled on a quiet, tree-lined street in Scarborough's sought-after Guildwood community, this charming, raised bungalow sits on a generous 46.5 x 114-foot lot surrounded by mature trees and established landscaping. The private backyard offers an ideal setting for family living and entertaining, featuring a party-sized wood deck, lush green space, and plenty of room for children and pets to play. Inside, the bright and inviting home offers a functional layout with two bedrooms, originally designed as a three-bedroom residence and easily converted back if desired. The spacious eat-in kitchen provides ample room for family gatherings, while the combined living and dining area is enhanced by elegant crown moulding and large windows that fill the home with natural light. The rear bedroom offers convenient walkout access to the backyard deck, creating a seamless connection between indoor and outdoor living. The finished lower level expands the living space with a separate entrance, a large recreation room featuring a cozy stone fireplace, a spacious bedroom, and a three-piece bathroom. With its independent access and flexible layout, the basement presents excellent potential for an in-law suite, multigenerational living, or future income opportunities. Located in one of Scarborough's most established and picturesque neighbourhoods, residents enjoy close proximity to the scenic Guild Park and Gardens, the beautiful waterfront bluffs along Lake Ontario, and the extensive trail network of Grey Abbey Trail. Just minutes from shopping, schools, parks, public transit, and the convenient Guildwood GO Station, commuters will appreciate easy access to downtown Toronto and Highway 401. A wonderful opportunity to enjoy a family-friendly lifestyle in one of east Toronto's most treasured communities! More detailsListed by RE/MAX HALLMARK REALTY LTD.- JARROD ARMSTRONG
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16 Earswick Drive in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13714864
16 Earswick Drive Toronto M1E 1C6
$1,199,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13714864
- Bedrooms:
- 4
- Bathrooms:
- 2
Welcome to 16 Earswick Drive, an elevated retreat in the coveted Guildwood Village, known for its tree-lined streets, timeless architecture, strong sense of community, and convenient access to Guildwood GO Station. This beautifully updated 3-level backsplit offers a perfect blend of modern style, functionality, and versatile living. The spacious open-concept living and dining area features warm hardwood floors, a custom feature wall, and an oversized window that fills the space with natural light. The newly renovated kitchen boasts custom cabinetry, sleek quartz countertops, premium stainless steel appliances, and a generous layout ideal for everyday living and entertaining. The home offers three well-sized bedrooms with large closets and a tastefully renovated bathroom. The primary suite features a private walkout to an impressive 300 sq. ft. two-tier deck overlooking the fully private backyard, surrounded by mature greenery and approximately 18-foot privacy trees for a peaceful, secluded setting. A separate side entrance leads to a beautifully finished in-law suite with its own kitchen, bedroom, and full bathroom-ideal for extended family, guests, or potential income. The lower level includes an approximately 500 sq. ft. crawl space for abundant storage, while a spacious garden shed provides additional outdoor storage. The fully interlocked front yard offers parking for up to four vehicles, plus a private attached garage. Ideally located minutes from the Scarborough Bluffs and Guild Park & Gardens, enjoy nearby trails, green space, historic architecture, and lakefront views. With easy access to Guildwood GO Station and Sir Wilfrid Laurier Collegiate, 16 Earswick Drive offers an exceptional combination of privacy, space, modern updates, and convenience in one of Scarborough's most established communities. More detailsListed by ROYAL LEPAGE SIGNATURE REALTY- JARROD ARMSTRONG
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414 20 GUILDWOOD Parkway in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13710132
414 20 GUILDWOOD Parkway Toronto M1E 5B6
$839,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13710132
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to the Gates of Guildwood, resort-style living at its finest! 20 Guildwood Parkway is situated on 13 Exclusive Acres of lush, landscaped grounds with expansive walking paths and a gazebo to sit and enjoy the view. The highly sought-after Rowatson model offers 1540 square feet of luxurious light-filled living space in a peaceful, secure, 24-hour Gated Community. This 2+1 Bedroom, 2-Bathroom Suite has been extensively and elegantly renovated and features the Total Removal of Popcorn Ceilings and the installation of modern Pot-Lighting throughout. The heart of the home is a completely remodeled, open-concept Kitchen that overlooks the dining room -- perfect for entertaining! The light-filled Solarium is an ideal space for a morning coffee, a quiet home office or guest room. Suite 414 includes: Walk-In laundry Room with shelving, New Window Shades in every room and a Walk-In Closet in the Primary Bedroom. Monthly maintenance fees cover All Utilities, WiFi and Cable TV! Live steps from everything you need, with the TTC at your doorstep (a quick 30 minute to Union Station) and the Historied Scarborough Golf Club is, literally around the corner. Enjoy world-class including an Indoor Salt-Water Pool, Whirlpool, Sauna, Fitness Centre, Newly Resurfaced Tennis courts, Picleball, Squash, Basketball Courts, Putting Green, Car Wash and communal BBQ patio. Your new home comes with 2 Side-By-Side Parking Spaces and an Extra Large Storage Locker. 20 Guildwood is an extremely well-maintained building, the Superintendent lives in the building and the Social Life is beyond compare. Join the many social clubs and organized social activities -- everything from Aquifit to Euchre! Please Note: This is strictly no-dogs building. (Cats are welcome). More detailsListed by KELLER WILLIAMS ADVANTAGE REALTY- JARROD ARMSTRONG
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11 Guildpark Pathway in Toronto: Guildwood Condo Townhouse for sale (Toronto E08) : MLS®# E13708290
11 Guildpark Pathway Toronto M1J 3P1
$819,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13708290
- Bedrooms:
- 3
- Bathrooms:
- 3
Welcome to this beautifully upgraded semi-detached condo, tucked away on a quiet court in the highly sought-after Guildwood community. Designed with both style and functionality in mind, this 3-bedroom home features a smart open-concept layout, hardwood floors, soaring 12-foot ceilings and tasteful upgrades throughout. The spacious L-shaped kitchen flows seamlessly into the family room, while the elevated living and dining areas overlook the space below, creating an open and airy feel. Upstairs, the generous primary suite features a walk-in closet and a 4-piece ensuite complete with a soaker tub and separate shower. The finished walkout basement provides additional living space with direct access to the fully fenced backyard-perfect for entertaining, relaxing or family enjoyment. Direct garage access adds everyday convenience. Ideally located just minutes from Guildwood GO Station, TTC, schools, the University of Toronto Scarborough, Centennial College, shopping, restaurants and the renowned Guild Park & Gardens. A rare opportunity to enjoy space, style and convenience in one of Scarborough's most desirable neighbourhoods. More detailsListed by CENTURY 21 LEADING EDGE REALTY INC.- JARROD ARMSTRONG
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6 Greyabbey Trail in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13703976
6 Greyabbey Trail Toronto M1E 1V7
$999,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13703976
- Bedrooms:
- 6
- Bathrooms:
- 3
Attention to new home buyer. Fully Renovated Open Concept, Stunning Kit. W/ Center Island, Coffered Ceiling In L.R.,2 Newer Baths, Upgraded Windows, 200 Amp Electrical Service, New Furnace & Gas (Dec 21),Prof. Water Proofing Basement. With Life Time Warranty Certificate($19K), Separate Entrance To Basement. Apt. 3+3 Bedrooms, 2 Kitchens, 2 Ldry,9 Appliances, Min. To TTC, Go, Schools, Shopping, Scarborough, T.C., Grey-Abbey Park, Guild-Inn Estate Lake. And One Bus To U Of T. Beautiful basement 3 bedrooms apartment is ready for rent to support as additional income. More detailsListed by ROYAL LEPAGE IGNITE REALTY- JARROD ARMSTRONG
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40 Toynbee Trail in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13701496
40 Toynbee Trail Toronto M1E 1E9
$1,099,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13701496
- Bedrooms:
- 7
- Bathrooms:
- 4
Bright & Spacious Bungalow In Sought After Guildwood...Situated On A Premium 60 ft Frontage. Features Hardwood Flooring Throughout, A Stunning Gourmet Kitchen With Quartz Countertops, Granite Tile Flooring & Stainless Steel Appliances. Four Beautifully Updated Bathrooms, Newer Windows & Doors. Professionally Finished Basement With Separate Entrance, 4 Bedrooms and 2 Full Washroom - Offering Excellent In-Law Or Income Potential. Move-In Ready! Conveniently Located Close To Top-Rated Schools, Parks, TTC, Shopping & Beautiful Lake Ontario. More detailsListed by RE/MAX REALTRON REALTY INC.- JARROD ARMSTRONG
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7 Lyncroft Drive in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13696258
7 Lyncroft Drive Toronto M1E 1X6
$1,049,900Residential Freehold- Status:
- Active
- MLS® Num:
- E13696258
- Bedrooms:
- 4
- Bathrooms:
- 2
Your own private retreat in the heart of Guildwood, where tranquil lakeside living meets an effortless connection to the city. Set in one of Scarborough's most established and coveted family communities, this four-bedroom detached home pairs a fantastic family layout with a private backyard oasis featuring a heated inground pool, mature trees, and plenty of space to entertain and unwind. It's a home designed to make the most of every season, with summers that feel like a getaway without leaving home. Inside, the bright main floor features open-concept living and dining rooms with hardwood floors, a spacious eat-in kitchen, and a sun-filled solarium with a walkout to the backyard. Upstairs, four well-sized bedrooms provide plenty of room for a growing family, including a primary bedroom overlooking the yard and another bedroom with a walkout to a large deck over the carport, creating yet another inviting outdoor space. The finished basement adds valuable flexibility with a recreation room and plenty of storage. Step outside and the backyard delivers on that first impression. Fully fenced and surrounded by mature greenery, the heated pool, patio, and generous outdoor space create an exceptional setting for summer entertaining, family gatherings, or quiet afternoons by the water. And then there's Guildwood, one of the east end's most desirable places to put down roots. Enjoy the tranquility of living close to Lake Ontario and the lakeshore trail system, along with beautiful parks, mature streets, and fantastic local schools. Guildwood GO Station is a short walk away for an easy commute downtown, while Highway 401 is just a short drive away for convenient travel across the GTA. It's a rare combination: peaceful lakeside surroundings with the city still comfortably within reach. A true family home with an unforgettable backyard, exceptional connectivity, and the relaxed lakeside lifestyle that makes Guildwood such a special place to call home. More detailsListed by Signature Elite Realty Ltd.- JARROD ARMSTRONG
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207 20 guildwood Parkway in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13694614
207 20 guildwood Parkway Toronto M1B 5E6
$699,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13694614
- Bedrooms:
- 2
- Bathrooms:
- 2
LUXURY CONDO LIVING IN THE GATES OF GUILDWOOD, Welcome home to resort-style living in one of Scarborough's most prestigious addresses. This bright, spacious 2-bedroom, 2-bathroom condo offers comfort, security, and an unbeatable lifestyle.The Lifestyle You Deserve:The Gates of Guildwood isn't just a condo - it's a community. Enjoy peace of mind with 24-hour gatehouse security and access to an unmatched suite of amenities:Indoor Resort Amenities: Salt water pool & hot tub Full fitness center Billiards room & library Party room for entertaining Virtual golf + putting green Indoor racquet courts, 10+ Acres of Meticulously Maintained Grounds: Scenic walking trails & lush gardens Tennis & pickleball courts. BBQ areas & patios for summer evenings Beautifully landscaped outdoor spacePrime Location:Steps to the GO, TTC, Guildwood Village shops & restaurants, parks, and the Bluffs. Commuting or unwinding - you're perfectly placed.Whether you're downsizing without compromise, investing, or buying your first home, this condo delivers the rare combo of security, space, and lifestyle. Maintenance Fees Incl:All Utilities,Cable & Internet. The Unit features New kitchen w/quatrz counters & stainless steel Appliances 2021 main bathroom renovated 2021, new flooring throughout 2021, ensuite bathroom new vanity w/ quartz counters 2021, Freshly painted new closet organizers 2026 More detailsListed by ROYAL HERITAGE REALTY LTD.- JARROD ARMSTRONG
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Data was last updated September 8, 2026 at 12:15 PM (UTC)
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