Guildwood Real Estate

Guildwood Real Estate

Welcome to Guildwood, a hidden gem nestled in the heart of Toronto, Ontario. This picturesque neighborhood, bordered by the stunning shores of Lake Ontario, offers a unique blend of natural beauty and community spirit. Known for its lush green spaces, Guildwood is home to the breathtaking Guildwood Park, where residents can stroll through beautifully landscaped gardens, explore scenic walking trails, and admire the stunning views of the lake.

Guildwood’s charm lies not only in its natural surroundings but also in its rich history. Originally developed in the 1950s as a planned community, it features a delightful mix of architectural styles, from mid-century modern homes to elegant bungalows, each contributing to the neighborhood's distinctive character. The streets are lined with mature trees, creating a serene atmosphere that invites leisurely walks and friendly chats with neighbors.

Families are drawn to Guildwood for its excellent schools and community-oriented spirit. Local parks, such as the popular Guildwood Village Park, provide ample opportunities for outdoor activities and social gatherings. The neighborhood is also conveniently located near shopping centers, cafes, and restaurants, ensuring that residents have easy access to all their daily needs.

With its close-knit community, stunning natural landscapes, and vibrant local culture, Guildwood is more than just a place to live; it’s a lifestyle. Whether you’re looking to raise a family or enjoy a peaceful retirement, Guildwood offers an idyllic setting that feels like home. Discover the charm of Guildwood and see why so many have chosen to call this enchanting neighborhood their own!

Newest Listings in Guildwood

$1,199,000
3 Beds ⋅ 2 Baths ⋅ E13768592 MLS
A quiet street, an exceptional property and the waterfront just a short walk away-69 Regency Square delivers the kind of Guildwood setting that is becoming increasingly hard to find. Tucked onto a picturesque loop with minimal through traffic, this three-bedroom home sits on an impressive, beautifully treed lot with a large, fenced west-facing backyard, established gardens and plenty of room to play, entertain or simply enjoy the outdoors. Inside, crisp, clean design, hardwood floors and an abundance of natural light create a relaxed, breezy feel throughout, complemented by an easy-flowing layout that feels equally suited to everyday living and entertaining. A series of thoughtful updates means much of the work has already been done. The kitchen features quartz countertops and was updated alongside the bathroom and flooring in 2023, followed by a new deck in 2024 and windows in 2025. Three bedrooms and a full bathroom provide a comfortable main-floor layout, while the finished lower level adds valuable flexibility with a large rec room with bright above-grade windows, a second bathroom and additional living space for movie nights, working from home, overnight guests or a growing family. An attached garage and three-car driveway provide up to four valuable parking spaces. But it's the location that really sets this home apart. Schools, parks, transit, local shops and restaurants are all close by, with the historic Guild Inn Estate, Guild Park and Gardens and the Lake Ontario waterfront within an easy walk. Guildwood GO is also nearby, putting downtown Toronto within convenient reach while letting you come home to mature trees, generous properties and a neighbourhood that feels distinctly removed from the pace of the city. Updated where it counts and sitting on a remarkable property in one of Guildwood's most desirable pockets, this is a home with the space, setting and location to enjoy for years to come.

69 Regency Square, Toronto
$1,195,000
4 Beds ⋅ 2 Baths ⋅ E13766470 MLS
Set in the heart of Guildwood, this spacious detached home delivers the kind of layout, lot, and location that make this neighbourhood so sought after. Bright principal rooms are filled with natural light, enhanced by a skylight at the centre of the home. The generous living room features a fireplace, large windows, hardwood floors, and a graceful archway that add character and style to this highly functional layout. The kitchen, with its walkout to the private deck, features a breakfast area, granite countertops, and plenty of workspace. Three bedrooms and two bathrooms upstairs provide comfortable separation for everyday family living. Downstairs, the expansive open lower level adds exceptional flexibility and options with two large rooms, a full bathroom, and plenty of space for a recreation area, home office, guest space, or extended family. There's a full bathroom, and plenty of space for a recreation area, home office, guest space, or extended family. Hardwood flooring runs throughout the upper level, complemented by durable vinyl flooring below. Outside, a private driveway with parking for four and an attached double-car garage add everyday practicality. All of this in one of east Toronto's most enduring residential communities, surrounded by mature trees and close to Guildwood GO, TTC, schools, parks, trails, the waterfront, and historic Guild Park & Gardens. With generous living space, a versatile lower level, and a peaceful Guildwood setting, 48 Toynbee Trail offers the space to settle in, grow, and make your own.

48 Toynbee Trail, Toronto
$829,900
3 Beds ⋅ 2 Baths ⋅ E13759736 MLS ⋅ Gates Of Guildwood BLDG.
Don't miss this bright, beautiful, and spacious corner suite! Immaculately maintained and thoughtfully upgraded throughout, this desirable Rowatson model offers 1,542 sq. ft. of well-designed living space with an exceptional split-bedroom floor plan, generously sized principal rooms, an inviting eat-in kitchen, and three walkouts to an lovely balcony where you can enjoy sensational sunsets! Enjoy breathtaking panoramic views from virtually every room! Features include gorgeous engineered wood flooring, granite countertops, upgraded bathroom fixtures, and three new fan coils. The Gates of Guildwood is set on 10 acres of beautifully landscaped grounds and award-winning gardens. An outstanding recreation centre offers brand-new tennis and pickleball courts, an indoor salt-water pool, gym, billiards, squash, and an active social calendar with something for everyone. With TTC at your door and the GO Train just steps away, enjoy a quick 25-minute commute downtown. All-inclusive maintenance fees include Rogers Xfinity cable and internet. Come experience an exceptional lifestyle at The Gates - you'll love calling it home! Please note: the Gates of Guildwood has a strict no dog policy.

10 Guildwood Parkway Unit 730, Toronto
$1,199,000
6 Beds ⋅ 4 Baths ⋅ E13751578 MLS
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!

59 Galloway Road, Toronto
$429,800
2 Beds ⋅ 2 Baths ⋅ E13734714 MLS ⋅ Prominence Point BLDG.
WOW! THIS ONE IS A STUNNER...Welcome to Suite 1503 at 90 Dale Avenue with breathtaking lake views, ideally located at the top of highly sought-after 'Guildwood Village' - Completely $$Renovated Top-to-Bottom! Offering almost 1,000 sq. ft. of beautifully finished living space, this home showcases luxurious upgrades throughout! The open living and dining area is wrapped in expansive floor-to-ceiling windows with clear panoramic unobstructed south-east views, creating an airy, sun-filled space with elevated sightlines. Open $$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! ** Virtual Staging in Some Photos **

90 Dale Avenue Unit 1503, Toronto
$585,000
2 Beds ⋅ 2 Baths ⋅ E13726786 MLS ⋅ Gates Of Guildwood BLDG.
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!

20 Guildwood Parkway Unit PH1, Toronto
$1,777,000
6 Beds ⋅ 5 Baths ⋅ E13720656 MLS
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.

21 Toynbee Trail, Toronto
$1,199,000
4 Beds ⋅ 2 Baths ⋅ E13714864 MLS
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.

16 Earswick Drive, Toronto
$839,000
3 Beds ⋅ 2 Baths ⋅ E13710132 MLS ⋅ Gates Of Guildwoodd BLDG.
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).

20 GUILDWOOD Parkway Unit 414, Toronto
$819,000
3 Beds ⋅ 3 Baths ⋅ E13708290 MLS
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.

11 Guildpark Pathway, Toronto
$999,000
6 Beds ⋅ 3 Baths ⋅ E13703976 MLS
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.

6 Greyabbey Trail, Toronto
$1,099,000
7 Beds ⋅ 4 Baths ⋅ E13701496 MLS
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.

40 Toynbee Trail, Toronto
Start Your Search