Guildwood Homes for Sale

Guildwood Homes for Sale

Welcome to Guildwood, a picturesque neighborhood nestled in the heart of Toronto, Ontario. Known for its serene landscapes and vibrant community spirit, Guildwood offers a unique blend of suburban tranquility and urban accessibility. This charming enclave is bordered by the stunning shores of Lake Ontario, providing residents with breathtaking waterfront views and ample opportunities for outdoor recreation. The area is characterized by its lush parks, including the renowned Guildwood Park, which features beautiful gardens, walking trails, and historical sculptures, making it a perfect spot for family outings or leisurely strolls.

Guildwood is also home to a diverse array of architectural styles, from cozy bungalows to elegant two-storey homes, catering to various tastes and lifestyles. The real estate market here is thriving, with an assortment of homes for sale that promise both comfort and convenience. Whether you're a first-time buyer, a growing family, or looking to downsize, Guildwood offers properties that meet your needs and desires.

Residents enjoy easy access to local amenities, including shopping centers, schools, and dining options, all within a short drive or a pleasant walk. The community is well-connected by public transit, making commuting to downtown Toronto a breeze. With its friendly atmosphere and strong sense of community, Guildwood is more than just a neighborhood; it's a place where you can truly feel at home. Explore the homes for sale in Guildwood today and discover the perfect place to start your next chapter in this enchanting corner of Toronto!

Newest Guildwood Homes for Sale

$1,349,000
6 Beds ⋅ 4 Baths ⋅ E13794938 MLS
Welcome to this exceptional, fully renovated 4+2 bedroom, 4-bathroom luxury home nestled on an impressive 70' x 105' lot in desirable Guildwood. The home offers a spacious and versatile layout designed for today's families. Move-in ready. Renovated in 2026, high-end finish, new kitchen, quartz countertop, quartz backsplash, new furnace, new tankless hot water system, new floor, separate laundry. Approximately 2,000 sq. ft. above grade. walkout to backyard, walk-out basement, 2 Br Basement apt. can be rented. Specious living space for big families. Large outdoor space. Abundant natural Light, ideal for families looking for space, Located Within Walking Distance to High Ranking Schools, Groceries, Restaurants,, Shops, Worship place, TTC., minutes from the Waterfront & Trails. Friendly neighbourhood, A home that truly deserves to be seen.

166 Guildwood Parkway, Toronto
$1,450,000
8 Beds ⋅ 4 Baths ⋅ E13785504 MLS
Rarely Offered in Sought After Guildwood Village. Welcome to this beautiful home, situated on a quiet cul-de-sac yet steps from the Guildwood Go station for a convenient commute. This detached four bedroom, four bathroom home boasts many features such as, two car garage, main floor laundry, large dining room adjacent to open concept custom built kitchen for easy entertaining, breakfast area, functional living area with one of three fireplaces and large walk out to large elevated deck w/awning and glass railings for seamless outdoor entertaining. Built in ceiling speakers on the main and lower floors. Large primary bedroom boasts walk in closet and ensuite bath w/jacuzzi tub and a spectacular private primary suite (listed as "Other") w/vaulted ceiling and a built in gas fireplace. Finished basement rec room with gas fireplace, wet bar and walk out to back yard. Three piece bathroom and tons of storage space. Beautiful established perennial gardens, outdoor sheds and lots of under deck covered storage. The home has been extensively renovated over the present owners' 34 yrs here, showing pride of ownership throughout. Guildwood has many features also, Go Station, shops, conveniences, parks including the historic Guild Inn Estate, trails, golf club. This picturesque property is on a large irregular lot. Pre-listing Carson & Dunlop home inspection available.

8 Chantrey Court, Toronto
$1,699,900
5 Beds ⋅ 3 Baths ⋅ E13784038 MLS
An Entertainer's Delight! Ultra Private Backyard Retreat Featuring An Inviting 16x38 ft Inground Pool, Huge Stone Patio, Gazebo W/Firetable, Kids Treehouse, Cabana/Change Room, 2 Pool Sheds And Lush Green Space w/Inground Sprinklers!Thoughtfully Designed & Newly Upgraded Throughout, This Home Is Waiting For You To Make It Yours! 4+1 Bedroom, 3-Bathroom Side-Split Home Offering An Incredible 3,129 Sq Ft of Total Living Space. Separate Entry to Finished Basement Steps to Lake, Bluffs, GO! Prime Location on a Child Friendly Quiet Cul-de-Sac. With A Deep Double Car Garage, Large Interlock Driveway & Walkway, Outdoor Pot Lights and Fantastic Curb Appeal.This Property Makes An Immediate Impression. Step Inside To A Bright Wide Entry W/ Direct Garage Access And A Flowing Spacious Layout. Natural Light Pours In Through 3 Skylights And Walls of Windows, Highlighting The Rich Hardwood Floors Throughout. The Main Level Offers An Inviting Living/Dining Area With A Picture-Perfect Bow Window with Cali Shutters Which Flows Seamlessly Into The O/Sized Kitchen, Complete With High End Stainless Steel Appliances, B/I Floor To Ceiling Wine-Beverage Fridge, Coffee Bar, Stone Counters, Gas Cooktop W/Pop Up Exhaust Fan, Breakfast Bar And Open Sightlines To The Family Room. The Family Room Is The Heart Of The Home, Vaulted Ceilings With Pot Lights, Gas Fireplace, And A Walk-Out To The Backyard Deck & Pool. Perfect For Indoor-Outdoor Living And Entertaining. A Unique Bonus: A Main Floor Bedroom Or Sitting Room With A Private 2-Piece(Ez 3 Pc) Bath And Direct Walk-Out To The Rear Yard, Ideal For Guests, A Home Office, Or Multi-Generational Living. Upstairs, You'll Find 3 Bedrooms, Including A Serene Primary Retreat With Bay Window Seating O/Looking The Backyard. A Separate Side Entrance and Loft (EZ Office) Leads to The Finished Lower Level W/Spacious Liv/Dining w/ Gas Fireplace,3Pc Bath, Reimagined Potential Kitchen Plus A Finished 5th Bedroom With)Or Change to 2 Bdrm In-Law Suite!

3 Wythenshawe Wood, Toronto
$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
$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
$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
$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
$1,398,000
6 Beds ⋅ 3 Baths ⋅ E13655286 MLS
Stunning 5 Level Back Split on a Premium Corner Lot. This spacious and versatile home sits on a large corner lot in one of the area's most welcoming and convenient neighbourhood. Newly renovated over 100K spend. Just minutes from the GO Train, TTC, shops, and a minute walk to beautiful Lake Ontario, the location truly can't be beat. Inside, the unique 5. level back split layout offers exceptional space and flexibility - perfect for large families or those seeking great income potential. Surrounded by schools, a mosque, church, parks, and all essential amenities, this property delivers comfort, community, and convenience in one package. A rare opportunity to own a home with size, location, and future potential - all in a highly desirable neighborhood. Separate Living Room, Family Room, Back Yard has Cover Deck, Basement finish with 1+1 Bed Room. Basement has separate Laundry line set up. Camera's line are installed ( Buyer needs to add the Camera ). Opportunity to make a garden suit or six split unit.

289 Livingston Road, Toronto
$995,000
5 Beds ⋅ 3 Baths ⋅ E13622168 MLS
Welcome to 24 Lalton Place, a stunning 4+1 bedroom home situated in the sought-after Guildwood community. This home presents a unique opportunity to indulge in a sophisticated lifestyle, featuring a carefully curated design. The main floor offers a bright and inviting dining and living area, enhanced by the large windows that frame the picturesque landscaped gardens. The upper level is home to FOUR generously sized bedrooms, each boasting elegant laminate flooring. With two separate entrances to both the backyard and side yard, you'll have seamless access to the outdoor space, perfect for enjoying the private interlocked patio. Recent improvements include New Updated kitchen, New counter tops , New flooring and New finished basement a roof Shingles 2022 , accompanied by a furnace and AC system 2023, New Bathtub ,New Paint. The basement is a standout feature, complete with a spacious sitting room, an additional bedroom, and a kitchen-ideal for generating rental income to help pay your mortgage faster. This prime location is just a stone's throw from beautiful parks and scenic trails, including Guild Park & Gardens and lakeside paths. You'll also find top-rated schools, convenient shopping along Kingston Rd, and the Guildwood GO train station nearby, ensuring a quick commute to downtown. With easy access to Highway 401 just minutes away, travel is a breeze. Don't let this chance slip away-schedule your showing today and step into your dream home!

24 Lalton Place, Toronto
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