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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68 Regency Square in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13128886
68 Regency Square Toronto M1E 1N3 
$1,274,900Residential Freehold- Status:
- Active
- MLS® Num:
- E13128886
- Bedrooms:
- 4
- Bathrooms:
- 2
Nestled on a quiet, tree-lined street in one of Scarborough's most beloved communities, 68 Regency Square is the home you've been waiting for. Offering the perfect combination of timeless character and modern upgrades, this exceptional property is move-in ready and designed to impress. The heart of the home is a beautifully renovated kitchen - a true showpiece that will delight any home chef, featuring quality finishes and a layout that makes cooking and entertaining a pleasure. And in a detail rarely seen, the designer laundry room elevates an everyday chore into a genuinely enjoyable space. Every inch of this home has been considered. Three comfortable bedrooms and two well-appointed bathrooms provide plenty of space for families of all sizes, while the bright lower-level family room offers the bonus living space everyone craves - perfect for movie nights, a playroom, a home office, or hosting guests. Step outside and fall in love all over again. The meticulously landscaped yard, complete with an irrigation system, is a true gardener's paradise - ready for you to enjoy from day one. Whether you're an avid green thumb or simply love beautiful outdoor living, this yard will exceed your expectations through every season. All of this in the heart of Guildwood, steps from Guild Park and Gardens, Morningside Park, local shops, and transit - with the Scarborough Bluffs and the best of lakeside living just minutes away. Homes of this calibre on Regency Square are a rare find. Come see it before it's gone. More detailsListed by Signature Elite Realty Ltd.- JARROD ARMSTRONG
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253 Catalina Drive in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13128180
253 Catalina Drive Toronto M1E 1B8
$999,999Residential Freehold- Status:
- Active
- MLS® Num:
- E13128180
- Bedrooms:
- 7
- Bathrooms:
- 3
Welcome to 253 Catalina Drive, where luxury meets affordability in the heart of Guildwood Village. This exceptional, move in newly renovated home offers an incredible opportunity for large families and or savvy investors alike. Boasting a spacious layout with 7 bedrooms, 2 kitchens, 3 bathrooms and 2 laundry rooms, this home is deigned for comfort flexibility and convenience. A separate entrance leads to a self contained large 2 bedrooms suite - ideal for extended family or potential rental income. One of the 2 bedroom is a walkout to an attached pergola, perfect for relaxing or entertaining. Located in one of Scarborough's most sought-after communities. This property is surrounded by top-rated public and high school that deliver a private-school-caliber education without the private school fees. Enjoy unbeatable conveniences with close proximity to public transit and the GO train, making commuting effortless. Nature and recreation are just steps from your door, includes park, tennis courts, and the renowned Scarborough Golf Club. Your also minutes from shopping, hospital, grocery stores and a wide variety of restaurants. A rare blend of space and versatlity, location and value. You don't want to miss out of the home. More detailsListed by TRUSTWELL REALTY INC.- JARROD ARMSTRONG
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21 Regency Square in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13122628
21 Regency Square Toronto M1E 1N4
$1,224,900Residential Freehold- Status:
- Active
- MLS® Num:
- E13122628
- Bedrooms:
- 4
- Bathrooms:
- 2
Set in the heart of highly sought-after Guildwood, this detached bungalow with in-law suite, offers the rare opportunity to own in an established and desirable neighbourhood - where quiet tree-lined streets, waterfront parks, top-rated schools, and commuter convenience all come together. Just minutes to Guildwood GO Station, the lakefront, scenic walking trails, shopping, dining, and everyday essentials, this is a location known for its unmatched balance of lifestyle and connectivity. Positioned on a quiet residential street surrounded by mature homes and greenery, the property offers exceptional flexibility with a fully finished lower level featuring a separate entrance and excellent in-law suite or income potential. The main floor is warm, bright, and functional, with hardwood floors throughout, a spacious living and dining area anchored by a gas fireplace, and a large picture window that fills the home with natural light. The eat-in kitchen features stone countertops and generous space for everyday living and entertaining, while three well-sized bedrooms provide a comfortable family-friendly layout. Downstairs, the finished basement with separate entrance expands the living space significantly with its own kitchen, dining area, living room, and oversized bedroom - Whether used for extended family living, multi-generational households, or rental income, the setup adds tremendous long-term value. Outside, the private pie shaped fenced yard offers plenty of room to relax, entertain, or garden, while the attached garage and parking for four vehicles provide everyday practicality rarely found this close to the city. Guildwood remains one of Toronto's hidden gems - offering a true community feel, exceptional access to nature and the waterfront, and a seamless downtown commute. Spacious, versatile, and exceptionally located, this is the kind of property that delivers both immediate lifestyle appeal and lasting value for years to come. More detailsListed by Signature Elite Realty Ltd.- JARROD ARMSTRONG
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24 Lalton Place in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13119210
24 Lalton Place Toronto M1E 1T4
$1,138,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13119210
- Bedrooms:
- 5
- Bathrooms:
- 3
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! More detailsListed by REMAX CONNECT REALTY- JARROD ARMSTRONG
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64 Dale Avenue in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13114950
64 Dale Avenue Toronto M1J 3J5
$849,900Residential Freehold- Status:
- Active
- MLS® Num:
- E13114950
- Bedrooms:
- 7
- Bathrooms:
- 4
Welcome to 64 Dale Ave! Renovated detached bungalow in highly sought-after Guildwood Village. This home sits on an extraordinary 49.5 xx 290.66 ft lot, offering endless possibilities for future expansion or development. The main level features 3 spacious bedrooms, an inviting open-concept living and dining area. Finished basement with a separate entrance, provides 4 additional bedrooms. The massive backyard offers ample space to create even more value. Tons of potential. More detailsListed by RE/MAX HALLMARK REALTY LTD.- JARROD ARMSTRONG
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51 Greyabbey Trail in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13113966
51 Greyabbey Trail Toronto M1E 1V8
$789,900Residential Freehold- Status:
- Active
- MLS® Num:
- E13113966
- Bedrooms:
- 6
- Bathrooms:
- 3
Welcome to 51 Greyabbey Trail, a fantastic opportunity in the highly sought-after Guildwood community! This spacious home with separate entrance & +1 kitchen is perfect for investors or savvy buyers looking to offset their mortgage. Featuring a functional and versatile layout, it's ideal for a growing family seeking comfort and flexibility. Nestled in a quiet, family-friendly neighbourhood, this property provides the perfect balance of peace and convenience. With generous living spaces and a solid structure, it's ready for your personal touch-just a little TLC will transform it into your dream home or a high-performing investment. Close to schools, parks, transit, and all essential amenities, this is a rare chance to own in one of Scarborough's most desirable pockets. Don't miss out on this investor's delight with endless potential! More detailsListed by RE/MAX METROPOLIS REALTY- JARROD ARMSTRONG
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105 Catalina Drive in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13089244
105 Catalina Drive Toronto M1M 1K7 OPEN HOUSE: May 17, 202602:00 PM - 04:00 PM EDTOpen House on Sunday, May 17, 2026 2:00PM - 4:00PM
$1,264,000Residential Freehold- Status:
- Active
- MLS® Num:
- E13089244
- Bedrooms:
- 3
- Bathrooms:
- 3
Welcome to 105 Catalina Drive, where comfort meets style and every day feels like a getaway! Step into this beautiful, sun-filled home, an entertainer's dream tucked away in one of the most sought-after neighbourhoods. Move-in ready and full of charm, this home blends function, warmth, and lifestyle perfectly. You'll find 3 spacious bedrooms (originally 4) and 3 bathrooms, with hardwood floors throughout, granite countertops, newer appliances, and an updated furnace, all (2020/2021). From the moment you walk in, it just feels like home, the kind of place where you can truly relax and make lasting memories. The bright, above-grade basement is a bonus, featuring a wall-mounted TV and built-in speakers, a full bathroom and laundry area, plus a walkout to the backyard. Step outside to your private backyard oasis - the perfect setting for summer gatherings. Lounge by the pool, unwind under the pergola, or host friends on the wrap-around deck. You'll also enjoy the convenience of direct garage access from the main floor. Elizabeth Simcoe Public School is known for offering a private-school experience without the private-school fees. You're also just steps away from parks, tennis courts, a splash pad, nature trails, the marina, and Scarborough Golf Club. With the Guildwood GO Station nearby, easy access to shopping, hospitals, grocery stores, and restaurants, everything you need is right here.105 Catalina Drive isn't just a house, it's the home you've been waiting for. More detailsListed by ROYAL LEPAGE SIGNATURE REALTY- JARROD ARMSTRONG
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1120 10 Guildwood Parkway in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13088840
1120 10 Guildwood Parkway Toronto M1E 5B5
$1,050,000Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13088840
- Bedrooms:
- 3
- Bathrooms:
- 2
Welcome to this DROP DEAD GORGEOUS Rowatson Suite - where Luxury meets BREATHTAKING VIEWS OF LAKE ONTARIO! Bathed in natural light and positioned for privacy, this fully reimagined suite has been masterfully renovated from top to bottom with an uncompromising commitment to quality and craftsmanship. Every detail has been curated to create a home that is sophisticated and serene! The designer Kitchen is a statement in modern elegance, featuring premium LG appliances, sleek custom cabinetry, and clean architectural lines that blend beauty with functionality! Ideal for intimate evenings or elevated entertaining, the space flows seamlessly into open-concept Living and Dining areas framed by mesmerizing Lake vistas. The Primary retreat is a sanctuary unto itself, complete with a spa-inspired Ensuite showcasing a spacious glass walk-in shower and indulgent jacuzzi tub - a tranquil escape at day's end. A second fully renovated bath mirrors the same timeless aesthetic. Luxury finishes elevate every corner: wide-plank quality vinyl flooring, smooth ceilings, crown moulding, designer lighting, motorized window treatments, three new fan coil units, and a gas fireplace that adds warmth and ambiance year-round! Beyond the suite, enjoy a Lifestyle reserved for the discerning few. Set within 10 acres of beautifully manicured grounds, residents experience a true resort atmosphere with access to an exceptional Recreation Centre and an array of fabulous amenities - including indoor salt-water pool & whirlpool, gym, billiards, indoor golf practice & outdoor putting green, tennis, pickleball, squash & social clubs & classes! Completing this rare offering are two premium parking spaces, a private EV charger, and a spacious storage locker - practical luxuries that enhance effortless living. This is waterfront sophistication without compromise - an exceptional residence for those who expect nothing less than extraordinary. More detailsListed by EVANOFF REAL ESTATE LTD.- JARROD ARMSTRONG
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207 20 guildwood Parkway in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13082490
207 20 guildwood Parkway Toronto M1B 5E6
$749,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13082490
- Bedrooms:
- 2
- Bathrooms:
- 2
Welcome To The sought after Gates Of Guildwood, Where The Amenities & Grounds Have So Much To Offer! 24 Hour Gatehouse Security, Close To Ttc, Subway, Go Train, Shopping & Golf Course. 2 Bedroom, 2 Full Bathrooms, 2 w/o to balcony Maintenance Fees Incl:All Utilities,Cable & Internet. 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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- 1 (416) 457-1722
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5 Greyabbey Trail in Toronto: Guildwood House for sale (Toronto E08) : MLS®# E13087440
5 Greyabbey Trail Toronto M1E 1V6 OPEN HOUSE: May 16, 202602:00 PM - 04:00 PM EDTOpen House on Saturday, May 16, 2026 2:00PM - 4:00PM
$889,900Residential Freehold- Status:
- Active
- MLS® Num:
- E13087440
- Bedrooms:
- 4
- Bathrooms:
- 2
This beautifully maintained 3+1 bedroom, 2 bathroom home has been thoughtfully cared for and tastefully updated, offering the kind of quality and warmth that's immediately felt the moment you walk through the door. The main floor shines with brand new appliances in a well-appointed kitchen, and a fully renovated bathroom that strikes the perfect balance of style and function. Fresh, neutral paint throughout gives the home a crisp, move-in ready feel, while new flooring in the basement rec room adds a polished finish to the additional living space below. A brand new washer and dryer round out the updates - the big-ticket items are already done for you. This generous lot is a standout feature for those with a love of gardening or outdoor living, offering space to create something truly special through the seasons. All of this is set within the heart of Guildwood - one of Toronto's most cherished communities, known for its neighbourly spirit, proximity to the Scarborough Bluffs, scenic walking trails, and top-rated schools. It's the kind of street where people stay for decades, and it's easy to see why. A rare opportunity at this price point - don't wait. More detailsListed by SUTTON GROUP OLD MILL REALTY INC.- JARROD ARMSTRONG
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PH1 20 Guildwood Parkway in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13083520
PH1 20 Guildwood Parkway Toronto M1E 5B6
$624,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13083520
- 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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- 1 (416) 457-1722
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222 10 Guildwood Parkway in Toronto: Guildwood Condo Apartment for sale (Toronto E08) : MLS®# E13082766
222 10 Guildwood Parkway Toronto M1E 5B5
$819,900Residential Condo & Other- Status:
- Active
- MLS® Num:
- E13082766
- Bedrooms:
- 3
- Bathrooms:
- 2
What value!! This is your prime opportunity to own a fantastic, expansive and sophisticated suite in the prestigious Gates of Guildwood condos where you will experience resort style living within an exclusive gated complex. Situated on the 2nd floor, this unit offers peace of mind with very quick and easy access to the lobby/exterior and wonderful privacy on its balcony. With 1620 sq.ft. of upgraded living space, a large marble tiled entry foyer, 2 bedrooms/2 baths this highly desirable "Avonmore model" offers a comfortable care free lifestyle for the discerning buyer. The large open living/dining space features a rare, cozy gas fireplace with an adjacent four season solarium. The well appointed renovated kitchen with granite counters and built in appliances is ideal for entertaining. The primary bedroom features a walk-in closet with additional his/ her closets and a beautiful four piece ensuite bath. The second bedroom/den features a walk-out to a very private covered balcony, as do the primary bedroom and solarium... 3 walk-outs in total! This fabulous suite ticks all the boxes and with separate ensuite storage/laundry rooms and a bonus additional owned locker, storage space will never be a concern. The exceptional and abundant amenties include an indoor pool, seperate hot tub, work out gym, billiards room, library, party room, virtual golf and indoor racquet courts and much more. Explore the outdoors of this 11 acre private property with extensive gardens, walking trails, tennis/pickle ball courts, BBQ area, patio, gazebo and even more. With gate house access and 24 hour security this amazing condo at 10 Guildwood Pkwy is the perfect home for you. More detailsListed by RE/MAX HALLMARK REALTY LTD.- JARROD ARMSTRONG
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Data was last updated May 16, 2026 at 04:15 AM (UTC)
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