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A once-in-a-lifetime opportunity, 220 Greyabbey Trail is one of Toronto's most extraordinary private waterfront estates. Beyond elegant wrought-iron gates, nearly 6 acres of breathtaking park-like grounds unfold, framed by mature trees and 11 magnificent Blaze Maples lining the 660-foot street frontage create an unforgettable arrival. With approximately 770 feet of unobstructed Lake Ontario frontage, one of the longest privately owned waterfronts within the City of Toronto, and your own private beach, this is an offering of exceptional scale, privacy and natural beauty that is impossible to replicate. Lovingly held by the same family since 1967, the home has evolved into an exceptional residence offering over 5,500 sq. ft. of living space with 5 bedrooms + den and 4.5 bathrooms. The heart of the home is a spacious family kitchen with a grand centre island, premium appliances and generous dining area, flowing into a spectacular glass-enclosed solarium with floor-to-ceiling folding doors that create seamless indoor-outdoor living. A formal living room with gas fireplace, private office with custom built-ins, family room and sunfilled breezeway/foyer complete the main level. Upstairs, four well appointed bedrooms include three with private balconies, while the primary suite offers rooftop access and a spa-inspired ensuite with lake views. A three-car garage is complemented by a self-contained guest or nanny suite above. Whether entertaining on a grand scale or enjoying the luxury of your private waterfront, this is more than a home-it's a legacy.

One-Of-A-Kind Home Situated On An Impressive 70-Ft Wide Lot, This Exceptional Home Enjoys An Unobstructed, Direct-Facing View Of Lake Ontario From The Backyard, With Breathtaking Lake Views From Every Bedroom. The Spacious Layout Features Soaring Vaulted Ceilings, A Striking Statement Window In The Kitchen, And Oversized Living And Family Rooms With A Walk-Out To The Beautifully Landscaped Backyard. Relax On The Expansive Deck Or Upper Balcony And Enjoy Your Morning Coffee While Watching Sailboats Glide Across The Lake. Additional Highlights Include A Double-Car Garage, Two Fireplaces, And A Grand Open-Concept Foyer Featuring Stained Glass And A Soaring Vaulted Ceiling.

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.

HGTV's Top of the Block winner, recognized for its sleek modern design, thoughtful functionality, natural light and exceptional attention to detail. Fully rebuilt in 2023 by a reputable builder with premium materials sourced from around the world. Bright, open-concept living and dining with European tilt-and-turn windows and expansive lift-and-slide doors. Chef-inspired kitchen with sleek cabinetry, quartz waterfall island and top-of-the-line appliances. Private pool-size 50 x 110 ft lot with a beautifully landscaped backyard oasis. Fully finished basement featuring a spacious bedroom and stunning bathroom. A true gem in Guildwood Village, one of Toronto's hidden paradises by the lake- Minutes from beaches, waterfront trails and Rouge National Urban Park, offering an incredible combination of nature and city living.

If you've been waiting for a truly one-of-a-kind Terrace suite, this is the one you've been dreaming of! This exceptional "mansion in the sky" offers an impressive 2,194 sq. ft. of luxurious single-level living, complemented by an extraordinary 600 sq. ft. private terrace (with 5 walk-outs!!) showcasing unparalleled panoramic Lake views. Rarely does an opportunity of this calibre come along! With its generous proportions and five walk-outs to the expansive outdoor space and breathtaking setting, this remarkable residence offers the ultimate blank canvas for discerning Buyers to create a spectacular home tailored entirely to their own vision and lifestyle. Imagine morning coffee overlooking the lake, sunset cocktails on your private terrace, and effortless indoor-outdoor entertaining on a grand scale. Whether you envision a sophisticated contemporary retreat, an elegant entertainer's paradise or your own private forever home, the possibilities are virtually limitless. A truly rare offering where exceptional space, extraordinary views and endless potential come together to create your own personal paradise in the sky. You'll also enjoy the Gates of Guildwood's fabulous amenities - including an indoor salt-water pool & whirlpool, Billiards, Gym, Squash, Tennis, Pickleball, indoor Golf practice & outdoor putting green & more! Stroll through 10 acres of meticulously manicured grounds & gardens! Easy access to Go Train, TTC & local shopping! This Suite also comes with a huge ensuite storage rm, a separate locker and two side-by-side parking spots! Don't miss this one!

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.

Highly Sought-After Guildwood Village. A Rare Opportunity. This Home Has Been Beautifully Renevated With Upgraded Kitchen, All New MainFloor Bathroom, Brand New 3pc Bathroom With Glass Shower. Private Well Designed And Spacious In-Law Apartment (Possible Income Potetial) With High Ceilings, May Also Be Used For Office Spaces Or Those Work-From-Home Needs . Large + Bright Laundry Room And Spacious Cold-Celler. Rec-Room/Family Room With Beautifull Designed Stone FirePlace For Cozy Family Gatherings and Holiday Celebbrations. Main Floor Kitchen Has Walk-Out To A Spacious and Private Yard For Gardening and Has Large Patio For Entertaining, Summer Gatherings, BRBque And Safe Family Fun. An *Additional 2nd Detatched Garage* That Can Be Converted Into A Home Studio or Space For A Home Business And/or WorkShop - Garage Has Lower Level. All New Roof - 2025, New Up-Grade Electrical 200 Amp -2025, Newer Furnace 2021, New Hot Water Tank -2023 (Owend). This Home Has an Abundance of Natural Light With Large Wall To Wall Windows in Living Area, Dinning Room and Kitchen and Bedrooms. Renovated Main Floor Kitchen with New Stainless Steel Appliances i.e. Two-Door Large Refridgerater, New Built-In Dishwasher and Newer 4 Burnner Gas Stove and Oven. 3 Very Spacious and Bright Bedrooms With Ample Closet/Storage Space. Main Floor Has Hardwood Throughout.This Home Delivers! Just Steps Away From Incredible Parks, Top-Rated Schools - Elementary , Middle School and High School, and The Scenic/Historic Guild Inn and Park With Beautiful Views of The Famouse Scarborough Bluffs and Lake Ontario.You Will Love The Lifestyle The Neighbourhood Offers. For Commuters, Guildwood GO Station Is A Mere 2 Minute Drive Away, Making Your Journey To Work A Breeze. This Home Is a Must See, Situated In One of The Most Desireble Pockets Of The City. **Dont Miss This Opportunity.

Visit REALTOR website for additional information: Much larger than it appears! Welcome to this charming, bright back split nestled on a quiet, tree-lined street in the highly desirable Guildwood Village community. This spacious home features an inviting open-concept living and dining room, complete with a cozy gas fireplace and an elegant bay window. Step down into the sunken family room, which boasts brand-new vinyl flooring and a seamless walk-out toa private patio and back garden.With a separate side entrance, a classic hardwood foot print throughout, a durable lifetime tiled roof, and a massive crawl space for extra storage, this property offers incredible layout potential.It also presents a proven income opportunity, consistently designated as a top-performing short-term rental guest favorite. Enjoy un matched neighborhood lifestyle value with an easy walk to the Guildwood GOTrain, TTC transit, top-rated schools, local boutique shops, the historic Guild Inn park, scenic trails, and the shores of Lake Ontario!