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58 Old Forest Hill Road, Toronto
$6,380,000
6 Beds ⋅ 6 Baths ⋅ C13806110 MLS
A Rare Offering On Prestigious Old Forest Hill Road! This Elegant 3 Storey Residence Offers Timeless Character, Gracious Proportions And An Exceptional Family Lifestyle. Hardwood Floors, Classic Millwork, Wainscoting throughout main and second floor. four Fireplaces And An Abundance Of Natural Light. The Spacious Eat-In Kitchen Features A Large Centre Island And Opens To A Sun-Filled Family Room, Multiple Walk-Outs Provide A Seamless Connection To The Private Rear Garden. The Upper Levels Offer Five Generously Proportioned Bedrooms, Including An Impressive Primary Retreat With Fireplace, Ensuite And A Bright Sitting Room Overlooking The garden. Two Additional Bedrooms on third floor with Ralph Lauren Broadloom provides Excellent Flexibility For Family, Guests Or Home Office Use. Finished basement With Recreation Room, Fireplace And nanny's room. Private Backyard Oasis Surrounded By Mature Greenery, Complete With Stone Patio, An Exceptional Setting For Summer Entertaining And Relaxed Family Living. Moments From Forest Hill Village, Parks, Transit And Some Of Toronto's Most Respected Schools, Including Upper Canada College And The Bishop Strachan School. A Wonderful Opportunity To Enjoy A Classic Forest Hill Residence Today, With Outstanding Potential To Personalize And Create A Home For Generations To Come. Check virtual tour for more photos!

58 Old Forest Hill Road, Toronto

29 Tarlton Road, Toronto
$2,795,000
5 Beds ⋅ 4 Baths ⋅ C13784406 MLS
Large 4+1 bedroom updated home in South Forest Hill/Chaplin Estates. Large 35' lot with private driveway, over 3,000 sq/ft of living space, close to UCC and BSS. This home has a 2 level addition to provide an oversize family room with wood burning fireplace and walk out to the professionally landscaped backyard and a primary bedroom with a new luxurious 5 piece ensuite bath with his/her shower and a standalone soaker tub. Large formal Living room, Dining room and a main floor powder room. Finished basement with a rec room and an additional bedroom/office as well as a proper laundry room with sink. This home is entirely move-in ready but with the potential to modernize the kitchen and secondary bathroom. Walking distance to both Avenue and Chaplin Eglinton LRT stations and shops and restaurants on Eglinton West. Interior pictures from prior Staging.

29 Tarlton Road, Toronto

523 Vesta Drive, Toronto
$5,995,000
5 Beds ⋅ 7 Baths ⋅ C13779646 MLS
Welcome to 523 Vesta Drive, an exceptional Forest Hill residence offering over 5,000 sf of beautifully designed living space across 3 levels. A dramatic double-height foyer introduces a light-filled, open-concept interior designed for sophisticated entertaining & comfortable family living. At the heart of the home is a chef-inspired kitchen with a centre island, quartz countertops, a Wolf 6-burner gas range, Sub-Zero refrigerator, and Miele dishwasher. A separate butler's pantry with sink, glass-front cabinetry & additional prep space adds function & elegance. The main level also features a family room with a gas fireplace and direct access to the deck overlooking the landscaped backyard, a private home office with custom built-ins and a functional mudroom. Upstairs are 4 bedrooms, each with its own ensuite & heated bathroom floors. The expansive primary retreat offers a coffee bar with sink, two walk-in closets & spa-inspired ensuite with heated floors, gas fireplace, soaker tub, steam & rain shower, heated towel rack & enclosed water closet. The custom dressing room features a skylight, centre island & vanity. The walkout lower level features heated floors, private home theatre with projector & surround sound, wet bar, climate-controlled glass-enclosed wine cellar, recreation space & private guest or nanny suite with ensuite. Exceptional comfort continues with a private elevator servicing all 3 levels, whole-home Sonos sound system, four gas fireplaces, motorized window coverings, central vacuum & security system. Outside, enjoy a landscaped backyard with in-ground pool, deck & lounge areas. A heated driveway leads to the double car garage. Ideally located in prestigious Forest Hill, close to BSS, UCC, parks, shops, transit & amenities, this is a rare opportunity to own a substantial family residence offering exceptional space, technology & luxury in one of Toronto's most coveted communities.

523 Vesta Drive, Toronto

94 Dunvegan Road, Toronto
$11,995,000
4 Beds ⋅ 7 Baths ⋅ C13763100 MLS
A Rare Offering in Forest Hill, welcome to 94 Dunvegan Road an exceptional home and lot on one of the neighbourhood's most prestigious and tightly held blocks. Situated on a remarkable 70 x 174 ft lot, this distinguished residence designed by acclaimed architect Joe Brennan offers an extraordinary combination of scale, presence, and future potential. From its impressive proportions to its rare underground 5 car garage, the home stands as a true statement property. Elegant principle rooms, soaring ceilings, wood-burning fireplaces, and oversized windows overlooking the landscaped grounds create a sense of timeless character and warmth throughout. The expansive layout across four levels offers exceptional family living, including a luxurious primary retreat, spacious ensuite bedrooms, and a spectacular third-floor loft with skylights, sauna, and wet bar. Whether you choose to enjoy the residence in its current form, undertake a thoughtful renovation, or create a custom-built legacy estate, the possibilities here are as expansive as the lot itself. Opportunities of this size and caliber on Dunvegan Road are exceedingly rare.

94 Dunvegan Road, Toronto

105 Dunvegan Road, Toronto
$13,500,000
5 Beds ⋅ 7 Baths ⋅ C13752980 MLS
Set amongst Forest Hill's most distinguished estates, 105 Dunvegan Road is an exceptional 29-year-old residence on a 65 x 170-foot lot, featuring a stately façade and semi-circular drive. An elegant entry opens to a dramatic foyer with baby grand piano, sweeping staircase, breathtaking skylight and soaring 12-foot ceilings. Grand principal rooms and gallery-like walls create an ideal setting for art lovers and effortless entertaining. The main floor offers a living room with gas fireplace and adjoining dining room, oversized kitchen with centre island and servery, mudroom and two powder rooms. A bright breakfast room beneath a skylight walks out to the terrace. The fully panelled library features a gas fireplace, coffered ceiling, wall-to-wall built-ins and herringbone floors with French doors to a covered terrace. A sun-filled family room with three sets of French doors and extensive built-ins provides a seamless connection to the outdoors. Upstairs, the primary suite spans the rear of the home overlooking the private, mature grounds with a spacious bedroom, sitting room w/fireplace, private terrace and spectacular seven-piece ensuite. Three additional bedrooms complete this level. The lower level is designed for entertaining and extended family living, featuring a billiard room with garden walk-out, vaulted recreation room with built-ins, mirrored exercise room and fifth bedroom with four-piece ensuite and kitchenette. Direct access to the underground three-car garage adds convenience. Multiple walk-outs lead to a stone terrace and exceptionally private garden with inground pool and a 3 room cabana* -a true urban retreat for entertaining and summer enjoyment. Ideally located in Forest Hill, within walking distance of UCC, BSS and Forest Hill Public School, plus parks, shops, restaurants, transit and neighbourhood amenities. A rare opportunity to enjoy exceptional space and privacy in one of Toronto's most coveted communities.

105 Dunvegan Road, Toronto

474 Russell Hill Road, Toronto
$17,200,000
5 Beds ⋅ 7 Baths ⋅ C13732176 MLS
An Exceptional Custom Residence On Prestigious Russell Hill Road, In The Heart Of Forest Hill Village. Surrounded By Distinguished Homes And Steps From The Village's Shops, Cafés, Restaurants, Parks, Transit And Renowned Private And Public Schools, This Is A Rare Opportunity To Enjoy One Of Toronto's Most Established Residential Settings. Only Four Years Old And Offering Over 7,500 Sq. Ft. Of Living Space, The Home Pairs A Timeless Limestone Exterior And Slate Roof With A Warm, Contemporary Interior. An Elevator Provides Convenient Access To Every Level. Twelve-Foot Ceilings On The Main And Upper Floors, Soaring Black-Framed Windows And A Serene Neutral Palette Create A Wonderful Sense Of Light And Space. The Generous Kitchen Features Integrated Appliances, Sleek White Oak Cabinetry, A Large Centre Island And Separate Servery, Opening To The Family Room With Fireplace. The Main Level Also Offers A Gracious Living Room With Gas Fireplace And An Elegant Formal Dining Room Enhanced By Its Own Wine Cellar. Book-Matched Italian Porcelain, Solid White Oak Floors And A Floating White Oak Staircase With Glass Railings Add Quiet Sophistication Throughout. The Primary Suite Features A Spacious Walk-In Closet And A Beautifully Appointed Ensuite With Freestanding Tub, Double Vanity And Glass-Enclosed Shower. Two Separate Laundry Rooms, Conveniently Located On The Upper And Lower Levels, Support Effortless Family Living. The Heated Lower Level Features A Gym, Recreation Room With Built-In Bar, Second Wine Cellar And Private Housekeeper Suite. Complete With A Crestron Smart-Home System, Sony Audio With Bosch Speakers Throughout, Heated Driveway And Landscaped Backyard-A Thoughtfully Designed Modern Home In A Coveted Forest Hill Location.

474 Russell Hill Road, Toronto

40 Thelma Avenue, Toronto
$4,888,000
4 Beds ⋅ 6 Baths ⋅ C13713204 MLS
Welcome to 40 Thelma Avenue, a masterfully designed four-level home in the heart of Forest Hill Village. Just steps from the neighbourhood's beloved shops, cafes, and restaurants, and moments from prestigious private schools including Upper Canada College and The Bishop Strachan School, this residence offers an exceptional blend of luxury, location, and lifestyle. Designed by renowned architect Richard Wengle and completed in 2023, this custom-built home spans over 4,500 square feet of beautifully curated living space. Exquisite custom cabinetry and millwork elevate every room, while a fully integrated smart home system provides seamless control of lighting, audio, TVs, window coverings, climate, and security. Generous ceiling heights and floor-to-ceiling windows on every level flood the home with natural light, while built-in surround sound enhances the living experience throughout. Outside, a heated driveway and heated rear patio provide year-round comfort and convenience, complemented by discreet security bollards for added peace of mind. The stunning kitchen is designed for both everyday living and entertaining, complemented by a temperature-controlled wine cabinet ideal for collectors. The second floor features two spacious bedrooms, each with an ensuite, plus a versatile den or play area with its own ensuite that can easily be converted into a fourth bedroom. A dedicated laundry room adds convenience. Occupying the entire top floor, the primary suite is a luxurious private sanctuary featuring a spacious bedroom with walkout balcony, oversized glass-enclosed shower, separate soaking tub, double vanity, custom makeup station, private office, and dedicated wellness space. With timeless architecture, exceptional finishes, intelligent design, and an unparalleled location, 40 Thelma Avenue is a rare opportunity to own an extraordinary home in one of Toronto's most prestigious and walkable neighbourhoods.

40 Thelma Avenue, Toronto

84 Old Forest Hill Road, Toronto
$14,880,000
6 Beds ⋅ 8 Baths ⋅ C13693884 MLS
A modern masterpiece of understated grandeur, the award-winning 84 Old Forest Hill Rd estate is a triumph of monumental architecture and elegance, capturing the prestigious Society of British International Interior Design Award. Spanning over 10,500 SF of crafted living space by visionary designer Omid Taba of OE Design, this custom residence commands an impressive 60-foot frontage with a circular driveway in Toronto's most exclusive enclave. Defined by a Show-Stopping Spiral Staircase, curved architectural transitions and rounded doorways, and soaring 23-ft windows, the sophisticated interior introduces a dramatic sense of scale while bathing the principal spaces in natural light. Tailored for elite hosting, the main level features a limestone fireplace, stylish dining, and a chef's kitchen with Miele appliances, custom cabinetry, leathered marble, butler's pantry and a family room with a hidden bar and speakeasy lounge. An elevator connects every floor, allowing the home to function as a refined family environment that instantly transforms for high-end entertaining. The subterranean wellness ecosystem features a serene indoor pool, custom porcelain spa, dry sauna and gym, built-in wet bar and wine cellar, alongside a state-of-the-art home theatre with a walkout to a private garden and two-level stone patios. Accommodations boast five luxurious bedrooms with dedicated ensuites, anchored by a primary retreat with dual French walk-in wardrobes and a 6-piece sanctuary in Silver White Honed Marble.This smart home integrates whole-home Lutron lighting and audio with premium conveniences, including an EV-ready garage with lift potential, a heated patio, and a heated driveway ready for double-gates. Offering an uncompromised entry into the affluent Forest Hill lifestyle, this elegant estate places top-tier schools, fine dining, and scenic ravines at your doorstep, while keeping Yorkville, Summerhill, and downtown just moments away.

84 Old Forest Hill Road, Toronto

139 Dunvegan Road, Toronto
$17,995,000
6 Beds ⋅ 8 Baths ⋅ C13619112 MLS
A rare commission in Forest Hill's most coveted enclave, this custom-built estate is a masterclass in enduring construction and considered design. Engineered with commercial-grade steel and concrete, the residence has undergone a comprehensive renovation executed with uncompromising attention to detail. The grand foyer's floor-to-ceiling windows and doors flood the space with light, while 12-foot ceilings carry across the main floor, giving scale to principal rooms that are massive by any measure. Multiple walk-outs connect the interior seamlessly to the grounds.The newly renovated kitchen, with its oversized breakfast table and family area, anchors daily life. The formal dining room impresses with intricate crown moulding and walls of windows. A panelled office with fireplace offers a refined work retreat. Upstairs, the primary suite occupies its own private wing with a fireplace, his-and-hers separate ensuites, dual walk-in closets, and views overlooking the pool. A secondary wing offers four oversized bedrooms. A heated circular driveway leads to a 2,000-sq-ft, six-car underground garage with direct access to the lower-level mudroom. The Basement features a professional-grade home gym and theater and 500 bottle wine cellar as well as nanny's quarters with walk-in closet and oversized ensuite. A commercial-grade roof and windows crown the exterior. Outdoors, the recently refinished pool is the estate's centre piece, complemented by a private cabana with two-piece bath and a summer kitchen with built-in BBQ. A 6-person outdoor sauna nestled gently into the garden completes the wellness offering. 139 Dunvegan Road is a legacy address on the best block in Forest Hill, offered for the family ready to make it their own.

139 Dunvegan Road, Toronto

39 Burton Road, Toronto
$10,180,000
5 Beds ⋅ 7 Baths ⋅ C13603996 MLS
39 Burton Road is a landmark residence, gracefully positioned within one of the most exclusive and prestigious enclaves in Forest Hill. Set on a rare 100x170.5 FT lot, this extraordinary estate offers appx 5,982 SF above grade plus partially renovated lower level, presenting a remarkable opportunity for both luxury living and scarcity investment. The expansive 17,000 SF grounds are nestled with a dense canopy of mature trees and exquisitely landscaped gardens that provide a private and sensational oasis. Approved severance allows two premium lots, effectively transforming one prominent residence into two and maximizing land value on one of the finest streets. The current mansion was built for an exceptional luxurious lifestyle that balances sumptuous entertaining and personal relaxation. Indulgence recreational amenities highlight an indoor saltwater pool, a circular hot tub, and a sauna that opens to a serene alfresco retreat for maximum comfort and wellness. Originally a Georgian, the mansion was reimagined by acclaimed architect Stanley Shenkman and interior designer Robert Dirstein into an epic modernist statement, defined by bold geometry, sweeping curves, and flat rooflines. Recognized for its distinctive aesthetic, once-famous black-changing-to-white exterior, the residence became a design icon after the radical redesign. Today, the home reflects a celebrated eclecticism and modernism, starring a teak paneled foyer, retro mid-century details, wall-to-wall windows and extensive use of skylights that bathed interiors with natural light. This excellent location is also known for its extreme proximity to walkable social hubs, places of worship, and top-tier schools such as UCC, BSS, Holy Rosary, St Michael's, Robbins, Bialik, Leo Baeck, Forest Hill CI and more. Rich in architectural significance and cultural character, the legendary residence is a rarity offering in a highly coveted row renowned for its affluent scale, influential prestige, and enduring grandeur.

39 Burton Road, Toronto

204 Richview Avenue, Toronto
$4,080,000
5 Beds ⋅ 4 Baths ⋅ C13545286 MLS
Welcome to elevated Forest Hill living in this fully renovated 4+1 bedroom, 4 bathroom home, where timeless style, thoughtful design, and exceptional behind-the-scenes quality come together beautifully. Completely gutted and renovated in 2018, this home was designed for modern family living with premium finishes, smart technology, and everyday comfort in mind. Inside, you'll find elegant principal rooms and a warm, inviting layout designed for both relaxed family life and effortless entertaining. The chef's kitchen is a true showpiece, featuring a Wolf 48" dual fuel range with charbroiler, custom teppanyaki grill with stainless steel hood, Sub-Zero fridge/freezer, Sub-Zero drink cabinet, Sub-Zero wine fridge, Miele dishwasher, Grohe fixtures, reverse osmosis water system, and water softener. A well-appointed butler kitchen adds even more function for hosting, prep, storage, and keeping the main kitchen looking effortlessly polished.Thoughtful upgrades continue throughout the home, including heated floors in select rooms and bathrooms, Lutron lighting control, triple-pane windows, CCTV, network wiring, 200-amp electrical service, EV-ready connection, Copper front eavestrough/soffit and fascia, and a 22KW Generac backup generator. With spacious bedrooms, beautifully renovated bathrooms, double laundry, and a finished lower level with an additional bedroom, every detail has been carefully considered. Outside, enjoy a private drive with manual bollards, garage and spacious backyard, raccoon-proof vents, and even a dog washing station - because muddy paws deserve their own spa moment too. Set in prestigious Forest Hill, surrounded by beautiful homes, top schools, parks, shops, restaurants, and transit, this is a rare move-in-ready opportunity in one of Toronto's most coveted neighbourhoods. See attached for a full list of features & upgrades.

204 Richview Avenue, Toronto

470 Russell Hill Road, Toronto
$6,495,000
6 Beds ⋅ 5 Baths ⋅ C13426984 MLS
Welcome home to 470 Russell Hill Rd. Located On One Of The Most Prestigious Streets In Forest Hill. This Well-Appointed Classic Georgian Home Is Perfect For Entertaining. With Grand Living, Dining & Family Rooms, This Home is Turn-Key & Move In Ready. Private Garden That Feels completely secluded. Modern Kitchen With Top Of The Line Wolf & Sub Zero Appliances. Heated Drive In The Front with electric car charger, And Double Car Garage At Rear with additional driveway space. The detached two-car garage is accessible from Old Forest Hill Rd. 5 Large Bedrooms, 2 Laundries, Top Of The Line Finishes Throughout. Steps To Upper Canada College & Bishop Strachan School, Canada's Top Private Schools. A Short walk to the Forest Hill Village shops & restaurants. This home has been lovingly maintained, and is ready for you to move right in. Property is currently tenanted until August 31, 2026 at $22,500.00 Per Month. The Tenants are willing to extend for an additional year if the Buyer agrees until August 31, 2027.

470 Russell Hill Road, Toronto

5 Dewbourne Avenue, Toronto
$13,950,000
6 Beds ⋅ 6 Baths ⋅ C13142424 MLS
Welcome to 5 Dewbourne Avenue - a Lorne Rose - designed architectural masterpiece completed in 2023, nestled in the prestigious enclave of Forest Hill. This bespoke contemporary estate on 63 ft south lot offers a seamless fusion of modern luxury and timeless sophistication, encompassing over 7800 sqft. of impeccably crafted living space with 10-15ft ceiling heights throughout. Featuring 5+1 BR with custom Poliform closets and 6 opulent bathrooms, the home is complete with a private home theatre, fitness studio, & mudroom, all thoughtfully distributed across four spectacular levels & accessible by private elevator. A heated driveway with electric gate accommodates up to 6 vehicles, in addition to a heated 2-car garage.Floor-to-ceiling glass walls invite nature indoors, creating a seamless blend of light, space, & natural beauty. At the heart of the home lies a state-of-the-art Scavolini kitchen imported from Italy, paired with Gaggenau appliances & elegant Laminam porcelain surfaces-a chef's dream blending form & function. Thoughtfully designed interiors feature Rimadesio sliding glass doors, expansive windows, creating bright, airy spaces that flow effortlessly.Step outside to your own private resort: a professionally landscaped backyard oasis with a heated saltwater pool and spa, a covered terrace with Bromic radiant heating, integrated surround sound, and a fully equipped Urban Bonfire, outdoor kitchen and bar-ideal for entertaining or quiet relaxation.Additional highlights include fully integrated Control4 smart system, Radiant in-floor heating on the main and lower levels, heated bathroom floors, Hunter Douglas automated shades, 2 Lennox HVAC systems, Generac generator, & an automated irrigation system.Located just steps from Forest Hill Village & some of Toronto's top private and public schools, including UCC, BSS, & Forest Hill Collegiate, this residence is a rare offering in one of the city's most coveted neighbourhoods.

5 Dewbourne Avenue, Toronto

42 Glenayr Road, Toronto
$4,500,000
5 Beds ⋅ 4 Baths ⋅ C13081206 MLS
An extraordinary opportunity to create a landmark residence in one of Toronto's most prestigious neighbourhoods. Set on a prime, highly coveted west-facing lot, this offering sits on the iconic curved red cobblestone section of Glenayr Road - one of Forest Hill's most distinguished and sought-after streets, just moments from Forest Hill Village. The property boasts a rare and generous land parcel, beginning at 40 ft of frontage and widening to approximately 71 ft, with a depth of 172.6 ft and a total area of approximately 8,600+ sq ft, offering exceptional scale and presence. This unique offering comes with Committee of Adjustment approvals for a striking custom-designed three-storey estate by renowned architect Richard Wengle, envisioned at approximately 6,000+ sq ft above grade and over 10,000 sq ft of total living space. The proposed design showcases expansive principal rooms, an integral garage, and a resort-inspired outdoor setting complete with pool, cabana, and curated entertaining spaces. Full architectural plans have been thoughtfully prepared, presenting a rare opportunity to bring a sophisticated vision to life with much of the groundwork already in place. The existing residence has been extensively prepared, offering flexibility for those who wish to proceed with the approved new build or explore a tailored transformation of the current structure. For the discerning builder, investor, or end-user, this is a rare chance to secure a premier property and step into an advanced-stage luxury project in an exceptional location. Property and improvements being sold in as-is, where-is condition. The current home has been demo'd back to the brick and is not liveable.

42 Glenayr Road, Toronto

11 Dewbourne Avenue, Toronto
$5,660,000
5 Beds ⋅ 8 Baths ⋅ C13000962 MLS
**Captivating residence/exquisite estate--Classic Elegance--This magical home has been meticulously cared for, remodeled/upgraded, and maintained by its owners--Classic/charm centre hall design offers spaces of refined and elegant comfort--5,511 sq.ft (3 storey) + 1,007 sq.ft (basement)---total 6,518 sq.ft of luxurious--where every impeccable detail has been carefully crafted and preserved. The grand principal rooms are designed for both elegance and comfort, a formal dining room and a living room with marble mantle fireplace. The functional gourmet kitchen is equipped with built-in appliances (Sub-Zero/Wolf brand), custom cabinetry & granite countertops. The adjoining family/sun room features a HEATED LIMESTONE floor and 16 ft high glass ceilings, allowing natural sunlight and French doors walkout to south exposure private garden. Upstairs, the hand-carved antique pine paneled library elaborates a story of this home, perfect for versatile use such as 2nd family room and adjoining a mahogany paneled office for a private space. The primary bedroom offers a dressing room, 6 pcs ensuite. The family gym on 2nd floor offers a 18 ft high ceiling with skylights for convenience and comfort. On 3rd floor, the additional all 3 bedrooms provide their own private ensuites, closets, and feature a 3rd furnace and 2nd laundry area. The lower level offers an entertainment room, music and studio room, wine cellar with climate control. Outside, the landscaped lush garden features cheerful trees for privacy and relaxation, and a heated driveway for 5 vehicles, and 2 cars in garage. Surrounded by top ranking private and public schools-UCC/BSS/Havergal College/Forest Hill Junior & Senior PS & Forest Hill CI. A short walk brings you to Forest Hill Village with shops, restaurants & cafes, minutes to sunway station, hwys & more!

11 Dewbourne Avenue, Toronto

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