Ravine Whitby Homes For Sale

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House for sale: 64 CLOSSON DRIVE, Whitby

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$1,900,000

64 Closson Drive, Whitby (Rural Whitby), Ontario L1P 0M9

5 beds
4 baths
43 days

Rossland Rd W & Des Newman Blvd Spectacular and rare home situated on a premium ravine lot overlooking a tranquil pond setting, 64 Closson Drive is a study in refined living and modernism. Impeccably upgraded, a 5-bedroom, 4-bathroom residence where designer finishes meets the serenity of nature.

House for sale: 1048 MCQUAY BOULEVARD, Whitby

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$1,449,000

1048 Mcquay Boulevard, Whitby (Lynde Creek), Ontario L1P 1R8

5 beds
5 baths
11 days

Rossland & Mcquay Ravine lot offers privacy and resort-style living: Beautiful 5 Bedrooms 5 Baths Monarch Built Detached home with rare to find features like *Backing Onto Greenbelt, W/O Bsmt*, *Main Floor Master Bedroom Boasts W/O To Deck, Updated 4Pc Ensuite W/Quartz Counters, W/I Closet**Soaring

Listed by: Benny Singh ,Right At Home Realty (905) 665-2500
House for sale: 82 CLOSSON DRIVE, Whitby

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$1,179,000

82 Closson Drive, Whitby (Lynde Creek), Ontario L1N 9Y6

4 beds
3 baths
27 days

Rossland Rd W/Des Newman Blvd Luxurious 4-Bedroom Home on Private Ravine Lot Modern Elegance Awaits! ** Step into **82 Closson Dr, Whibty**, where luxury meets tranquility. This stunning **4-bedroom, 3.5-bathroom home** sits on a serene ravine lot, offering privacy and breathtaking views. Boasting

House for sale: 133 AUCKLAND DRIVE, Whitby

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$1,300,000

133 Auckland Drive, Whitby (Rural Whitby), Ontario L1P 0H4

5 beds
4 baths
38 days

Coronation Rd & Rossland Rd W Welcome to **133 Auckland Drive, Whitby** - a beautifully upgraded home that blends modern elegance with everyday comfort. Step inside to a bright and spacious open-concept layout featuring stunning wide-plank flooring, pot lights throughout, and a chef-inspired

Ruena Corpuz Reotutar,Re/max Metropolis Realty
Listed by: Ruena Corpuz Reotutar ,Re/max Metropolis Realty (905) 824-0788
House for sale: 6540 CORONATION ROAD, Whitby

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$1

6540 Coronation Road, Whitby (Rural Whitby), Ontario L0B 1C0

5 beds
8 baths
78 days

Coronation Road/ Columbus Road Brand New Custom-Built Luxury Estate On Premium 2.25-Acre East-Facing Lot !! Approx. 8,500 Sq Ft Of Finished Living Space. Featuring 4+1 Bedrooms And 8 Bathrooms With Exceptional Craftsmanship And High-End Finishes Throughout. Main Floor Offers 12-Ft Ceilings

Listed by: Harmeet Neelon ,Re/max Gold Realty Inc. (905) 672-0003
House for sale: 106 BARKERVILLE DRIVE, Whitby

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$1,119,900

106 Barkerville Drive, Whitby (Rural Whitby), Ontario L1P 0L8

5 beds
3 baths
77 days

Cross Streets: Rossland And 412. ** Directions: E. Less than 5 Year Old*** Still under Tarion's Warranty ** Fabulous 4 Bedroom Detached House***Loft On 2nd Floor Can Be Used As Office or extra bedroom *** Backing On Ravine With Deep Back Yard *** Huge And Bright Great Room *** Spacious Master

Listed by: Luke Zhou ,Homelife Landmark Realty Inc. (905) 305-1600
House for sale: 15 SHEPHERD ROAD, Whitby

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$2,647,000

15 Shepherd Road, Whitby (Rural Whitby), Ontario L1M 1G8

7 beds
7 baths
8 days

Coronation and Highway 7 Macedonian Village Opportunity - Bungalow Living on a Premium Conservation Lot, this custom-built bungalow offers exceptional space, privacy, and long-term versatility on a premium 102.48 ft x 352.51 ft lot backing onto the natural beauty of Heber Down Conservation

Eldon King,Re/max Hallmark First Group Realty Ltd.
Listed by: Eldon King ,Re/max Hallmark First Group Realty Ltd. (905) 668-3800
Row / Townhouse for sale: 1 RADIANCE WAY, Whitby

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$719,500

1 Radiance Way, Whitby (Rural Whitby), Ontario L1P 0S2

3 beds
2 baths
9 days

Taunton Rd W & Coronation Rd Welcome home to The Whitby Meadows Community. This brand new never lived in end unit townhome in highly sought-after North Whitby. Wide streets connecting you to parks, beautiful Ravine trails and the $30 Million West Whitby Public School and Licensed Childcare

Listed by: Mitchinson Small ,Re/max Metropolis Realty (905) 824-0788
House for sale: 106 BARKERVILLE DRIVE, Whitby

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$1,079,000

106 Barkerville Drive, Whitby (Rural Whitby), Ontario L1P 0L8

5 beds
3 baths
Today

Cross Streets: Rossland And 412. ** Directions: E. Less than 5 Year Old*** Still under Tarion's Warranty ** Fabulous 4 Bedroom Detached House***Loft On 2nd Floor Can Be Used As Office or extra bedroom *** Backing On Ravine With Deep Back Yard *** Huge And Bright Great Room *** Spacious Master

Listed by: Luke Zhou ,Homelife Landmark Realty Inc. (905) 305-1600
House for sale: 8 ST PHILIP COURT, Whitby

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$1,574,000

8 St Philip Court, Whitby (Williamsburg), Ontario L1P 0A5

7 beds
6 baths
114 days

Taunton & Baycliffe Absolutely Stunning Detached Home Situated In The Heart Of The Prestigious Williamsburg Neighbourhood, Boasting Over 3,000 Sq Ft Of Luxurious Living Space On A Rare And Serene Ravine Lot With A Spectacular Inground Pool, Double Waterfall Features, And Breathtaking Western

Listed by: Ram Krishnamurthy ,Re/max Rouge River Realty Ltd. (416) 427-5555
House for sale: 30 HANOVER COURT, Whitby

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$1,999,000

30 Hanover Court, Whitby (Lynde Creek), Ontario L1N 7J2

5 beds
5 baths
10 days

Cross Streets: Bonacord & Cochrane. ** Directions: Bonacord to Hanover Crt. Welcome to 30 Hanover Court, Whitby-a custom-built bungaloft nestled in the highly sought-after Lynde Creek ravine community. Set on a premium ravine lot, this exceptional home offers the perfect blend of elegance,

Listed by: Kendra Foley ,Re/max Rouge River Realty Ltd. (905) 623-6000
House for sale: 16 BEAVERDAMS DRIVE, Whitby

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$1,699,900

16 Beaverdams Drive, Whitby (Rural Whitby), Ontario L1P 0C4

5 beds
5 baths
10 days

Cross Streets: Country Lane and Taunton Rd. ** Directions: From Taunton Rd north on Country Lane, East on Micklefield Ave to Beaverdams Dr., West on Beaver Dams Dr. Backing onto protected ravine green space in Whitby's prestigious Country Lane community, this magnificent Beechfield model delivers

Carmine Cupelli,Re/max Hallmark First Group Realty Ltd.
Listed by: Carmine Cupelli ,Re/max Hallmark First Group Realty Ltd. (905) 718-0173
Row / Townhouse for sale: 78 BONELLO CRESCENT, Whitby

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$799,000

78 Bonello Crescent, Whitby (Taunton North), Ontario L1R 3N7

3 beds
4 baths
20 days

Cross Streets: Anderson St. / Taunton Rd E. ** Directions: Intersection of Bonello Cres/Toscana Dr. Welcome to this beautifully maintained end-unit townhome that shows like a model home, ideally situated in a sought-after North Taunton neighbourhood and backing onto a tranquil ravine setting.

William Yao,Homelife Landmark Realty Inc.
Listed by: William Yao ,Homelife Landmark Realty Inc. (416) 606-2738
House for sale: 27 KENNETT DRIVE, Whitby

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$1,539,900

27 Kennett Drive, Whitby (Lynde Creek), Ontario L1P 1L5

5 beds
5 baths
14 days

Cross Streets: McQuay Blvd and Kennett. ** Directions: McQuay to Kennett. Stately 5 bedroom, three-story 4571sq ft (finished area) brick home backing to ravine on an extra deep private matured treed lot (49.26' x 212.72') with finished bsmt, inground pool and fabulous 3rd level in-law suite.

Row / Townhouse for sale: 16 EDISON WAY, Whitby

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$799,900

16 Edison Way, Whitby (Taunton North), Ontario L1R 0M3

3 beds
4 baths
26 days

Cross Streets: Thickson Rd / Taunton Rd E. ** Directions: Thickson Rd N / Edison Way. Stunning all-brick end-unit townhome backing onto a private ravine in one of Whitby's most sought-after family-friendly communities. This bright 2-storey home offers exceptional natural light and added privacy,

Row / Townhouse for sale: 14 - 1640 NICHOL AVENUE S, Whitby

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$599,000

14 - 1640 Nichol Avenue S, Whitby (Blue Grass Meadows), Ontario L1N 8P6

3 beds
2 baths
10 days

Springwood/Thickson Welcome to 1460 Nichol #14 this end unit townhome is spacious and finished on all levels. Approx 1600 Sqft. This 3 bdrm - 2 bath all brick sits on a large corner lot, with a spacious back and side yard onto the Ravine. Single car garage with visitor parking beside your exclusive

Listed by: Eileen Dodd ,Royal Heritage Realty Ltd. (289) 404-2541
House for sale: 7 INVERLYNN WAY, Whitby

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$1,589,999

7 Inverlynn Way, Whitby (Lynde Creek), Ontario L1N 2S6

5 beds
4 baths
11 days

Cross Streets: Raglan St & Dundas St W. ** Directions: North of Dundas St W, off of Raglan & Giffard St. Presenting the McGillivray on lot #4. Turn Key - Move-in ready! Award Winning builder! MODEL HOME - Loaded with upgrades... 2,701sqft + fully finished basement with coffee bar, sink, beverage

House for sale: 12 LABRIOLA COURT, Whitby

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$1,575,000

12 Labriola Court, Whitby (Taunton North), Ontario L1R 0N1

4 beds
4 baths
38 days

Cross Streets: Thickson Rd & Taunton Rd E. ** Directions: East of Thickson, north of Taunton. Discover your dream home, nestled at the end of a tree-lined cul-de-sac on a rare premium lot that exudes privacy and warmth. Situated in a family-friendly neighborhood, this custom single-family home

Listed by: Philip Ming-tim Leung ,Right At Home Realty (416) 391-3232
470 LYNDEBROOK ROAD, Whitby
Vacant land

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$1,199,999

470 Lyndebrook Road, Whitby (Rural Whitby), Ontario L1P 2A3

33 days

Country Lane and Taunton A truly rare offering to build your dream estate on approximately 4.5 breathtaking acres backing directly onto Heber Down Conservation Area. With towering trees and a breathtaking woodland setting as your backdrop, this incredible property delivers unmatched privacy,

Listed by: Hend Ali ,Century 21 Percy Fulton Ltd. (905) 903-2905
House for sale: 28 CONARTY CRESCENT, Whitby

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$899,000

28 Conarty Crescent, Whitby (Rural Whitby), Ontario L1P 0L4

3 beds
3 baths
23 days

Cochrane St & Taunton Rd W Welcome to this beautifully maintained family home thoughtfully designed living space, plus an additional basement with sep entrance for your personal touches. A grand double-door entry welcomes you into a bright, open-concept layout filled with natural light from

House for sale: 18 BUGELLI DRIVE, Whitby

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$1,250,000

18 Bugelli Drive, Whitby (Taunton North), Ontario L1R 3B7

5 beds
4 baths
10 days

Baldwin / Taunton Welcome to this stunning fully renovated Tormina-built home, ideally located in one of North Whitby's most sought-after neighbourhoods, just minutes from Highway 407, shopping, transit, parks, and top-rated schools. Showcasing exceptional craftsmanship and modern finishes

Lisa Fayle,Re/max Rouge River Realty Ltd.
Listed by: Lisa Fayle ,Re/max Rouge River Realty Ltd. (905) 668-1800
House for sale: 7475 GARRARD ROAD, Whitby

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$2,349,000

7475 Garrard Road, Whitby (Rural Whitby), Ontario L1M 2B6

5 beds
5 baths
14 days

Cross Streets: Columbus / Garrard. ** Directions: -. Privately set on approximately 10 rolling acres just minutes from Brooklin, this custom-built estate offers a rare balance of seclusion, natural beauty, and convenience. Surrounded by mature woods, streams and sweeping southern views, the

Listed by: Kevin Cahill ,Re/max Hallmark First Group Realty Ltd. (905) 683-5000
House for sale: 5 INVERLYNN WAY, Whitby

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$1,299,900

5 Inverlynn Way, Whitby (Lynde Creek), Ontario L1N 2S6

5 beds
3 baths
2 days

Cross Streets: Raglan St & Dundas St W. ** Directions: North of Dundas St W, off of Raglan & Giffard St. Presenting the McGillivray on lot #3. Award Winning builder! 2,701sqft. Downtown Whitby - exclusive gated community. Located within a great neighbourhood and school district on Lynde Creek.

House for sale: 10 THISTLEDOWN CRESCENT, Whitby

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$998,000

10 Thistledown Crescent, Whitby (Taunton North), Ontario L1R 3P2

6 beds
4 baths
36 days

Cross Streets: Garrard / Taunton. ** Directions: Taunton Rd & Garrard Rd. Functional Detached house in a quiet community. Upgraded home with finished basement, offering an exquisite blend of elegance and comfort. Enjoy the grandeur and sophistication of high cathedral ceilings complemented

Ravine Whitby: practical guidance for buyers, investors, and cottage‑style seekers

If you're exploring ravine Whitby properties, you're likely balancing privacy and green views with questions about regulations, insurance, and long‑term value. Whitby sits within Durham Region and benefits from commuter convenience, established neighbourhoods, and protected natural corridors such as Lynde Creek, Pringle Creek, and the Heber Down and Lynde Shores conservation areas. This mix creates genuine lifestyle appeal—but it also introduces conservation authority oversight, top‑of‑bank setbacks, and construction limits that every purchaser should understand. Market data from resources like KeyHomes.ca suggests ravine lot premiums are real, but condition, slope stability, and access are just as important as the view.

Ravine Whitby: zoning, conservation authority rules, and building reality

In Whitby, ravines, valleys, and floodplains are regulated primarily by the Central Lake Ontario Conservation Authority (CLOCA). If a property touches a valleyland, wetland, or watercourse, expect CLOCA permit requirements for most site alterations, including additions, decks, pools, retaining walls, walkouts, and tree removals. Top‑of‑bank and erosion hazard lines are property‑specific; setbacks are not one‑size‑fits‑all and are established through technical review (often including a geomorphology or geotechnical report). Do not assume a neighbour's approval transfers to your lot.

Municipally, Whitby maintains multiple zoning by‑laws across its urban and rural areas (notably By‑law 1784 and By‑law 2585, with site‑specific exceptions). The Town has been moving toward a comprehensive update—buyers should confirm the current zoning for the specific parcel, permitted uses (including additional residential units), and any site plan control. Private tree protection by‑laws and site alteration by‑laws may also apply; removing mature trees along a ravine edge often requires permits.

Buyer takeaway: before waiving conditions, obtain written confirmation on the location of the stable top‑of‑bank, whether the lot is in a regulated area, and what approvals are needed for your intended use. Budget time for CLOCA and municipal reviews.

Neighbourhoods and corridors: Inverlynn, Lynde Creek, and Lakeridge Road Whitby

The Inverlynn Whitby area is known for mature estate lots, heritage character, and proximity to Lynde Creek's wooded valley—high in charm, but with heightened sensitivity to conservation rules. Along the Lakeridge Road Whitby corridor, some pockets back onto green space or conservation lands near Heber Down; these locations trade convenience to Highway 401/407/412 (now toll‑free) with potential traffic exposure depending on siting. Elsewhere, parts of Pringle Creek, Williamsburg, and Whitby Shores back onto protected corridors or stormwater‑fed greenspaces that can feel “ravine‑like” even if they're engineered valleys.

Walkout basements are common on sloping lots, which can add daylight and rental potential. However, check that walkouts, decks, and hardscaping were permitted and inspected—especially where retaining walls or drainage features stabilize grades.

Resale potential and product types on a ravine lot

Ravine lots typically command a premium for privacy and view. The strongest resale candidates combine gentle slopes, usable yard space, sufficient lot width for side access, and minimal exposure to road or rail noise. South‑ or west‑facing rears capture light over the treeline, while deep, narrow lots may feel boxed‑in if the slope is steep. Townhomes backing onto greenbelts can capture much of the appeal at a lower price point; see examples of Whitby townhouses that back onto protected green space to understand how these sell relative to interior units.

Buyers interested in condo living without sacrificing greenery may look at Whitby apartments with treed ravine views, balancing maintenance ease with walkability to trails. For multi‑generational households, Whitby homes with elevators can future‑proof mobility in multi‑storey designs where grades enable side or rear entries. Within older pockets near downtown, you can also research the Coronation neighbourhood listings to compare lot size, canopy coverage, and resale velocity across tree‑lined streets.

Supply for compact footprints is tighter; tracking 2‑bedroom homes in Whitby can reveal how downsizers and first‑timers bid up low‑maintenance options near parks and trails.

Lifestyle appeal: daily advantages and small trade‑offs

Access to woodland trails, birdsong, and natural privacy are everyday benefits. In Whitby, residents frequently mention Lynde Shores and Heber Down for quick hikes and wildlife viewing. The Whitby GO Station and Highway 401 keep downtown Toronto reachable for commuters, and the 412/407 connectors improve east‑west mobility. The main trade‑offs: yard use can be limited by slope; mosquitos can be seasonal; and fallen leaves and tree roots demand ongoing maintenance. Expect to budget for tree care, gutter cleaning, and possibly slope monitoring where retaining structures are present.

Seasonal market rhythms and showing strategy

Durham Region's freehold market is most active in spring and early fall. Ravine settings show differently by season: in spring, snowmelt reveals drainage paths and high water tables; in lush summer foliage, privacy peaks but ground conditions are harder to assess; in winter, slopes and steps can be icy, obscuring grading and erosion signs. If you can, view a property twice—once in wet weather and once in dry. Bring footwear to walk the yard's rear edge (where safe) and note runoff, soft soils, or evidence of bank movement.

Investor lens: rents, ARUs, and short‑term rental rules

Tenants value quiet treed outlooks and proximity to transit. Ontario now permits additional residential units more broadly, but local rules still govern parking, egress, servicing, and lot coverage. Walkout basements can be excellent candidates if legally created; review examples of legal basement suites in Whitby to benchmark rents and finishes. Near the core, bungalows with deep lots sometimes mirror the appeal seen in Toronto ravine bungalows, though price points and tenant profiles differ.

Short‑term rental bylaws vary by municipality and can change. In Durham Region, licensing, taxation, and primary‑residence restrictions may apply, and enforcement is increasing. Confirm Whitby's current STR rules with the Town before underwriting nightly rates; do not assume a walkout to a ravine deck can be monetized through STR without approvals.

Financing, insurance, and inspections: reduce surprises

Lenders and insurers scrutinize properties within floodplains or erosion hazard limits. Overland flood endorsements are available in Canada, but coverage can be limited or more expensive for high‑risk locations near watercourses. Some insurers may decline coverage if the dwelling sits too close to a hazard zone. Secure an insurance quote during your conditional period and disclose the property's proximity to a ravine.

On due diligence, order a current survey or reference plan if the top‑of‑bank and easements are unclear, and consider a geotechnical assessment where structures sit near slopes. Ask for permits and final inspections for decks, walkouts, retaining walls, pools, and drainage tiles. In rural pockets north of Taunton and around Brooklin, some ravine‑adjacent homes rely on private wells and septic systems; budget for water potability tests, flow rate assessments, and septic inspections (including tank age and leaching bed location) before firming up. Example: a purchaser planning an accessory suite on a rural ravine lot may need to confirm whether the existing septic can handle added load and whether CLOCA will allow any expansion.

Regional comparisons and price discovery

Ravine markets behave differently across the GTA and beyond. Comparing Whitby to Newmarket ravine options can highlight how York Region's price points and lot widths diverge. West of the city, reviewing ravine inventory in Halton Hills helps calibrate premiums for escarpment‑adjacent settings. Even outside Ontario, places like Mill Creek Ravine in Edmonton show how trail systems and conservation corridors influence values and rental demand. Cross‑checking these markets on KeyHomes.ca is useful for understanding appreciation patterns, days on market, and how sharply buyers discount steep or heavily regulated lots versus gentle, usable ones.

Practical add‑ons and renovation planning

Before budgeting for a pool, accessory building, or large deck, verify whether the lot lies within a regulated area and whether site plan or CLOCA approvals are needed; you may also need a grading plan and engineering sign‑off. New hardscaping near slopes can alter runoff, so permeable surfaces and swales are often required. If the property has a walkout, ask for the grading certificate and any underpinning documentation. For townhouse or condo buyers seeking greenery without the maintenance, a unit with a treed exposure can deliver most of the feel at lower risk—screen available apartment listings in Whitby with ravine‑style views to see how premiums track by floor height and exposure.

As you research, leverage data and neighbourhood context. KeyHomes.ca is widely used by Ontario buyers to explore listings, map conservation areas, and connect with licensed professionals who understand CLOCA processes and Whitby's zoning nuances. With the right due diligence—and an appreciation for what can and cannot be altered on a ravine lot—you can align the romance of a treed outlook with solid, province‑aware investment decisions.