Ravine-Whitby Homes For Sale

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House for sale: 54 BLENHEIM CIRCLE, Whitby

49 photos

$1,579,000

54 Blenheim Circle, Whitby (Rural Whitby), Ontario L1P 0E2

6 beds
5 baths
9 days

Country Lane North of Taunton ONE OF A KIND ABSOLUTE SHOW STOPPER. Don't miss out. Heathwood's flagship 4509 square foot Beech field model in Country Lane's ONLY private enclave. School bus directly to the street, and ZERO through traffic. Designed for comfort, this bespoke home is an entertainer's

Listed by: Zakir Hussain ,Century 21 Innovative Realty Inc. (416) 298-8383
House for sale: 133 AUCKLAND DRIVE, Whitby

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$1,449,000

133 Auckland Drive, Whitby (Rural Whitby), Ontario L1P 0J4

6 beds
4 baths
26 days

Soltys & Auckland Welcome To 133 Auckland Drive, An Exquisite Arista-Built Residence Offering Over 3000 Sq Ft Of Refined Living In The Prestigious Williamsburg Neighbourhood Of Whitby. Completed In December 2020, This Elegant 4-Year-New Home Showcases Exceptional Craftsmanship, Modern Design,

Listed by: Vidhi Parikh ,Realtris Inc. (866) 511-7171
House for sale: 36 BLENHEIM CIRCLE, Whitby

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$1,895,000

36 Blenheim Circle, Whitby (Rural Whitby), Ontario L1P 0E3

5 beds
4 baths
35 days

Cross Streets: Taunton and country lane. ** Directions: Turn into country lane from taunton and make a left onto Blenheim circle. Welcome to 36 Blenheim Circle-an exceptional 4+1 bed, 4-bath full-brick home offering over 4,700 sq ft of beautifully finished living space. Set on a rare ravine

Listed by: James Tasca ,Ici Source Real Asset Services Inc. (800) 253-1787
House for sale: 47 FRUITFUL CRESCENT, Whitby

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$1,499,990

47 Fruitful Crescent, Whitby (Rural Whitby), Ontario L1P 0N3

5 beds
4 baths
131 days

Rossland Rd/ HWY 412 Welcome To This Exceptional 5-Bedroom, 4-Bathroom Detached Home Nestled In A Family-Friendly Neighbourhood, Backing Onto A Scenic Ravine With No Neighbours On One Side. This Thoughtfully Designed Home Combines Natural Beauty, Functionality, And Luxury, Offering A Peaceful

Mairaj Ahmed,Re/max Hallmark First Group Realty Ltd.
Listed by: Mairaj Ahmed ,Re/max Hallmark First Group Realty Ltd. (833) 819-1548
House for sale: 15 SHEPHERD ROAD, Whitby

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$2,800,000

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

7 beds
7 baths
21 days

Coronation and Highway 7 Discover winter luxury at 15 Shepherd Road, a custom luxury bungalow set on a premium 102.48 ft x 352.51 ft lot backing onto the peaceful winter landscape of Heber Down Conservation Area. This beautifully updated home features four main-floor bedrooms, each with its

Eldon King,Re/max Hallmark First Group Realty Ltd.
Listed by: Eldon King ,Re/max Hallmark First Group Realty Ltd. (905) 668-3800
House for sale: 50 BLUEBELL CRESCENT, Whitby

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$1,275,000

50 Bluebell Crescent, Whitby (Lynde Creek), Ontario L1P 1K9

7 beds
5 baths
76 days

Cross Streets: Dundas St. W & Fothergill Ct. ** Directions: 0. Welcome to 50 Bluebell Crescent, a spacious family home situated on a quiet cul-de-sac in an upscale neighbourhood of beautifully maintained homes in the highly desirable West Lynde community. This well-maintained property features

House for sale: 3 COVINGTON DRIVE, Whitby

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$1,779,000

3 Covington Drive, Whitby (Brooklin), Ontario L1M 2K4

4 beds
5 baths
41 days

Cross Streets: Thickson and Winchester. ** Directions: Thickson North to Winchester. Winchester East to Cachet, Cachet North to Helston. East on Helston to Covington. Set on one of Brooklin's most coveted streets, this exceptional Southampton Model Queensgate home offers over 4,000 sq. ft.

House for sale: LOT 11 INVERLYNN WAY, Whitby

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$1,699,999

Lot 11 Inverlynn Way, Whitby (Lynde Creek), Ontario L1N 2S6

3 beds
3 baths
96 days

Cross Streets: Raglan St & Dundas St W. ** Directions: North of Dundas St W, off of Raglan & Giffard St. Presenting the McGillivray on Lot #11 in Whitby's Exclusive Gated Community! *** Limited-Time Builder Incentive: Enjoy $75,000 in free upgrades from The DeNoble Homes Décor & Design Centre

House for sale: 40 ENDEAVOUR COURT, Whitby

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$2,375,000

40 Endeavour Court, Whitby (Williamsburg), Ontario L1P 0B5

6 beds
5 baths
23 days

Cross Streets: Country Lane and Rossland Rd. ** Directions: Country Lane to Constance Drive, West on Constance Drive, South on Endeavour Court. Welcome to 40 Endeavour Court, a rare offering tucked at the end of a quiet court and bordered by ravine on two sides. This custom 5+1 bedroom, 5 bath

Carmine Frank Cupelli,Re/max Hallmark First Group Realty Ltd.
Listed by: Carmine Frank Cupelli ,Re/max Hallmark First Group Realty Ltd. (905) 668-3800
House for sale: LOT 13 INVERLYNN WAY, Whitby

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$1,850,000

Lot 13 Inverlynn Way, Whitby (Lynde Creek), Ontario L1N 2S6

4 beds
5 baths
108 days

Cross Streets: Raglan St & Dundas St W. ** Directions: North of Dundas St W, off of Raglan & Giffard St. Turn Key - Move-in ready! Award Winning builder! *Elevator* Another Inverlynn Model - THE JALNA! Secure Gated Community...Only 14 Lots on a dead end enclave. This Particular lot has a multimillion

House for sale: LOT 4 INVERLYNN WAY, Whitby

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$1,825,000

Lot 4 Inverlynn Way, Whitby (Lynde Creek), Ontario L1N 2S6

5 beds
4 baths
108 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: 8 ST PHILIP COURT, Whitby

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$1,649,000

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

7 beds
6 baths
86 days

Cross Streets: Taunton & Baycliff. ** Directions: 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,

Row / Townhouse for sale: 60 - 1610 CRAWFORTH STREET, Whitby

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$699,999

60 - 1610 Crawforth Street, Whitby (Blue Grass Meadows), Ontario L1N 9B1

4 beds
3 baths
90 days

Thickson & Dundas Welcome to 1610 Crawforth St Unit 60. A beautifully renovated 4-bedroom, 3-bath condo townhouse offering over 1,200 sq ft of stylish, low-maintenance living in Whitby"s sought-after Blue Grass Meadows community. Enjoy a bright and functional layout featuring a modern kitchen

Row / Townhouse for sale: 4 PARADISE WAY, Whitby

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$839,999

4 Paradise Way, Whitby (Rolling Acres), Ontario L1R 0R7

3 beds
3 baths
9 days

Thickson Rd & Dryden Blvd Style meets everyday comfort in this beautifully updated townhome located in Whitby's highly desired Rolling Acres community. With over 2,000 sq. ft. of finished living space, this home is designed for buyers who want a modern look without lifting a finger. Step inside

House for sale: 165 RIVERS EDGE PLACE, Whitby

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$1,399,900

165 Rivers Edge Place, Whitby (Taunton North), Ontario L1R 0G4

5 beds
4 baths
33 days

Taunton & Thickson Rd Prestigious executive home on a premium treed ravine lot, offering unparalleled privacy and resort-style living. This luxurious 4+1 bedroom home showcases manicured perennial gardens, gated access on both sides, and a serene wooded pond - your own private sanctuary! Step

House for sale: 50 CARNWITH DRIVE W, Whitby

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$2,495,000

50 Carnwith Drive W, Whitby (Brooklin), Ontario L1M 2N1

4 beds
6 baths
42 days

Carnwith Dr West & Montgomery Ave Backing onto a picturesque wooded ravine, this exceptional Fulton Homes "Flatbush" Elevation B sits on a rare 52x133 ft premium lot with a desirable walk-up basement-perfect for future in-law or multi-generational living. Offering approximately 4,220 sq ft

House for sale: 35 MARKWOOD CRESCENT, Whitby

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$899,800

35 Markwood Crescent, Whitby (Rolling Acres), Ontario L1R 2S3

5 beds
4 baths
13 days

Tom Edward & Taunton 3+2 Bedroom 4 Bath Detached Home in Desirable Rolling Acres Community * Backs Onto Ravine * Freshly Painted * 1,811 Sq Ft* Family Room with Gas Fireplace * Modern Kitchen with Quartz Counters & Walk-Out to Deck * New Oak Stairs with Wrought Iron Pickets * Recently Finished

Shiv Bansal,Century 21 Percy Fulton Ltd.
Listed by: Shiv Bansal ,Century 21 Percy Fulton Ltd. (416) 298-8200
House for sale: 10 THISTLEDOWN CRESCENT, Whitby

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$1,358,888

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

6 beds
4 baths
111 days

Cross Streets: Garrard / Taunton. ** Directions: Southeast. Beautiful Detached house in a quiet community. Upgraded home with finished basement, offering an exquisite blend of elegance and comfort. Cathedral Ceilings & Crown Moulding: Enjoy the grandeur and sophistication of high cathedral

Listed by: Howard Yang ,Anjia Realty (905) 808-6000
2950 9TH CONCESSION ROAD, Pickering

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$4,900,000

2950 9th Concession Road, Pickering (Rural Pickering), Ontario L1Y 1G3

0 beds
0 baths
50 days

Cross Streets: 9th Concession Rd & Balsam Rd. ** Directions: 9th Concession & East of Brock Rd. A rare chance to secure more than 122 acres of picturesque land in the sought-after Balsam Village area. Set along a year-round municipal road, this expansive property features roughly 43 acres of

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.