Ravine-Whitby Homes For Sale

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House for sale: 36 BLENHEIM CIRCLE, Whitby

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$2,195,000

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

5 beds
5 baths
17 days

Cross Streets: Country Lane & Taunton Rd W. ** Directions: East on Dagenham Dr from Country Ln then East on Blenheim Cir. This Is The Kind Of Home That Makes An Impression Before You Even Step Inside. Set On A Stunning Ravine Lot, This Executive 4+1 Bedroom, 5 Bathroom Home Delivers Serious

Listed by: Dan Plowman ,Dan Plowman Team Realty Inc. (905) 668-1511
House for sale: 141 AUCKLAND DRIVE, Whitby

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$1,388,800

141 Auckland Drive, Whitby (Rural Whitby), Ontario L1P 0J2

7 beds
5 baths
10 days

CORONATION AND ROSSLAND Beautifully upgraded 4+3 bedroom home on a rare ravine lot in one of Whitby's most desirable neighborhoods. This rare offering features three full kitchens, five washrooms, one den in the master bedroom. A walk-out to a fully finished basement, and flexible living

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
177 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
67 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: 25 INVERLYNN WAY, Whitby

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$1,799,000

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

4 beds
5 baths
32 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: 103 WYCOMBE STREET, Whitby

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$1,149,900

103 Wycombe Street, Whitby (Brooklin), Ontario L1M 0H4

3 beds
3 baths
1 day

Carnwith & Thickson OPEN HOUSE CANCELLED! SOLD FIRM AWAITING DEPOSIT.Set on a picturesque deep lot offering unobstructed views of a serene ravine and walking trail, this exceptional bungalow is truly a rare find. Designed for entertaining, with an open-concept floor plan with large windows,

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
39 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,

Listed by: Ram Krishnamurthy ,Re/max Rouge River Realty Ltd. (416) 427-5555
Row / Townhouse for sale: 4 PARADISE WAY, Whitby

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$749,999

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

3 beds
3 baths
10 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: 50 BLUEBELL CRESCENT, Whitby

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$1,275,000

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

7 beds
5 baths
122 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: 7 INVERLYNN WAY, Whitby

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$1,775,000

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

5 beds
4 baths
39 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: 27 KENNETT DRIVE, Whitby

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$1,599,900

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

5 beds
5 baths
12 days

Cross Streets: McQuay Blvd and Kennett. ** Directions: Dundas St to 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

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
142 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: 139 TREMOUNT STREET, Whitby

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$999,000

139 Tremount Street, Whitby (Brooklin), Ontario L1M 1E9

5 beds
4 baths
41 days

Cross Streets: Anderson St. / Winchester Rd. E. ** Directions: . Tucked away on a premium ravine lot in the heart of Brooklin, this all-brick 4+1 bedroom home offers a rare blend of privacy, space, and everyday livability. Backing onto mature green space, the property enjoys a peaceful, natural

Evan Blainey,Re/max Rouge River Realty Ltd.
Listed by: Evan Blainey ,Re/max Rouge River Realty Ltd. (905) 668-1800
Row / Townhouse for sale: 3 HADLEIGH WAY, Whitby

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$819,900

3 Hadleigh Way, Whitby (Brooklin), Ontario L1M 0L4

4 beds
4 baths
23 days

Cross Streets: Thichkson Rd & Canwith Dr. E. ** Directions: North of Carnwith Dr.E, east of Thickson Rd. Welcome to this elegant and well-appointed 3+1 bedroom 4 bath 11 year old home, nestled on a private and quiet cul-de-sac bordering a beautiful ravine and walking path. This home features

Chris Gray,Century 21 Leading Edge Realty Inc.
Listed by: Chris Gray ,Century 21 Leading Edge Realty Inc. (905) 471-2121
House for sale: 48 CARNWITH DRIVE W, Whitby

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$2,179,000

48 Carnwith Drive W, Whitby (Brooklin), Ontario L1M 2L1

4 beds
6 baths
24 days

Carnwith Dr W & Montgomery Ave Special opportunity to fully customize your brand new Brooklin home! Fulton Homes 'Bedford' model (elevation a) welcomes you to a world of possibility. Backing onto a protected woodlot on extra deep 50 foot wide lot with a fully finished walk-out basement with

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
79 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
88 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: 20 CAPSTAN COURT, Whitby

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$1,300,000

20 Capstan Court, Whitby (Lynde Creek), Ontario L1P 0K5

5 beds
4 baths
5 days

Cross Streets: Hwy 412 And Dundas St W. ** Directions: . LOOK NO FURTHER! PRIME LOCATION** This P-R-E-M-I-U-M- L-O-T. Widens to almost 60Ft At Back With No Neighbours Behind. Court Location Perfect For Privacy. No Sidewalk. The Grand Essex Model Offers Approx 3000 Sq Ft Of Total Living Space.

Dorothy Harrison,Re/max Hallmark First Group Realty Ltd.
Listed by: Dorothy Harrison ,Re/max Hallmark First Group Realty Ltd. (416) 258-2140
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
157 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
96 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

House for sale: 57 POTTERS LANE, Clarington

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$1,399,000

57 Potters Lane, Clarington (Rural Clarington), Ontario L0B 1J0

3 beds
3 baths
24 days

Cross Streets: Bowmanville Ave & County Rd 3. ** Directions: From Bwmn Ave, travel WEST on Cty Rd 3 to 1st LEFT onto Potters Lane, home is 5th on LEFT. Welcome to life in Enniskillen! This charming 3 bedroom 3 bath home is situated on a picturesque 1.2 acre ravine lot complete with in-ground

Nate Brouwer,Keller Williams Energy Real Estate
Listed by: Nate Brouwer ,Keller Williams Energy Real Estate (905) 723-5944

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.