Whitby Walkout Basement Homes

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House for sale: 19 SHEPHERD ROAD, Whitby

1 photos

$1,535,000

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

6 beds
5 baths
69 days

Cross Streets: Hwy 7 & Coronation Rd. ** Directions: Coronation Rd. south of Hwy 7. Executive Estate Living in Northwest Whitby w/Private Oasis.Welcome home to this magnificent, beautifully maintained 4-level side split residence, situated within a prestigious enclave of multi-million dollar

Ricardo Khan,Right At Home Realty
Listed by: Ricardo Khan ,Right At Home Realty (416) 391-3232
House for sale: 31 FOUR WINDS DRIVE, Whitby

47 photos

$975,000

31 Four Winds Drive, Whitby (Port Whitby), Ontario L1N 9R8

3 beds
3 baths
31 days

Cross Streets: Whitby Shores Greenway & Four Winds. ** Directions: Whitby Shores Greenway to Four Winds Drive. Welcome to Whitby Shores, Whitby's most sought-after waterfront community! This beautifully updated 3 bedroom, 3 bathroom detached home offers move-in-ready living just steps from

Listed by: Shelby Nicole Densmore ,Real Broker Ontario Ltd. (905) 906-5227
House for sale: 6540 CORONATION ROAD, Whitby

45 photos

$3,499,999

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

5 beds
8 baths
6 days

Coronation Road/ Columbus Road Welcome to this brand new custom-built luxury home offering over 8,500 sq. ft. of elegant living space with top-of-the-line finishes throughout. The main floor features 12-ft ceilings, a spacious open-concept layout with a grand 24-ft open-to-above living room,

Listed by: Nitin Angrish ,King Realty Inc. (905) 793-5464
House for sale: 62 STARGELL DRIVE, Whitby

42 photos

$1,280,000

62 Stargell Drive, Whitby (Pringle Creek), Ontario L1N 7X5

6 beds
5 baths
67 days

Garden St. & Manning Rd. Welcome to 62 Stargell Drive, a stunning and spacious home located in Whitby's highly sought-after Pringle Creek neighborhood. This beautifully renovated property features 4+2 bedrooms, 5 washrooms and a thoughtfully designed layout with an expansive living and dining

Listed by: Omar Ali ,Century 21 Millennium Inc. (416) 885-1800
House for sale: 31 FOUR WINDS Drive, Whitby

47 photos

$975,000

31 Four Winds Drive, Whitby, Ontario L1N 9R8

3 beds
3 baths
31 days

Whitby Shores Greenway to Four Winds Drive Welcome to Whitby Shores, Whitby's most sought-after waterfront community! This beautifully updated 3 bedroom, 3 bathroom detached home offers move-in-ready living just steps from the lake. With tons of natural light and tastefully updated throughout,

Listed by: Shelby Nicole Densmore ,Real Broker Ontario Ltd. (905) 906-5227
Row / Townhouse for sale: 42 LAKE TRAIL WAY, Whitby

31 photos

$699,999

42 Lake Trail Way, Whitby (Brooklin), Ontario L1M 0M3

3 beds
4 baths
25 days

Cross Streets: Carnwith Dr E and Thickson Rd N. ** Directions: 42 Lake Trail Way, Whitby L1M 0M3. Client RemarksStunning 3-year-old townhouse located in the highly sought-after Brooklin community! This home offers the perfect blend of modern elegance, functional living, and unmatched convenience.

Aakash Lalith Kumar,Homelife Landmark Realty Inc.
Listed by: Aakash Lalith Kumar ,Homelife Landmark Realty Inc. (647) 901-5773
House for sale: 43 BELLWOOD DRIVE, Whitby

33 photos

$1,150,000

43 Bellwood Drive, Whitby (Blue Grass Meadows), Ontario L1N 2E3

3 beds
3 baths
61 days

Near Thickson and Burns st lots of upgrades a must see investment property.insulated garage Doors and 40' Entrance door. All windows were replaced in 2021.updated Kitchen,washrooms and floors through out the house.Basement is Fire Seperated Built According to by law. Hvac and plumbing has been

Listed by: Anees Chaudhry ,Homelife Elite Services Realty Inc. (416) 283-1555
House for sale: 59 WESTFIELD DRIVE, Whitby

38 photos

$1,599,999

59 Westfield Drive, Whitby (Lynde Creek), Ontario L1P 0E9

7 beds
6 baths
2 days

Cross Streets: Rossland Rd. E. / Lakeridge Rd. N. ** Directions: Des Newman Blvd. / Westfield Dr. Step into luxury and comfort in this stunning detached home featuring a legal basement apartment with its own private side entrance - perfect for large families, in-law/nanny suite or investors.

Listed by: Rahim Rajab Ali ,International Realty Firm, Inc. (647) 494-8012
House for sale: 34 SAWDON DRIVE, Whitby

20 photos

$799,999

34 Sawdon Drive, Whitby (Blue Grass Meadows), Ontario L1N 8C3

4 beds
4 baths
3 days

Thickson-Burns Well-maintained family home offering modern updates while preserving warmth and character. Features a gourmet kitchen with breakfast bar, quartz countertops, and stainless steel appliances, complemented by a spacious family room with cozy fireplace. California shutters are featured

Listed by: Alysah Lopez ,Property.ca Inc. (416) 583-1660
House for sale: 87 BARRISTER AVENUE, Whitby

40 photos

$949,999

87 Barrister Avenue, Whitby (Pringle Creek), Ontario L1R 0N3

4 beds
4 baths
10 days

Cross Streets: Brock Street & Rossland Rd. ** Directions: Vanier St & Barrister Ave. Introducing this exquisite, link home situated In a highly sought after community of Pringles Creek .Offering privacy, outdoor space, and the feel of a detached home with only a small shared foundation wall.Thoughtfully

Listed by: Maryam Habibi Shishavan ,Right At Home Realty (905) 665-2500
House for sale: 58 TEDDINGTON CRESCENT, Whitby

37 photos

$749,000

58 Teddington Crescent, Whitby (Pringle Creek), Ontario L1R 1S5

3 beds
3 baths
24 days

Cross Streets: Rossland Rd. East & Garden St. ** Directions: Rossland Rd. East & Garden St. to Bassett Blvd to Teddington Cres. Well-Maintained 3-Bedroom Home in Desirable Fallingbrook, Whitby. Welcome to this well-kept, move-in-ready home-ideal choice for first time buyers and those ready

Lijo George Perumpallil,Right At Home Realty
Listed by: Lijo George Perumpallil ,Right At Home Realty (416) 826-4364
House for sale: 73 KENILWORTH CRESCENT, Whitby

50 photos

$1,149,900

73 Kenilworth Crescent, Whitby (Brooklin), Ontario L1M 2M7

4 beds
4 baths
26 days

Thickson Rd N & Blackfriar Ave Welcome To 73 Kenilworth Crescent - A Beautiful Brooklin Gem! This Stunning 3+1 Bedroom And 4 Bathroom Home With A Double Car Garage Is Nestled In The Highly Sought-After Brooklin Community Surrounded By Excellent Schools, Parks, And Family-Friendly Amenities.

Adem Ozbek,Homelife Frontier Realty Inc.
Listed by: Adem Ozbek ,Homelife Frontier Realty Inc. (647) 533-2336
House for sale: 139 TREMOUNT STREET, Whitby

50 photos

$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
House for sale: 68 APPLEWOOD CRESCENT, Whitby

42 photos

$1,075,000

68 Applewood Crescent, Whitby (Blue Grass Meadows), Ontario L1N 2E6

4 beds
4 baths
15 days

Thickson Rd & Applewood Ave Welcome to this exceptional upgraded 4-bedroom home, nestled on a picturesque, park-like lot in a quiet cul-de-sac. Thoughtfully renovated and designed for modern living, this residence blends contemporary style with functional comfort, perfect for buyers seeking

Andrew Quinn Persaud,Revel Realty Inc.
Listed by: Andrew Quinn Persaud ,Revel Realty Inc. (416) 220-7045
House for sale: 30 GLENMOUNT COURT, Whitby

41 photos

$749,900

30 Glenmount Court, Whitby (Lynde Creek), Ontario L1N 5M8

4 beds
2 baths
3 days

Dundas St and Bell Dr Tucked away on a quiet, family friendly court, this beautifully maintained two story detached home offers the perfect blend of space, privacy & location, backing directly onto a park. Set on a premium pie-shaped lot, the property offers an abundance of outdoor space &

Lisa Joy Macdonald,Keller Williams Energy Real Estate
Listed by: Lisa Joy Macdonald ,Keller Williams Energy Real Estate (905) 723-5944
House for sale: 1016 MCQUAY BOULEVARD, Whitby

42 photos

$875,000

1016 Mcquay Boulevard, Whitby (Lynde Creek), Ontario L1P 1R7

3 beds
2 baths
5 days

Cross Streets: Rossland Rd W / Cochrane St. ** Directions: South on McQuay Blvd from Rossland Rd W. Set in a highly desirable Whitby neighbourhood, this welcoming bungalow delivers a comfortable, easygoing lifestyle with thoughtful modern touches throughout. Thoughtfully updated and beautifully

Lisa Fayle,Re/max Rouge River Realty Ltd.
Listed by: Lisa Fayle ,Re/max Rouge River Realty Ltd. (905) 655-8808
Row / Townhouse for sale: 112 CREEKWOOD CRESCENT, Whitby

25 photos

$839,000

112 Creekwood Crescent, Whitby (Rolling Acres), Ontario L1R 2K4

4 beds
4 baths
6 days

Cross Streets: Thickson Rd. & Dyden Blvd. ** Directions: North of Dryden Blvd., East of Bakerville St. Immaculate freehold townhouse located in a family-friendly neighbourhood. The main floor offers bright and spacious living and dining areas with a walkout to a private, fully fenced backyard-perfect

Listed by: Ardy Nikzad ,Right At Home Realty (416) 391-3232
Row / Townhouse for sale: 9 THREADGOLD COURT, Whitby

43 photos

$699,000

9 Threadgold Court, Whitby (Lynde Creek), Ontario L1P 1L9

4 beds
4 baths
10 days

McQuay Boulevard/ Bonacord Avenue Welcome To This Beautifully Maintained 3+1 Bed, 4 Bath Freehold Townhouse In The Desirable Lynde Creek Neighbourhood *Featuring A Bright Kitchen With White Cabinetry *This Home Flows Into A Warm And Inviting Living Space With A Gas Fireplace And Walkout To

Row / Townhouse for sale: 4 PARADISE WAY, Whitby

36 photos

$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

Row / Townhouse for sale: 8 OGLEVIE DRIVE, Whitby

41 photos

$650,000

8 Oglevie Drive, Whitby (Pringle Creek), Ontario L1R 2Y4

3 beds
3 baths
4 days

Cross Streets: Brock St N / Taunton Rd E. ** Directions: East on Joy Thompson Ave from Brock St N then North on Oglevie Dr. Welcome To This Beautifully Upgraded Freehold Townhome In Whitby's Highly Desirable Pringle Creek Neighbourhood - An Exceptional Opportunity With No Condo Fees And True

Listed by: Dan Plowman ,Dan Plowman Team Realty Inc. (905) 668-1511
House for sale: 82 VIPOND ROAD, Whitby

41 photos

$1,069,000

82 Vipond Road, Whitby (Brooklin), Ontario L1M 2P2

4 beds
3 baths
11 days

Cross Streets: Ferguson Avenue Vipond Road. ** Directions: Thickson Rd N. to Winchester, Left to Ferguson Ave., Right on Vipond Rd. Property on the left. Welcome to 82 Vipond Road, a beautifully maintained family home in the heart of Brooklin where thoughtful updates meet everyday comfort.

Stefan Melnychuk,Coldwell Banker - R.m.r. Real Estate
Listed by: Stefan Melnychuk ,Coldwell Banker - R.m.r. Real Estate (905) 430-6655
House for sale: 26 LUROSA CRESCENT, Whitby

25 photos

$899,900

26 Lurosa Crescent, Whitby (Taunton North), Ontario L1R 3A9

2 beds
2 baths
20 days

Cross Streets: Brock/Attersley. ** Directions: Robert Attersley/Baldwin. Welcome to 26 Lurosa Crescent, Whitby! Oversized all brick bungalow, 2-bedroom, 2 bathroom home. Large private corner lot with no sidewalk and features a two-car garage plus parking for four cars on the driveway.The stunning

Listed by: Annie V. Byles ,Re/max Crossroads Realty Inc. (905) 305-0505
House for sale: 6 RIBBLESDALE DRIVE, Whitby

43 photos

$999,900

6 Ribblesdale Drive, Whitby (Pringle Creek), Ontario L1N 6K6

4 beds
4 baths
63 days

Anderson & Manning Welcome To This Beautiful 3-Bdrm Detached Home W/ A Very Rare 55 Ft Front Lot Nestled In A Quiet And Highly Sought-After Pringle Neighborhood From The Moment You Step Into The Grand Foyer, You'1l Be Captivated By The Elegance & Charm Of This Home. A Main-Flr The Formal Living

House for sale: 97 DEVERELL STREET, Whitby

50 photos

$1,099,000

97 Deverell Street, Whitby (Rolling Acres), Ontario L1R 1V9

4 beds
4 baths
89 days

Dryden/Thickson Rd N Discover 97 Deverell Street, an upgraded 4-bed, 4-bath Rolling Acres standout with over $200K in improvements and a layout built for real family living. The main floor features an elegant open-concept dining area with hardwood floors, a bright living space with large windows

Adrian Gennuso,Keller Williams Energy Real Estate
Listed by: Adrian Gennuso ,Keller Williams Energy Real Estate (416) 888-2686

Whitby walkout basement: what buyers and investors should know

In Whitby and the broader Durham market, a whitby walkout basement offers more than extra square footage—it can mean brighter living space, multigenerational flexibility, and, when compliant, rental income potential. Whether you're seeking walkout basement homes for family use or scanning for a walkout basement for sale to support a house-hacking strategy, understanding zoning, building standards, and neighbourhood context is essential before you write an offer.

What a walkout really provides

A true walkout basement is built into a slope and opens at grade to the exterior via full-size doors. Compared with standard “lookout” or below-grade basements, walkouts tend to command a value premium due to natural light, direct yard access, and easier egress. For lifestyle, that can translate into a usable family room, home office with patio access, or an in-law suite. For investors, a walkout helps with tenant appeal—but only if the unit is legal and the building envelope is well managed for moisture and safety.

Whitby walkout basement: zoning, permits, and legal suite realities

Whitby permits second suites in many low-density zones, but rules vary by neighbourhood and bylaw updates do occur. If you intend to create or rent a basement suite, confirm:

  • Zone permissions for additional residential units (ARUs) and any parking minimums.
  • Ontario Building Code compliance: egress, ceiling height, fire separations, smoke/CO interconnects, and dedicated exits.
  • Electrical safety (ESA) and Fire Code inspections as applicable.
  • Registration or licensing requirements for a legal accessory unit.

Key point: A “separate entrance” isn't the same as a legal suite. Verify municipal approvals and permits on file. For current local inventory and context, review walkout basement homes in Whitby and compare with separate-entrance basement options in Whitby to see how listings present compliance.

Income potential and resale value

Legal, well-finished walkouts typically resell more readily than standard basements due to light, access, and flexibility. Investors often model returns using either rental add-back or offset methods, depending on lender. Owner-occupiers may value a bright lower level as an extension of main-floor living, which supports price resilience.

Example: A 3-bedroom with a bright, code-compliant basement one-bedroom in North Whitby near Dryden Blvd may appraise higher than a similar home without a walkout, provided the finishes and permits are documented. Conversely, an unpermitted “house for sale walk out basement” advertised as “potential income” can suffer a discount at appraisal or attract lender/insurer conditions. Always review the municipality's occupancy or registration status before projecting rent.

Neighbourhood nuance: slopes, ravines, and streets to watch

In Whitby, sloped lots near ravines or storm corridors often host walkouts. You'll see them in pockets around Dryden Blvd in the north end and along streets such as Closson Drive in newer subdivisions where the topography favours at-grade rear yards. Ravine-backed lots offer privacy but demand drainage vigilance (grading, swales kept clear). If you target “houses with big basements” or a “house with huge basement,” confirm that the added square footage is functional, permitted, and dry.

Seasonal market rhythms

GTA seasonality matters. Spring listings for houses with finished basements for sale surge; competition rises and so do multiple-offer probabilities. Summer can bring a slight lull as buyers turn to cottage country, while early fall often sees serious, mortgage-ready purchasers. Winter offers negotiating room, but snow can mask grading issues and ice can obscure foundation cracks—book a follow-up inspection once the thaw reveals drainage patterns. If you're searching “walkout basement near me,” set alerts for both late-winter and post-Labour Day windows to capture motivated sellers.

Build quality, moisture, and performance

Walkouts interact directly with soil and surface water. Inspect for:

  • Consistent grading that slopes away from the foundation; intact downspouts and extensions.
  • Properly flashed patio doors and thresholds; no softness at sills.
  • Sump pump, backwater valve, and evidence of past water ingress (staining, efflorescence).
  • Window well drainage; covers where needed.
  • Ventilation and insulation quality; dehumidification capacity.
  • Radon test results—Durham readings are often low to moderate, but every home is unique. Mitigation is straightforward if required.

Buyer takeaway: Even for new homes with finished basements, ask for builder warranties, permit records, and proof of inspection. A bright walkout that leaks will underperform on both enjoyment and resale.

Financing, appraisal, and insurance

Most lenders will recognize the contributory value of a quality walkout, and many accept a portion of legal-suite rent to qualify. Policies vary by institution and whether the suite is owner-occupied. Some scenarios:

  • Owner-occupied with legal basement suite: Lenders may use rental offset (e.g., 50–70% of lease) or add-back to income; insurer may require proof of legality.
  • Unpermitted suite: Financing risk rises; some lenders will reduce loan amounts or require unit decommissioning before closing.
  • Refinance for secondary suite build: Ensure your cost estimates include fire separations, egress, HVAC zoning, and sound attenuation; appraisers will look for code compliance to credit value.

Speak with your mortgage professional early. Appraisals hinge on comparable sales; in Whitby, sales near transit and good schools with proper walkouts set strong benchmarks.

Short-term rentals and use restrictions

If you plan to STR a basement walkout in Whitby, verify the Town's short-term rental bylaws and licensing rules. Some municipalities restrict STRs to principal residences or cap the number of rental days. Condominium townhomes may have additional bylaws. Never assume permissibility based on a prior owner's usage.

Urban versus rural edges: wells, septics, and services

Many Whitby addresses are fully serviced, but properties on the rural fringe (particularly north of Brooklin) may be on well and septic. A walkout basement adds potential occupancy; ensure the septic system is sized appropriately for bedroom count and consult recent pump/inspection records. Water quality and flow tests are prudent for wells. Budget for upgrades if you intend to add a legal suite with higher fixture loads.

Regional comparisons and search strategy

Inventory ebbs and flows across the GTA and beyond. Tracking nearby markets can help with pricing and timing. For regional context, compare Whitby with the broader Durham Region walkout basement inventory or specific submarkets such as Pickering walkout options. If you're flexible geographically, look at the Barrie basement walkout market, Kitchener walkout listings, and Newmarket walkout properties for alternative price points.

Outside Ontario, buyers sometimes benchmark GTA pricing against western or smaller markets to gauge value. For example, explore Langley, BC walkout inventory or Alberta choices like Beaumont walkout homes. Even mid-sized Ontario towns such as Orangeville walkout basements can offer instructive comparables when assessing replacement cost and rent potential.

KeyHomes.ca is a practical place to cross-reference these markets in one spot. You can scan data, compare finishes, and see how a basement walkout in Whitby is positioned versus similar listings nearby. When you need a licensed opinion, the platform connects you with professionals who understand local bylaws and valuation.

How to assess a listing description

Common phrases like “house for sale walk out basement,” “walkout basement homes,” and “houses with finished basements for sale” don't guarantee zoning compliance or quality. Read for:

  • Mentions of permits, inspections, and suite registration numbers.
  • Details about ceiling heights, separate HVAC controls, and independent laundry.
  • Photos that show proper exterior grading and door thresholds at grade (not sunken pits).
  • Notes on parking availability—especially relevant when adding a tenant.

For an organized view of available options, resources like Whitby walkout basement listings can help you filter for lot type, separate entrance, and finished area, saving time during your shortlisting process.

Offer strategy and conditions

When you find a promising basement walkout Whitby property, the following conditions are common and often prudent:

  • Financing condition reflecting potential rental income only if the suite is legal or will be legalized post-close with lender consent.
  • Home inspection with specific scope for moisture, grading, and foundation.
  • Review of municipal records for permits and, if applicable, second-suite registration.
  • Insurance confirmation for intended use (owner-occupied with tenant vs. full investment).

If competition is high, some buyers pre-arrange a lender review and conduct a pre-offer inspection to shorten timelines, but weigh the risk carefully.

Taxes and operating costs

In Ontario, adding a legal suite may have HST, development charge, or parkland nuances depending on the scope and municipality; in most low-density retrofits, HST on resale isn't triggered, but renovation inputs include HST and may be eligible for limited rebates. Factor utilities (separate metering versus cost sharing), maintenance of exterior stairs/patios, and potential increases in insurance premiums. For investors, confirm whether Whitby's property standards bylaw imposes additional inspection or licensing fees for rentals.

Practical checklist for due diligence

  • Confirm zoning and second-suite permissions for the exact address; bylaws vary by municipality and can change.
  • Obtain building permits and final inspections for any finished or altered space.
  • Assess water management: grading, eaves, sump/backwater valve, and historical moisture.
  • Validate egress, ceiling heights, and life-safety elements to Ontario Code standards.
  • If rural services: septic capacity and well quality/quantity testing.
  • Model financing with and without rental income; ensure appraisal support via relevant comparables (e.g., similar homes near Dryden Blvd or Closson Drive).

As you refine your search, platforms like KeyHomes.ca provide a coherent view of local and regional inventory, from Whitby-focused pages to broader Durham and cross-province comparisons, making it easier to contextualize price, quality, and compliance before you proceed.