RENOVATED LEGAL FOURPLEX WITH MAJOR UPGRADES, LAKE SIMCOE ACROSS THE ROAD & INCOME-PRODUCING POTENTIAL! Secure an income-focused legal fourplex on nearly half an acre, positioned across from Lake Simcoe with renovated suites, strong rental potential, and neighbouring higher-end homes adding to the area's appeal. Set on an impressive 87 x 203 ft lot, 22 Olive Crescent speaks to investors, entrepreneurs, and multi-family buyers looking beyond the ordinary income property. Live in one unit, keep family close in another, and generate rental income from the remaining suites, or lease all four to capture current market value. The property offers a versatile mix of one-bedroom, three-bedroom, one-bedroom plus den, and two-bedroom suites, with only one unit below grade. Three units are currently vacant, giving the next owner control over tenant selection and market rents from day one, while three of the four suites have been extensively renovated with updated kitchens, bathrooms, flooring, trim, interior doors, and appliances. With 8 parking spaces, separate utilities except water, a common coin-operated laundry, storage, and major improvements including the roof, insulation, siding, basement waterproofing, sump pump, and ongoing landscaping enhancements, much of the heavy lifting has already been done. Minutes from Kitchener Park, beaches, boat launches, downtown Orillia, Orillia Soldiers' Memorial Hospital, schools, shops, and local parks.
Finished walk-out basement with apartment and sump pump
Smoke and carbon monoxide detectors
Heating & cooling
Electric baseboard heating
Wall-mounted cooling units
Exterior features
Deck and porch
Dry, flat topography
Irregular lot with greenbelt and level areas
Publicly maintained road access
Home design
Residential income property (quadruplex / fourplex)
North-facing
Parking
8 parking spaces
Security
Smoke detector(s)
Carbon monoxide detector(s)
Construction
Brick and vinyl siding exterior
Asphalt roof
Utilities
Public water
Cable available
Sale and tax history for 22 Olive Cres
Sale History
Tax History
Date
Event
Price
TREB #S13649236
Aug 7, 2026
Listed
$1,179,000
TREB #S13160936
May 22, 2026
Listed
$1,245,000
TREB #S12382675
Mar 6, 2026
Delisted
—
Sep 4, 2025
Listed
$1,310,000
For Sale by Owner. Click on "More Information" Link Below. Welcome to 22 olive cres. This is a large single family home (plus) 2 in-law legal suites. The main home offers 5 bedrooms, 2 living rooms, 2 full bathrooms , open concept kitchen/dining/living room and 2 covered verandas with views of Lake Simcoe. The 2 in-law legal suites are fully equipped with their own full bathroom, kitchen, large bedroom and living room. This home is large enough for a multi-generational family. This still leaves 2 in-law suites for other family to visit or live there or rent them out to students at Lake University or Georgian College to help pay the mortgage (one is currently rented at $1149/mth). So many configurations to work with. It has a huge backyard for the family and pet. This home is being updated (TBF in Oct ) with NEW interior doors, flooring, trim, bathrooms, kitchen and appliances. It is located across the road from multi-million dollar lakefront homes. Great family fun can be found at city of Orillia Kitchener Park, located ~300ft away with a beach area and a boat launch. Use it to paddle board, canoe or ice fish in the winter or enjoy watching ball games at the park. It's on a huge, very private lot of 0.4 Acre that can possibly accommodate building another residence (garden suite) in the backyard, with the new owner getting proper approval. New shingles, attic insulation and siding 2015. Buyers or agents confirm all measurements.
TREB #S12280070
Jan 13, 2026
Delisted
—
Jul 11, 2025
Listed
$1,310,000
As the MLS and public records start to fill up, we'll list the details here.
Public record
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Lot size
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Style
Single Family Residential
Region
Simcoe County
Parking Spaces
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Accessible
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Last updated by owner on Aug 9, 2023.
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