Simcoe County Multi-Family Real Estate Listings

Looking For An Investment Property In Simcoe County?

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Jeff Gilbert, an experienced real estate broker with a focus on real estate investing.  

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Featured Property

Browse Current Multi-Family Listings

* For the Income/Expense, Rent Roll, Net Operating Income, Details of current tenancies and projected Return on Investment for any property listed below, Please Contact Jeff Direct.

89 results | Page 7 of 8
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For sale
$825,000
84 MISSISSAGA STREET W, Orillia, Ontario

84 Mississaga Street W

Orillia, Ontario

Downtown Orillia, Legal Fourplex, has been continually upgraded, offering great income producing potential. Secure an income-focused legal fourplex in downtown Orillia. Upgrades include all new decks, windows, and a new roof to the exterior of the property. The property offers a mix of 2 X two-bedroom units and, 2 X one-bedroom units. Additionally, the property is of a unique shape offering a double detached garage in the back corner of the lot. Three of the four units have been extensively renovated with updated kitchens, bathrooms, flooring, paint, and appliances and are tenanted; the last unit to be renovated has just become vacated. With 8 parking spaces, separate electrical meters. Located Downtown, close to beaches, schools, shopping and the Hospital. (id:67934)

6 Bedroom 4 Bathroom 3,500 - 5,000 sqft
For sale
$645,000
679 MONTREAL STREET, Midland, Ontario

679 Montreal Street

Midland, Ontario

Attention investors! Here is a rare, low-stress addition to your portfolio. Located in a desirable, high-demand neighborhood on Midland's west side, this exceptionally well-maintained duplex is completely optimized for independent tenant living. The property features two spacious units (a 3-bedroom upper unit and a 2-bedroom lower unit), each completely self-contained to minimize your landlord overhead.The smartest feature of this build? Absolutely everything is separate. Both units boast their own private driveways, separate hydro meters, independent gas furnaces, individual A/C units, dedicated hot water heaters, separate electrical panels, and in-suite laundry facilities.The grade-level entry lower unit is a bright, accessible space currently generating $1,400/month plus utilities. The expansive main-floor upper unit is currently vacant. With all appliances included and a structure built for minimal maintenance, you can sit back and collect immediate cash flow from day one! (id:67934)

5 Bedroom 2 Bathroom 700 - 1,100 sqft
For sale
$889,900
65 OTTAWAY AVENUE, Barrie, Ontario

65 Ottaway Avenue

Barrie, Ontario

**Turnkey Legal Duplex with Legal Registered Detached Garden Suite | Fully Tenanted | Exceptional Investment Opportunity**An outstanding opportunity to own a fully tenanted, income-producing legal duplex with a detached secondary garden suite in one of Barrie's most established and sought-after neighbourhoods. This rare turnkey investment offers immediate cash flow with quality tenants already in place, making it an ideal addition to any real estate portfolio.Thoughtfully maintained and recently updated, the property features new shingles on main house 2026 and some new floors in basement unit providing added value and reducing future capital. With three self-contained living spaces, this is a low-maintenance, high-performing asset designed to deliver strong and consistent rental income.Situated on a generous lot in a mature, family-friendly neighbourhood, the property is perfectly positioned close to Highway 400, schools, public transit, parks, shopping, and everyday amenities. Its desirable location continues to attract quality tenants while supporting long-term appreciation.For investors, this is the complete package-a fully leased, turnkey property with multiple income streams, recent capital improvements, and excellent future growth potential. For those looking to house hack, there is also the opportunity to occupy one unit in the future while continuing to generate income from the remaining suites.Whether you're expanding your investment portfolio or securing a high-quality income property in a thriving market, this is a rare chance to own a solid, fully tenanted asset in one of Barrie's strongest rental locations. Opportunities like this don't come along often. (id:67934)

8 Bedroom 4 Bathroom 700 - 1,100 sqft
For sale
$1,850,000
175 SECOND STREET, Collingwood, Ontario

175 Second Street

Collingwood, Ontario

Step back in time while securing your financial future with this remarkable century-old triplex. Located just two blocks from Collingwood's vibrant downtown core, this property perfectly blends historic character with income potential. It is an ideal find for savvy investors, multi-generational families, or buyers looking to live in one unit while renting the others. This grand century home exudes curb appeal with its welcoming covered front porch and timeless craftmanship. The building is thoughtfully divided into three distinct 2-bedroom self contained rental units. Location is everything and this property delivers the ultimate Collingwood lifestyle. A short stroll to Hurontario St's boutique shops, restaurants, cozy cafes and local farmer's market. As well just minutes from the shores of Georgian Bay, scenic walking and biking trails, and a short drive to the ski hills of Blue Mountain or the Beaches of Wasaga Beach. Three independent income streams in a high demand rental market. Separate Meters/utilities, Ample on stie parking for tenants, zoning and location protect long-term property value. Don't miss your chance to own a piece of Collingwood's history schedule your private viewing today. (id:67934)

6 Bedroom 5 Bathroom 3,000 - 3,500 sqft
For sale
$799,999
29 PEEL STREET, Barrie, Ontario

29 Peel Street

Barrie, Ontario

Rare opportunity to own a multi-unit investment property in a prime Barrie location, just steps to the waterfront and Georgian College. Set on a generously sized lot with no immediate neighbour to the right, this property backs onto a private, tree-lined ravine with nearby walking trails and a picturesque stream, offering a unique blend of privacy and urban convenience. Currently configured with four separate living areas (3 one-bedroom, 1 studio), the property offers strong income potential in a high-demand area. Financials attached. Recent updates include renovations to Unit 1 (kitchen, flooring, bathroom, dishwasher), new fridge (Unit 2), updated eavestroughs (2026), gutter guards at the front, and furnace (2021). Additional features include three separate hydro meters, three electrical panels, and two large hot water tanks. The unfinished basement offers further value-add potential with 8-foot ceilings, large above-grade windows, and partial framing already in place. Conveniently located minutes to Highway 400, downtown Barrie, and key amenities, making it an attractive option for both tenants and commuters. (id:67934)

4 Bedroom 4 Bathroom 2,000 - 2,500 sqft
For sale
$849,900
65 FRONT STREET S, Orillia, Ontario

65 Front Street S

Orillia, Ontario

Rare Opportunity! Legal triplex bungalow in the heart of Orillia. Steps to shopping, dining, library, trails, and the Lake Couchiching waterfront. Located in a rapidly redeveloping neighborhood, this turn-key property features extensive updates (last 2 years) across all units: newer kitchens, baths, flooring, paint, & LED lighting. Plus, updated front steps, decks, perimeter fencing, HWT, and a paved parking lot. Perfect for investors or live-in buyers! (id:67934)

3 Bedroom 3 Bathroom 1,100 - 1,500 sqft
For sale
$699,900
2082 CENTRE AVENUE, Severn, Ontario

2082 Centre Avenue

Severn, Ontario

This well-built 2022 duplex offers an outstanding opportunity for investors, multi-generational families, or homeowners looking to live in one unit while generating income from the other. Featuring two fully self-contained units with separate entrances, utilities, and completely independent utility access for each unit, the property provides privacy, convenience, and cost efficiency, along with ample parking and a private garage.Constructed with energy-efficient ICF, it ensures durability, comfort, and reduced operating costs. The upper unit includes a spacious eat-in kitchen, three bedrooms, and in-suite laundry, while the lower unit offers a bright open-concept layout, two bedrooms, and its own laundry-ideal for rental or extended family.Conveniently located just minutes from Orillia, Gravenhurst, and Barrie, this approximately 2,072 sq. ft. property is a turnkey investment in a great location. Lot Irregularities: 37.99 ft x 148.96 ft x 157.84 ft x 190.76 ft (id:67934)

5 Bedroom 2 Bathroom 1,100 - 1,500 sqft
For sale
$750,000
571 HIGH STREET, Orillia, Ontario

571 High Street

Orillia, Ontario

Welcome to 571 High Street. This turn-Key Triplex is Ideal for Multi-Generational Living or Smart Investors. Located in the heart of Orillia, just a short stroll from Lake Simcoe and offering quick access for commuters. This impressive home has been completely transformed by a highly regarded local custom home builder and features three fully fire coded, self-contained units making it as versatile as it is stylish. The Main floor features nearly 1400 sq.ft. of living area including 3 generous Bedrooms, fully updated 4pc. Bath, main floor Laundry, open concept Living area, new Rockwood Kitchen w/soft close cabinets, quartz countertops & backsplash & walkout to private deck overlooking the fenced rear portion of the 63 x 134 lot. The lower level features 2 separate 1 Bedroom Apartments each with full walkout to the backyard & patio area, newly installed high efficiency Baseboard heaters, modern and functional layout & updated Bathrooms. Steel roof, Forced Air Gas furnace (6 yrs. Old). The 2025 renovation updates include: Eavestrough, soffit and facia; upgraded, luxury siding (Hardie board); lighting throughout the home including pot lights; windows; interior and exterior doors; baseboard and trim throughout; Freshly painted throughout; Hardwood stairs; Luxury vinyl flooring throughout; Upgraded electrical with 3 separate meters and panels with breakers (ESA certified); Main floor kitchen; renovated bathrooms x 3 units including tubs, toilets, vanities, taps, etc.; New appliances throughout); Whether you're seeking a stunning multi-unit home for family, or a high-quality investment with incredible rental potential, this property offers many possibilities checks every box. Some photos are virtually staged. (id:67934)

5 Bedroom 3 Bathroom 1,100 - 1,500 sqft
For sale
$1,500,000
184 BORLAND STREET E, Orillia, Ontario

184 Borland Street E

Orillia, Ontario

This property performs and turns heads. 184 Borland St E presents a rare opportunity to acquire a renovated, well-maintained multi-residential asset in one of Orillia's most established neighbourhoods. Located in the prestigious and highly valued East Ward on a large in-town lot, this is a clean, stabilized investment with a proven track record of performance.The property consists of 6 legal residential units plus flex space delivering solid 6+ income streams with strong in-place tenancy and a historically low vacancy rate. Over the past three years, vacancy has been minimal, with near full occupancy outside of brief renovation periods.Based on 2026 projections from actuals, the property generates a Net Operating Income of $96,266.92 and is offered at $1,550,000, representing a 6.21% cap rate. Operating expenses of $30,946.36 reflect a combination of actual and projected costs, resulting in an efficient and well-controlled expense profile.Ownership has completed extensive capital improvements including renovated units, updated hallways, plumbing upgrades, lighting improvements, and the replacement of both owned hot water tanks in 2025. The asset has been actively improved with a focus on long-term performance and tenant retention.Recent leasing activity confirms strong rental demand, with a one-bedroom unit leased at $1,700 and a three-bedroom at $2,000. Current rents align with market levels while still offering room for gradual growth.Additional income from laundry and parking further supports overall returns, and the property benefits from a balanced tenant mix of long-term and newer occupants.Strong numbers, low vacancy rate, and a fully improved asset in a growing Simcoe County market make this a compelling turnkey investment with immediate cash flow and continued upside. (id:67934)

5,474 sqft
For sale
$1,500,000
184 BORLAND STREET E, Orillia, Ontario

184 Borland Street E

Orillia, Ontario

This property performs and turns heads. 184 Borland St E presents a rare opportunity to acquire a renovated, well-maintained multi-residential asset in one of Orillia's most established neighbourhoods. Located in the prestigious and highly valued East Ward on a large in-town lot, this is a clean, stabilized investment with a proven track record of performance.The property consists of 6 legal residential units plus flex space delivering solid 6+ income streams with strong in-place tenancy and a historically low vacancy rate. Over the past three years, vacancy has been minimal, with near full occupancy outside of brief renovation periods.Based on 2026 projections from actuals, the property generates a Net Operating Income of $96,266.92 and is offered at $1,550,000, representing a 6.21% cap rate. Operating expenses of $30,946.36 reflect a combination of actual and projected costs, resulting in an efficient and well-controlled expense profile.Ownership has completed extensive capital improvements including renovated units, updated hallways, plumbing upgrades, lighting improvements, and the replacement of both owned hot water tanks in 2025. The asset has been actively improved with a focus on long-term performance and tenant retention.Recent leasing activity confirms strong rental demand, with a one-bedroom unit leased at $1,700 and a three-bedroom at $2,000. Current rents align with market levels while still offering room for gradual growth.Additional income from laundry and parking further supports overall returns, and the property benefits from a balanced tenant mix of long-term and newer occupants.Strong numbers, low vacancy rate, and a fully improved asset in a growing Simcoe County market make this a compelling turnkey investment with immediate cash flow and continued upside. (id:67934)

9 Bedroom 7 Bathroom 5,000 - 100,000 sqft
For sale
$2,790,000
58 QUEEN ST STREET W, Springwater, Ontario

58 Queen St Street W

Springwater, Ontario

Excellent investment opportunity with over 10,000 Square Feet! Fully rented residential 8 plex with ground level 5400+ Square foot commercial retail warehouse space. Huge capital improvements done in the last 2 years. Including stucco/stone front facade, windows, doors, bathrooms, flooring, roofs, brand new asphalt parking lot, plumbing, exterior paint, storage units, covered porch entrance, new heat pumps in all upper apartments, new hot water heaters, new interior paint, and much more! Some units have newer kitchens and bathrooms. Rear truck level loading dock with elevator. Main floor tenant operates a reputable and successful Fireplace/HVAC business. All residential and commercial units fully occupied. Too many improvements to list. Turn key investment! (id:67934)

10 Bedroom 9 Bathroom 5,000 - 100,000 sqft
For sale
$1,899,000
268 HUME STREET, Collingwood, Ontario

268 Hume Street

Collingwood, Ontario

8 Unit multi residential apartment units plus commercial detailing shop on expansive grounds. All fully leased with reliable tenants providing good cash flow. Property includes coin laundry and all existing appliances. Detailed financial info available upon request (id:67934)

5,250 sqft
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