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$999,999
6 Beds ⋅ 4 Baths ⋅ S13752982 MLS
Top 5 Reasons You Will Love This Home: 1) Perfectly positioned in the heart of Orillia, this spacious legal duplex offers exceptional convenience, walkability, and the rare chance to own a high-quality multi-unit property in a highly desirable neighbourhood 2) Inside the main residence, you'll find a bright, open-concept layout complemented by a generous primary bedroom with a private ensuite, an ideal combination of comfort and modern style for families or those who love to entertain 3) The kitchen has been fully updated, featuring brand-new appliances, a refreshed upper-level flooring, upgraded stairs, stylish light fixtures, and sleek new blinds, resulting in a move-in-ready space with lasting appeal 4) A fully legal, self-contained lower-level suite provides outstanding flexibility for rental income, extended family, or multi-generational living, adding both convenience and financial value to the property 5) Rounding out this impressive home are a spacious two-car garage, an extended driveway, and elegant stamped concrete accents surrounding the exterior, delivering both functionality and striking curb appeal, with immediate possession of the main house ensures a smooth and seamless move. 2,455 above grade sq.ft plus a finished basement. *Please note some images have been virtually staged to show the potential of the home.

2 Vanessa Drive, Orillia
$3,799,000
6 Beds ⋅ 5 Baths ⋅ S13744674 MLS
Top 5 Reasons You Will Love This Home: 1) Experience executive waterfront living in one of Orillia's most prestigious communities, where sophisticated contemporary finishes carry throughout an impressive 6,339 square feet of finished living space, complemented by expansive open-concept principal rooms, generously sized bedrooms, and beautifully appointed bathrooms 2) Extend the living and entertaining space to the thoughtfully designed lower level, featuring a spacious walkout recreation room, private home theatre, and excellent in-law potential, offering exceptional versatility for multi-generational living, overnight guests, and memorable gatherings 3) Set on approximately one acre with an impressive 100 feet of pristine shoreline along Lake Couchiching, enjoy direct access to the renowned Trent-Severn Waterway and an unparalleled setting for boating, swimming, and four-season waterfront living 4) Embrace exceptional outdoor living with a private dock, inviting stone firepit patio, and charming gazebo, creating multiple spaces to entertain, unwind, and take in the beauty of the waterfront surroundings 5) Elevating the property's waterfront appeal is a recently built boathouse complete with a marine rail system, complemented by an expansive new deck and dedicated hot tub room below, creating an outstanding lakeside retreat designed for recreation, relaxation, and effortless enjoyment. 3,351 above grade sq.ft. plus a finished lower level.

354 Brewery Lane, Orillia
$849,000
6 Beds ⋅ 5 Baths ⋅ S13723024 MLS
Welcome to 3119 Emperor Drive, an extraordinary estate in Orillia's coveted Westridge community, where timeless elegance harmonizes with modern luxury. This impeccably maintained 6 bedrooms, 4 bathroom + 1 powder room residence showcases exceptional craftsmanship and thoughtful design throughout its expansive living spaces. Step into a grand foyer that flows seamlessly into a sun-drenched family room and formal dining area, perfect for sophisticated entertaining. The gourmet kitchen features premium appliances, custom cabinetry, and a walkout to an oversized deck with a pre-installed gas BBQ hookup-ideal for effortless outdoor dining and summer entertaining. Beyond, lush private grounds await, complete with two productive cherry trees and a flowering crabapple, offering seasonal beauty and homegrown delights. Ascend to the upper level, where a lavish primary suite with a luxurious private ensuite awaits, complemented by three additional generously sized bedrooms and abundant closet space. The fully finished walkout basement offers remarkable versatility with 2 bedrooms and a stackable washer and dryer bathroom, plus a raw cold cellar for wine storage or seasonal preserves-ideal for multigenerational living, rental income, or entertaining. Situated on one of the neighbourhood's most desirable streets, this home is moments from schools, scenic trails, parks, and Highway 11 access. With its attached double-car garage, premium finishes, and unbeatable location, 3119 Emperor Drive represents a rare opportunity to own a turnkey luxury home in Westridge. Schedule your private showing today and experience exceptional living at its finest.

3119 Emperor Drive, Orillia
$759,900
8 Beds ⋅ 4 Baths ⋅ S13699162 MLS
Well built three unit investment property offering a great opportunity for investors or owner occupiers. Constructed with ICF, the building features an insulated attached garage and is conveniently located close to the hospital and other amenities. The lower 2 bedroom unit is currently rented for $1,650/month, while the main floor unit rents for $1,800/month, both with great tenants in place. The upper 3 bedroom unit is currently vacant, providing flexibility to set your own rent or occupy the unit yourself. A solid income producing property with established rental income and additional upside from the vacant unit.

102 Dunlop Street, Orillia
$1,459,900
9 Beds ⋅ 6 Baths ⋅ S13685386 MLS
Exceptional opportunity to own a purpose-built triplex in a convenient Orillia location. Thoughtfully designed for today's rental market, this quality multi-residential property offers three spacious, self-contained, separate units, modern finishes and energy-efficient construction - an ideal addition to any investment portfolio. Each unit offers approximately 1,500 sq. ft. of living space with 3 bedrooms and 2 bathrooms, providing an impressive amount of space rarely found in rental accommodations. All three units feature private entrances, in-suite laundry and new appliances, along with bright, functional layouts and contemporary finishes designed for comfortable everyday living. Built using ICF (Insulated Concrete Form) construction, the property offers excellent insulation, energy efficiency and year-round comfort. With approximately 4,500 sq. ft. of combined living space, 9 bedrooms and 6 bathrooms across three separate residences, this property presents a compelling opportunity for investors seeking a low-maintenance income property. Conveniently situated on Barrie Road with easy access to shopping, restaurants, transit, schools and everyday amenities, while just minutes from downtown Orillia and the waterfront. An outstanding turnkey investment opportunity in Orillia.

165 Barrie Road, Orillia
$981,000
7 Beds ⋅ 5 Baths ⋅ S13650796 MLS
Welcome to this exceptional raised bungalow with a unique loft design, offering an impressive blend of luxury, functionality, and versatility. Set on a spectacular ravine lot, this beautifully appointed home features 4 spacious bedrooms above grade, including a private loft retreat complete with its own bedroom and full bathroom-ideal for guests, extended family, or a home office. The sun-filled main level showcases open to above family room, hardwood floors, and an open concept layout designed for both everyday living and entertaining. The modern kitchen is equipped with stainless steel appliances and overlooks the elegant living and dining spaces, all framed by picturesque ravine views.The professionally finished lower level offers incredible flexibility with 3 additional bedrooms, a kitchenette, pot lights throughout, and a separate layout with outstanding in-law or income potential. The oversized 3 car tandem garage provides ample parking and storage. Thoughtfully upgraded throughout with exceptional craftsmanship and attention to detail, this turnkey home leaves nothing to be desired. Ideally located just moments from Costco, Home Depot, shopping, restaurants, transit, parks, and every major convenience, this is a rare opportunity to own a one-of-a-kind home in an unbeatable location. A truly must-see property that perfectly combines elegant bungalow living with the added versatility of a loft.

3046 Monarch Drive, Orillia
$1,179,000
7 Beds ⋅ 4 Baths ⋅ S13649236 MLS
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.

22 Olive Crescent, Orillia
$1,879,000
6 Beds ⋅ 3 Baths ⋅ S13229844 MLS
A rare waterfront opportunity on the shores of Lake Couchiching (Trent System), featuring nearly 98 feet of pristine shoreline with a private dock, beach frontage, and unobstructed water views. Set on an irregular lot of approximately 97.81 210.36 ft (0.5-1.99 acres) within beautifully manicured, wooded grounds in a tranquil Orillia community (zoned R1).This distinguished 1.5-storey home - built c. 1914 with stone and wood construction and asphalt shingle roof - delivers over 4,980 finished sq ft across 6 bedrooms, 3 bathrooms, and 11 rooms. The main floor features a granite eat-in kitchen with centre island and maple cabinetry, a formal dining room with hardwood floors and crown moulding, a gas fireplace family room, and a sweeping 43-foot sunroom with walkout to the yard. The primary suite includes a 3-piece ensuite and walk-in closet. Two additional main-floor bedrooms open onto the sunroom. The upper level offers two bedrooms and a massive games room above the garage.Additional highlights: 4-car attached garage with upper loft, 12 total parking spaces, forced air gas heating, central A/C, municipal water and sewers, and a wired generator. Appliances, washer/dryer, and dock included (as is). HWT is a rental. Taxes $12,715 (2024). ** See Unbranded Virtual Tour URL for a full video**

345 Brewery Lane, Orillia
$825,000
6 Beds ⋅ 4 Baths ⋅ S13571966 MLS
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.

84 Mississaga Street W, Orillia
$2,490,000
6 Beds ⋅ 6 Baths ⋅ S13464810 MLS
83' of Lake Couchiching waterfront on a quiet family friendly sought after cul-de-sac. Stunning 5,700 sq. foot custom home built in 2018 with 6+ bedrooms & 6 bathrooms. Large welcoming foyer with a view straight to the water and walk in closet. The open concept main floor offers a chefs kitchen with tons of cabinet space, breakfast bar, double stainless farm sink and stone counters, spacious dining area with a walkout to the water view deck, and a living room with , a cathedral ceiling, floor to ceiling windows and gas stone fireplace. Main floor Principal suite overlooking the water with a spacious 5 piece ensuite and 14 x 10 closet with custom built-ins. Convenient pantry, laundry, 3 piece bath and mud room off the 3 car garage finish off the main floor. Upstairs there is 2 bedrooms with walk-in closets and private ensuites, an open loft area perfect for office space, a library etc plus a huge family/theatre room with a wet bar and 2 piece bath. Downstairs is finished with a fabulous space for a games room with a wet bar area, 3 bedrooms, a 3 piece bath plus a room for a gym or craft room etc.Perfect for entertaining, this home was built with space for everyone. Fabulous 4 Season Muskoka room with a gas fireplace to enjoy the water views. Great boating on the Trent Severn and easy access thru the Narrows to Lake Simcoe.If you are lucky you will see the beautiful swans in the area.

465 Mooney Crescent, Orillia
$1,098,000
10 Beds ⋅ 9 Baths ⋅ S13464316 MLS
Investor Alert! Seize a rare, high-yield opportunity with this modern, purpose-built legal duplex at 371 Barrie Street, Orillia. Constructed in 2018, this turnkey property is being sold as a corporation, offering savvy buyers significant tax savings on the purchase and the added financial advantage of a carry-forward loss. Designed for maximum rental efficiency and comfort, the building features two expansive above-ground floors housing a total of eight bedrooms-each uniquely equipped with its own private bathroom. These levels provide bright, spacious common living areas and well-appointed kitchens for residents. Adding even more value is the self-contained walk-out lower level, which serves as a full two-bedroom, two-bathroom apartment. With a realistic 7% cap rate and a layout optimized for low-vacancy this is a cornerstone asset for any portfolio. Don't miss out on this sophisticated blend of modern construction and strategic tax positioning.

371 Barrie Road, Orillia
$595,000
6 Beds ⋅ 2 Baths ⋅ S13226650 MLS
What If Homeownership Cost Less Than Renting? Step Up To 58 Nottawasaga Street. This Legal Duplex Features Two Bright And Spacious 3-Bedroom Units, Both Above Grade. Whether You're A First-Time Buyer Looking To Offset Your Housing Costs Or An Investor Seeking Strong Rental Potential, This Property Delivers Flexibility And Long-Term Value. Extensively Renovated Over The Past 10 Years, The Home Offers Modern Finishes And Updated Major Systems Without The Worry Of Immediate Capital Expenses. Bring Your Imagination To The Third Floor Loft, A Flexible Space With Potential For Additional Living Area, A Home Office, Studio, Or Storage. Enjoy A Lifestyle Just Minutes From Lake Couchiching, Downtown Shops And Restaurants, Parks, Trails, And All The Conveniences That Make Orillia One Of Ontario's Fastest-Growing Communities.

58 Nottawasaga Street, Orillia
$1,199,000
8 Beds ⋅ 4 Baths ⋅ S13078240 MLS
The Perfect Fourplex doesn't come around very often....Until Today!! 416 Gill Street is a purpose built, all brick fourplex with four 2 Bedroom , 1 Bath apartments, all the same, approximately 860 sqft each. The property is fully tenanted with four fantastic tenants. Property provides 8 parking spaces for your tenants. The updated apartments are in fantastic condition, three with newer kitchens. All units have separately metered forced air gas furnaces, separate hydro meters and a large in unit storage closet. Sound proofing added between upper and lower apartments for peaceful living. New 25 Year Architectural Shingles in 2014 and all new windows in 2017/18. On-site Coin Laundry for tenant convenience, two washers and two gas dryers, all owned. All units also have full size appliances. New back up generator installed in 2025 that powers part of the building including hot water. Very large lot for your tenants to enjoy the yard, but could also be large enough to add additional dwelling units on property (check with City of Orillia Planning). There is lots of upside on tenant turnovers as well. A great addition to your multi-unit investment portfolio or perfect hassle free investment to get started on your Landlord journey.

416 Gill Street, Orillia
$2,599,000
12 Beds ⋅ 12 Baths ⋅ S13075776 MLS
Incredible investment opportunity in Orillia. Fully occupied 12-unit apartment building with stable income from day one.The property generates approximately $189,322 annually and is supported by long-term, quality tenants. A well-balanced unit mix and strong occupancy make this a reliable asset with clear potential for future rent growth.One of the key advantages is the location. The building is within walking distance to the lakefront, parks, and scenic trails, offering easy access to nature, waterfront views, and outdoor activities. This lifestyle factor strongly attracts tenants and supports long-term demand.Located in a rapidly developing area, Orillia continues to grow, with expanding infrastructure and increasing interest from young professionals.This is a clean, straightforward investment with solid fundamentals, consistent cash flow, and long-term upside.

263 Canice Street, Orillia
$1,500,000
9 Beds ⋅ 7 Baths ⋅ S13034688 MLS
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.

184 Borland Street E, Orillia
$449,400
6 Beds ⋅ 3 Baths ⋅ S12994782 MLS
Opportunity awaits in this detached 1-storey family home located on a quiet residential street in south-central Orillia. Situated on a standard-sized lot measuring approximately 57.6 x 115 ft (irregular), this property offers a solid footprint with 1,472 sq. ft. above grade plus a full, mostly finished basement. The home features 4+1 bedrooms and three 3-piece bathrooms, providing flexible living space for families, multi-generational living, or renovation potential.The main level offers a functional layout with a combined living and dining area, kitchen, bedroom, and full bathroom. The upper level includes additional bedrooms with hardwood flooring. The partly finished basement includes a recreation room, bedroom, and a partially completed bathroom, offering added living space. Flooring throughout is a mix of hardwood, laminate, carpet, and vinyl.

345 LINWOOD Avenue, Orillia
$2,299,000
12 Beds ⋅ 7 Baths ⋅ S12994258 MLS
Exceptional opportunity to own a fully renovated 7-unit apartment building with high in-place income and excellent tenant profile. Completely occupied, this turnkey investment has been thoughtfully upgraded in 2023 with new doors, windows, flooring, water tank, modern appliances, and energy-efficient floor heating. A newly added retaining wall maximizes functionality by increasing available parking. The property includes 5 spacious 2-bedroom, condo-style apartments featuring wall A/C units and updated kitchens with dishwashers, one 1-bedroom apartment, and 1 bachelor. Designed for both tenant comfort and investor peace of mind, this well-maintained asset offers a compelling blend of stability, quality, and long-term growth potential. All tenants pay their own hydro. It is located within walking distance of the lake and marina.

235 Canice Street, Orillia