Simcoe County

Located just north of the Greater Toronto Area stretching from the shores of Lake Simcoe to the east and Georgian Bay to the West. Enjoy the natural beauty that Simcoe County has to offer along with over 50 golf courses and 50 marinas, 7 Provincial Parks and almost a dozen breweries/distillers and a dozen farmers markets. Simcoe County is your historic, cultural and outdoor recreation destination!

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Simcoe County 500K-1M

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  • 1614 Ridge Road E, Oro-Medonte

    1614 Ridge Road E Hawkestone Oro-Medonte L0L 1T0
    Main Photo: 1614 Ridge Road E, Oro-Medonte

    1614 Ridge Road E Oro-Medonte L0L 1T0 Hawkestone

    $3,299,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    S6142920
    Bedrooms:
    6
    Bathrooms:
    5
    Welcome To 'Hawkstone Manor' In Old Charm Historical Hawkestone, Oro-Medonte. First Time Offer For Sale After Completing A Full Preservation Of This Unique Century Grand Manor Home And Fully Renovated Suites. Stunning Curb Appeal With Keystone Brick, Soaring Ceilings, Exquisite Trim Work & Superior Interior Finishes. Ensuite Laundry, Fireplace. The Building Features State Of The Art Mechanical Systems And Offers The Most In Home Comfort And Efficiencies. 7 fireplaces. Metal roof. Fully spray-foam insulation. New glazing & doors. New paved driveway. All units are separately metered for hydro & separate Water purifications systems & hot water heater per unit. New HVAC, Electrical, Fire security, well & septic systems. This 4 Storey Dwelling Has 5 Executive Suites (See Schedule For Each Floor Plan). This Is A Lifestyle Building With Exceptional Finishes Both In And Out. This Along With Manicured & Groomed Grounds Welcome The Most Discerned Investor, Occupants And Guests! **EXTRAS** Unlike any other 5 plex building - Huge estate manor (over 6,000 square feet) on just under an acre of property. Exceptional investment that is ‘turn key’, fully renovated & free form any future capital improvements. More details
    Listed by CENTURY 21 FINE LIVING REALTY INC.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 507 90 Dean Avenue, Barrie

    507 90 Dean Avenue Painswick South Barrie L4N 0M3
    Main Photo: 507 90 Dean Avenue, Barrie

    507 90 Dean Avenue Barrie L4N 0M3 Painswick South

    $409,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    S9231440
    Bedrooms:
    1
    Bathrooms:
    2
    The Terraces of Heritage Square is a Adult over 60+ building. These buildings have lots to offer, Party rooms, library, computer room and a second level roof top gardens. Ground floor lockers and parking. |These buildings were built with wider hallways with hand rails and all wheel chair accessible to assist in those later years of life. It is independent living with all the amenities you will need. Walking distance to the library, restaurants and shopping. Barrie transit stops right out front of the building for easy transportation. This Allandale Suite is 1 Bedroom with ensuite bath with a one piece shower with seat and safety bars. There's also a convenient 2 piece powder room across from the Den. The kitchen overlooks the Living Rooms with convenient look through. In suite Laundry with added storage. Open House tour every Tuesday at 2pm Please meet in lobby of 94 Dean Ave More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 1614 Ridge Road E, Oro-Medonte

    1614 Ridge Road E Hawkestone Oro-Medonte L0L 1T0
    Main Photo: 1614 Ridge Road E, Oro-Medonte

    1614 Ridge Road E Oro-Medonte L0L 1T0 Hawkestone

    $3,299,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    S6142848
    Major Bus.:
    Apts - 2 To 5 Units
    Total Area:
    6,000 sq. ft.
    Welcome To 'Hawkstone Manor' In Old Charm Historical Hawkestone, Oro-Medonte. First Time Offer For Sale After Completing A Full Preservation Of This Unique Century Grand Manor Home And Fully Renovated Suites. Stunning Curb Appeal With Keystone Brick, Soaring Ceilings, Exquisite Trim Work & Superior Interior Finishes. Ensuite Laundry, Fireplace. The Building Features State Of The Art Mechanical Systems And Offers The Most In Home Comfort And Efficiencies. 7 fireplaces. Metal roof. Fully spray-foam insulation. New glazing & doors. New paved driveway. All units are separately metered for hydro & separate Water purifications systems & hot water heater per unit. New HVAC, Electrical, Fire security, well & septic systems. This 4 Storey Dwelling Has 5 Executive Suites (See Schedule For Each Floor Plan). This Is A Lifestyle Building With Exceptional Finishes Both In And Out. This Along With Manicured & Groomed Grounds Welcome The Most Discerned Investor, Occupants And Guests! **EXTRAS** Unlike any other 5 plex building - Huge estate manor (over 6,000 square feet) on just under an acre of property. Exceptional investment that is ‘turn key’, fully renovated & free form any future capital improvements. More details
    Listed by CENTURY 21 FINE LIVING REALTY INC.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 1430 COUNTY RD 50 S, Adjala-Tosorontio

    1430 COUNTY RD 50 S Rural Adjala-Tosorontio Adjala-Tosorontio L0N 1P0
    Main Photo: 1430 COUNTY RD 50 S, Adjala-Tosorontio

    1430 COUNTY RD 50 S Adjala-Tosorontio L0N 1P0 Rural Adjala-Tosorontio

    $800,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    N9362823
    This picturesque 10-acre parcel of rolling land in Adjala-Tosorontio Township offers stunning, clear views in every direction, making it the ideal location to build your dream home. Conveniently situated just 45 minutes from the Greater Toronto Area, it provides easy access to nearby towns such as Orangeville, Newmarket, Bolton, Alliston, and Hockley Valley. More details
    Listed by REAL ESTATE HOMEWARD
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 4352 124 COUNTY Road, Clearview

    4352 124 COUNTY Road Rural Clearview Clearview L9Y 3Z1
    Main Photo: 4352 124 COUNTY Road, Clearview

    4352 124 COUNTY Road Clearview L9Y 3Z1 Rural Clearview

    $1,900,000 /For Sale
    Residential Freehold
    Status:
    Active
    MLS® Num:
    S10902116
    Bedrooms:
    3
    Bathrooms:
    1
    7 PLUS ACRES ON THE NORTHERN EDGE OF NOTTAWA. CLOSE TO COLLINGWOOD AND THE SKI AREAS. UNIQUE ZONING!! FEATURES INCLUDE A GREAT LITTLE STARTER HOME, SMALL POND ON SITE, OPEN SIDED STORAGE SHED. THIS WOULD BE AN EXCELLENT PROPERTY TO BUILD YOUR DREAM HOME ON AN ESTATE LIKE SETTING IN THE QUAINT LITTLE VILLAGE OF NOTTAWA. More details
    Listed by Century 21 Millennium Inc.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • LOT 1-6 36/37 NOTTAWASAGA Side Road, Clearview

    LOT 1-6 36/37 NOTTAWASAGA Side Road Nottawa Clearview L9Y 3Z1
    Main Photo: LOT 1-6 36/37 NOTTAWASAGA Side Road, Clearview

    LOT 1-6 36/37 NOTTAWASAGA Side Road Clearview L9Y 3Z1 Nottawa

    $1,945,000 /For Sale
    Residential Freehold
    Status:
    Active
    MLS® Num:
    S10894577
    Great opportunity to build your dream home on 45 acres in the Village of Nottawa, just south of Collingwood. In an area of estate homes (this street is known as "Doctor's Row") and also has some rural farms. Or bank the property as an investment for it's future development potential. It's located just south of the proposed site of the Poplar Regional Health and Wellness Village and proposed site of the new Collingwood Hospital. That corner of Poplar Sideroad & Raglan St is already the current home of the Georgian College South Georgian Bay Campus. Features of this 45 acre property include a pond located on the south portion, potentially a great location for your building site and the popular Clearview/Collingwood Train Trail which borders the entire west side of this property. (Previously a rail line, but now a maintained trail where you can bike or walk to downtown Collingwood or to the town of Stayner to the south). The Clearview Planning Department has reported that it can likely be split into two building lots based on the zoning and the size of the road frontage, to be confirmed by the Buyer. There are approximately 10 wooded acres for good privacy, including a beautiful stand of white birch trees in the NW corner. Reduce your property taxes with the Farm Tax Credit, as the current owners have, by having a farmer use the property. Currently about 20-25 acres are farmed in this manner on the north part of the property, with another 10-15 acres of workable land available. High Speed Fiber Optics is installed on the street. Visit my REALTOR website for further information about this Listing (under my contact info). More details
    Listed by Royal LePage Locations North
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 1536 Tiny Beaches Road N, Tiny

    1536 Tiny Beaches Road N Rural Tiny Tiny L9M 0J2
    Main Photo: 1536 Tiny Beaches Road N, Tiny

    1536 Tiny Beaches Road N Tiny L9M 0J2 Rural Tiny

    $3,399,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    S11896365
    Bedrooms:
    4
    Bathrooms:
    1
    *** Visit the REALTOR website for further information about this Listing *** Your opportunity to own an awesome four season waterfront beach house with 102 feet of sandy shoreline! This well maintained house is directly on the beaches of Georgian Bay and has an excellent sandy lake bottom. Gradual crystal clear water entry and ideal lake bottom gradient leads to deep water outside of the protected bay. This bay has a swim area that is protected by two rock groins provides excellent snorkeling and protected launch for jet boats and other toys. This unique gem has private properties on either side insuring tranquility. This property does not have adjacent public right of ways to lake. Amazing location north of Lafontaine and survey available. Incredible open water views of Blue Mountain with the South Western exposure, providing unbeatable sunsets and great sunlight in winter months. The cottage has brand new flooring. The massive waterside deck is great for entertaining. Great drilled well and oversized approved septic system. New steel roof and aluminum siding provide an ultra low maintenance house. Only 90 mins from GTA. Midland is twenty minutes away from the beach house. Midland has many options including Foodland, Superstore Canadian Tire, Home Depot, Georgian Bay Hospital and attractions such as the King Warfs Theatre. Start making priceless memories at this ideal family home in the exclusive cove beach community! More details
    Listed by EASY LIST REALTY LTD.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 8 Summerset Place, Essa

    8 Summerset Place Angus Essa L3W 0G4
    Main Photo: 8 Summerset Place, Essa

    8 Summerset Place Essa L3W 0G4 Angus

    $624,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    N11945884
    Bedrooms:
    4
    Bathrooms:
    2
    2 Unit home (Duplex) on a massive in town property 82.30 ft x 164.99 ft/ 0.31 acres in a very nice Angus neighborhood across from retail. Each unit has its own entrance and electrical panel so tenants pay their own hydro. Both units are above grade, bright and spacious with 2 bedrooms & 1 full bath. Units are tenanted so they require 24 hour notice to tenants for showings so please book your viewing with that in mind. Note: This property is beside 190 and 192 Mill Street which are also available for sale making it even more interesting for future development considerations. More details
    Listed by CENTURY 21 B.J. ROTH REALTY LTD.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 4570 Penetanguishene Road, Springwater

    4570 Penetanguishene Road Hillsdale Springwater L0L 1V0
    Main Photo: 4570 Penetanguishene Road, Springwater

    4570 Penetanguishene Road Springwater L0L 1V0 Hillsdale

    $1,150,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    S12094014
    Total Area:
    4,600 sq. ft.
    Excellent Investment Property. Annual income potential $130,000. Three Commercial Units On Main plus Two Residential 2 Bedroom Units On Upper Floor (Stores connect to apartments above for perfect live above work opportunity). Tenants Pay TMI and Utilities, Ample Parking for 15 vehicles, Access from busy Penetanguishene Road and also From Martin Street. Roof Updated Approximately 10 Years Ago, Some Windows Replaced, Kitchen upgraded, Furnace Replaced In 2018 (Rental). Large backyard with BBQ and picnic table and space can be fenced. Room to build a shed. Building Approximately 4,600 Square Feet. Conveniently located 2 minutes drive from Highway 400 and exit 121. Minutes to Horseshoe Value, Mount St Louis Moonstone Resort, and other ski resorts. A short drive to Awenda, Muskoka, Orr Lake, Georgian Bay Islands, Balm Beach, Midland, Penetanguishene, Innisfil, Barrie, Elmvale, Orillia, Wasaga, Lake Simcoe, 1-hr from Toronto, and more. Currently 2/3 commercial units are leased and both apartments are leased. Total 5 units in the building (3 commercial plus 2 apartments above). Building appraised for 1.2 million in December 2025. More details
    Listed by COLDWELL BANKER THE REAL ESTATE CENTRE
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 159 11 Line N, Oro-Medonte

    159 11 Line N Rural Oro-Medonte Oro-Medonte L0L 1T0
    Main Photo: 159 11 Line N, Oro-Medonte

    159 11 Line N Oro-Medonte L0L 1T0 Rural Oro-Medonte

    $729,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    S12102994
    52.4 acre farmland & horsebarn less than a minute to Hwy 11 in a very desirable area based on its proximity to Orillia & Barrie! This flat parcel is newly severed from the existing house and ideal for equestrians, farmers or investors to consider especially if they are also interested in the 93.47 acres also for sale on Line 12. (See listing photos for more information on severance details and accessibility to acreage on line 12) Zoned Agricultural Rural & EP. More details
    Listed by CENTURY 21 B.J. ROTH REALTY LTD.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 10 12 Line N, Oro-Medonte

    10 12 Line N Rural Oro-Medonte Oro-Medonte L0L 1T0
    Main Photo: 10 12 Line N, Oro-Medonte

    10 12 Line N Oro-Medonte L0L 1T0 Rural Oro-Medonte

    $1,539,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    S12106183
    Bedrooms:
    5
    Bathrooms:
    2
    93.47 acres of farmland with amazing visual exposure of 1,555 feet right on busy Highway 11 perfectly positioned between Barrie and Orillia making this a prime piece of real estate for today and the future. Features a very large renovated barn and 2nd detached smaller barn. Also features $150K in fencing and is currently used as pasture. Great opportunity for farmers, equestrians and investors. Property recently had 2.9 acres severed from it and does not include the house or garage. Abutting 52.4 acres that is also for sale on Line 11. (See listing photos for more information on severance details and accessibility to acreage at 159 line 11 N) So much opportunity here in a sought after part of Oro only 10 minutes to Orillia, Costco and 15 minutes to Barrie. More details
    Listed by CENTURY 21 B.J. ROTH REALTY LTD.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)

  • 403 & 404 10 Keith Avenue, Collingwood

    403 & 404 10 Keith Avenue Collingwood Collingwood L9Y 0W5
    Main Photo: 403 & 404 10 Keith Avenue, Collingwood

    403 & 404 10 Keith Avenue Collingwood L9Y 0W5 Collingwood

    $599,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    S12119227
    Major Bus.:
    Restaurant
    Total Area:
    2,950 sq. ft.
    Welcome to Harbour Street Fish Bar a thriving, turn-key restaurant and bar now available for sale. This well-established business is ready for its next owner to carry on the legacy and make their mark in one of Collingwood's most dynamic west-end locations. Surrounded by vibrant residential neighborhoods and popular attractions, Harbour Street Fish Bar is a local staple known for its standout menu and unmatched live music scene. Ask any local where to go dancing in town, and you'll hear Harbour Street Fish Bar time and time again. With indoor seating for over 100 guests and an additional 55 seats on the patio, there's plenty of space to welcome loyal regulars and curious newcomers alike. The fully equipped kitchen and bar are ready for a smooth transition to new ownership. Rare opportunity to take the rein of a beloved local hotspot in the heart of Collingwood's vibrant business scene. More details
    Listed by Century 21 Millennium Inc.
    LISTING DETAILS
    NANCY PIERCE (Sales Representative)
    DAVE DUNCAN (Sales Representative)
1-12/1,500
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Data was last updated October 16, 2026 at 06:15 AM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.

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This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.