Welcome to your go-to resource for finding houses for sale in Simcoe, Ontario, a charming town in Norfolk County known for its vibrant community and beautiful landscapes. Whether you’re a first-time buyer, looking to upgrade, or seeking an investment property, our listings feature a variety of homes to meet your needs and budget. Discover the best houses in Simcoe with our curated selection, detailed information, and expert guidance.

Forgot password Extend Verify Contact

4950 Penetanguishene Road
Hillsdale Simcoe L0L 1V0

$1,399,900
Residential Freehold beds: 4 baths: 3.0

Main Photo: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 1: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 2: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 3: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 4: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 5: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 6: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 7: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 8: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 9: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 10: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 11: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 12: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 13: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 14: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 15: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 16: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 17: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 18: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 19: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 20: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 21: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 22: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 23: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 24: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 25: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 26: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 27: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 28: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 29: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 30: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 31: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 32: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 33: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 34: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 35: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 36: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 37: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 38: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 39: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 40: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 41: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 42: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 43: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 44: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 45: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 46: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 47: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Photo 48: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
S12374012
Bedrooms:
4
Bathrooms:
3
Welcome to one of Hillsdale's most prestigious century homes - a true hidden gem that blends timeless elegance with modern comfort. Nestled on over 5 acres of complete privacy, this extraordinary estate is surrounded by the magic of Simcoe Countys autumn colours, offering a front-row seat to natures most spectacular show.From the moment you arrive, the historic charm is undeniable original wood trim, rich hardwood floors, a gracious wraparound porch, and soaring ceilings all whisper stories of a bygone era. Imagine sipping tea on the porch while fiery maples and golden oaks dance around you, or strolling through your own secret garden as leaves crunch softly underfoot.Inside, a beautifully updated kitchen with a centre island anchors the main floor, while custom built-ins add warmth and character. The luxurious primary suite on the second level is a private haven, complete with spa-inspired ensuite and generous walk-in closets. Upstairs, the fully converted attic (an expansive 958 sq ft) floods with natural light, perfect for an inspiring studio, entertainment lounge, or additional bedrooms.The lower level is full of delightful surprises: a large workshop (15x23), a cozy den/man cave (13x15) with a secret door to hidden wine storage, and plenty of flexible space for hobbies or storage.Outdoors, the beauty of fall envelops you. Mature trees frame the property in brilliant reds, oranges, and yellows, while a peaceful Zen garden offers a quiet retreat. A massive barn/shop provides room for toys, tools, or even animals. And with Simcoe County forest trails backing directly onto the property, hiking, biking, or snowshoeing is just a step away.All this, while still being less than 20 minutes to Midland or Barrie, and just 5 minutes to Craighurst for essentials.This isnt just a home its an experience. A rare opportunity to embrace the slower, richer rhythms of country life, surrounded by the ever-changing beauty of the seasons.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2 1/2 Storey
Approx. Age:
100+
Total Approx Floor Area:
2500-3000
Lot Size:
5-9.99
Depth:
0'
Frontage:
408'10¾"
Lot Shape:
Irregular
Topography:
Hilly
Direction Faces:
East
Bedrooms:
4
Bathrooms:
3.0
Water supply:
Well
Kitchens:
1
Bedrooms Above Grade:
4
Kitchens Above Grade:
1
Rooms Above Grade:
7
Rooms Below Grade:
1
Zoning:
A-1
Heating type:
Forced Air
Heating Fuel:
Propane
Fireplaces:
1
Foundation:
Stone
Roof:
Asphalt Shingle
Basement:
Full, Partially Finished
Fireplace Features:
Propane
Fireplace/Stove:
Yes
Garage:
Carport
Garage Spaces:
2.0
Other Structures:
Barn
Parking Features:
Private
Parking Spaces:
10
Total Parking Spaces:
12.0
Family Room:
Yes
Pool:
None
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$3,750 / 2025
Assessment:
$- / -
Springwater
Hillsdale
Simcoe
Golf, Greenbelt/Conservation, Park, School, School Bus Route, Wooded/Treed
Built-In Oven, Storage, Water Softener
Landscaped, Porch, Privacy, Year Round Living
hot water heater, propane tank and water softener
Oven, Cook Top, Dishwasher, Fridge/Freezer, Light Fixtures, Washer, Dryer
Brick
No
None
Garden, Forest, Trees/Woods
Floor
Type
Size
Other
Main
Kitchen
17'2" × 14'5"
Main
Dining Room
17'3" × 15'5"
Main
Family Room
27'9" × 15'6"
Second
Primary Bedroom
17'1⅛" × 14'3"
Second
Bedroom 2
15'8" × 13'2"
Second
Bedroom 3
12'6" × 12'6"
Third
Loft
35' × 25'
Floor
Ensuite
Pieces
Other
Main
No
2
0' x 0' 2 Pc Bath
Upper
Yes
4
0' x 0' 4 Pc Ensuite
Upper
No
4
0' x 0' 4 Pc Bath
Utilities Water:
No
Water Supply Types:
Drilled Well
Sewers:
No
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Ensuite Laundry:
No
Laundry Level:
Main Level
Date Listed:
Sep 02, 2025
Original Price:
Previous Price:
  • Photo 1: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 1 of 48
  • Photo 2: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 2 of 48
  • Photo 3: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 3 of 48
  • Photo 4: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 4 of 48
  • Photo 5: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 5 of 48
  • Photo 6: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 6 of 48
  • Photo 7: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 7 of 48
  • Photo 8: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 8 of 48
  • Photo 9: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 9 of 48
  • Photo 10: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 10 of 48
  • Photo 11: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 11 of 48
  • Photo 12: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 12 of 48
  • Photo 13: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 13 of 48
  • Photo 14: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 14 of 48
  • Photo 15: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 15 of 48
  • Photo 16: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 16 of 48
  • Photo 17: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 17 of 48
  • Photo 18: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 18 of 48
  • Photo 19: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 19 of 48
  • Photo 20: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 20 of 48
  • Photo 21: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 21 of 48
  • Photo 22: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 22 of 48
  • Photo 23: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 23 of 48
  • Photo 24: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 24 of 48
  • Photo 25: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 25 of 48
  • Photo 26: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 26 of 48
  • Photo 27: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 27 of 48
  • Photo 28: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 28 of 48
  • Photo 29: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 29 of 48
  • Photo 30: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 30 of 48
  • Photo 31: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 31 of 48
  • Photo 32: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 32 of 48
  • Photo 33: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 33 of 48
  • Photo 34: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 34 of 48
  • Photo 35: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 35 of 48
  • Photo 36: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 36 of 48
  • Photo 37: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 37 of 48
  • Photo 38: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 38 of 48
  • Photo 39: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 39 of 48
  • Photo 40: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 40 of 48
  • Photo 41: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 41 of 48
  • Photo 42: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 42 of 48
  • Photo 43: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 43 of 48
  • Photo 44: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 44 of 48
  • Photo 45: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 45 of 48
  • Photo 46: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 46 of 48
  • Photo 47: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 47 of 48
  • Photo 48: 4950 Penetanguishene Road in Simcoe: Hillsdale House for sale (Springwater)  : MLS®# S12374012
    Photo 48 of 48
Listed by RE/MAX HALLMARK CHAY REALTY
Data was last updated September 7, 2025 at 06:15 PM (UTC)
Area Statistics
Listings on market:
14
Avg list price:
$1,064,900
Min list price:
$749,000
Max list price:
$2,175,000
Avg days on market:
48
Min days on market:
2
Max days on market:
345
These statistics are generated based on the current listing's property type and located in Hillsdale. Average values are derived using median calculations. This data is not produced by the MLS® system.
DARYL  KING
powered by myRealPage.com

Explore Houses for Sale in Simcoe, Ontario

Browse our comprehensive listings of houses for sale in Simcoe, offering a range of styles, sizes, and price points. Each listing includes detailed descriptions, high-quality photos, and essential information to help you make an informed decision. Whether you’re looking for a cozy family home, a spacious property with a large yard, or a modern residence, our listings cater to all preferences.

Why Buy a Home in Simcoe, Ontario?

Simcoe offers the perfect blend of small-town charm and modern amenities, making it an ideal place for families, retirees, and professionals. With excellent schools, beautiful parks, and a welcoming community, Simcoe is a great place to call home. Its location in Norfolk County provides easy access to nearby cities and recreational opportunities, including Lake Erie’s beaches and trails.

Navigating the Home Buying Process in Simcoe

Buying a home in Simcoe involves important considerations, such as financing options, market trends, and neighborhood amenities. Our expert team is here to guide you through each step, offering personalized advice on mortgages, property inspections, and long-term investment strategies to help you make the best decision.

Start Your Search for a Home in Simcoe Today

Begin your journey to find the perfect house in Simcoe with us. Our user-friendly platform and dedicated team are here to assist you every step of the way, ensuring a smooth and rewarding home-buying experience.

Explore our listings and discover the ideal property for your next move or investment. Let us help you find your dream home in Simcoe, Ontario.

Explore More Real Estate Options in the GTA:

Each of these links will guide you to a dedicated subpage with detailed listings and information tailored to your specific real estate needs.