NEXT Open House details
Oct 18, 2026 01:00 PM - 03:00 PM EDT

44 HIGHLAND Drive
Horseshoe Valley Oro-Medonte L0L 2L0

$1,599,000
Residential Freehold beds: 4+1 baths: 4.0

Over 4100 finished living space
Photo 1: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 2: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 3: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 4: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 5: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 6: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 7: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 8: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 9: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 10: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 11: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 12: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 13: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 14: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 15: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 16: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 17: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 18: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 19: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 20: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 21: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 22: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 23: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 24: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 25: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 26: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 27: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 28: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 29: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 30: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 31: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 32: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 33: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 34: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 35: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 36: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 37: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 38: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 39: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 40: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 41: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 42: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 43: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 44: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 45: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 46: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 47: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 48: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Photo 49: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
Open House - Oct 18, 2026
01:00 PM - 03:00 PM EDT
NOTES: Open House on Sunday, October 18, 2026 1:00PM - 3:00PM
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
S14084702
Bedrooms:
4+1
Bathrooms:
4
Welcome to your home in paradise with all the luxurious extras you'd put on your wish-list! Home inspected, thumbs up! This heavenly, one acre parcel has a backyard retreat which includes a 16 x 32 foot, saltwater pool (high efficiency radiant heating), oversized Hot Tub, large enclosed patio area with rust proof fenced enclosure. Add the large outbuilding with built-in cabana, an overnight bunkie room, plus storage area for the pool equipment etc. There are several walk-outs to a large deck area for family get togethers and just a few steps down on your private forested ravine, you have a custom stone firepit setting for those evening smores! Trails throughout this area in the Highland Hills (sunset views!). Now step into your custom built residence with beautiful slate and hardwood flooring, cathedral ceilings and a layout that breathes luxury. Perfect space here to work from home (office with granite topped, built-in desk) or bring extended family with the separate entrance access to in-law space in the fully finished basement (bedroom, bath, kitchenette and gas fireplace). The kitchen is a chef's dream with professionally refinished cabinetry (2025), huge working island (granite c/tops throughout), breakfast bar, pantry, and endless cupboards. Open concept here as it overlooks the living room (fireplace and walk out to deck) and your backyard bliss. Moving up to the second floor, the master bedroom is truly a delight with cozy double sided gas fireplace adjoining your private sitting room, huge and say it again, huge walk-in closet, and a walkout to the balcony overlooking the backyard pool, ravine and beautiful skyline. The spa-like master bath features wifi thermostat and heated floors. The oversize drive is interlock paved with plenty of room for your truck, toys and guest parking. The 3 car garage doors are wifi entry and upgraded wiring is installed for an electric charger. This is a 'must visit' property you won't want to miss!
Under Contract:
Hot Water Heater, Security System
Property Type:
Residential Freehold
Property Sub Type:
Detached
Property Attached:
No
Home Style:
2-Storey
Approx. Age:
16-30
Total Approx Floor Area:
3000-3500
Lot Size:
.50-1.99
Lot Depth:
446'10"
Lot Frontage:
108'5"
Lot Shape:
Irregular
Lot Details:
401.87 x 108.4
Topography:
Terraced, Wooded/Treed
Direction Faces:
West
Bedrooms:
4+1
Bathrooms:
4.0
Water supply:
Municipal
Kitchens:
1
Kitchens in Basement:
0
Bedrooms Above Grade:
4
Bedrooms Below Grade:
1
Kitchens Above Grade:
1
Rooms Above Grade:
14
Rooms Below Grade:
3
Rooms:
17
Zoning:
R1 Residential
Heating type:
Forced Air
Heating Fuel:
Gas
Fireplaces:
4
Foundation:
Poured Concrete
Roof:
Asphalt Shingle
Basement:
Full, Walk-Up, Finished, Separate Entrance
Fireplace Features:
Living Room, Family Room, Natural Gas
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
3.0
Other Structures:
Out Buildings
Parking Features:
Private Double, Inside Entry
Parking Spaces:
10
Total Parking Spaces:
13.0
Family Room:
Yes
Possession Details:
Flexible
Lot Irregularities:
irregular
Pool:
Inground, Salt
Link:
No
HST Applicable To Sale Price:
Included In
Assessment:
$896,000
Assessment Year:
2026
Taxes:
$9,468.33 / 2026
Assessment:
$896,000.00 / 2026
Simcoe
Oro-Medonte
Horseshoe Valley
Fenced Yard, Golf, Ravine, Wooded/Treed
Built-In Oven, Auto Garage Door Remote, Countertop Range, Central Vacuum, In-Law Capability, Storage, Water Softener, Sump Pump
Hot Tub, Deck, Landscaped, Patio, Lawn Sprinkler System, Recreational Area
Carbon Monoxide Detectors, Smoke Detector, Security System
Two hot water tanks
Built-in fridge, oven, microwave, countertop gas range, dishwasher, wine fridge, washer, dryer, Hot tub, Pool equipment, water softener
Personal belongings
None
Stucco (Plaster)
No
None
Forest, Panoramic, Golf Course, Trees/Woods
Floor
Type
Size
Other
Main
Kitchen
21'11¾" × 14'8"
Centre Island, Breakfast Bar, Granite Counters
Main
Family Room
21'11¾" × 13'
Gas Fireplace, Hardwood Floor, W/O To Deck
Main
Dining Room
15'1" × 12'6"
Hardwood Floor
Main
Living Room
19'6" × 14'
W/O To Pool, Gas Fireplace, Broadloom
Main
Office
13'5" × 11'
Granite Counters, B/I Desk
Main
Laundry
8'2" × 8'2"
Slate Flooring, 2 Pc Bath
Second
Primary Bedroom
17'2" × 16'6"
Walk-In Closet(s), Gas Fireplace, W/O To Balcony
Second
Sitting
16'2" × 9'10"
Gas Fireplace
Second
Bedroom
12'10" × 12'
Second
Bedroom
12'8¾" × 12'6"
Second
Bedroom
13'1" × 11'
Basement
Bedroom
12' × 10'6"
Basement
Living Room
27' × 26'
Walk-Up, Combined w/Dining, Breakfast Bar
Floor
Ensuite
Pieces
Other
Second
Yes
5
7'5¾" x 16'2⅞" 5 Pc Ensuite
Second
No
4
11'1" x 7'9" 4 Pc Bath
Basement
No
4
6'11" x 6'2" 4 Pc Bath
UFFI:
No
Utilities Gas:
Yes
Utilities Hydro:
Yes
Utilities Water:
Yes
Sewers:
No
Special Designation:
Unknown
Sewers:
Septic
Air Conditioning:
Central Air
Central Vacuum:
Yes
Seller Property Info Statement:
No
Laundry Level:
Main Level
Date Listed:
Oct 16, 2026
  • Photo 1: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Over 4100 finished living space
  • Photo 2: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 2 of 49
  • Photo 3: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    All fenced patio/pool with no-rust fencing.
  • Photo 4: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Main floor family/living area
  • Photo 5: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Huge custom kitchen open to extra fam/living room
  • Photo 6: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Triple garage -wired wifi and for electric charger
  • Photo 7: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 7 of 49
  • Photo 8: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 8 of 49
  • Photo 9: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Cathedral height entry area
  • Photo 10: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Built-in, granite topped desk in office
  • Photo 11: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 11 of 49
  • Photo 12: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Separate Dining room overlooks front gardens
  • Photo 13: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Gas fireplace, w/out to large deck
  • Photo 14: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Large island workspace, double sinks
  • Photo 15: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Built-in stainless steel appliances
  • Photo 16: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    All new cabinetry 2025, wine fridge
  • Photo 17: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Picture perfect, w/out to side deck
  • Photo 18: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Open concept to kitchen, note second island/bar
  • Photo 19: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 19 of 49
  • Photo 20: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 20 of 49
  • Photo 21: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Large master -w/out to balcony overlooking pool
  • Photo 22: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 22 of 49
  • Photo 23: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Double sided gas fireplace
  • Photo 24: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Huge walk-in closet, built-in shelving/storage
  • Photo 25: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Sitting room, fireplace
  • Photo 26: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Sitting room off master
  • Photo 27: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Spa-size 5 pc ensuite to Master BR
  • Photo 28: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 28 of 49
  • Photo 29: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    2nd Bedroom
  • Photo 30: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    2nd Bedroom o/looks backyard
  • Photo 31: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Main bathroom, 5 pc on 2nd floor
  • Photo 32: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    3rd Bedroom
  • Photo 33: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Bsmt level 5th Bedroom
  • Photo 34: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    4th bedroom
  • Photo 35: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Bsmt level - 4pc
  • Photo 36: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Built-in granite toppe breakfast bar with bar sink
  • Photo 37: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Dinette area/Bsmt
  • Photo 38: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Bsmt living area, gas fireplace, Sep Entrance
  • Photo 39: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Large deck off fam & Living rooms
  • Photo 40: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Huge i/lock patio/sitting area, Hot Tub
  • Photo 41: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Outbuilding with cabana, mini-bunkie, pump room
  • Photo 42: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    16x32 ft saltwater pool
  • Photo 43: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Photo 43 of 49
  • Photo 44: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Mini bunkie in outbuilding
  • Photo 45: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Cabana room in outbuilding
  • Photo 46: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Custom firepit area sequestered in the trees
  • Photo 47: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Aerial photo
  • Photo 48: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Horseshoe Highlands
  • Photo 49: 44 HIGHLAND Drive in Oro-Medonte: Horseshoe Valley House for sale : MLS®# S14084702
    Lot backs onto trails, golf and more!
Listed by RIGHT AT HOME REALTY
Data was last updated October 16, 2026 at 06:15 AM (UTC)
Area Statistics
Listings on market:
21
Avg list price:
$1,198,000
Min list price:
$749,900
Max list price:
$1,775,000
Avg days on market:
38
Min days on market:
0
Max days on market:
647
These statistics are generated based on the current listing's property type and located in Horseshoe Valley. Average values are derived using median calculations. This data is not produced by the MLS® system.
ANTHONY OLIVERA
ANN RAHINEL
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.