Over 4100 finished living space
44 HIGHLAND Drive photo 2
All fenced patio/pool with no-rust fencing.
Main floor family/living area
Huge custom kitchen open to extra fam/living room
44 HIGHLAND Drive photo 6
Triple garage -wired wifi and for electric charger
44 HIGHLAND Drive photo 8
44 HIGHLAND Drive photo 9
44 HIGHLAND Drive photo 10
44 HIGHLAND Drive photo 11
Separate Dining room overlooks front gardens
Gas fireplace, w/out to large deck
Large island workspace, double sinks
Built-in stainless steel appliances
All new cabinetry 2025, wine fridge
Picture perfect, w/out to side deck
Open concept to kitchen, note second island/bar
44 HIGHLAND Drive photo 19
44 HIGHLAND Drive photo 20
Large master -w/out to balcony overlooking pool
44 HIGHLAND Drive photo 22
Double sided gas fireplace
Huge walk-in closet, built-in shelving/storage
Sitting room, fireplace
Sitting room off master
Spa-size 5 pc ensuite to Master BR
44 HIGHLAND Drive photo 28
2nd Bedroom
2nd Bedroom o/looks backyard
Main bathroom, 5 pc on 2nd floor
3rd Bedroom
Bsmt level 5th Bedroom
4th bedroom
Bsmt level - 4pc
Built-in granite toppe breakfast bar with bar sink
Dinette area/Bsmt
Bsmt living area, gas fireplace, Sep Entrance
Large deck off fam & Living rooms
Huge i/lock patio/sitting area, Hot Tub
Outbuilding with cabana, mini-bunkie, pump room
16x32 ft saltwater pool
44 HIGHLAND Drive photo 43
Mini bunkie in outbuilding
Cabana room in outbuilding
Custom firepit area sequestered in the trees
Aerial photo
Horseshoe Highlands
Lot backs onto trails, golf and more!
44 HIGHLAND Drive photo 50

44 HIGHLAND Drive

Horseshoe Valley / Oro-Medonte, ON L0L 2L0

ActiveFor Sale
5 Beds
4 Baths
3,000 Sq Ft
1 Lot Sq Ft
Single Family Home
Virtual Tour Available

About This Property

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 (ski hills and 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!

Property Details

StatusActive
Property TypeSingle Family Home
Listing TypeFor Sale
Interior Size3,000 sq ft
Lot Size1 sq ft
Bedrooms5
Bathrooms4
Taxes (2026)$9,468
Postal CodeL0L 2L0
Last UpdatedOct 28, 2026 · 12:52 p.m.

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Features & Amenities

  • Pool
  • View
  • Fireplace
  • Air Conditioning
  • Basement

Buying or selling in Oro-Medonte?

Filipe & Isabel Ferreira and the Team Filipe (RE/MAX Ultimate Realty Inc., Brokerage) represent buyers and sellers here. Local guides and live listings below.

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TRREB MLS® Attribution

MLS® S14084702

Listed by RIGHT AT HOME REALTY

The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. The trademarks REALTOR®, REALTORS® and the REALTOR® logo are controlled by CREA and identify real estate professionals who are members of CREA. Listing data provided by the Toronto Regional Real Estate Board (TRREB). The information contained herein is from sources believed to be reliable but is not guaranteed. Information deemed reliable but not guaranteed accurate by TRREB or Team Filipe / RE/MAX.

$1,599,000

asking price

MLS®S14084702
TypeSingle Family Home
CityOro-Medonte
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Team Filipe · RE/MAX · (647) 210-6070

Mortgage Estimate

Est. Monthly Payment

$7,808

/month · $1,279,200 mortgage

Down Payment20% — $319,800
Interest Rate5.5%

Amortization

Total Interest

$1,063,238

Total Cost

$2,342,438

Estimate only. Based on Canadian semi-annual compounding, 25-yr amortization at 5.5%.

Full Mortgage Calculator →

Listed By

RIGHT AT HOME REALTY