Orangeville Real Estate Search

Orangeville Homes with a Pool for Sale

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Newest Orangeville Homes with a Pool for Sale

$1,999,900
4 Beds 2 Baths W13771778 MLS
A prime asset in one of Orangeville's most sought-after historic neighbourhoods. Positioned on an expansive parcel within the newly designated Heritage Conservation District, this property combines immediate residential charm with exceptional long-term strategic value. You may have read about this unique "U-shaped" property at 11A York Street in recent months and please inquire for details regarding planning insights and site potential. See attached property sketch and aerial view for this rare .7 acre town lot with approx. 151.8 ft across rear which backs onto Kay Cee Gardens and offers a prime location near local amenities, shops, cafes, restaurants and Theatre. The existing bungalow features 3 bedrooms, spacious updated kitchen/dining room with large pantry, built-in desk and convenient closet laundry. Bright open concept family room with walkout to upper sundeck and living room with cozy gas fireplace. The lower level features a massive recreation room with 2nd gas fireplace, 4th bedroom, office and 3 piece bathroom. There is also a large workshop and lots of dedicated storage for hobbies and off season items. The lower level offers the potential of an in-law suite with it's separate side entrance/mudroom and garage access. The west frontage of the property is approx. 9.5 ft. and has a paved driveway that leads to the spacious garage and parking area, as well as the sprawling rear yard with towering, mature trees and gardens.

11A York Street, Orangeville

$970,000
7 Beds 4 Baths W13752400 MLS
Welcome to this updated and well maintained all-brick, two-storey detached home, located in Orangeville's most sought-after, family-friendly neighbourhood. Main level features an updated family-sized eat-in kitchen with a walk-out to a large size deck, overlooking the scenic greenery and beautifully landscaped backyard. Step outside to your own private summer oasis, complete with a stunning inground salt-water pool and generous lounging area, perfect for relaxing, sunbathing, entertaining and creating lasting memories with family and friends. The main floor of this beautiful home also offers spacious living and dining rooms, a comfortable family room with fireplace, convenient main-floor laundry and a 2-piece powder room. Upstairs, the very spacious primary suite features a walk-in closet and a 4-piece ensuite with a freestanding tub. Three additional well-sized bedrooms all come with large size windows and closets; Basement: The finished walk-out lower level features two generous-sized rooms plus a third versatile room ideal for a bedroom or home office. A full-size kitchen and walk-out access make the basement particularly appealing with excellent potential for an income generating, in-law suite or nanny suite. Ideally located close to schools, parks, shopping, restaurants, trails and everyday amenities, with convenient access to Highways 9 & 10. This is the home with the complete package awaiting you: a beautiful 4bed, move-in-ready home, featuring an incredible backyard retreat and a finished basement with rental potential in a great neighbourhood. *photos are virtually staged to show the home's full potential and beauty.*

292 Lisa Marie Drive, Orangeville

$735,000
4 Beds 2 Baths W13506774 MLS
When Lot Size Matters to you. Opportunities like this don't come along often! This spacious and beautifully maintained 4-bedroom family home offers exceptional value in a sought-after neighborhood. With parking for up to 6 vehicles and a large, private backyard with no rear neighbors, you'll have all the space your family needs. The outdoor oasis features a large above-ground pool (approx. 2020), multiple decks and patios, storage sheds, and plenty of room for entertaining, relaxing, and enjoying summer with family and friends. Inside, you'll find a bright, open-concept layout designed for comfortable family living. The welcoming foyer features a new front door in 2025, pot lights, with additional pot lighting in the family room and finished basement. The cozy family room showcases a beautiful wood-burning fireplace with an iron insert and offers a walkout to the fully fenced backyard. The spacious living and dining rooms flow seamlessly into the kitchen, creating an ideal space for both everyday living and entertaining. The primary bedroom features his-and-hers closets with convenient semi-Ensuite access to the main bathroom. Interior access to the garage from the foyer adds everyday convenience. This home has been lovingly cared for and updated throughout, including: Furnace, central air conditioning, and on-demand water heater (2021), roof (2023), paved driveway (2023), patio door (2020), front door (2025), and above-ground pool (approx. 2020).Ideally located within walking distance to shopping, schools, the recreation centre, public transit, and other everyday amenities, this move-in-ready home truly offers the perfect combination of space, privacy, location, and value. Don't miss your chance to make this exceptional family home your own! PS the big front tree is a beautiful Mulberry Tree. Basement also has a huge Storage area for all your stuff and more.

111 Diane Drive, Orangeville

$718,000
4 Beds 2 Baths W13206198 MLS
Welcome To 44 Madison Ave In The Heart Of Orangeville. A Warm And Inviting 3level Backsplit Nestled In A Quiet, Family-Friendly Neighbourhood Just Steps From Parks, Trails, And Parkinson Centennial Public School At The End Of The Street, Offering JK Through Gr 8. This Home Offers An Excellent Opportunity For Growing Families, First-Time Buyers, Downsizers, Or Investors Looking To Get Into The Market.Step Inside To Find Bright And Spacious Principal Rooms Filled With Natural Light, New Windows Throughout (Except 2nd Flr Bath) Warm Hardwood Floors, And A Practical Layout Designed For Everyday Living. The Kitchen Offers Plenty Of Cabinet Space, A Functional Eat-In Area, And An Easy Flow Into The Dining Space, Making It Ideal For Family Dinners Or Entertaining. The Cozy Living Room Creates The Perfect Spot To Unwind. The Finished Basement Features A Spacious Rec Room, Convenient 2-Piece Bathroom, Laundry Room, Expansive Storage Space, And An Additional Room That Can Easily Function As A Fourth Bedroom, Home Office, Guest Room, Or Hobby Room. The Walkout From The Basement To The 3-Season Sunroom Adds Versatility And Creates A Seamless Connection Between Indoor And Outdoor Living.Outside Is Where This Property Truly Shines. The Fully Fenced Backyard Features A Brand-New Privacy Fence, Expansive Multi-Level Deck, 3-Season Sunroom, Above-Ground Pool, Mature Trees, And Plenty Of Green Space For Children And Pets To Enjoy. Whether You're Hosting Summer Bbqs, Relaxing Poolside, Gardening, Or Enjoying Quiet Evenings Outdoors, This Backyard Offers The Perfect Setting For Making Lasting Memories With Family And Friends.Located Close To Schools, Parks, Recreation Centres, Shopping, Restaurants, And Scenic Walking Trails, This Home Offers The Lifestyle So Many Buyers Are Searching For. With A Welcoming Community Atmosphere And Easy Access To Everyday Amenities, This Is A Fantastic Opportunity To Own A Well-Loved Home In One Of Orangeville's Desirable Family-Oriented Neighbourhoods.

44 Madison Avenue, Orangeville

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