Chris Assaff, Sales Representative

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Chris Assaff, Sales Representative I'm a Sales Representative working at Chestnut Park Real Estate Brokerage in Collingwood, Ontario. He has been a licensed REALTOR® since 2010.

Born and raised in Collingwood, Chris’ diverse connections and experience has helped him establish a residential foothold. Chris has a degree in Finance from Dalhousie University and has extensive work experience in commercial real estate, having concentrated on urban retail and office leasing at Colliers International’s Downtown Toronto office. Living an active lifestyle and being an outdoor enthusiast, you can often find Chris playing a round of golf, skiing, playing squash and hiking. Chris looks forward to serving you as he continues to build his residential real estate clientele in South Georgian Bay.

🌳 COUNTRY LIVING WITH CHARACTER, SPACE & ENDLESS POSSIBILITIES 🌳📍 1164 Fairgrounds Road North, Stayner, OntarioMLS Numbe...
09/30/2026

🌳 COUNTRY LIVING WITH CHARACTER, SPACE & ENDLESS POSSIBILITIES 🌳

📍 1164 Fairgrounds Road North, Stayner, Ontario

MLS Number S13845130 • Offered at $1,499,900

Set amongst mature trees and beautifully landscaped grounds, this exceptional 8.024-acre country property offers the timeless character of a circa-1900 red brick farmhouse, combined with the space, amenities and outbuildings to suit a variety of lifestyles.

The approximately 3,020 sq. ft. home features 4 bedrooms, 2.5 bathrooms, a generous custom kitchen with high-end Miele appliances, fireplace, multiple porches and decks, and an attached 3-car garage.

A thoughtfully designed addition completed in 2010 incorporates authentic reclaimed antique bricks, carefully sourced to complement the original farmhouse and create a seamless blend of historic charm and modern living. The original farmhouse’s metal roof was also replaced in 2010.

🌿 Outside, the possibilities continue:
• Insulated shop with propane boiler-fired hydronic in-floor heating
• Two extra-large overhead doors
• Older barn & workshop
• Unique “beach-house” trailer beside the pond
• Beautiful pond views & incredible sunsets
• 8+ acres offering privacy, space and versatility

Whether you’re dreaming of a private country retreat, hobby farm, workshop space, family property or simply room to spread out, this is a truly special opportunity.

📍 Just 2 km to downtown Stayner
⛷️ 10 km to Collingwood
⛳ 8 km to Mad River Golf Club
✈️ Approx. 90 minutes to Pearson International Airport

The property is serviced by a drilled well and septic system, with the septic serviced and pumped in June 2026.

Estate sale — property being sold strictly “as-is, where-is.” Seller makes no representations or warranties regarding the condition or operation of the heating, cooling, plumbing, electrical systems or appliances.

OntarioRealEstate Farmhouse CountryHome HobbyFarm RuralProperty Acreage SouthernGeorgianBay BlueMountainRealEstate MuskokaLifestyle DreamProperty

08/07/2026

🌅 Wake up to Georgian Bay. End your day with unforgettable sunsets.

Welcome to Penthouse 618 at Harbour House—where luxury meets the waterfront in the heart of downtown Collingwood.

Imagine sipping your morning coffee on your private terrace, spending the afternoon exploring the harbour, marina, boutiques and restaurants just steps away, then coming home to soaring 20-foot ceilings, a stunning chef’s kitchen, and panoramic views of Georgian Bay and the Niagara Escarpment.

✨ 2 Bedrooms + 2 Full Bathrooms
✨ 1,010 Sq. Ft. + 150 Sq. Ft. Private Terrace
✨ Rare 2 Underground Parking Spaces (1 with EV Charging)
✨ Luxury building amenities including a rooftop terrace, fitness centre, guest suites & pet spa

This isn’t just a penthouse—it’s one of Collingwood’s most exceptional waterfront lifestyles.

📩 DM me today to book your private tour before this incredible opportunity is gone.

Penthouse GeorgianBay OntarioRealEstate DowntownCollingwood LuxuryRealEstate LiveTheLifestyle DreamHome

Doesn’t get any better! Downtown Collingwood/Waterfront living, combined with a Penthouse featuring a large 150 Sq Ft. t...
08/07/2026

Doesn’t get any better! Downtown Collingwood/Waterfront living, combined with a Penthouse featuring a large 150 Sq Ft. terrace with unimpeded/protected views of the Escarpment from Duntroon to Georgian Peaks + North views to the Collingwood Terminals 🌅 ⛰️🛥️ ⛷️ Full details coming in my next post…. #
homedesign forsale chestnutpark investinstyle lovewhereyoulive luxuryrealestate

🚨 PRICE IMPROVEMENT 🚨Suite 304 at 1 Chamberlain Crescent, Collingwood is now available at a newly reduced and incredibly...
06/26/2026

🚨 PRICE IMPROVEMENT 🚨

Suite 304 at 1 Chamberlain Crescent, Collingwood is now available at a newly reduced and incredibly attractive price!

This is your opportunity to own one of the most desirable floorplans in the building—a RARE 3-bedroom, 2 full bathroom suite offering over 1,200 sq.ft. of beautifully upgraded living space.

✨ Why you’ll love it:
✔️ Top-floor location means exceptional privacy and quiet living
✔️ Stunning escarpment views from your suite
✔️ Flexible layout – use the 3rd bedroom as a spacious home office
✔️ Bright open-concept kitchen, dining & living area
✔️ Private 94 sq.ft. terrace overlooking a peaceful pond
✔️ Over $50,000 in premium builder upgrades

Notable upgrades include:
• California shutters throughout
• Quartz countertops in kitchen & both bathrooms
• Extended ceiling-height kitchen cabinetry
• Designer-upgraded bathrooms
• Premium flooring
• Dedicated laundry room with stackable washer & dryer

Additional conveniences:
🚗 Designated parking plus guest parking
🚲 Assigned locker & bicycle storage
🚗 Optional second parking space available ($50/month)
🏡 Residents’ lounge with kitchenette for gatherings and meetings

Whether you’re looking for a full-time residence, weekend retreat, or a work-from-home lifestyle in the heart of Collingwood, this rare top-floor suite checks all the boxes.

📩 Contact me today for pricing details or to book your private showing before this opportunity is gone.

🚨 LAST REMAINING COMMERCIAL SPACE AVAILABLE! 🚨An exceptional leasing opportunity in one of Collingwood’s most prominent ...
06/08/2026

🚨 LAST REMAINING COMMERCIAL SPACE AVAILABLE! 🚨

An exceptional leasing opportunity in one of Collingwood’s most prominent mixed-use developments!

📍 Harbour House Condominium Commercial
31 Huron Street, Collingwood

✔️ 2,675 SF of premium retail or office space
✔️ Base Rent: $35.00 PSF
✔️ Estimated TMI: $10.00 PSF
✔️ Wide range of permitted commercial uses
✔️ 4 private reserved surface parking spaces included
✔️ Access to 100 additional paid public parking spaces in the underground garage
✔️ Outstanding signage exposure on both the East and South elevations facing busy Highway 26

This location continues to attract strong commercial tenants. I recently completed a lease for 3,000 SF to a major financial institution, joining an excellent mix of established businesses including Bocado Restaurant, Westland Insurance, and Peaks Family Dentistry.

With significant daily traffic exposure, excellent parking, and a growing professional and retail tenant base, this is a rare opportunity to secure space in one of Collingwood’s most visible commercial properties.

⏳ This is the final available commercial unit in the building.

Interested in learning more or arranging a tour?

📱 705-446-6440
📧 [email protected]

CommercialLease Highway26 CollingwoodOntario OfficeSpace RetailOpportunity BusinessGrowth CommercialProperty ForLease SouthernGeorgianBay ChestnutParkRealEstate

🏡 SOLD! 🎉Congratulations to my clients on the successful sale of their home at 10 Archer Avenue in Collingwood!In a mark...
06/08/2026

🏡 SOLD! 🎉

Congratulations to my clients on the successful sale of their home at 10 Archer Avenue in Collingwood!

In a market where inventory is up, prices have softened, and buyers have more choices than ever, getting a home sold takes the right strategy, marketing, and ex*****on. I’m proud to share that this property sold in just over one month—a great result in today’s challenging real estate environment.

Thinking about buying or selling? I’d be happy to help you navigate the market and achieve your real estate goals.

📱 Call or text: 705-446-6440
📧 [email protected]

OntarioRealEstate ChestnutParkRealEstate HomeSold RealEstateAgent SouthernGeorgianBay BuyWithConfidence SellWithConfidence

🔥🏡 Hot New Listing in Summit View Community 🔥🏡 ✔️ Meticulously maintained two-storey semi-detached in the sought-after S...
04/11/2026

🔥🏡 Hot New Listing in Summit View Community 🔥🏡

✔️ Meticulously maintained two-storey semi-detached in the sought-after Summit View community
✔️ Built by award-winning Devonleigh Homes, this home was built in 2020
✔️ This property offers a rare combination of a west-facing bright, sunny, fully fenced and landscaped rear yard - as well as backing directly onto neighbourhood parkland
✔️ 1,448 SF finished space above grade, and 2,016 SF finished including the basement
✔️ Bright and inviting open-concept main floor, complete with a convenient powder room and inside entry from the attached garage-ideal for everyday living
✔️ The combo kitchen, living, dining area features tasteful hardwood floors which adds a luxurious touch to the space
✔️ Upstairs, you’ll find 3 generously sized bedrooms, a full 4-piece bathroom, and the added convenience of second-floor laundry
✔️ Fully finished basement extends your living space with a large recreation room and an additional 3-piece bathroom, providing flexibility for family gatherings, a home office, or guests
✔️ Just minutes from schools, scenic trails, and local shops, with easy access to ski hills, beaches, and golf courses
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homedesign forsale chestnutpark investinstyle lovewhereyoulive luxuryrealestate

01/28/2026

Address

393 First Street, Suite 100
Collingwood, ON

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