Chris Assaff, Sales Representative

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 enth

usiast, 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.

🔥🏡 New Ultra-Rare 3 Bedroom Just Listed at Dwell at Creekside! MLS S12187057✅ Perfectly positioned between Blue Mountain...
06/26/2025

🔥🏡 New Ultra-Rare 3 Bedroom Just Listed at Dwell at Creekside! MLS S12187057
✅ Perfectly positioned between Blue Mountain, Georgian Bay, and the Historic Downtown Collingwood
✅ This rarely available 3-bed/2-bath top-floor condo offers the best of nature, featuring a South facing private terrace with gorgeous views to the escarpment and Osler Bluff
✅ Spanning over 1,200 SF, this residence features a bright and airy open-concept kitchen, dining, and living space
✅ Step out onto your private 94 sq.ft. terrace and enjoy serene views of the escarpment
✅ Over $50,000 in builder upgrades including: California shutters throughout, Quartz countertops in kitchen & both bathrooms, extended kitchen cabinetry to the ceiling, Designer-upgraded washrooms and premium flooring
✅ Dedicated laundry room with convenient stackable washer & dryer
✅ Additional features include: Designated outdoor parking + guest parking, Assigned lower-level locker and extra bicycle storage, and Residents lounge with kitchenette for gatherings and meetings. Whether you’re seeking a year-round residence, a weekend getaway, or a sophisticated investment, this rare third-floor, 3-bedroom condo offers comfort, style, and a coveted location. Don’t miss your chance to own a piece of Dwell at Creekside-where refined living meets the natural beauty of Southern Georgian Bay.
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📌 New Office Space Available in the Heart of Downtown Collingwood!Suite 205 - 186 Hurontario St - MLS S12242988* 714 SF ...
06/26/2025

📌 New Office Space Available in the Heart of Downtown Collingwood!
Suite 205 - 186 Hurontario St - MLS S12242988
* 714 SF of improved, functional office space
Features include:
✅ 2 private offices
✅ Extra-large reception area
✅ Recently painted + new commercial grade carpet
✅ Potential for a staff/lunch room with a large vanity with tap comes with the lease space
✅ Common men’s & women’s washrooms
✅ 1 private reserved parking spot
✅ Bright, professional space perfect for a variety of business uses
✅ Prime downtown location - steps from shops, restaurants, and amenities!
DM for more info or to schedule a tour. Don’t miss out on this rare opportunity in the core of Collingwood!

🚨 NEW LISTING in Downtown Collingwood! 🏡At nearly 4,000 sq.ft., this spacious raised bungalow is the definition of flexi...
04/17/2025

🚨 NEW LISTING in Downtown Collingwood! 🏡
At nearly 4,000 sq.ft., this spacious raised bungalow is the definition of flexibility + potential! With legal duplex status and triplex conversion potential, this property is a rare gem for investors, first-time buyers, or multi-generational families.
✨ Features Include:
🔹 Two 1,000 sq.ft. upper units — each w/ 2 beds, 2 baths, & deck access to a private, treed backyard
🔹 Lower level: 5 beds, 2 full baths + roughed-in plumbing for a future kitchen (this is currently part of the right side upper unit)
🔹 Potential to convert into a triplex with 4-bed third lower unit or keep it as-is for additional space
🔹 9 total bedrooms & 6 full bathrooms
🔹 Separate hydro meters, 1 gas & water meter
🔹 Parking for 4 vehicles + plans to pave driveway in May
🔹 Backyard makeover coming soon with fresh sod
💡 Whether you’re looking to house-hack, generate rental income, or accommodate a large family with in-laws, this home checks all the boxes.
📍Located in the heart of Downtown Collingwood — steps to shops, restaurants, and trails. Located in the Mountainview Elementary School District
📲 Don’t miss this unique opportunity! DM me for a private tour or more details.

✨SOLD!✨Thrilled to report that 556 Hurontario St, Collingwood has sold. Congratulations to the new homeowners! 🎄••• ...
12/16/2024

✨SOLD!✨Thrilled to report that 556 Hurontario St, Collingwood has sold. Congratulations to the new homeowners! 🎄
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Happy Thanksgiving to you and your family and loved ones! 🦃 🥘 🌽 🥧
10/14/2024

Happy Thanksgiving to you and your family and loved ones! 🦃 🥘 🌽 🥧

Welcome to your dream home, an ENERGY STAR® Certified property nestled on 5.53 acres of serene rural land, Built in 2019...
07/03/2024

Welcome to your dream home, an ENERGY STAR® Certified property nestled on 5.53 acres of serene rural land, Built in 2019 🏡 🌾
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Step inside and be captivated by the modern elegance of polished concrete floors, equipped with radiant in-floor heating throughout both levels, ensuring comfort and efficiency year-round. $1,200/year for heating and $1,200/year for hydro! ⚡️
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The open-concept design of the kitchen, living, and dining areas boasts soaring 14-foot ceilings, creating a grand and airy atmosphere. The heart of the home is the cozy living area, where a wood stove adds warmth and charm, making it the perfect spot for relaxation and gatherings 🔥
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Outside, the expansive 5.53 acres provide
ample space for outdoor activities, gardening, and enjoying the natural beauty of the countryside. Brand new Bunkie with wood stove is being completed as we speak 🛏️
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1hr 30min to Pearson International 🛩️ • 20min (24km) from Beaver Valley Ski Club ⛷️ • 14min to Markdale (hospital, schools, shopping, etc) 🏫
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Whether you’re looking for a peaceful retreat or a place to entertain family and friends, this property offers endless possibilities. Don’t miss the opportunity to own this exceptional energy-efficient home that combines modern luxury with rural tranquility
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Schedule your viewing today and experience the perfect blend of comfort, style, and sustainability. Offered at $1,295,000. MLS: 40613472
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🏙️ Congrats to my Client on her new beautiful space at the Cranberry Mews Plaza! I represented the Tenant in this transa...
04/11/2024

🏙️ Congrats to my Client on her new beautiful space at the Cranberry Mews Plaza! I represented the Tenant in this transaction
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1,738 SF located in a busy plaza with direct Highway 26 exposure and lots of parking
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Contact me directly if you’re looking for commercial space to lease in Collingwood & Area
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Just Listed! 1814 Quantz Crescent, Innisfil 🏡•Executive Bungalow with 5,000 fin sq.ft. on a very private 2.3 acre ravine...
04/10/2024

Just Listed! 1814 Quantz Crescent, Innisfil 🏡
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Executive Bungalow with 5,000 fin sq.ft. on a very private 2.3 acre ravine estate located in an enclave of upscale residences
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MLS # 40553006 • Offered at $2,299,000
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5 🛏 , 5 🛀 , 5,000 SQ.FT. 🏠
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Luxury Living literally just minutes to Friday Harbour ⛵️ and downtown Barrie (7KM to both) & very close to Catholic and public schools and neighbourhood shopping centre
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New kitchen feat. Quartzite Counters, high end SS appliances, 14’ island and gas stove witu double ovens
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Hardwood floors throughout, newer windows and doors, entire house was recently painted and has all LED lighting
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Beautiful circular driveway holds a dozen cars and 3-car garage has epoxy floors and a loft for extra storage
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2 master suites to choose from: one on the main floor with balcony overlooking the gorgeous property, or the secluded lower level master w/ all new 6-piece ensuite and large walk in closets
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For more information feel free to DM me
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🏙️ New Commercial Lease Listing in Downtown Collingwood at 49 Huron Street•MLS # 40546985 • Offered at $18/SF Net + $7....
04/10/2024

🏙️ New Commercial Lease Listing in Downtown Collingwood at 49 Huron Street
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MLS # 40546985 • Offered at $18/SF Net + $7.80/SF T.M.I.
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2,386 SF unit is located directly on Highway
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Directly adjacent to both Sobey’s Supermarket and Sunset Point Park in Collingwood
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The space can be used for either office or retail. It’s presently set up with 2 private offices, large reception area, very large retail area, and a private bathroom
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Ample parking with 105 parking spots shared among the 4 tenants of this building.
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Current tenants of the building include the Ontario Court of Justice, Iron Skillet Restaurant, and Granite Homes.
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This space is available immediately. Lease Term not to run any longer than June 30, 2026, and will go month to month after that until site is redeveloped
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Central Collingwood location with great exposure directly on Highway 26!
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🏙️ New Commercial Lease Listing in Collingwood at 100 Pretty River Parkway South•MLS # 40568292 • Offered at $23/SF Net...
04/10/2024

🏙️ New Commercial Lease Listing in Collingwood at 100 Pretty River Parkway South
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MLS # 40568292 • Offered at $23/SF Net + $6.50/SF T.M.I.
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4,570 sq.ft. of very high end, fully finished & furnished office space. Very functional and tastefully built out!
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11 offices, 1 boardroom, 2 washrooms, a kitchenette, large reception & waiting area, a bright bullpen area, and a large storage area in
a busy commercial multi unit complex
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Central Collingwood location with easy access to HWY 26
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I want to take this opportunity to thank all my clients for such a great year, it was an interesting one but we got it d...
02/16/2024

I want to take this opportunity to thank all my clients for such a great year, it was an interesting one but we got it done! I am feeling grateful to be receiving the 2023 President’s Award! This Spring marks my 12th year in Real Estate and I can’t imagine doing anything else. I think we are in for a really great 2024, and I’d like to wish everyone a very happy, healthy and successful year! 🎉🏡
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3 New Commercial Lease Listings. Any of these can accommodate Retail or Office uses. Message me for more info, these wil...
11/15/2023

3 New Commercial Lease Listings. Any of these can accommodate Retail or Office uses. Message me for more info, these will not last long on the market… 🏙️🔥
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Address

393 First Street, Suite 100
Collingwood, ON

Telephone

+17054466440

Website

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