Pretty River Collingwood Homes

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House for sale: 34 ROBERTSON STREET, Collingwood

37 photos

$675,000

34 Robertson Street, Collingwood (Collingwood), Ontario L9Y 0X1

3 beds
3 baths
15 days

Cross Streets: Hughes and Robertson. ** Directions: Poplar Side Road to Pretty River Estates onto Hughes then onto Robertson. PRETTY RIVER ESTATES: A very popular location close to Collingwood and only a short drive to Blue Mountain and The Village. This freshly painted end semi offers 3 Beds

Vanessa Burgess - Mason,Chestnut Park Real Estate
Listed by: Vanessa Burgess - Mason ,Chestnut Park Real Estate (705) 888-9625
326 - 31 HURON STREET, Collingwood

26 photos

$895,000

326 - 31 Huron Street, Collingwood (Collingwood), Ontario L9Y 0E8

2 beds
2 baths
51 days

Cross Streets: Pretty River Parkway to Heritage Drive. ** Directions: First St or Pretty River Parkway (hwy 26) to Heritage Drive. Discover unparalleled waterfront living with gorgeous views of Georgian Bay from stunning one-bedroom plus den, two-bathroom unit. Step inside to a custom-designed

Listed by: Wispy Boivin ,Forest Hill Real Estate Inc. (705) 999-5590
Apartment for sale: 401 - 16 RAGLAN STREET, Collingwood

35 photos

$665,000

401 - 16 Raglan Street, Collingwood (Collingwood), Ontario L9Y 4Y2

2 beds
2 baths
16 days

Cross Streets: Pretty River Pkwy. ** Directions: Hwy 26 West. North on to Raglan St. Collingwood's Exclusive Sunset Cove Waterfront Condo Community has a rare offering; an updated end unit with unobstructed PANORAMIC Georgian Bay Views! Located in a private, quiet corner of the 4th floor, this

Carrie Rys,Royal Lepage Locations North
Listed by: Carrie Rys ,Royal Lepage Locations North (519) 831-7796
House for sale: 2 EVERGREEN ROAD, Collingwood

45 photos

$1,599,000

2 Evergreen Road, Collingwood (Collingwood), Ontario L9Y 5A8

4 beds
3 baths
41 days

Cross Streets: Grey Rd 19 (Mountain Rd) and Evergreen Rd. ** Directions: Mountain Rd (Grey Rd 19) from Collingwood to Evergreen Road, turn right to sign and first driveway on the left (Evergreen Estates). Imagine living just two minutes from Blue Mountain's ski hills, golf courses, shops, restaurants,

Apartment for sale: 202 - 460 ONTARIO STREET, Collingwood

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$285,000

202 - 460 Ontario Street, Collingwood (Collingwood), Ontario L9Y 4E5

2 beds
1 baths
27 days

Cross Streets: Ontario St & Niagara St. ** Directions: Pretty River Parkway to Ontario St. Best buy in Collingwood in this two bedroom, second floor, west facing, elevatored apartment condo. Bayview Terrace is a clean, quiet well maintained building on the bus route and is a 5 minute walk to

Lisa Scott,Century 21 Millennium Inc.
Listed by: Lisa Scott ,Century 21 Millennium Inc. (705) 606-2557
Apartment for sale: 405 - 460 ONTARIO STREET, Collingwood

36 photos

$299,000

405 - 460 Ontario Street, Collingwood (Collingwood), Ontario L9Y 4E5

0 beds
1 baths
43 days

Cross Streets: Pretty River parkway. ** Directions: Pretty River Parkway to Ontario Street. Welcome to Bayview Terrace unit 405, This fully updated studio condo is the perfect blend of style, simplicity, and unbeatable value - with your monthly utilities included in the purchase price! This

Kelly Caldwell,Royal Lepage Locations North
Listed by: Kelly Caldwell ,Royal Lepage Locations North (705) 445-5520
House for sale: 24 OLIVER CRESCENT, Collingwood

50 photos

$1,895,000

24 Oliver Crescent, Collingwood (Collingwood), Ontario L9Y 3Z1

5 beds
4 baths
50 days

Cross Streets: Ontario and Raglan. ** Directions: Hwy 26, North on Raglan, Right onto Ontario St. Ontario turns into Oliver. Take to #24 (no sign). Welcome to 24 Oliver Crescent, a charming log home nestled on a spacious 120 x 225 lot backing onto the tranquil Pretty River. This unique property

Greg Weeks,Royal Lepage Locations North
Listed by: Greg Weeks ,Royal Lepage Locations North (705) 445-5520
House for sale: 22 HUGHES STREET, Collingwood

35 photos

$899,900

22 Hughes Street, Collingwood (Collingwood), Ontario L9Y 3Z1

4 beds
3 baths
44 days

Poplar Sdrd / Hurontario St. Welcome to Pretty River Estates, a move-in ready Detached Home tucked away in a Peaceful Neighborhood Convenient to Everything Collingwood has to Offer. This Raised Bungalow Boasts Approx. 1266 sq/ft Above Grade & 1217 sq/ft Below Grade of Meticulously Finished

Row / Townhouse for sale: 35 KIRBY AVENUE, Collingwood

50 photos

$785,000

35 Kirby Avenue, Collingwood (Collingwood), Ontario L9Y 3W8

4 beds
3 baths
49 days

Cross Streets: Albany St/Kirby Ave. ** Directions: Hurontario to Tracey Lane to Kirby Avenue. Welcome to this immaculate freehold end unit, perfectly positioned on a premium corner lot and only attached at the garage for maximum privacy. Fully fenced, landscaped, and completely finished from

Sara White,Re/max Four Seasons Realty Limited
Listed by: Sara White ,Re/max Four Seasons Realty Limited (705) 445-8500
7475 POPLAR SIDE ROAD, Clearview

22 photos

$7,500,000

7475 Poplar Side Road, Clearview (Rural Clearview), Ontario L9Y 3Z1

0 beds
1 baths
20 days

Cross Streets: Hurontario or Hwy 26 to Poplar. ** Directions: Hurontario or Hwy 26 to Poplar on South Side. Future Development Opportunity on 84.6 acres on Poplar Sideroad with the Pretty River flowing through the land and abutting the Train Trail. A very busy location with lots of residential

Greg Weeks,Royal Lepage Locations North
Listed by: Greg Weeks ,Royal Lepage Locations North (705) 445-5520
7639 36/37 NOTTAWASAGA SIDE ROAD, Clearview

10 photos

$579,000

7639 36/37 Nottawasaga Side Road, Clearview (Nottawa), Ontario L0M 1P0

0 beds
0 baths
78 days

Cross Streets: County Rd 124 & 36/37 Sideroad West. ** Directions: County Rd 124 to 36/37 Sideroad west, turn west to sign on left. Just steps from the tranquil Pretty River, this exceptional 0.77-acre property offers a rare opportunity to bring your vision to life. The gently sloping, mostly

House for sale: 589108 GREY ROAD 19, Blue Mountains

47 photos

$2,360,000

589108 Grey Road 19, Blue Mountains (Blue Mountains), Ontario N0H 2E0

6 beds
5 baths
20 days

Cross Streets: Grey Road 19 & Grey Road 2. ** Directions: Runs off Grey Road 19. Down a winding drive, hidden among 13 acres of towering trees, sits a home that feels like a private retreat yet keeps you close to everything. Crafted by the Legendary Group in timeless Post & Beam style, this

Darice Lush,Re/max Four Seasons Realty Limited
Listed by: Darice Lush ,Re/max Four Seasons Realty Limited (705) 443-0741
8483 36/37 NOTTAWASAGA SIDE ROAD, Clearview

22 photos

$2,750,000

8483 36/37 Nottawasaga Side Road, Clearview (Rural Clearview), Ontario L0M 1P0

0 beds
0 baths
95 days

Cross Streets: Highway 124 to Nottawa Side Road W~ Pass Tenth Concession to 36/37 Nottawasaga Side Road to Sign on the South Side. ** Directions: HWY 124. WEST ON 36/37 SIDE ROAD. Build your Dream Home on this 32.6 Acre One of a Kind Property~ Spectacular Panoramic Views to Georgian Bay, Pretty

Loretta Mcinnis,Re/max Four Seasons Realty Limited
Listed by: Loretta Mcinnis ,Re/max Four Seasons Realty Limited (705) 445-8500

Understanding Pretty River, Collingwood: Lifestyle and Investment Basics

Pretty River Collingwood refers both to the watercourse that threads into Georgian Bay and to the family-oriented neighbourhoods south and east of town, including the well-known Pretty River Estates. For buyers and investors, the area offers in-town convenience, quick access to trails and ski country, and a steady pull from the Toronto/Barrie corridor. The combination of residential zoning, conservation considerations along the river corridor, and Collingwood's maturing amenities requires a clear plan before you write an offer.

Neighbourhood Snapshot: Pretty River Estates Collingwood

Pretty River Estates in Collingwood is a modern subdivision of detached and townhomes, generally on municipal water/sewer with natural gas, sidewalks, and proximity to schools, parks, and commercial services along Highway 26. Homes typically appeal to move-up families, local professionals, and downsizers seeking lower-maintenance living without sacrificing square footage. The walkability and school catchments support consistent resale interest, while the relative affordability (versus waterfront Blue Mountain or custom escarpment builds) keeps entry points accessible to first- and second-time buyers.

Zoning, Conservation, and Approvals

Within town limits, lands are regulated by the Town of Collingwood's Zoning By-law and Official Plan, with site-specific provisions on setbacks, height, accessory units, and parking. Properties adjacent to watercourses like the Pretty River may fall under Nottawasaga Valley Conservation Authority (NVCA) regulation. That can introduce permitting for additions, decks, pools, or grading if you are within regulated hazard lands or floodplains. Where the Niagara Escarpment Commission (NEC) boundary overlaps rural parcels closer to Pretty River Valley Provincial Park, additional development controls, tree cutting rules, and visual impact assessments can apply. Buyers should:

  • Pull a zoning compliance letter and confirm legal use, setbacks, and whether a secondary suite is permitted on your specific lot.
  • Check NVCA regulated area maps and ask for any prior permits, engineered grading plans, and drainage easements.
  • Verify if the property is within a Source Protection Area that could affect wells or future fuel storage.

Key takeaway: A seemingly simple deck or walkout may require conservation sign-off; build timelines and budgets should reflect this.

Short-Term Rentals and Use Permissions

Collingwood has generally restricted short-term rentals (STRs) in most residential zones. Owner-occupied Bed & Breakfasts may be permitted with licensing, and commercial accommodations operate in appropriate zones. The stricter STR framework—especially compared with neighbouring The Blue Mountains—means the Pretty River Estates Collingwood buyer profile leans toward end-users and long-term landlords rather than nightly rental investors. Regulations evolve, so verify with the Town's by-law team before assuming any rental income model.

Property Types and Due Diligence

In-town Pretty River Estates homes offer municipal services and standardized building envelopes, often simplifying maintenance and financing. Just beyond town, rural parcels edging the valley can involve private wells, septic systems, and private or seasonally maintained roads.

Examples:

  • Septic and well: For a rural detached backing onto woodland, you'll want a flow-rate test, recent water potability results, and a third-party septic inspection/pump-out verification. Lenders may require more conservative down payments on properties with functional obsolescence (e.g., undersized septic or non-winterized structures).
  • Snowbelt reality: Collingwood receives significant lake-effect snowfall. Inspect attic insulation, roof ventilation, and ice-dam mitigation details. A back-up sump system and surge-protected panel are wise adds.
  • Flood risk: Even if a home is set back from the Pretty River, review overland water coverage and sewer backup endorsements with your insurer.

Market and Seasonal Trends

Seasonality in Collingwood is real: winter demand rises with ski season proximity; late spring to early summer brings another surge as families target school-year transitions. List-to-sale times can compress during these windows, whereas late summer and mid-winter shoulder periods may present negotiation opportunities—particularly for homes without turnkey finishes. Investors focused on long-term rentals see steadier year-round demand from healthcare, education, construction trades, and remote workers who choose Collingwood's lifestyle while maintaining GTA ties via Barrie.

For perspective, some buyers compare Collingwood family properties with urban options such as a 5-level backsplit in Toronto or student-adjacent housing like a 3-bedroom near York University, weighing appreciation prospects against Collingwood's quality-of-life premium.

Resale Potential: What Performs Well

Resale strength in Pretty River Estates is driven by functional family layouts (3–4 beds, attached garage), updated kitchens/baths, and finished basements with egress. Quiet interior streets and lots with trail access or southern exposure also draw interest. Homes that are “turnkey” and energy-efficient command the broadest buyer pool. Conversely, properties backing onto arterial traffic, with small yards, or needing big-ticket updates may lag unless priced with precision.

For investors, long-term leases to stable tenants (healthcare staff, teachers, retirees) remain the most predictable play given STR restrictions. If you prefer recreational exposure, consider cottage markets within a two-hour drive; KeyHomes.ca publishes active data for northern pockets like Novar near Huntsville and waterfront-centric regions such as Seguin cottages, which offer a different seasonality profile.

Financing Nuances and Ownership

Lenders categorize properties by use and services. Many banks view in-town Collingwood homes as conventional “Type A” residences, eligible for standard amortizations and competitive rates. Recreational or rural properties can be under “Type B” with tighter down payment and insurance rules. Practical notes:

  • Primary residence vs. investment: Expect 20% down or more for rentals. Second homes used by family can sometimes qualify with lower down payments if they meet year-round standards.
  • Private roads/condo elements: If a property relies on a private lane, a road maintenance agreement may be required for financing. For common element condominiums, review the budget, reserve fund, and rules (pets, parking, rentals).
  • Fractional ownership: Not common in Pretty River Estates, but exists in some resort markets. Review specific financing constraints if exploring fractional ownership opportunities.

Comparative Context Across Ontario

Portfolio-focused buyers sometimes benchmark Pretty River homes against other lifestyle regions. Georgian Bay boaters might look south through the locks to Port Severn houses, while those prioritizing small-town value investigate Huron-Kinloss listings. Commuter-friendly lake towns like Port Perry three-bedroom homes provide a Durham Region alternative with different property tax and transit dynamics. Even neighbourhoods such as Woodridge or the community around Richardson can serve as pricing comparables if you're balancing investment diversification with lifestyle goals. KeyHomes.ca is frequently used by clients to scan these markets side-by-side, pairing listings with recent sales data and local by-law notes.

Lifestyle Appeal and Everyday Conveniences

Pretty River Estates residents enjoy quick trips to Collingwood's downtown restaurants, waterfront trails, and the Georgian Trail. The neighbourhood is within reach of Collingwood General and Marine Hospital, community centres, and schools such as Collingwood Collegiate Institute. Skiing at Blue Mountain and Nordic centres, mountain biking, and paddling all sit within a short drive. The no-camping, day-use Pretty River Valley Provincial Park is a quiet draw for hikers seeking a natural escape without weekend chaos.

Commuting options include County LINX bus service connections and highway access toward Barrie (and GO Train links from there). Remote workers appreciate robust internet coverage in-town; rural pockets vary, so confirm service before firming up conditions.

Practical Risk Management

  • Home inspection: Prioritize roofs, attic ventilation, and foundation drainage given freeze-thaw cycles and snow loads.
  • Insurance: Ask specifically about overland flood endorsements and premiums for properties near watercourses.
  • Title review: Confirm easements for trails, drainage, or utilities common in planned subdivisions.
  • Energy costs: Gas furnaces are common; consider energy audits for incentives that improve resale and operating costs.

Planning Horizon: What Could Influence Value Next

Municipal planning work continues through Collingwood's Official Plan updates, with attention on intensification around serviced areas and protection of natural heritage systems like the Pretty River corridor. Transportation refinements along Highway 26 and ongoing discussions around healthcare infrastructure (including the long-discussed hospital redevelopment) remain medium-term variables. For any add-on, infill, or suite conversion, confirm the latest rules—policy can shift, particularly around stormwater and secondary units.

Putting It Together

For most buyers, Pretty River Estates offers a practical blend of “close-to-everything” convenience and predictable ownership costs within Collingwood's growth story. Investors prioritizing nightly rentals will find the regulatory framework limiting, but long-term tenancy and personal-use ownership work well. If you're weighing Pretty River against cottage-first markets, browsing the data-driven neighbourhood pages on KeyHomes.ca—whether that's Georgian Bay-adjacent searches or smaller communities further north—helps align expectations around price, rental viability, and operating complexity.