Pretty River Collingwood Homes

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House for sale: 21 EVA CRESCENT, Collingwood

39 photos

$899,900

21 Eva Crescent, Collingwood (Collingwood), Ontario L9Y 5R1

2 beds
1 baths
2 days

Cross Streets: Hwy 26 and Eva Cres. ** Directions: Hwy 26 to Eva Cres. Rare .8 acre Riverfront Opportunity on the Pretty River leading into Georgian Bay! Whether you are a contractor looking for your next project or a retiree dreaming of a custom-built four-season 2 bedroom home, this Riverfront

Greg Weeks,Royal Lepage Locations North
Listed by: Greg Weeks ,Royal Lepage Locations North (705) 445-5520
House for sale: 34 ROBERTSON STREET, Collingwood

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$645,500

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

3 beds
3 baths
11 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
House for sale: 44 HUGHES STREET, Collingwood

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$1,237,000

44 Hughes Street, Collingwood (Collingwood), Ontario L9Y 0W7

4 beds
5 baths
16 days

Cross Streets: Poplar SDRD & Hurontario St. ** Directions: Hurontario St to Poplar sdrd, turn east, enter Pretty River Estates, North to Hughes. Welcome to this exceptional south-facing back yard residence in the heart of Collingwood, offering the perfect blend of luxury, functionality, and

House for sale: 47 GLEN ROAD, Collingwood

49 photos

$2,150,000

47 Glen Road, Collingwood (Collingwood), Ontario L9Y 0X2

3 beds
3 baths
58 days

Cross Streets: Beachwood & York St. ** Directions: Pretty River Parkway to Hwy 26 to Beachwood Rd turn left on York St., turn right on Glen Rd to #47 and sign at property. Outstanding waterfront residence in Collingwood! Spectacular panoramic waterfront views from this custom-built home close

House for sale: 81 ST LAWRENCE STREET, Collingwood

40 photos

$2,299,000

81 St Lawrence Street, Collingwood (Collingwood), Ontario L9Y 4Y3

4 beds
4 baths
6 days

Cross Streets: Pretty River Parkway and Niagara Street. ** Directions: Hwy 26 Pretty River Parkway to Niagara to St Lawrence. Ready to enjoy this summer at the coveted and magical Sunset Point neighbourhood in the heart of Collingwood - where waterfront living, nature, and downtown convenience

Listed by: Wispy Boivin ,Forest Hill Real Estate Inc. (705) 999-5590
326 - 31 HURON STREET, Collingwood

25 photos

$895,000

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

2 beds
2 baths
74 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: 405 - 460 ONTARIO STREET, Collingwood

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$247,000

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

0 beds
1 baths
125 days

Cross Streets: Pretty River parkway. ** Directions: Pretty River Parkway to Ontario Street. One of Collingwood's best-kept secrets just got even better. This fully renovated studio condo at 460 Ontario Street, Unit 405 offers exceptional value with utilities included in the condo fees, making

Kelly Caldwell,Royal Lepage Locations North
Listed by: Kelly Caldwell ,Royal Lepage Locations North (705) 445-5520
45 GLEN ROAD, Collingwood

11 photos

$900,000

45 Glen Road, Collingwood (Collingwood), Ontario L9Y 0X2

0 beds
0 baths
58 days

Cross Streets: Beachwood Road and York Street. ** Directions: Pretty River Parkway to Hwy 26 to Beachwood Rd, turn left on York St., turn right on Glen Rd. to #45 and sign at property. Outstanding waterfront vacant lot (50' x 323' irregular) in Collingwood! Spectacular panoramic waterfront

Apartment for sale: 303 - 91 RAGLAN STREET, Collingwood

18 photos

$450,000

303 - 91 Raglan Street, Collingwood (Collingwood), Ontario L9Y 4V3

2 beds
2 baths
82 days

Cross Streets: HUME & RAGLAN. ** Directions: Pretty River Parkway West to Ontario Street, Turn left on to Raglan Condo development is ahead on the West side. Located in Raglan Heights (Raglan Village), one of Collingwood's premier adult lifestyle communities, this spacious condo offers an open-concept

House for sale: 30 COOPER STREET, Collingwood

33 photos

$875,000

30 Cooper Street, Collingwood (Collingwood), Ontario L9Y 0W9

3 beds
3 baths
135 days

Hughes Street and Poplar Side Road Welcome to coveted Pretty River Estates, a peaceful neighbourhood perfectly situated near everything the charming town of Collingwood has to offer. This beautifully maintained home is nestled on a sun-filled, south-facing lot on a quiet, child-friendly street.

House for sale: 22 HUGHES STREET, Collingwood

35 photos

$859,000

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

4 beds
3 baths
10 days

Poplar Sideroad And Hurontario 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

House for sale: 74 RODNEY STREET, Collingwood

37 photos

$499,900

74 Rodney Street, Collingwood (Collingwood), Ontario L9Y 1C8

2 beds
1 baths
23 days

Cross Streets: Pretty River Parkway to Rodney St. ** Directions: Pretty River Pkwy to Rodney St. Short walk to Downtown and Sunset Point ! This two story - 2 Bedroom plus office/guest room home is located on a corner lot with mature trees providing shade and privacy. Some upgrades include

Chad Campbell,Royal Lepage Locations North
Listed by: Chad Campbell ,Royal Lepage Locations North (705) 429-4800
11589 26 HIGHWAY, Collingwood

35 photos

$5,980,000

11589 26 Highway, Collingwood (Collingwood), Ontario L9Y 5E7

0 beds
0 baths
2 days

West of Greentree Emporium Hwy 26 Rare shovel-ready residential development opportunity in the heart of Collingwood. Cranberry Marsh Estates offers a conditionally approved executive freehold townhome development with strong market potential in one of Ontario's most sought-after four-season

Candace Armstrong,Royal Lepage Locations North
Listed by: Candace Armstrong ,Royal Lepage Locations North (705) 817-1007
House for sale: 24 OLIVER CRESCENT, Collingwood

50 photos

$1,875,000

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

5 beds
4 baths
30 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). 24 Oliver Crescent, a charming log home nestled on a spacious 120 x 225 lot backing onto the tranquil Pretty River. This unique property offers

Greg Weeks,Royal Lepage Locations North
Listed by: Greg Weeks ,Royal Lepage Locations North (705) 445-5520
House for sale: 553763 ROAD 55, Grey Highlands

50 photos

$1,899,900

553763 Road 55, Grey Highlands (Grey Highlands), Ontario N0C 1J0

5 beds
5 baths
10 days

Cross Streets: 4th Concession B. ** Directions: https://maps.app.goo.gl/oyWhiAutWKorQaSEA. Welcome to one of Grey County's most extraordinary properties - a masterfully restored 1884 red brick schoolhouse transformed into a remarkable country estate with over 5,000 sf of living space where

7475 POPLAR SIDE ROAD, Clearview

22 photos

$7,500,000

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

0 beds
1 baths
157 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

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.