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Houses for Sale in Simcoe Under $500K - P4

Showing results 91 - 120 of 224
Last Updated: May 15, 2026
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  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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8 Photos
Last Updated : 16 Days ago
1879 Lakeshore Drive, Simcoe, ON , MLS #S13058808 , Image - 1
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1879 Lakeshore Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13058808

Residential Freehold (Vacant Land)

$374900.0
An exceptional opportunity a 100 x 150 ft. building lot just 250 meters from shared residents' access to the pristine shores of Lake Simcoe. Nestled a
13 Photos
Last Updated : 16 Days ago
891 River Road W, Simcoe, ON , MLS #S12380460 , Image - 1

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Unit-1, 891 River Road W Wasaga Beach, Simcoe, ON MLS® S12380460

Residential Condo & Other (Condo Apartment)

$339000.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Location, Lifestyle and Easy Living in Wasaga Beach! Just minutes from the sandy shores of Wasaga Beach and surrounded by endless recreational opportu
23 Photos
Last Updated : 16 Days ago
382 West Street N, Simcoe, ON , MLS #S13057842 , Image - 1

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382 West Street N Orillia, Simcoe, ON MLS® S13057842

Residential Freehold (Detached)

$375000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Attention Builders/Developers/Investors. This may be the development/investment property you've been looking for. Property is being sold primarily as
47 Photos
Last Updated : 16 Days ago
85 Theme Park Drive, Simcoe, ON , MLS #S12949140 , Image - 1

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Unit-G4, 85 Theme Park Drive Wasaga Beach, Simcoe, ON MLS® S12949140

Residential Freehold (MobileTrailer)

$149999.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Nestled in a secluded haven on a corner lot within the beloved Countrylife Resort, this Huron Ridge Resort Cottage (2001) invites you into a world whe
Pre-Construction
Rosehaven Simcoe Woods
6 Photos

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard
From $879,990 - $1,339,990
project size image
Project Info
  • Units
  • Townhouses
building outline
Property Mix
Floorplans coming soon
Developer:Rosehaven Homes
32 Photos
Last Updated : 17 Days ago
299 Cundles Road E, Simcoe, ON , MLS #S12951644 , Image - 1

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Unit-102, 299 Cundles Road E Alliance, Barrie, Simcoe, ON MLS® S12951644

Residential Condo & Other (Condo Apartment)

$475000.0
  • 3 Beds
  • 2 Baths
  • 1200-1399 sq-ft
This beautiful and well-maintained ground-level condo offers 1,244 square feet of bright, open-concept living. Featuring three spacious bedrooms, this
34 Photos
Last Updated : 17 Days ago
295 Cundles Road E, Simcoe, ON , MLS #S13054188 , Image - 1

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Unit-404, 295 Cundles Road E Little Lake, Barrie, Simcoe, ON MLS® S13054188

Residential Condo & Other (Condo Apartment)

$449900.0
  • 2 +1 Beds
  • 2 Baths
  • 1000-1199 sq-ft
SPACIOUS 2 BEDROOM + DEN CONDO WITH IMPECCABLY MAINTAINED INTERIOR, SKYLINE VIEWS & A HIGHLY WALKABLE LOCATION! Living here feels like stepping into a
10 Photos
Last Updated : 17 Days ago
6411 Concession 4 Road, Simcoe, ON , MLS #N13054118 , Image - 1

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6411 Concession 4 Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13054118

Residential Freehold (Vacant Land)

$399900.0
  • < 700 sq-ft
Scenic 1 Acre Building Lot ready for you to build your dream home. Surrounded by nature and tranquil views, and century old mature oak trees, this lot
7 Photos
Last Updated : 17 Days ago
257 Robins Point Road, Simcoe, ON , MLS #S13051686 , Image - 1

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257 Robins Point Road Victoria Harbour, Tay, Simcoe, ON MLS® S13051686

Residential Freehold (Vacant Land)

$289000.0
  • < 700 sq-ft
An incredible parcel of land awaits to build your dream home, perfectly situated across from the stunning shores of Georgian Bay! This lot offers peac
34 Photos
Last Updated : 17 Days ago
275 BROWARD Way, Simcoe, ON , MLS #N13051586 , Image - 1

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275 BROWARD Way
Unit-60, 275 BROWARD Way Rural Innisfil, Innisfil, Simcoe, ON MLS® N13051586

Residential Condo & Other (Condo Apartment)

$300000.0
  • 0 +1 Beds
  • 1 Baths
  • 0-499 sq-ft
Friday Harbour is a stunning waterside community that gives a one of a kind experience for homeowners, guest and visitors. Are you a Golfer? Join the
32 Photos
Last Updated : 17 Days ago
85 Theme Park Drive, Simcoe, ON , MLS #S12898318 , Image - 1

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Unit-154, 85 Theme Park Drive Wasaga Beach, Simcoe, ON MLS® S12898318

Residential Freehold (Detached)

$78000.0
price drop iconPrice drop by 17.9%
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Beautifully maintained and priced to sell. Sellers are extremely motivated due to relocation. Experience the perfect seasonal retreat at the popular C
5 Photos
Last Updated : 17 Days ago
3585 Peter Street, Simcoe, ON , MLS #S13051208 , Image - 1
3585 Peter Street Rural Ramara, Ramara, Simcoe, ON MLS® S13051208

Residential Freehold (Vacant Land)

$199999.0
Build your dream home on this prime vacant lot located at 3585 Peter Street in Ramara, just moments from the desirable Bayshore Village community. Off
41 Photos
Last Updated : 18 Days ago
8 Carmans Cove N/A, Simcoe, ON , MLS #N12990486 , Image - 1

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8 Carmans Cove N/A Rural Innisfil, Innisfil, Simcoe, ON MLS® N12990486

Residential Freehold (Modular Home)

$299900.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
WELL-KEPT 2-BEDROOM HOME IN AN AMENITY-RICH ADULT LIFESTYLE COMMUNITY! Enjoy relaxed living in this charming Monaco II model bungalow nestled on a qui
25 Photos
Last Updated : 18 Days ago
375 Sea Ray Avenue, Simcoe, ON , MLS #N13046632 , Image - 1

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Unit-116, 375 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13046632

Residential Condo & Other (Condo Apartment)

$499900.0
  • 2 Beds
  • 2 Baths
  • 800-899 sq-ft
Beautiful 2 Bedroom, 2 Bathroom Newly Renovated Unit in the Aquarius Building at Friday Harbour. Unit Boast 9ft Ceilings, Designer Lighting Fixtures T
44 Photos
Last Updated : 20 Days ago
330 Third Street, Simcoe, ON , MLS #S13044912 , Image - 1

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330 Third Street Midland, Simcoe, ON MLS® S13044912

Residential Freehold (Detached)

$479000.0
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Timeless Charm & Modern Comfort in the Heart of Midland! Welcome to a home that instantly feels just right. This beautifully updated 2-storey century
11 Photos
Last Updated : 21 Days ago
5216 County 90 Road, Simcoe, ON , MLS #S13040020 , Image - 1

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Unit-51, 5216 County 90 Road Rural Springwater, Springwater, Simcoe, ON MLS® S13040020

Residential Freehold (MobileTrailer)

$15000.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Welcome to Unit #51 at 5216 County 90 Road a bright and cozy 1-bed, 1-bath. In a well-maintained seasonal park. Enjoy open-concept living, a private d
27 Photos
Last Updated : 22 Days ago
157 Wellington Street E, Simcoe, ON , MLS #N13031522 , Image - 1

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Unit-109, 157 Wellington Street E Alliston, New Tecumseth, Simcoe, ON MLS® N13031522

Residential Condo & Other (Condo Apartment)

$429000.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Main floor executive condo in the heart of Alliston. Walking distance to shops, restaurants, school, and the recreation center. This beautiful one-bed
13 Photos
Last Updated : 22 Days ago
5703 10th Side Road, Simcoe, ON , MLS #N12882638 , Image - 1

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5703 10th Side Road Rural Essa, Essa, Simcoe, ON MLS® N12882638

Residential Freehold (Vacant Land)

$399900.0
  • < 700 sq-ft
A rare opportunity to build with a head start. Set on over an acre along 10th Side Road in Essa Township, this property offers the space and privacy o
40 Photos
Last Updated : 22 Days ago
56 Birch Trail, Simcoe, ON , MLS #S13036556 , Image - 1

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56 Birch Trail Wasaga Beach, Simcoe, ON MLS® S13036556

Residential Freehold (Detached)

$499777.0
  • 1 Beds
  • 2 Baths
  • < 700 sq-ft
Charming A-Frame Cottage Just a 9-Minute Walk from Allenwood Beach. Nestled at the end of a tranquil cul-de-sac, this delightful A-frame cottage is on
34 Photos
Last Updated : 22 Days ago
90 Dean Avenue, Simcoe, ON , MLS #S9231440 , Image - 1

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Unit-507, 90 Dean Avenue Painswick South, Barrie, Simcoe, ON MLS® S9231440

Residential Condo & Other (Leasehold Condo)

$419900.0
price drop iconPrice drop by 7.7%
  • 1 Beds
  • 2 Baths
  • 900-999 sq-ft
The Terraces of Heritage Square is a Adult over 60+ building. These buildings have lots to offer, Party rooms, library, computer room and a second lev
46 Photos
Last Updated : 23 Days ago
14 Dawson Drive, Simcoe, ON , MLS #S13028014 , Image - 1

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Unit-415, 14 Dawson Drive Collingwood, Simcoe, ON MLS® S13028014

Residential Condo & Other (Condo Townhouse)

$440000.0
  • 2 Beds
  • 2 Baths
  • 900-999 sq-ft
Beautifully updated townhome in a prime Collingwood location, tucked among the trees for added privacy and a true four-season feel. This two-storey ho
4 Photos
Last Updated : 25 Days ago
15 Tiny Beaches Road N, Simcoe, ON , MLS #S12236229 , Image - 1
15 Tiny Beaches Road N Rural Tiny, Tiny, Simcoe, ON MLS® S12236229

Residential Freehold (Vacant Land)

$299900.0
Prime building lot located next to a park and just steps from the shores of Georgian Bay. Enjoy the convenience of being minutes from a marina and Pro
48 Photos
Last Updated : 25 Days ago
36 Tecumseth Pines Drive, Simcoe, ON , MLS #N12426310 , Image - 1

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36 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N12426310

Residential Freehold (Detached)

$499000.0
price drop iconPrice drop by 1.2%
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Tecumseth Pines, where peaceful country surroundings meet an active and welcoming 55+ lifestyle! Nestled in a beautiful community just minu
42 Photos
Last Updated : 25 Days ago
112 Loggers Run, Simcoe, ON , MLS #S13014570 , Image - 1

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Unit-38, 112 Loggers Run Ardagh, Barrie, Simcoe, ON MLS® S13014570

Residential Condo & Other (Condo Townhouse)

$405000.0
  • 3 +1 Beds
  • 3 Baths
  • 1200-1399 sq-ft
This open concept town home is ideal for first-time home buyers, investors or that busy professional who needs close and easy access to the highway. T
45 Photos
Last Updated : 28 Days ago
333 LAFONTAINE Road W, Simcoe, ON , MLS #S13012886 , Image - 1

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Unit-102, 333 LAFONTAINE Road W Rural Tiny, Tiny, Simcoe, ON MLS® S13012886

Residential Condo & Other (Other)

$175000.0
  • 1 +0 Beds
  • 1 Baths
  • 600-699 sq-ft
Welcome to Unit 102 at The Villageois in Tiny Township, near Georgian Bay. This ground-floor, 1-bedroom, 1-bathroom life lease condo offers just under
46 Photos
Last Updated : 28 Days ago
333 LAFONTAINE Road W, Simcoe, ON , MLS #S13012692 , Image - 1

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Unit-310, 333 LAFONTAINE Road W Rural Tiny, Tiny, Simcoe, ON MLS® S13012692

Residential Condo & Other (Other)

$199900.0
  • 1 +0 Beds
  • 1 Baths
  • 800-899 sq-ft
Welcome to Unit 310 at The Villageois, a peaceful retirement community near Georgian Bay in Tiny Township. This spacious 1-bedroom, 1-bathroom life le
40 Photos
Last Updated : 28 Days ago
1 Paradise Boulevard, Simcoe, ON , MLS #S12957462 , Image - 1

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Unit-Unit 14, 1 Paradise Boulevard Rural Ramara, Ramara, Simcoe, ON MLS® S12957462

Residential Condo & Other (Condo Townhouse)

$429000.0
price drop iconPrice drop by 7.7%
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Don't Miss this Exceptional Waterfront Opportunity on Lake Simcoe. This Beautifully Appointed 2-bedroom, Two-Storey Waterfront Condominium on Paradise
18 Photos
Last Updated : 28 Days ago
525 Midland Point Road, Simcoe, ON , MLS #S13011760 , Image - 1

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Unit-36, 525 Midland Point Road Midland, Simcoe, ON MLS® S13011760

Residential Freehold (MobileTrailer)

$255900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Easy living at its best in popular Leeshore Estates, Midland. This unit is located in Midland's prime waterfront community on Georgian Bay. Two bedroo
6 Photos
Last Updated : 28 Days ago
14 Barbara Avenue, Simcoe, ON , MLS #S13010966 , Image - 1

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14 Barbara Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13010966

Residential Freehold (Vacant Land)

$344000.0
  • < 700 sq-ft
Here's an Easy Choice.With an ideal location, a level ready-to-build residential lot, development charges paid (approx. $41,245 value), two driveways,
16 Photos
Last Updated : 29 Days ago
150 AMANDA Street, Simcoe, ON , MLS #S12676848 , Image - 1

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150 AMANDA Street Waubaushene, Tay, Simcoe, ON MLS® S12676848

Residential Freehold (Vacant Land)

$159900.0
Build your dream home on this exceptional corner lot, tucked away on a quiet, low-traffic street in the welcoming community of Waubaushene. Just a sho
24 Photos
Last Updated : 29 Days ago
21 Hawthorne Drive, Simcoe, ON , MLS #N13005520 , Image - 1

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21 Hawthorne Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13005520

Residential Freehold (Detached)

$299999.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Top 5 Reasons You Will Love This Home: 1) An upgrade packed home that delivers exceptional value at every turn, even before stepping inside you'll not
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