416-800-1055
Are You a Realtor? JOIN US
FOR SALE
FOR RENT
LIST PROPERTY FOR SALE
Property Type
Municipality
see all
|
Bedrooms
Minimum
0-Beds 989
1-Bed 986
2-Beds 835
3-Beds 623
4-Beds 361
5-Beds 45
6-Beds 6
7-Beds 2
Maximum
0-Beds 3
1-Bed 154
2-Beds 366
3-Beds 628
4-Beds 944
5-Beds 983
6-Beds 987
7-Beds 989
Bathrooms
Price Range
Maximum
$300k 0
$400k 2
$500k 38
$600k 149
$700k 231
$800k 302
$900k 339
$1.00m 376
$1.25m 465
$1.50m 561
$1.75m 638
$2.00m 729
$2.50m 802
$3.00m 859
$4.00m 927
$5.00m 952
$7.50m 980
$10.0m 982
$15.0m 984
$20.0m 986
$30.0m 987
2144 Winding Woods Dr, Oakville
Home Oakville River Oaks Winding Woods Dr

2144 Winding Woods Dr
NOT FOR SALE FOR INFORMATION PURPOSES ONLY $400k$800k$1.20m$1.60m$2.00m$2.40m2000200120022003200420052006200720082009201020112012201320142015201620172018201920202021202220232144 Winding Woods Dr, Oakville - Comparative Market Analysis on Apr 1, 2025 is $2,289,151 2144 Winding Woods Dr, Oakville - Comparative Market Analysis on Apr 1, 2025 is $2,289,151 [Source: Listing.ca] © 2025 Listing.ca
Save Graph
How is this Graph Generated?
SIMILAR PROPERTIES FOR SALE
391 March Cres, Oakville
5 beds
5 baths
$2,099,999
391 March Cres, Oakville
Rarely does a home of this size come to market in this premium neighbourhood! This home welcomes you to a serene lifestyle. Situated on a quiet...
85 Howell Rd, Oakville
5 beds
3 baths
$1,939,900
85 Howell Rd, Oakville
Welcome to 85 Howell Rd, a warm & spacious 5 bedroom executive home located in the highly sought after River Oaks community. This well cared for home...
60 River Glen Blvd, Oakville
5+1 beds
4 baths
$1,899,000
Located in the highly desirable River Oaks neighborhood, this stunning home is set on a beautifully landscaped lot, exuding exceptional curb appeal...
238 Elderwood Tr, Oakville
4 beds
4 baths
$2,100,000
Don't miss your chance to own this stunning and meticulously renovated River Oaks home at 238 Elderwood. Nestled on a quiet, family-friendly street...
2196 Grand Ravine Dr, Oakville
4 beds
3 baths
$1,975,000
Discover an exceptional lifestyle in River Oaks, where woodlands, scenic trails, & lush parks create a picturesque setting. Just minutes from the...
2103 Grand Ravine Dr, Oakville
4 beds
4 baths
$1,650,000
Fabulous, BRIGHT, upgraded house in River Oaks on the lovliest, quiet part of Grand Ravine Drive without a residential neighbour behind! Pack your...
67 River Oaks Blvd, Oakville
4 beds
4 baths
$1,499,998
Perfect Blend of Nature & Urban Convenience. This stunning executive home offers luxury, comfort & an unbeatable location. Surrounded by scenic...
2124 Nipigon Dr, Oakville
4+1 beds
4 baths
$2,179,900
2124 Nipigon Dr, Oakville
Stunning back to ravine property located in sought after river oaks Oakville. Conveniently closed to shopping, parks, nature trails, schools, public...
2163 Towne Blvd, Oakville
4+1 beds
4 baths
$1,995,000
2163 Towne Blvd, Oakville
A rare gem awaits in River Oaks, Oakville, yours to call home! This meticulously maintained 4+1 bedroom detached home offering over 3500 sq/ft of...
2080 Sixth Line, Oakville
4+1 beds
4 baths
$1,599,900
2080 Sixth Line, Oakville
Nestled in the heart of the family-friendly River Oaks community this 4+1 bedroom and 3.5 bathroom home offers over 4,200sf of living space...
2080 Sixth Line, Oakville
4+1 beds
4 baths
$1,599,900
2080 Sixth Line, Oakville
Nestled in the heart of the family-friendly River Oaks community this 4+1 bedroom and 3.5 bathroom home offers over 4,200sf of living space...
265 River Glen Blvd, Oakville
4+1 beds
4 baths
$1,588,000
Discover River Oaks - a vibrant neighbourhood offering the perfect blend of convenience and charm. Within walking distance of schools and recreation...
2116 Munns Ave, Oakville
4+2 beds
5 baths
$2,150,000
2116 Munns Ave, Oakville
Private backyard oasis! This luxury 4 + 2 Bed, 4 +1 bath home backs on and is beside Oakridge Park with its lush forested walking trails. You will...
560 Marlatt Dr, Oakville
3 beds
4 baths
$1,399,000
560 Marlatt Dr, Oakville
Welcome to your new home 560 Marlatt Drive, a spacious 3 bedroom, 4-bath family home nestled on a quiet street in the sought-after River Oaks...
2353 Mowat Ave, Oakville
3+1 beds
4 baths
$1,298,000
2353 Mowat Ave, Oakville
Beautiful Family Home In The Prestigious River Oak Neighborhood. Impeccably Maintained & Elegantly Upgraded Throughout, This Gorgeous Home Is...
5
BEDROOMS
5
BATHROOMS
1
KITCHENS
ADDRESS
2144 Winding Woods Dr, River Oaks, Oakville L6H5T8
PROPERTY TYPE
Detached House
LOT SIZE
56.00 x 111.00
STATUS
NOT AN ACTIVE LISTING
COMPARATIVE MARKET ANALYSIS
$2,289,151
Refinance Your Property
Comparative Market Analysis of 2144 Winding Woods Dr is based on market trends for River Oaks community of Oakville community and recent sales in the area. The sold statistics information is provided by Toronto Real Estate Board (Reference: Competition Bureau vs. TREB in Federal Court of Appeal - 27 April, 2016; TREB's appeal was dismissed and it is now mandated to provide sold data to the public).
Comparative Market Analysis is provided for reference purposes only and may be different from the actual market sold price or an appraised value. Comparative Market Analysis does not take into account recent home improvements that have been carried out to the property. Listing.ca does not bare any responsibility to the accuracy of the provided opinion. The graph represents a seasonally adjusted long term valuation trends and may not immediately reflect short term market fluctuations.
SALES HISTORY
XX/XX/20XX
SOLD
$XXX,000
Request Sold History
MARKET STATS
PROPERTY DESCRIPTION
2144 Winding Woods Dr is a 5-bedroom 5-washroom detached house located in River Oaks community of Oakville. It is currently NOT FOR SALE, but is worth in our opinion around $2,289,151 .

The property is situated on a 56' frontage by 111' deep lot. 2144 Winding Woods Dr is currently not for sale and is not an active listing on Listing.ca.
NEARBY SCHOOLS
Glenashton Daycare Centre Ltd 2.5 km
2200 Trafalgar Rd, L6H7H2
Phone: (905) 338-9019
Halton Catholic District School Board 1.8 km
145 Millbank Dr, L6H6G3
Phone: (905) 257-7102
Halton Catholic District School Board 1.5 km
2420 Sixth Line, L6H5Z8
Phone: (905) 257-3534
Halton Catholic District School Board 0.8 km
391 River Glen Blvd, L6H5X5
Phone: (905) 257-2791
Halton District School Board 0.7 km
2173 Munn's Ave, L6H3S9
Phone: (905) 842-7430
Halton District School Board 1.8 km
2220 Caldwell Dr, L6H6B5
Phone: (905) 845-1661
Montclair Public School - Halton District School Board 2.2 km
1285 Montclair Dr, L6H1Z3
Phone: (905) 845-9590
NEARBY MEDICAL CENTRES
Dr Heather Cockwell 3.0 km
627 Lyons Lane, L6J5Z7
Phone: (905) 844-7238
MCI The Doctor's Office 3.6 km
1011 Upper Middle Rd E, L6H4L2
Phone: (905) 849-7007
Oakville Fertility & Women's Health Center 3.0 km
627 Lyons Lane, L6J5Z7
Phone: (905) 844-7238
NEARBY PHARMACIES
Walmart Supercentre 2.5 km
234 Hays Boul, L6H6M4
Phone: (905) 257-5742
NEARBY COFFEE SHOPS
Tim Hortons - Oakville 3.6 km
1011 Upper Middle Rd E, L6H4L2
Phone: (905) 844-1519
NEARBY BANKS
Manulife Financial 0.8 km
410 River Glen Blvd, L6H5X5
Phone: (905) 582-5562
RBC - Oakville 7.6 km
2460 Winston Churchill Blvd, L6H6J5
Phone: (905) 829-8665
RBC Royal Bank 7.6 km
2460 Winston Churchill blvd, L6H6J5
Phone: (905) 829-8665
NEARBY HEALTH AND FITNESS FACILITIES
Cycle of Health 0.8 km
201 River Oaks Blvd W, L6H3S7
Phone: (905) 334-9305
Highway To Health 1.5 km
17 Inverhuron Trail, L6H5Z6
Phone: (905) 877-1999
Are You a Licensed Real Estate Agent or Broker?
© 2011-2025 Real Estate Bay Realty Inc, Brokerage
The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial or any other purpose. Information is deemed reliable but is not guaranteed accurate by TREB, Listing.ca or Real Estate Bay Realty, Brokerage.
The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA. Used under license.
Real Estate Bay Realty, Brokerage
220 Duncan Mill Road, Suite 209
Toronto, ON M3B 3J5
Phone: 416-800-1055
info@listing.ca
Listing.ca on Twitter
RealEstateBay.ca on Facebook