Skip to content
×
Pro Members Get
Full Access!
Get off the sidelines and take action in real estate investing with BiggerPockets Pro. Our comprehensive suite of tools and resources minimize mistakes, support informed decisions, and propel you to success.
Advanced networking features
Market and Deal Finder tools
Property analysis calculators
Landlord Command Center
ANNUAL Save 16%
$32.50 /mo
$390 billed annualy
MONTHLY
$39 /mo
billed monthly
7 day free trial. Cancel anytime

Filters

Price

Price Range

$
  • $0
  • $50,000
  • $100,000
  • $150,000
  • $200,000
  • $250,000
  • $300,000
  • $350,000
  • $400,000
  • $450,000
  • $500,000
  • $550,000
  • $600,000
  • $650,000
  • $700,000
  • $750,000
  • $800,000
  • $850,000
  • $900,000
  • $950,000
  • $1M
  • $1.25M
  • $1.5M
  • $1.75M
  • $2M
  • $2.25M
  • $2.5M
  • $2.75M
  • $3M
  • $4M
  • $5M+
$
  • $0
  • $50,000
  • $100,000
  • $150,000
  • $200,000
  • $250,000
  • $300,000
  • $350,000
  • $400,000
  • $450,000
  • $500,000
  • $550,000
  • $600,000
  • $650,000
  • $700,000
  • $750,000
  • $800,000
  • $850,000
  • $900,000
  • $950,000
  • $1M
  • $1.25M
  • $1.5M
  • $1.75M
  • $2M
  • $2.25M
  • $2.5M
  • $2.75M
  • $3M
  • $4M
  • $5M+
Beds/Baths

Bedrooms

Bathrooms

For Sale

Status

Property Type (6)

Property Type

More

Square Feet

Lot Size

Year Built

Projected Rent

Cash on Cash Return

Monthly Cash Flow

Cap Rate

Copied

Winter Garden, FL Investment Properties for Sale

Browse homes for sale and investment properties in Winter Garden, FL. Refine your search by price, property type, or more.

302 out of 340 properties for sale in Winter Garden, FL

Limited Results Shown

Create a free account, or log in to reveal all property listings and enjoy the complete experience.

Property photo
Active
StellarMLS

$1,599,900

5 bds | 4 ba | 3,910 sqft | built 2018
10303 Atwater Bay Dr, Winter Garden, FL 34787
$-6,125
Cash flow
-20.0%
Cash-on-Cash Return

1.6%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Pending
StellarMLS

$750,000

4 bds | 4 ba | 2,704 sqft | built 2018
8872 Bismarck Palm Dr, Winter Garden, FL 34787
$-2,455
Cash flow
-17.1%
Cash-on-Cash Return

2.2%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$765,000

4 bds | 3 ba | 2,893 sqft | built 2023
18381 Oliver Twist Way, Winter Garden, FL 34787
$-2,347
Cash flow
-16.0%
Cash-on-Cash Return

2.5%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$435,000

3 bds | 3 ba | 1,710 sqft | built 2015
15580 Blackbead St, Winter Garden, FL 34787
$-1,097
Cash flow
-13.2%
Cash-on-Cash Return

3.1%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$535,000

3 bds | 3 ba | 1,904 sqft | built 2016
9149 Grand Island Way, Winter Garden, FL 34787
$-1,358
Cash flow
-13.2%
Cash-on-Cash Return

3.1%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,410,000

5 bds | 4 ba | 3,465 sqft | built 2003
17117 Heartwood Loop, Winter Garden, FL 34787
$-3,736
Cash flow
-13.8%
Cash-on-Cash Return

3.0%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,150,000

4 bds | 5 ba | 2,954 sqft | built 2017
16736 Broadwater Ave, Winter Garden, FL 34787
$-3,402
Cash flow
-15.4%
Cash-on-Cash Return

2.6%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$2,185,000

4 bds | 5 ba | 3,836 sqft | built 2023
60 N Park Ave, Winter Garden, FL 34787
$-6,918
Cash flow
-16.5%
Cash-on-Cash Return

2.3%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
StellarMLS

$569,999

3 bds | 2 ba | 2,120 sqft | built 2017
3242 Irish Peach Dr, Winter Garden, FL 34787
$-1,528
Cash flow
-14.0%
Cash-on-Cash Return

2.9%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$435,000

4 bds | 3 ba | 2,200 sqft | built 2021
10316 Spring Arbor Ln, Winter Garden, FL 34787
$-1,006
Cash flow
-12.1%
Cash-on-Cash Return

3.4%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$429,900

3 bds | 3 ba | 1,732 sqft | built 2020
10400 Spring Arbor Ln, Winter Garden, FL 34787
$-1,027
Cash flow
-12.5%
Cash-on-Cash Return

3.3%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$599,000

5 bds | 3 ba | 2,940 sqft | built 2002
181 Zachary Wade St, Winter Garden, FL 34787
$-1,483
Cash flow
-12.9%
Cash-on-Cash Return

3.2%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$515,000

3 bds | 3 ba | 1,774 sqft | built 2020
17087 Wynford Ln, Winter Garden, FL 34787
$-1,449
Cash flow
-14.7%
Cash-on-Cash Return

2.8%
Cap rate
0.5%
Rent to Value Ratio
Active
StellarMLS

$409,000

3 bds | 3 ba | 1,868 sqft | built 2017
15687 Kinnow Mandarin Ln, Winter Garden, FL 34787
$-1,348
Cash flow
-17.2%
Cash-on-Cash Return

2.2%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Pending
StellarMLS

$630,000

4 bds | 2 ba | 2,153 sqft | built 2005
15144 Spinnaker Cove Ln, Winter Garden, FL 34787
$-1,323
Cash flow
-11.0%
Cash-on-Cash Return

3.6%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$693,000

3 bds | 3 ba | 2,336 sqft | built 2022
3186 Sailing Pier Ave, Winter Garden, FL 34787
$-1,484
Cash flow
-11.2%
Cash-on-Cash Return

3.6%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$2,450,000

7 bds | 7 ba | 5,976 sqft | built 2020
15469 Shorebird Ln, Winter Garden, FL 34787
$-11,349
Cash flow
-24.2%
Cash-on-Cash Return

0.6%
Cap rate
0.2%
Rent to Value Ratio
Property photo
Active
StellarMLS

$335,000

3 bds | 3 ba | 1,544 sqft | built 2007
1552 Broken Oak Dr, Winter Garden, FL 34787
$-702
Cash flow
-10.9%
Cash-on-Cash Return

3.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$680,000

4 bds | 3 ba | 2,470 sqft | built 2018
16144 Parkwyn St, Winter Garden, FL 34787
$-1,884
Cash flow
-14.5%
Cash-on-Cash Return

2.8%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,199,000

5 bds | 5 ba | 4,114 sqft | built 2021
9947 Summerlake Groves St, Winter Garden, FL 34787
$-4,484
Cash flow
-19.5%
Cash-on-Cash Return

1.7%
Cap rate
0.3%
Rent to Value Ratio
Property photo
Active
StellarMLS

$910,000

4 bds | 4 ba | 3,115 sqft | built 2023
11206 Pixie Mandarin Ct, Winter Garden, FL 34787
$-3,241
Cash flow
-18.6%
Cash-on-Cash Return

1.9%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,489,000

5 bds | 6 ba | 4,453 sqft | built 2019
15644 Panther Lake Dr, Winter Garden, FL 34787
$-3,042
Cash flow
-10.7%
Cash-on-Cash Return

3.7%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$780,000

5 bds | 3 ba | 2,514 sqft | built 2017
14419 Magnolia Ridge Loop, Winter Garden, FL 34787
$-2,244
Cash flow
-15.0%
Cash-on-Cash Return

2.7%
Cap rate
0.4%
Rent to Value Ratio
Property photo
Active
StellarMLS

$750,000

4 bds | 4 ba | 3,568 sqft | built 2014
1073 Vinsetta Cir, Winter Garden, FL 34787
$-1,636
Cash flow
-11.4%
Cash-on-Cash Return

3.5%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$219,900

2 bds | 2 ba | 930 sqft | built 1988
320 Eron Way, Winter Garden, FL 34787
$-257
Cash flow
-6.1%
Cash-on-Cash Return

4.7%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$899,990

5 bds | 4 ba | 4,069 sqft | built 2019
14504 Sunbridge Cir, Winter Garden, FL 34787
$-2,334
Cash flow
-13.5%
Cash-on-Cash Return

3.0%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$380,000

2 bds | 3 ba | 1,345 sqft | built 2006
14448 Pleach St, Winter Garden, FL 34787
$-1,212
Cash flow
-16.6%
Cash-on-Cash Return

2.3%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$342,000

2 bds | 1 ba | 914 sqft | built 1952
636 Coke Ave, Winter Garden, FL 34787
$-486
Cash flow
-7.4%
Cash-on-Cash Return

4.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
Beaches

$238,900

2 bds | 2 ba | 918 sqft | built 1984
142 Windtree Ln, Winter Garden, FL 34787
$-612
Cash flow
-13.4%
Cash-on-Cash Return

3.1%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$699,000

4 bds | 4 ba | 2,656 sqft | built 2001
1024 Harbor Hill St, Winter Garden, FL 34787
$-1,859
Cash flow
-13.9%
Cash-on-Cash Return

3.0%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$910,000

5 bds | 5 ba | 3,602 sqft | built 2019
14150 Aldford Dr, Winter Garden, FL 34787
$-1,897
Cash flow
-10.9%
Cash-on-Cash Return

3.6%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Pending
StellarMLS

$274,900

2 bds | 2 ba | 1,216 sqft | built 2012
1555 Scarlet Oak Loop, Winter Garden, FL 34787
$-580
Cash flow
-11.0%
Cash-on-Cash Return

3.6%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$400,000

3 bds | 2 ba | 1,339 sqft | built 1960
425 S Woodland St, Winter Garden, FL 34787
$-377
Cash flow
-4.9%
Cash-on-Cash Return

5.0%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$799,999

4 bds | 4 ba | 3,093 sqft | built 2018
16150 Parkwyn St, Winter Garden, FL 34787
$-2,118
Cash flow
-13.8%
Cash-on-Cash Return

3.0%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$585,000

3 bds | 3 ba | 1,892 sqft | built 2019
9918 Pallida Hickory Way, Winter Garden, FL 34787
$-1,406
Cash flow
-12.5%
Cash-on-Cash Return

3.3%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$665,000

4 bds | 3 ba | 2,701 sqft | built 2014
14664 Spotted Sandpiper Blvd, Winter Garden, FL 34787
$-1,691
Cash flow
-13.3%
Cash-on-Cash Return

3.1%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$1,025,000

5 bds | 4 ba | 3,911 sqft | built 2017
16310 Rock Coast Dr, Winter Garden, FL 34787
$-2,937
Cash flow
-14.9%
Cash-on-Cash Return

2.7%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$529,000

3 bds | 3 ba | 2,199 sqft | built 2017
15088 Night Heron Dr, Winter Garden, FL 34787
$-1,588
Cash flow
-15.7%
Cash-on-Cash Return

2.5%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$565,000

3 bds | 3 ba | 2,196 sqft | built 2018
14214 Shocklach Dr, Winter Garden, FL 34787
$-1,221
Cash flow
-11.3%
Cash-on-Cash Return

3.6%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$875,000

4 bds | 4 ba | 2,799 sqft | built 2017
15672 Shorebird Ln, Winter Garden, FL 34787
$-2,036
Cash flow
-12.1%
Cash-on-Cash Return

3.4%
Cap rate
0.6%
Rent to Value Ratio