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

Townhouse (1)

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.

49 out of 51 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

$658,900

3 bds | 3 ba | 2,581 sqft | built 2017
8919 Lakeshore Pointe Dr, Winter Garden, FL 34787
$-1,650
Cash flow
-13.1%
Cash-on-Cash Return

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

$430,000

3 bds | 3 ba | 1,717 sqft | built 2023
15579 Water Spring Blvd, Winter Garden, FL 34787
$-1,131
Cash flow
-13.7%
Cash-on-Cash Return

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

$424,500

3 bds | 3 ba | 1,567 sqft | built 2023
12035 Holystone St, Winter Garden, FL 34787
$-1,185
Cash flow
-14.6%
Cash-on-Cash Return

2.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$460,000

4 bds | 3 ba | 1,992 sqft | built 2023
10624 Words Dr, Winter Garden, FL 34787
$-1,286
Cash flow
-14.6%
Cash-on-Cash Return

2.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$445,000

3 bds | 3 ba | 1,868 sqft | built 2021
11054 Hanlon Terrace Aly, Winter Garden, FL 34787
$-1,235
Cash flow
-14.5%
Cash-on-Cash Return

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

$445,000

3 bds | 3 ba | 1,784 sqft | built 2018
15477 Blackbead St, Winter Garden, FL 34787
$-1,260
Cash flow
-14.8%
Cash-on-Cash Return

2.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$234,500

2 bds | 2 ba | 1,140 sqft | built 1984
460 Sand Lime Rd, Winter Garden, FL 34787
$-233
Cash flow
-5.2%
Cash-on-Cash Return

5.1%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
StellarMLS

$408,000

3 bds | 3 ba | 1,717 sqft | built 2021
9909 Alliteration Aly, Winter Garden, FL 34787
$-1,168
Cash flow
-14.9%
Cash-on-Cash Return

2.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$425,000

3 bds | 3 ba | 1,751 sqft | built 2011
15483 Avenue Of The Arbors, Winter Garden, FL 34787
$-1,169
Cash flow
-14.4%
Cash-on-Cash Return

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

$449,900

3 bds | 3 ba | 1,902 sqft | built 2019
15241 Sunrise Grove Ct, Winter Garden, FL 34787
$-1,180
Cash flow
-13.7%
Cash-on-Cash Return

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

$449,900

4 bds | 3 ba | 2,033 sqft | built 2017
15693 Kinnow Mandarin Ln, Winter Garden, FL 34787
$-1,329
Cash flow
-15.4%
Cash-on-Cash Return

2.7%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$486,000

3 bds | 3 ba | 1,814 sqft | built 2023
13452 Sagestone Dr, Winter Garden, FL 34787
$-1,430
Cash flow
-15.4%
Cash-on-Cash Return

2.8%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$479,900

3 bds | 3 ba | 2,076 sqft | built 2020
15946 Marina Bay Dr, Winter Garden, FL 34787
$-1,211
Cash flow
-13.2%
Cash-on-Cash Return

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

$394,990

3 bds | 3 ba | 1,748 sqft | built 2008
1122 Priory Cir, Winter Garden, FL 34787
$-1,153
Cash flow
-15.2%
Cash-on-Cash Return

2.8%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$515,700

4 bds | 3 ba | 1,917 sqft | built 2019
8042 Glenlloyd Ave, Winter Garden, FL 34787
$-1,254
Cash flow
-12.7%
Cash-on-Cash Return

3.4%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$499,999

3 bds | 3 ba | 2,070 sqft | built 2020
15975 Marina Bay Dr, Winter Garden, FL 34787
$-1,344
Cash flow
-14.0%
Cash-on-Cash Return

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

$410,000

3 bds | 3 ba | 1,568 sqft | built 2019
16162 Arbor Crest Aly, Winter Garden, FL 34787
$-1,099
Cash flow
-14.0%
Cash-on-Cash Return

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

$444,900

3 bds | 3 ba | 1,568 sqft | built 2023
17081 Water Spring Blvd, Winter Garden, FL 34787
$-1,292
Cash flow
-15.2%
Cash-on-Cash Return

2.8%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$325,000

2 bds | 3 ba | 1,145 sqft | built 2005
13758 Daniels Landing Cir, Winter Garden, FL 34787
$-940
Cash flow
-15.1%
Cash-on-Cash Return

2.8%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$210,000

2 bds | 1 ba | 761 sqft | built 1988
963 Stucki Ter, Winter Garden, FL 34787
$-252
Cash flow
-6.3%
Cash-on-Cash Return

4.8%
Cap rate
0.8%
Rent to Value Ratio
Property photo
Active
StellarMLS

$418,900

3 bds | 3 ba | 1,560 sqft | built 2020
6013 Blue Lily Way, Winter Garden, FL 34787
$-1,284
Cash flow
-16.0%
Cash-on-Cash Return

2.6%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$300,000

2 bds | 3 ba | 1,236 sqft | built 2005
13329 Harbor Shore Ln, Winter Garden, FL 34787
$-798
Cash flow
-13.9%
Cash-on-Cash Return

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

$415,000

3 bds | 3 ba | 1,748 sqft | built 2015
14867 Driftwater Dr, Winter Garden, FL 34787
$-1,188
Cash flow
-14.9%
Cash-on-Cash Return

2.8%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$400,000

3 bds | 3 ba | 1,568 sqft | built 2018
16518 Brook Springs Aly, Winter Garden, FL 34787
$-1,117
Cash flow
-14.6%
Cash-on-Cash Return

2.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$549,000

3 bds | 3 ba | 2,067 sqft | built 2006
6632 Pasturelands Pl, Winter Garden, FL 34787
$-2,156
Cash flow
-20.5%
Cash-on-Cash Return

1.6%
Cap rate
0.5%
Rent to Value Ratio
Property photo
Active
StellarMLS

$439,000

3 bds | 3 ba | 1,844 sqft | built 2019
15237 Sunrise Grove Ct, Winter Garden, FL 34787
$-1,143
Cash flow
-13.6%
Cash-on-Cash Return

3.2%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$453,000

3 bds | 3 ba | 1,814 sqft | built 2020
16261 Admirals Cove Ln, Winter Garden, FL 34787
$-1,210
Cash flow
-13.9%
Cash-on-Cash Return

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

$470,000

3 bds | 3 ba | 1,881 sqft | built 2019
11162 Hanlon Terrace Aly, Winter Garden, FL 34787
$-1,267
Cash flow
-14.1%
Cash-on-Cash Return

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

$429,900

3 bds | 3 ba | 1,560 sqft | built 2021
6165 Juneberry Way, Winter Garden, FL 34787
$-1,357
Cash flow
-16.5%
Cash-on-Cash Return

2.5%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$435,000

3 bds | 3 ba | 1,792 sqft | built 2020
16217 Prairie School Dr, Winter Garden, FL 34787
$-1,239
Cash flow
-14.9%
Cash-on-Cash Return

2.9%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$340,000

3 bds | 3 ba | 1,558 sqft | built 2006
509 Westpoint Garden Cir, Winter Garden, FL 34787
$-574
Cash flow
-8.8%
Cash-on-Cash Return

4.3%
Cap rate
0.7%
Rent to Value Ratio
Property photo
Active
StellarMLS

$425,000

3 bds | 3 ba | 1,636 sqft | built 2023
10684 Words Dr Dr, Winter Garden, FL 34787
n/a
Cash flow
n/a
Cash-on-Cash Return

n/a
Cap rate
n/a
Rent to Value Ratio
Property photo
Active
StellarMLS

$449,900

3 bds | 3 ba | 1,626 sqft | built 2019
9790 Amber Chestnut Way, Winter Garden, FL 34787
$-1,525
Cash flow
-17.7%
Cash-on-Cash Return

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

$224,900

3 bds | 2 ba | 1,156 sqft | built 1987
1270 Westside Dr, Winter Garden, FL 34787
$-72
Cash flow
-1.7%
Cash-on-Cash Return

5.9%
Cap rate
0.9%
Rent to Value Ratio
Property photo
Active
StellarMLS

$438,000

3 bds | 3 ba | 1,568 sqft | built 2019
16180 Arbor Crest Aly, Winter Garden, FL 34787
$-1,314
Cash flow
-15.7%
Cash-on-Cash Return

2.7%
Cap rate
0.6%
Rent to Value Ratio
Property photo
Active
StellarMLS

$429,000

3 bds | 3 ba | 1,639 sqft | built 2006
14433 Pleach St, Winter Garden, FL 34787
$-1,214
Cash flow
-14.8%
Cash-on-Cash Return

2.9%
Cap rate
0.7%
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
$-2,541
Cash flow
-17.7%
Cash-on-Cash Return

2.2%
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
$-1,147
Cash flow
-13.8%
Cash-on-Cash Return

3.1%
Cap rate
0.6%
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
$-7,167
Cash flow
-17.1%
Cash-on-Cash Return

2.3%
Cap rate
0.4%
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
$-1,056
Cash flow
-12.7%
Cash-on-Cash Return

3.4%
Cap rate
0.7%
Rent to Value Ratio