Rent to own Homes in Winter Park, FL

Nestled in the heart of the Orlando metro area, just a few miles away from the city's vibrant downtown, is Winter Park, Florida. Winter Park boasts a serene, natural setting, which you can take in at one of the city's dozen parks. Cultural and community events abound in Winter Park, from the annual art festival to the community's Fourth of July Celebration. The city is a hub for fine dining and shopping, and has something for everyone to enjoy.

Winter Park, FL is a great place for affordable rent-to-own homes! With a median household income of over $80,500 and a median rent of $1,372, the Winter Park, FL rent-to-own market is more affordable than the traditional housing market which has shown tremendous growth across the U.S. and with it, aggressive competition for home purchases. With the current housing shortage trend it can make it harder to become a homeowner, including in Winter Park, FL. This means higher than average down payments for homes and higher qualification standards for conventional home loans. With a rent-to-own property, tenants are also buyers. You can live in the house for a set amount of time before you purchase it, meaning that you get to know the house, your neighbors, and your community before making the final purchase. This enables you and your family to make the right choice based on both information and experience. Rent-to-own is also a great alternative way to get into a home if you have bad credit or don't have enough saved for a down payment.

Check out Winter Park, FL rent to own homes for sale, which may include auction properties, for sale by owner, and more.
Showing 1 - 44 of 176
2149 RIDGE DR
Rent To Own
Casselberry
Single Family Home
Winter Park, FL 32792
3
1
1478 ft2
1959
311 E MORSE BLVD #8-1
Rent To Own
 
Townhouse/Condo
Winter Park, FL 32789
3
3
2350 ft2
1960
1613 CUMBIE AVE
Rent To Own
Fairvilla Park
Single Family Home
Orlando, FL 32804
2
1
660 ft2
1957
1 of 214 530 E Central Blvd
Rent To Own
South Eola
Townhouse/Condo
Orlando, FL 32801
2
2
1304 ft2
1985
207 ROBIN RD
Rent To Own
Altamonte Springs
Single Family Home
Altamonte Springs, FL 32701
3
3
2438 ft2
1968
5321 CYPRESS RESERVE PL
Rent To Own
 
Single Family Home
Winter Park, FL 32792
4
2
2283 ft2
1997
1144 Delaney Ave
Rent To Own
Delaney Park
Townhouse/Condo
Orlando, FL 32806
2
2
1500 ft2
1986
440 MISTY OAKS RUN
Rent To Own
Casselberry
Single Family Home
Casselberry, FL 32707
4
3
2335 ft2
2003
(Undisclosed Address)
Rent To Own
 
Single Family Home
Orlando, FL 32806
3
2
1953 ft2
1 of 23 6517 AUTUMN COVE DR
Rent To Own
Ventura
Single Family Home
Orlando, FL 32822
3
2
1604 ft2
1992
2900 PERSHING AVE
Rent To Own
Conway
Single Family Home
Orlando, FL 32806
3
2
1311 ft2
1958
1166 PIEDMONT WEKIWA RD
Rent To Own
Apopka
Single Family Home
Apopka, FL 32703
3
2
1521 ft2
1921
New
414 Candler Ave
Rent To Own
 
Single Family Home
Orlando, FL 32835
3
2
1400 ft2
1985
1631 SUNSET VIEW CIR
Rent To Own
Apopka
Single Family Home
Apopka, FL 32703
3
2
1222 ft2
1995
771 DACOMA CT
Rent To Own
Apopka
Townhouse/Condo
Apopka, FL 32703
2
2
1163 ft2
1988
9660 DORIS LN
Rent To Own
Vista Park
Townhouse/Condo
Orlando, FL 32829
2
3
1273 ft2
2005
1706 DOREEN AVE
Rent To Own
Ocoee
Single Family Home
Ocoee, FL 34761
2
1
1021 ft2
1961
2730 MIDSUMMER DR
Rent To Own
Lake Butler
Single Family Home
Windermere, FL 34786
4
4
3452 ft2
1984
7914 SUMMER RIDGE PL
Rent To Own
 
Single Family Home
Orlando, FL 32819
5
4
3903 ft2
1998
503 E 11TH ST
Rent To Own
Sanford
Single Family Home
Sanford, FL 32771
3
2
816 ft2
1989
8820 BAY VILLA CT
Rent To Own
 
Single Family Home
Orlando, FL 32836
4
4
3711 ft2
1985
1533 AMHERST LN
Rent To Own
Oak Hollow
Single Family Home
Kissimmee, FL 34744
3
2
1682 ft2
1989
Hot
8026 WOOD SAGE DR
Rent To Own
Village Of Bridgewater
Single Family Home
Winter Garden, FL 34787
3
3
2004 ft2
2017
(Undisclosed Address)
Rent To Own
Deltona Lakes
Single Family Home
Deltona, FL 32725
3
2
1345 ft2
712 GOLFPARK DR
Rent To Own
Celebration
Single Family Home
Kissimmee, FL 34747
5
5
4620 ft2
1999
260 REESE CT
Rent To Own
 
Townhouse/Condo
Saint Cloud, FL 34769
3
2
1380 ft2
2020
266 REESE CT
Rent To Own
 
Townhouse/Condo
Saint Cloud, FL 34769
3
2
1380 ft2
2020
182 JOCELYN DR
Rent To Own
 
Single Family Home
Davenport, FL 33897
4
2
0 ft2
2005
Hot
1 of 30 313 SALAMANCA RD
Rent To Own
Loughman
Single Family Home
Davenport, FL 33837
3
2
1702 ft2
2015
100 W MYRTLE ST
Rent To Own
Howey In The Hills
Single Family Home
Howey In The Hills, FL 34737
2
1
1456 ft2
1926
Coventry Ct
Rent To Own
 
Single Family Home
Kissimmee, FL 34758
4
3
2215 ft2
18750 REA WAY
Rent To Own
Altoona
Single Family Home
Altoona, FL 32702
2
2
1136 ft2
1947
12451 INSIM LN
Rent To Own
 
Single Family Home
Leesburg, FL 34788
3
4
3183 ft2
2015
9720 FAIRWAY CIR
Rent To Own
Silver Lake
Single Family Home
Leesburg, FL 34788
5
4
2983 ft2
1986
3361 PONETA AVE
Rent To Own
Venetian Bay
Single Family Home
New Smyrna Beach, FL 32168
4
2
2165 ft2
2015
1 of 257 424 LUNA BELLA LN
Rent To Own
Venetian Bay
Townhouse/Condo
New Smyrna Beach, FL 32168
2
2
1575 ft2
2007
10944 AUTUMN LN
Rent To Own
 
Single Family Home
Clermont, FL 34711
4
4
4501 ft2
1994
New
1248 S Pennsylvania Ave
Rent to Own Eligible
 
Townhouse/Condo
Winter Park, FL 32789
3
3
1957 ft2
2007
New
1695 LEE RD
Rent to Own Eligible
 
Townhouse/Condo
Winter Park, FL 32789
2
1
881 ft2
2001
New
814 HAMILTON PLACE CT
Rent to Own Eligible
 
Single Family Home
Winter Park, FL 32789
4
4
2703 ft2
2007
101 S New York Ave
Rent to Own Eligible
 
Townhouse/Condo
Winter Park, FL 32789
3
4
2966 ft2
2008
New
230 Killarney Bay Ct
Rent to Own Eligible
 
Townhouse/Condo
Winter Park, FL 32789
2
3
1536 ft2
1986
200 S Interlachen Ave
Rent to Own Eligible
 
Townhouse/Condo
Winter Park, FL 32789
3
4
3074 ft2
2001
New
210 E LAKE SUE AVE
Rent to Own Eligible
 
Single Family Home
Winter Park, FL 32789
4
3
2582 ft2
1951
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Buying a Home in Winter Park, FL

Winter Park, FL is seeing rapid growth and Winter Park, FL's' housing market remains not optimal with an average home price that is 116% above the 2024 national average. Winter Park, FL is part of Orange county and taxes are an important factor to consider when purchasing a home whether through rent to own or a traditional purchase. The average tax rate as of 2024 for county Orange is 0.94% which is below the national average, which is 0.99%.

Median Home Price in Winter Park, FL

Median Rent in Winter Park, FL

Rent to own homes offer low monthly payments and flexible terms.

Top 4 Reasons to Live in Winter Park, Florida

Cultural opportunities abound! Art lovers will rejoice when they explore Winter Park's cultural offerings. The Morse Museum offers the largest collection of works, including jewelry and pottery, paintings by artist Louis Comfort Tiffany, and pottery, paintings and decorative art from other late 19th and early 20th century artists. The Winter Park Playhouse, which is Central Florida's only musical theater, offers musical comedies, revues and cabarets performed by talented live musicians. The Rollins College Cornell Fine Arts Museum boasts a collection of more than 5,000 pieces, ranging from paintings to archaeological fragments to sketches and drawings.

Shopping and dining on Park Avenue! Stroll down the brick-paved Park Avenue and shop at stores such as Lily Pulitzer, Williams-Sonoma and Bay Hill Jewelers. Grab a plate of pasta at Pannullo's Italian Restaurant or enjoy new American cuisine at 310 Park South. Finish your Park Avenue adventure at The Wine Room, where you can choose from hundreds of wines on tap.

Great housing options available! Winter Park is a much sought-after address in the Orlando area and home prices reflect the area's desirability. This densely populated suburb offers hundreds of homes for sale, with the average price per square foot at $163 and rising, making homes here an excellent investment. Although the average listing price of homes for sale in Winter Park exceeds $600,000, housing prices vary widely depending on the part of Winter Park you choose. Look outside of the popular and trendy heart of this suburb for attractively priced homes, such as in Winter Park Pines. The further away from Park Avenue, the better the deals. You might even find rent to own homes.

Pedestrian friendly housing options! Even though you're nestled in the heart of Orlando, Winter Park can put shops and dining just a short walk away if you choose the right neighborhoods. If walking or biking around this suburb is important to you, focus your housing search on the center of Winter Park. Check out housing options along Fairbanks Avenue near Park Avenue. Look at neighborhoods such as Windsong in the center of old Winter Park, or homes near Hannibal Square on Winter Park's west end.