Real Estate Investment Properties for Sale in Winter Springs, FL
Looking for investment property in Winter Springs, FL with high ROI ?
Explore a variety of short-term homes & houses in Winter Springs, FL. Invest wisely with VRBO & Winter Springs, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winter Springs, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
710 BRIARWOOD DriveWinter Springs, FLVirtually Staged. MOVE-IN READY WITH BRAND-NEW HVAC SYSTEM! Welcome to this beautifully up... |
4 beds | 2 baths | 1,769 sq.ft. |
$355,000 |
Airbnb cash on cash: 9.86%
|
440 BUCKSKIN CourtWinter Springs, FLPAID-OFF SOLAR + 2018 ROOF + WHOLE-HOME 10Gb ETHERNET all on a corner lot in the heart of ... |
4 beds | 3 baths | 1,922 sq.ft. |
$499,000 |
Airbnb cash on cash: 6.58%
|
113 KRISTI ANN CourtWinter Springs, FLWelcome to this charming townhouse located in the desirable Winter Springs area! This 2-be... |
2 beds | 2 baths | 898 sq.ft. |
$210,000 |
Airbnb cash on cash: 0.55%
|
1162 E WINGED FOOT CircleWinter Springs, FLWelcome to this beautifully maintained 3-bedroom, 2-bath POOL home nestled on a quiet, tre... |
3 beds | 2 baths | 1,574 sq.ft. |
$439,000 |
Airbnb cash on cash: 4.21%
|
1201 WOLVERINE TrailWinter Springs, FLWelcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighbo... |
4 beds | 2 baths | 1,979 sq.ft. |
$490,000 |
Airbnb cash on cash: 6.79%
|
758 N GRETNA CourtWinter Springs, FLWelcome to this versatile and beautifully updated 4-bedroom, 3-bathroom home offering both... |
4 beds | 3 baths | 2,150 sq.ft. |
$400,000 |
Airbnb cash on cash: 8.58%
|
1024 DINERO DriveWinter Springs, FLBeautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates ... |
3 beds | 2 baths | 1,463 sq.ft. |
$394,000 |
Airbnb cash on cash: 5.43%
|
499 CLUB DriveWinter Springs, FLBeautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices fo... |
2 beds | 2 baths | 1,224 sq.ft. |
$210,000 |
Airbnb cash on cash: -1.23%
|
1329 HERITAGE COMMONS DriveWinter Springs, FLBuilt by Beazer Homes in 2010, this beautifully maintained townhome sits in a gated neighb... |
3 beds | 3 baths | 1,492 sq.ft. |
$290,000 |
Airbnb cash on cash: 7.36%
|
572 PINEBRANCH CircleWinter Springs, FLThis beautiful 3 bedroom 2.5 bath townhome is located in Winter Springs near 417 plenty of... |
3 beds | 3 baths | 1,564 sq.ft. |
$330,000 |
Airbnb cash on cash: 6.14%
|
1314 Augusta National BlvdWinter Springs, FLPay in Bitcoin for this modern, yet cozy family home in Tuscawilla, for sale by owner! Sp... |
3 beds | 3 baths | 2,004 sq.ft. |
$600,000 |
Airbnb cash on cash: 3.03%
|
212 S CORTEZ AvenueWinter Springs, FLPOOL HOME WITH PRIVATE IN-LAW SUITE! Welcome to this beautifully updated 4-bedroom, 3-bath... |
4 beds | 3 baths | 1,344 sq.ft. |
$375,000 |
Airbnb cash on cash: 9.31%
|
276 SAN GABRIEL StreetWinter Springs, FLPriced to Sell! This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity f... |
3 beds | 2 baths | 1,089 sq.ft. |
$278,900 |
Airbnb cash on cash: 8.03%
|
611 CASA PARK A CourtWinter Springs, FLWelcome to 611 Casa Court, Unit A, a well-located 2-bedroom, 2.5-bath condo offering 1,156... |
2 beds | 3 baths | 1,156 sq.ft. |
$234,900 |
Airbnb cash on cash: -0.03%
|
142 BAYBERRY CourtWinter Springs, FLPRICE IMPROVEMENT: This 4 bedroom 2 bath home located on a quiet cul de sac is perfect for... |
4 beds | 2 baths | 1,425 sq.ft. |
$365,000 |
Airbnb cash on cash: 9.76%
|
140 SEVILLE CHASE DriveWinter Springs, FLWelcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - a... |
5 beds | 4 baths | 3,129 sq.ft. |
$755,000 |
Airbnb cash on cash: 7.16%
|
506 CLUB DriveWinter Springs, FLMove-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! ... |
2 beds | 2 baths | 1,002 sq.ft. |
$215,000 |
Airbnb cash on cash: -0.33%
|
717 LANCEWOOD DriveWinter Springs, FLMOVE-IN READY HOME on an amazing 0.3-acre corner lot! In the heart of Seminole County's Wi... |
3 beds | 2 baths | 1,616 sq.ft. |
$359,900 |
Airbnb cash on cash: 7.1%
|
717 ADIDAS RoadWinter Springs, FLVirtually Staged. Welcome home to this absolutely charming and move-in-ready 2-bedroom, 2-... |
2 beds | 2 baths | 1,812 sq.ft. |
$419,900 |
Airbnb cash on cash: -0.72%
|
476 TRADITION LaneWinter Springs, FLWelcome to this beautifully maintained 3-bedroom, 2.5-bath townhome located in the desirab... |
3 beds | 3 baths | 1,468 sq.ft. |
$289,900 |
Airbnb cash on cash: 8.05%
|
632 BLENHEIM LoopWinter Springs, FLJUST REDUCED, This home is updated, renovated, well maintained in a beautiful and a family... |
4 beds | 3 baths | 1,996 sq.ft. |
$484,900 |
Airbnb cash on cash: 7.11%
|
120 E BAHAMA RoadWinter Springs, FLMid-Century Modern Paradise!! A Beautiful, well-designed home with spectacular architectur... |
4 beds | 3 baths | 4,464 sq.ft. |
$959,000 |
Airbnb cash on cash: 2.3%
|
116 PHILADELPHIA WayWinter Springs, FLSeller Motivated!!!! Well-appointed 3-bedroom, 2.5-bath townhome for sale in a gated commu... |
3 beds | 3 baths | 1,468 sq.ft. |
$304,900 |
Airbnb cash on cash: 6.45%
|
421 HORIZON DriveWinter Springs, FLMOTIVATED SELLERS!!! Welcome to 421 Horizon Drive in Winter Springs, located in The Season... |
3 beds | 2 baths | 1,069 sq.ft. |
$285,000 |
Airbnb cash on cash: 7.79%
|
2 La Vista Drive #2Winter Springs, FLStep into modern comfort and effortless style with The Solara, a beautifully designed bran... |
2 beds | 2 baths | N/A |
$132,500 |
Airbnb cash on cash: 4.07%
|
77 Majorca Drive #77Winter Springs, FLDiscover The Riviera, a beautifully designed brand-new 2026 home filled with stylish finis... |
2 beds | 2 baths | N/A |
$135,500 |
Airbnb cash on cash: 3.95%
|
67 Majorca Drive #67Winter Springs, FLStep into modern comfort and effortless style with The Solara, a beautifully designed bran... |
2 beds | 2 baths | N/A |
$132,500 |
Airbnb cash on cash: 4.07%
|
63 Majorca Drive #63Winter Springs, FLWelcome Home to The Laguna - Brand-New for 2026! Step into modern comfort and effortless s... |
2 beds | 2 baths | N/A |
$135,500 |
Airbnb cash on cash: 3.95%
|
Real Estate investment in Winter-springs, FL
There are 104 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $441,736 and the average price per square foot is $241. In September 2026, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,278.