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 |
|---|---|---|---|
477 GREEN SPRING CIRCLEWinter Springs, FLUnder contract-accepting backup offers. Conveniently located in Winter Springs, this prope... |
3 beds | 2 baths | 1,280 sq.ft. |
$234,999 |
Airbnb cash on cash: 2.88%
|
710 BRIARWOOD DRIVEWinter Springs, FLMOVE-IN READY WITH NEW ROOF & HVAC SYSTEM TO BE COMPLETED PRIOR TO CLOSING. Beautifully... |
4 beds | 2 baths | 1,769 sq.ft. |
$365,000 |
Airbnb cash on cash: 6.1%
|
440 BUCKSKIN COURTWinter Springs, FL**This house comes with a REDUCED RATE through the seller's preferred lender. This is a le... |
4 beds | 3 baths | 1,922 sq.ft. |
$534,900 |
Airbnb cash on cash: 3.7%
|
1331 AUGUSTA NATIONAL BOULEVARDWinter Springs, FLUnder contract-accepting backup offers. 3 BED + OFFICE | BRAND NEW ROOF | WOODED LOT | TUS... |
3 beds | 2 baths | 1,657 sq.ft. |
$450,000 |
Airbnb cash on cash: 0.52%
|
451 HARBOR WINDS COURTWinter Springs, FLOne or more photo(s) has been virtually staged. Welcome to 451 Harbor Winds Court, located... |
3 beds | 3 baths | 1,914 sq.ft. |
$357,500 |
Airbnb cash on cash: 0.65%
|
337 KIRKCALDY DRIVEWinter Springs, FLWarm and inviting home located in the highly sought-after Highland Village community of Wi... |
2 beds | 2 baths | 974 sq.ft. |
$284,900 |
Airbnb cash on cash: 2.55%
|
471 HARBOR WINDS COURTWinter Springs, FLExperience the perfect blend of location and low-maintenance living at 471 Harbor Winds Co... |
3 beds | 3 baths | 1,680 sq.ft. |
$330,000 |
Airbnb cash on cash: 0.57%
|
131 LISA LOOPWinter Springs, FLCheck out this spacious 4-bedroom, 2.5 bath home in Winter Springs, located in the highly ... |
4 beds | 3 baths | 2,309 sq.ft. |
$489,000 |
Airbnb cash on cash: 4.04%
|
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. |
$430,000 |
Airbnb cash on cash: 5.04%
|
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. |
$424,000 |
Airbnb cash on cash: 0.9%
|
299 WOODGREEN LANEWinter Springs, FLWelcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Gre... |
3 beds | 3 baths | 1,326 sq.ft. |
$285,000 |
Airbnb cash on cash: 2.11%
|
499 CLUB DRIVEWinter Springs, FLBeautiful 2 bedroom 2 bathroom townhome within The Highlands Community. The 20ft high ceil... |
2 beds | 2 baths | 1,224 sq.ft. |
$235,000 |
Airbnb cash on cash: 0.48%
|
412 BLUE BAYOU LANEWinter Springs, FLQuick move in available. Welcome to 412 Blue Bayou Lane in the highly desirable Jesups Res... |
3 beds | 4 baths | 1,854 sq.ft. |
$385,000 |
Airbnb cash on cash: 0.58%
|
613 BONITA ROADWinter Springs, FLNestled beneath a canopy of mature trees in a charming ranch-style setting in Winter Sprin... |
4 beds | 4 baths | 3,281 sq.ft. |
$719,000 |
Airbnb cash on cash: 2.19%
|
429 SHEOAH BOULEVARD #12Winter Springs, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
3 beds | 2 baths | 1,187 sq.ft. |
$180,000 |
Airbnb cash on cash: 1.98%
|
4991 COURTLAND LOOPWinter Springs, FLUnder contract-accepting backup offers. MULTIPLE OFFERS : HIGHEST AND BEST DUE BY SATURDAY... |
4 beds | 3 baths | 3,217 sq.ft. |
$750,000 |
Airbnb cash on cash: 2.21%
|
622 ANHINGA ROADWinter Springs, FLNEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MIN... |
3 beds | 3 baths | 1,721 sq.ft. |
$384,900 |
Airbnb cash on cash: 1.06%
|
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: 0.91%
|
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: 0.14%
|
600 NORTHERN WAY #302Winter Springs, FLOne or more photo(s) has been virtually staged. Seller may consider buyer concessions if m... |
3 beds | 2 baths | 1,425 sq.ft. |
$269,900 |
Airbnb cash on cash: -0.33%
|
403 MURPHY ROADWinter Springs, FLWelcome home to this beautiful 3 bedrooms, 2 bathrooms house with a pool. Come and enjoy t... |
3 beds | 2 baths | 1,520 sq.ft. |
$408,500 |
Airbnb cash on cash: 0.96%
|
276 SAN GABRIEL STREETWinter Springs, FLPrice Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportuni... |
3 beds | 2 baths | 1,089 sq.ft. |
$285,000 |
Airbnb cash on cash: 1.8%
|
130 SEVILLE CHASE DRIVEWinter Springs, FLDiscover the perfect blend of comfort, privacy, and luxury in the sought-after gated commu... |
4 beds | 3 baths | 2,433 sq.ft. |
$739,900 |
Airbnb cash on cash: 1.95%
|
444 BLUE BAYOU LANEWinter Springs, FLWelcome to 444 Blue Bayou Lane, a fully renovated 3-story end-unit townhome in a prime loc... |
3 beds | 4 baths | 1,854 sq.ft. |
$385,000 |
Airbnb cash on cash: -0.26%
|
201 BURGESS DRIVEWinter Springs, FLWelcome to Avery Park! This is a STUNNING 4-bedroom, 2.5-bath residence that spans more th... |
4 beds | 3 baths | 3,046 sq.ft. |
$650,000 |
Airbnb cash on cash: 2.23%
|
424 FLATWOOD DRIVEWinter Springs, FLExcellent opportunity in desirable Tusca Oaks/Tuscawilla area. Spacious 4BR/2.5BA with fun... |
4 beds | 4 baths | 2,164 sq.ft. |
$525,000 |
Airbnb cash on cash: 4.17%
|
1551 WESCOTT LOOPWinter Springs, FLWelcome to Barrington Estates, where this light-filled home with an open floor plan instan... |
4 beds | 3 baths | 2,803 sq.ft. |
$750,000 |
Airbnb cash on cash: 1.92%
|
600 NORTHERN WAY #502Winter Springs, FLMOTIVATED SELLER!!! Seller offering concession toward buyer closing cost. Location! Loca... |
3 beds | 2 baths | 1,425 sq.ft. |
$265,000 |
Airbnb cash on cash: 1.9%
|
122 STONE GABLE CIRWinter Springs, FLPRICED TO SELL + $15,000 INCENTIVE!!. WELCOME TO YOUR COMPLETELY WORRY-FREE OASIS. SELLER ... |
3 beds | 3 baths | 2,147 sq.ft. |
$485,000 |
Airbnb cash on cash: 0.33%
|
294 SAN GABRIEL STREETWinter Springs, FLBeautifully maintained 2-bedroom, 2-bath single-family home located in the desirable Deers... |
2 beds | 2 baths | 1,105 sq.ft. |
$249,990 |
Airbnb cash on cash: 1.61%
|
702 GLASGOW COURTWinter Springs, FLWelcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac ... |
4 beds | 3 baths | 1,878 sq.ft. |
$313,700 |
Airbnb cash on cash: 6.14%
|
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. |
$779,900 |
Airbnb cash on cash: N/A
|
30 MOREE LOOP #39Winter Springs, FLWelcome to your move-in ready 3-bedroom, 2.5-bath townhome-style condo located in the desi... |
3 beds | 3 baths | 1,400 sq.ft. |
$210,000 |
Airbnb cash on cash: 1.32%
|
998 EL LAGO TERRACEWinter Springs, FLWelcome to Sunrise Estates and your opportunity to own a truly unique property in the hea... |
4 beds | 2 baths | 2,126 sq.ft. |
$650,000 |
Airbnb cash on cash: 3.52%
|
1360 VIA VILLA NOVA WAYWinter Springs, FLLocation, Location, Location... Don't miss out this opportunity to own a turn-key home in ... |
4 beds | 2 baths | 2,064 sq.ft. |
$539,999 |
Airbnb cash on cash: 4.19%
|
934 TORREY PINE DRIVEWinter Springs, FLOne or more photo(s) has been virtually staged. Beautifully remodeled golf course home in ... |
3 beds | 3 baths | 1,678 sq.ft. |
$514,000 |
Airbnb cash on cash: 0.85%
|
314 SAN GABRIEL STREETWinter Springs, FLSeller offering $2,500.00 toward Buyers Closing costs with an acceptable offer. Welcome t... |
3 beds | 2 baths | 1,091 sq.ft. |
$279,990 |
Airbnb cash on cash: 2.38%
|
126 SEVILLE CHASE DRIVEWinter Springs, FL**Price Improvement** and a $20,000.00 SELLER CONCESSION towards buyer's closing costs ** ... |
5 beds | 4 baths | 3,205 sq.ft. |
$769,000 |
Airbnb cash on cash: N/A
|
270 SAN GABRIEL STREETWinter Springs, FLPrice Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street... |
3 beds | 2 baths | 1,089 sq.ft. |
$259,000 |
Airbnb cash on cash: 3.39%
|
114 SUNDANCE COURTWinter Springs, FLOne or more photo(s) has been virtually staged. If youâve been searching for space, loca... |
4 beds | 2 baths | 1,356 sq.ft. |
$305,500 |
Airbnb cash on cash: 7.35%
|
Real Estate investment in Winter-springs, FL
There are 128 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $419,783 and the average price per square foot is $218. In June 2026, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,554.