Airbnb Properties for Sale in Winter Springs, FL

Looking for a vacation rental investment in Winter Springs, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Springs, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb Single Family Residential For Sale in Winter Springs, FL

Search for Single Family Residential for Sale in Winter Springs, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 32 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1024 DINERO DRIVE Winter Springs, FL Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates ...	3 beds \| 2 baths \| 1,463 sq.ft.	$419,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.49% Airbnb Rental Income: $3583 Traditional Rental Income: $2341 Airbnb ROI: 4.65% Traditional ROI: 3.49%
622 ANHINGA ROAD Winter Springs, FL $374,900 NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMAT...	3 beds \| 3 baths \| 1,721 sq.ft.	$374,900	Airbnb cash on cash: 5.27% Traditional cash on cash: 5.02% Airbnb Rental Income: $3583 Traditional Rental Income: $2709 Airbnb ROI: 5.27% Traditional ROI: 5.02%
1314 Augusta National Blvd Winter Springs, FL Pay 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: 2.75% Traditional cash on cash: 2.23% Airbnb Rental Income: $3583 Traditional Rental Income: $2508 Airbnb ROI: 2.75% Traditional ROI: 2.23%
276 SAN GABRIEL STREET Winter Springs, FL Price 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: 7.25% Traditional cash on cash: 4.28% Airbnb Rental Income: $3583 Traditional Rental Income: $1998 Airbnb ROI: 7.25% Traditional ROI: 4.28%
140 SEVILLE CHASE DRIVE Winter Springs, FL Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - a...	5 beds \| 4 baths \| 3,129 sq.ft.	$769,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 3.28% Airbnb Rental Income: $5023 Traditional Rental Income: $3908 Airbnb ROI: 3.4% Traditional ROI: 3.28%
934 TORREY PINE DRIVE Winter Springs, FL Virtually Staged. Beautifully remodeled golf course home in the highly desirable Tuscawill...	3 beds \| 2 baths \| 1,678 sq.ft.	$499,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.89% Airbnb Rental Income: $3583 Traditional Rental Income: $2726 Airbnb ROI: 4.04% Traditional ROI: 3.89%
314 SAN GABRIEL STREET Winter Springs, FL **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE ...	3 beds \| 2 baths \| 1,091 sq.ft.	$279,990	Airbnb cash on cash: 7.93% Traditional cash on cash: 5.5% Airbnb Rental Income: $3583 Traditional Rental Income: $2157 Airbnb ROI: 7.93% Traditional ROI: 5.5%
270 SAN GABRIEL STREET Winter Springs, FL Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springsânow offered...	3 beds \| 2 baths \| 1,089 sq.ft.	$249,900	Airbnb cash on cash: 9.75% Traditional cash on cash: 7.55% Airbnb Rental Income: $3583 Traditional Rental Income: $2278 Airbnb ROI: 9.75% Traditional ROI: 7.55%
421 HORIZON DRIVE Winter Springs, FL Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This mov...	3 beds \| 2 baths \| 1,069 sq.ft.	$294,900	Airbnb cash on cash: 6.93% Traditional cash on cash: 4.8% Airbnb Rental Income: $3583 Traditional Rental Income: $2205 Airbnb ROI: 6.93% Traditional ROI: 4.8%
130 DEER SONG DRIVE Winter Springs, FL Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to o...	3 beds \| 2 baths \| 1,105 sq.ft.	$310,000	Airbnb cash on cash: 6.79% Traditional cash on cash: 5.17% Airbnb Rental Income: $3583 Traditional Rental Income: $2323 Airbnb ROI: 6.79% Traditional ROI: 5.17%
1328 ANDES DRIVE Winter Springs, FL Welcome to 1328 Andes Dr! Tile floors run throughout this well-maintained 4-bed, 2-bath in...	4 beds \| 2 baths \| 1,582 sq.ft.	$373,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 4.5% Airbnb Rental Income: $3298 Traditional Rental Income: $2340 Airbnb ROI: 5.12% Traditional ROI: 4.5%
560 PLEASANT GROVE DRIVE Winter Springs, FL Welcome to Tuska Oaksâa well-established community in the heart of Winter Springs known ...	3 beds \| 2 baths \| 1,654 sq.ft.	$425,000	Airbnb cash on cash: 4.25% Traditional cash on cash: 3.02% Airbnb Rental Income: $3583 Traditional Rental Income: $2305 Airbnb ROI: 4.25% Traditional ROI: 3.02%
807 BUCKIE DRIVE Winter Springs, FL Move Right In this Updated Highlands Home! Desirable Gas Stove in Kitchen along with newer...	3 beds \| 2 baths \| 1,574 sq.ft.	$375,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 3.77% Airbnb Rental Income: $3583 Traditional Rental Income: $2228 Airbnb ROI: 5.39% Traditional ROI: 3.77%
335 KIRKCALDY DRIVE Winter Springs, FL Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like...	3 beds \| 2 baths \| 1,178 sq.ft.	$329,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 3.88% Airbnb Rental Income: $3583 Traditional Rental Income: $1991 Airbnb ROI: 6.48% Traditional ROI: 3.88%
820 WAKULLA LANE Winter Springs, FL Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath home offers bright, comfort...	3 beds \| 3 baths \| 1,658 sq.ft.	$419,900	Airbnb cash on cash: 4.07% Traditional cash on cash: 2.65% Airbnb Rental Income: $3583 Traditional Rental Income: $2241 Airbnb ROI: 4.07% Traditional ROI: 2.65%
629 RYAN COURT Winter Springs, FL Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highl...	3 beds \| 2 baths \| 1,857 sq.ft.	$475,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.88% Airbnb Rental Income: $3583 Traditional Rental Income: $2479 Airbnb ROI: 4.6% Traditional ROI: 3.88%
65 S DEVON AVENUE Winter Springs, FL Discover the charm and convenience of life in Winter Springs at 65 S Devon Avenue â a mo...	3 beds \| 2 baths \| 1,075 sq.ft.	$314,900	Airbnb cash on cash: 7.43% Traditional cash on cash: 4.41% Airbnb Rental Income: $3583 Traditional Rental Income: $1903 Airbnb ROI: 7.43% Traditional ROI: 4.41%
143 HAYES ROAD Winter Springs, FL Welcome to 143 Hayes Rd, Winter Springs a rare opportunity to own a beautifully renovated...	3 beds \| 2 baths \| 1,649 sq.ft.	$479,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 3.92% Airbnb Rental Income: $3583 Traditional Rental Income: $2463 Airbnb ROI: 4.66% Traditional ROI: 3.92%
618 LOCUST COURT Winter Springs, FL The seller is currently in a multiple offer scenario related to the Buyer/Property Address...	3 beds \| 2 baths \| 1,326 sq.ft.	$228,800	Airbnb cash on cash: 9.58% Traditional cash on cash: 6.79% Airbnb Rental Income: $3583 Traditional Rental Income: $2193 Airbnb ROI: 9.58% Traditional ROI: 6.79%
1018 WEATHERED WOOD CIRCLE Winter Springs, FL Welcome to refined, low-maintenance living in the highly sought-after Wedgewood Golf Villa...	3 beds \| 2 baths \| 1,718 sq.ft.	$369,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 4.81% Airbnb Rental Income: $3583 Traditional Rental Income: $2348 Airbnb ROI: 6.11% Traditional ROI: 4.81%
1020 TAPROOT DRIVE Winter Springs, FL Under contract-accepting backup offers. Welcome to highly sought-after Oak Forest in Winte...	3 beds \| 3 baths \| 1,905 sq.ft.	$509,900	Airbnb cash on cash: 3.71% Traditional cash on cash: 3.29% Airbnb Rental Income: $3583 Traditional Rental Income: $2599 Airbnb ROI: 3.71% Traditional ROI: 3.29%
984 TURKEY HOLLOW CIRCLE Winter Springs, FL Under contract-accepting backup offers. Virtually Staged. A spacious 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 1,821 sq.ft.	$410,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.29% Airbnb Rental Income: $3583 Traditional Rental Income: $2419 Airbnb ROI: 5.28% Traditional ROI: 4.29%
877 BENCHWOOD DRIVE Winter Springs, FL Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool hom...	3 beds \| 2 baths \| 1,612 sq.ft.	$450,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 3.89% Airbnb Rental Income: $3583 Traditional Rental Income: $2447 Airbnb ROI: 4.72% Traditional ROI: 3.89%
907 GLEN ABBEY CIRCLE Winter Springs, FL Welcome home to this beautiful, move-in-ready residence nestled in the highly sought-after...	3 beds \| 2 baths \| 1,791 sq.ft.	$410,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 4.13% Airbnb Rental Income: $3583 Traditional Rental Income: $2400 Airbnb ROI: 5.17% Traditional ROI: 4.13%
324 DORNOCH COURT Winter Springs, FL Welcome Home to Dornoch Ct in The Highlands of Winter Springs. Situated among tree lined s...	3 beds \| 2 baths \| 1,579 sq.ft.	$399,000	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.19% Airbnb Rental Income: $3583 Traditional Rental Income: $2257 Airbnb ROI: 5.64% Traditional ROI: 4.19%
339 INGLENOOK CIRCLE Winter Springs, FL Under contract-accepting backup offers. ACCEPTING BACK-UP OFFERS! New Roof Being Installed...	3 beds \| 2 baths \| 1,437 sq.ft.	$359,900	Airbnb cash on cash: 5.61% Traditional cash on cash: 3.77% Airbnb Rental Income: $3583 Traditional Rental Income: $2177 Airbnb ROI: 5.61% Traditional ROI: 3.77%
101 MELTON DRIVE Winter Springs, FL Charming 4-Bedroom Home in the Heart of Winter Springs! Welcome to this well-positioned 4-...	4 beds \| 2 baths \| 1,212 sq.ft.	$285,000	Airbnb cash on cash: 7.56% Traditional cash on cash: 5.85% Airbnb Rental Income: $3298 Traditional Rental Income: $2101 Airbnb ROI: 7.56% Traditional ROI: 5.85%
1055 CHESTERFIELD CIRCLE Winter Springs, FL Under contract-accepting backup offers. Beautiful pool home located in the highly desirabl...	3 beds \| 2 baths \| 1,665 sq.ft.	$499,900	Airbnb cash on cash: 3.72% Traditional cash on cash: 3.05% Airbnb Rental Income: $3583 Traditional Rental Income: $2481 Airbnb ROI: 3.72% Traditional ROI: 3.05%
811 MAPLE LEAF LOOP Winter Springs, FL Explore 811 Maple Leaf Loop, recently enhanced with fresh interior paint. The kitchen incl...	5 beds \| 3 baths \| 2,852 sq.ft.	$545,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 3.77% Airbnb Rental Income: $5023 Traditional Rental Income: $3013 Airbnb ROI: 5.7% Traditional ROI: 3.77%
240 N DEVON AVENUE Winter Springs, FL Welcome to 240 N Devon Avenue, a fully updated three-bedroom, two-bath home in the heart o...	3 beds \| 2 baths \| 1,238 sq.ft.	$375,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 4.58% Airbnb Rental Income: $3583 Traditional Rental Income: $2102 Airbnb ROI: 6.55% Traditional ROI: 4.58%
1441 FOREST HILLS DRIVE Winter Springs, FL Welcome to this beautifully maintained and updated 3 bedroom, 2 bath home with a 2-car gar...	3 beds \| 2 baths \| 1,731 sq.ft.	$420,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.63% Airbnb Rental Income: $3583 Traditional Rental Income: $2645 Airbnb ROI: 5.01% Traditional ROI: 4.63%
1335 SAN FELIPE COURT Winter Springs, FL Under contract-accepting backup offers. Welcome home to this move-in-ready 4-bedroom, 2-ba...	4 beds \| 2 baths \| 1,571 sq.ft.	$450,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.7% Airbnb Rental Income: $3298 Traditional Rental Income: $2541 Airbnb ROI: 3.74% Traditional ROI: 3.7%

Your search for investment property begins and ends here

Airbnb Single Family Residential For Sale in Winter Springs, FL

1024 DINERO DRIVE

Winter Springs, FL

3 beds | 2 baths | 1,463 sq.ft.

$419,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $3583

Traditional Rental Income: $2341

Airbnb ROI: 4.65%

Traditional ROI: 3.49%

622 ANHINGA ROAD

Winter Springs, FL

3 beds | 3 baths | 1,721 sq.ft.

$374,900

Airbnb cash on cash: 5.27%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $3583

Traditional Rental Income: $2709

Airbnb ROI: 5.27%

Traditional ROI: 5.02%

1314 Augusta National Blvd

Winter Springs, FL

3 beds | 3 baths | 2,004 sq.ft.

$600,000

Airbnb cash on cash: 2.75%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $3583

Traditional Rental Income: $2508

Airbnb ROI: 2.75%

Traditional ROI: 2.23%

276 SAN GABRIEL STREET

Winter Springs, FL

3 beds | 2 baths | 1,089 sq.ft.

$285,000

Airbnb cash on cash: 7.25%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $3583

Traditional Rental Income: $1998

Airbnb ROI: 7.25%

Traditional ROI: 4.28%

140 SEVILLE CHASE DRIVE

Winter Springs, FL

5 beds | 4 baths | 3,129 sq.ft.

$769,900

Airbnb cash on cash: 3.4%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $5023

Traditional Rental Income: $3908

Airbnb ROI: 3.4%

Traditional ROI: 3.28%

934 TORREY PINE DRIVE

Winter Springs, FL

3 beds | 2 baths | 1,678 sq.ft.

$499,000

Airbnb cash on cash: 4.04%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $3583

Traditional Rental Income: $2726

Airbnb ROI: 4.04%

Traditional ROI: 3.89%

314 SAN GABRIEL STREET

Winter Springs, FL

3 beds | 2 baths | 1,091 sq.ft.

$279,990

Airbnb cash on cash: 7.93%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $3583

Traditional Rental Income: $2157

Airbnb ROI: 7.93%

Traditional ROI: 5.5%

270 SAN GABRIEL STREET

Winter Springs, FL

3 beds | 2 baths | 1,089 sq.ft.

$249,900

Airbnb cash on cash: 9.75%

Traditional cash on cash: 7.55%

Airbnb Rental Income: $3583

Traditional Rental Income: $2278

Airbnb ROI: 9.75%