Real Estate Investments for Sale in Winter Springs, FL With High ROI

Are you looking for a vacation rental in Winter Springs, FL? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
308 TWELVE OAKS DRIVE Winter Springs, FL LOCATION, LOCATION, LOCATION!! PRIDE OF OWNERSHIP is EVIDENT EVERYWHERE in this SINGLE STO...	4 beds \| 2 baths \| 2,284 sq.ft.	$624,800	Airbnb cash on cash: 3.91% Traditional cash on cash: 2.98% Airbnb Rental Income: $4334 Traditional Rental Income: $2883 Airbnb ROI: 3.91% Traditional ROI: 2.98%
415 TRADITION LANE Winter Springs, FL Welcome home to this spacious MOVE-IN ready 3-bedroom, 2.5-bathroom END UNIT townhome in t...	3 beds \| 3 baths \| 1,888 sq.ft.	$369,900	Airbnb cash on cash: 3.54% Traditional cash on cash: 2.87% Airbnb Rental Income: $3361 Traditional Rental Income: $2379 Airbnb ROI: 3.54% Traditional ROI: 2.87%
511 S EDGEMON AVENUE Winter Springs, FL Under contract-accepting backup offers. Price Drop - This home in the heart of old Winter ...	3 beds \| 2 baths \| 1,529 sq.ft.	$380,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.87% Airbnb Rental Income: $3361 Traditional Rental Income: $2264 Airbnb ROI: 4.85% Traditional ROI: 3.87%
304 BRIDIE COURT Winter Springs, FL Welcome to your dream home nestled at the end of a serene cul-de-sac in the highly sought-...	3 beds \| 2 baths \| 1,613 sq.ft.	$365,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.71% Airbnb Rental Income: $3361 Traditional Rental Income: $2361 Airbnb ROI: 5.44% Traditional ROI: 4.71%
564 JESUP SPRINGS LANE Winter Springs, FL This move-in ready 2-story townhome nestled in Jesup's Landing, has 3 bedrooms and 2 1/2 b...	3 beds \| 2 baths \| 1,668 sq.ft.	$415,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.71% Airbnb Rental Income: $3361 Traditional Rental Income: $2337 Airbnb ROI: 3.42% Traditional ROI: 2.71%
355 LANSBROOK LANE Winter Springs, FL Location, Location, Location and GREAT GREAT INCENTIVE from the seller ******* Seller will...	3 beds \| 3 baths \| 1,504 sq.ft.	$387,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 2.11% Airbnb Rental Income: $3361 Traditional Rental Income: $2165 Airbnb ROI: 3.35% Traditional ROI: 2.11%
413 DAVID STREET Winter Springs, FL Welcome to 413 David St, a delightful 3-bedroom, 2-bathroom single-family home located in ...	3 beds \| 2 baths \| 1,136 sq.ft.	$329,900	Airbnb cash on cash: 6.12% Traditional cash on cash: 4.72% Airbnb Rental Income: $3361 Traditional Rental Income: $2178 Airbnb ROI: 6.12% Traditional ROI: 4.72%
132 BAYBERRY COURT Winter Springs, FL Welcome to this beautiful 3 bedroom 2 full bath house in Winter Springs, Florida. Features...	3 beds \| 2 baths \| 1,458 sq.ft.	$394,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 3.76% Airbnb Rental Income: $3356 Traditional Rental Income: $2208 Airbnb ROI: 4.85% Traditional ROI: 3.76%
30 SHEOAH BOULEVARD #19 Winter Springs, FL This 1- Bedroom, 1- Bath Condo offers a garden view off the private patio along with a sce...	1 beds \| 1 baths \| 710 sq.ft.	$152,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 2.33% Airbnb Rental Income: $1982 Traditional Rental Income: $1335 Airbnb ROI: 3.21% Traditional ROI: 2.33%
481 BUCKHORN DRIVE Winter Springs, FL Under contract-accepting backup offers. 4 bedroom plus LOFT home in the desirable Winter S...	4 beds \| 3 baths \| 2,076 sq.ft.	$549,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 2.7% Airbnb Rental Income: $4334 Traditional Rental Income: $2870 Airbnb ROI: 3.78% Traditional ROI: 2.7%
718 GLEN EAGLE DRIVE Winter Springs, FL YOUR PRIVATE OASIS IN TUSCAWILLA. This elegant Glen Eagle custom pool home is stunning and...	4 beds \| 5 baths \| 3,004 sq.ft.	$895,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 3.04% Airbnb Rental Income: $4334 Traditional Rental Income: $4416 Airbnb ROI: 1.84% Traditional ROI: 3.04%
553 SHADOW GLENN PLACE Winter Springs, FL This townhouse, nestled in the heart of Winter Springs' Tuskawilla/Red Bug area, showcases...	3 beds \| 3 baths \| 1,348 sq.ft.	$289,900	Airbnb cash on cash: 3.75% Traditional cash on cash: 1.94% Airbnb Rental Income: $3361 Traditional Rental Income: $2118 Airbnb ROI: 3.75% Traditional ROI: 1.94%
768 MAPLE LEAF LOOP Winter Springs, FL PRICE IMPROVEMENT! This contemporary-style single-family home in the Seven Oaks community ...	5 beds \| 4 baths \| 3,092 sq.ft.	$649,900	Airbnb cash on cash: 5.66% Traditional cash on cash: 3.38% Airbnb Rental Income: $6195 Traditional Rental Income: $3588 Airbnb ROI: 5.66% Traditional ROI: 3.38%
966 LOGENBERRY TRAIL Winter Springs, FL Florida living at its finest! ~ Welcome to this beautiful, spacious 3-bedroom 2.5 bath POO...	3 beds \| 3 baths \| 2,525 sq.ft.	$579,900	Airbnb cash on cash: 2.58% Traditional cash on cash: 3.51% Airbnb Rental Income: $3361 Traditional Rental Income: $3114 Airbnb ROI: 2.58% Traditional ROI: 3.51%
4408 BROOK HOLLOW CIRCLE Winter Springs, FL Welcome to the beautifully kept 4408 Brook Hollow Circle. Location is everything and this ...	2 beds \| 2 baths \| 1,088 sq.ft.	$280,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 1.86% Airbnb Rental Income: $2131 Traditional Rental Income: $1629 Airbnb ROI: 1.71% Traditional ROI: 1.86%
421 RINGWOOD CIRCLE Winter Springs, FL Under contract-accepting backup offers. Welcome home! This beautiful house sits proudly i...	4 beds \| 2 baths \| 2,029 sq.ft.	$500,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 3.58% Airbnb Rental Income: $4334 Traditional Rental Income: $2771 Airbnb ROI: 4.97% Traditional ROI: 3.58%
1109 SEAFARER LANE Winter Springs, FL Back on Market. Buyers home sale fell through. Come see this strikingly beautiful pool hom...	3 beds \| 2 baths \| 1,927 sq.ft.	$525,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 2.8% Airbnb Rental Income: $3361 Traditional Rental Income: $2553 Airbnb ROI: 2.92% Traditional ROI: 2.8%
4105 Hedge Maple Place Winter Springs, FL Enjoy maintenance free living in this move in ready townhouse featuring two master suites,...	2 beds \| 3 baths \| 1,330 sq.ft.	$310,000	Airbnb cash on cash: 3.17% Traditional cash on cash: 4.38% Airbnb Rental Income: $2131 Traditional Rental Income: $1942 Airbnb ROI: 3.17% Traditional ROI: 4.38%
327 STREAMVIEW WAY Winter Springs, FL Under contract-accepting backup offers. If you want a WOW House, this is it! A beautiful, ...	3 beds \| 2 baths \| 1,549 sq.ft.	$469,900	Airbnb cash on cash: 3.38% Traditional cash on cash: 2.55% Airbnb Rental Income: $3361 Traditional Rental Income: $2247 Airbnb ROI: 3.38% Traditional ROI: 2.55%
1314 Augusta National Blvd Winter Springs, FL	3 beds \| 3 baths \| N/A	$600,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 2.7% Airbnb Rental Income: $3356 Traditional Rental Income: $2663 Airbnb ROI: 2.61% Traditional ROI: 2.7%
1314 Augusta National Blvd Winter Springs, FL	3 beds \| 3 baths \| N/A	$600,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 2.7% Airbnb Rental Income: $3356 Traditional Rental Income: $2663 Airbnb ROI: 2.61% Traditional ROI: 2.7%
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: 2.41% Traditional cash on cash: 2.53% Airbnb Rental Income: $3356 Traditional Rental Income: $2676 Airbnb ROI: 2.41% Traditional ROI: 2.53%
517 SHADOW GLENN PL Winter Springs, FL This beautiful 3 bedroom/2.5 bathroom townhouse is perfect for entertaining or family life...	3 beds \| 3 baths \| 1,344 sq.ft.	$315,900	Airbnb cash on cash: 5.29% Traditional cash on cash: 3.73% Airbnb Rental Income: $3361 Traditional Rental Income: $2150 Airbnb ROI: 5.29% Traditional ROI: 3.73%
602 BONITA ROAD Winter Springs, FL DRASTIC PRICE REDUCTION! Submit Your Best Offer! Seller is Motivated! FULLY RENOVATED home...	4 beds \| 3 baths \| 1,634 sq.ft.	$465,000	Airbnb cash on cash: 5.89% Traditional cash on cash: 3.7% Airbnb Rental Income: $4334 Traditional Rental Income: $2472 Airbnb ROI: 5.89% Traditional ROI: 3.7%
330 STREAMVIEW WAY Winter Springs, FL Nestled in a sought-after gated community in Winter Springs, this charming 3-bedroom, 2-ba...	3 beds \| 2 baths \| 1,995 sq.ft.	$480,000	Airbnb cash on cash: 3.77% Traditional cash on cash: 3.61% Airbnb Rental Income: $3361 Traditional Rental Income: $2540 Airbnb ROI: 3.77% Traditional ROI: 3.61%
1437 CREEKSIDE CIRCLE Winter Springs, FL One or more photo(s) has been virtually staged. This beautiful home offers a natural and i...	3 beds \| 2 baths \| 1,225 sq.ft.	$368,000	Airbnb cash on cash: 5.23% Traditional cash on cash: 3.83% Airbnb Rental Income: $3361 Traditional Rental Income: $2128 Airbnb ROI: 5.23% Traditional ROI: 3.83%
393 TWELVE OAKS DRIVE Winter Springs, FL Under contract-accepting backup offers. Charming one-story, fully renovated pool home in t...	4 beds \| 3 baths \| 2,361 sq.ft.	$695,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 2.97% Airbnb Rental Income: $4334 Traditional Rental Income: $3074 Airbnb ROI: 3.51% Traditional ROI: 2.97%
4961 COURTLAND LOOP Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 4 baths \| 3,456 sq.ft.	$774,900	Airbnb cash on cash: 2.9% Traditional cash on cash: 3.41% Airbnb Rental Income: $4334 Traditional Rental Income: $3793 Airbnb ROI: 2.9% Traditional ROI: 3.41%
706 ADIDAS ROAD Winter Springs, FL Welcome to 706 Adidas Rd in Winter Springs Fl. A charming 2 bedroom + 2 bathroom POOL home...	2 beds \| 2 baths \| 1,459 sq.ft.	$379,900	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.86% Airbnb Rental Income: $2131 Traditional Rental Income: $1909 Airbnb ROI: 1.96% Traditional ROI: 2.86%
1365 ANDES DRIVE Winter Springs, FL This beautiful remodeled 3 bedrooms, 3-bath, 2 car garage home offers many features. The o...	3 beds \| 3 baths \| 1,427 sq.ft.	$399,900	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.18% Airbnb Rental Income: $3361 Traditional Rental Income: $2284 Airbnb ROI: 5.06% Traditional ROI: 4.18%
1115 DUNCAN DRIVE Winter Springs, FL Come be enchanted by 1115 Duncan Drive. Let the whimsy of the oak trees pull you in. Nestl...	3 beds \| 2 baths \| 1,802 sq.ft.	$550,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 2.49% Airbnb Rental Income: $3361 Traditional Rental Income: $2482 Airbnb ROI: 2.74% Traditional ROI: 2.49%
1328 AVENUE DEL SOL Winter Springs, FL Under contract-accepting backup offers. Welcome to this well-maintained move-in-ready 3-be...	3 beds \| 2 baths \| 1,721 sq.ft.	$399,995	Airbnb cash on cash: 4.81% Traditional cash on cash: 4.32% Airbnb Rental Income: $3361 Traditional Rental Income: $2430 Airbnb ROI: 4.81% Traditional ROI: 4.32%
80 S CORTEZ AVENUE Winter Springs, FL REDUCED! Winter Springs POOL home! No HOA! Move right in this beautiful 3 bedroom 2 bath h...	3 beds \| 2 baths \| 1,315 sq.ft.	$349,000	Airbnb cash on cash: 6.55% Traditional cash on cash: 5.23% Airbnb Rental Income: $3361 Traditional Rental Income: $2179 Airbnb ROI: 6.55% Traditional ROI: 5.23%
510 CLUB DRIVE Winter Springs, FL Under contract-accepting backup offers. Move Right in this Bright One-Story End Unit Villa...	3 beds \| 2 baths \| 1,222 sq.ft.	$255,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 3.68% Airbnb Rental Income: $3361 Traditional Rental Income: $2077 Airbnb ROI: 5.9% Traditional ROI: 3.68%
1416 WINTER WHARF LANE Winter Springs, FL Under contract-accepting backup offers. Youâre going to love this beautiful 3 bedroom 3 ...	3 beds \| 4 baths \| 1,932 sq.ft.	$400,000	Airbnb cash on cash: 3.09% Traditional cash on cash: 3.11% Airbnb Rental Income: $3361 Traditional Rental Income: $2619 Airbnb ROI: 3.09% Traditional ROI: 3.11%
424 FLATWOOD DRIVE Winter Springs, FL Under contract-accepting backup offers. Welcome to Tusca Oaks, your gateway to a lifestyle...	4 beds \| 3 baths \| 2,138 sq.ft.	$499,000	Airbnb cash on cash: 5.2% Traditional cash on cash: 4.05% Airbnb Rental Income: $4334 Traditional Rental Income: $2889 Airbnb ROI: 5.2% Traditional ROI: 4.05%
1001 SAPLING DRIVE Winter Springs, FL Located in the beautifully mature neighborhood of Oak Forest - This 3/2 is move-in ready. ...	3 beds \| 2 baths \| 1,831 sq.ft.	$474,999	Airbnb cash on cash: 4.36% Traditional cash on cash: 4.08% Airbnb Rental Income: $3361 Traditional Rental Income: $2490 Airbnb ROI: 4.36% Traditional ROI: 4.08%
1124 CITRUS OAKS RUN Winter Springs, FL This home has everything you need! It offers a great location complimented by incredible i...	5 beds \| 3 baths \| 3,456 sq.ft.	$825,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 2.1% Airbnb Rental Income: $6195 Traditional Rental Income: $3284 Airbnb ROI: 4.3% Traditional ROI: 2.1%
146 NANDINA Terrace Winter Springs, FL BRAND NEW ROOF! Gorgeous well maintained move in ready home in gated community of Howell C...	5 beds \| 3 baths \| 3,251 sq.ft.	$750,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 2.67% Airbnb Rental Income: $6195 Traditional Rental Income: $3286 Airbnb ROI: 5.09% Traditional ROI: 2.67%
377 TWELVE OAKS DRIVE Winter Springs, FL Welcome to 377 Twelve Oaks Drive, a stunning 4-bedroom, 2.5-bathroom residence spanning 2,...	4 beds \| 3 baths \| 2,157 sq.ft.	$575,000	Airbnb cash on cash: 4.42% Traditional cash on cash: 3.56% Airbnb Rental Income: $4334 Traditional Rental Income: $2958 Airbnb ROI: 4.42% Traditional ROI: 3.56%

Real Estate investment in Winter-springs, FL

There are 103 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $447,450 and the average price per square foot is $235. In April 2024, the average monthly cash on cash return in Winter Springs is 3.00%. The average monthly rental income in Winter Springs is $2,430.

Winter-springs, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 103 investment properties available for sale in Winter-springs.

In 2024, the best neighborhood to buy investment property is Winter Springs.

The ROI for Short-Term is higher than the Long-Term in Winter-springs with average rental income of $3,361.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Springs, FL

308 TWELVE OAKS DRIVE

Winter Springs, FL

4 beds | 2 baths | 2,284 sq.ft.

$624,800

Airbnb cash on cash: 3.91%

Traditional cash on cash: 2.98%

Airbnb Rental Income: $4334

Traditional Rental Income: $2883

Airbnb ROI: 3.91%

Traditional ROI: 2.98%

415 TRADITION LANE

Winter Springs, FL

3 beds | 3 baths | 1,888 sq.ft.

$369,900

Airbnb cash on cash: 3.54%

Traditional cash on cash: 2.87%

Airbnb Rental Income: $3361

Traditional Rental Income: $2379

Airbnb ROI: 3.54%

Traditional ROI: 2.87%

511 S EDGEMON AVENUE

Winter Springs, FL

3 beds | 2 baths | 1,529 sq.ft.

$380,000

Airbnb cash on cash: 4.85%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $3361

Traditional Rental Income: $2264

Airbnb ROI: 4.85%

Traditional ROI: 3.87%

304 BRIDIE COURT

Winter Springs, FL

3 beds | 2 baths | 1,613 sq.ft.

$365,000

Airbnb cash on cash: 5.44%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $3361

Traditional Rental Income: $2361

Airbnb ROI: 5.44%

Traditional ROI: 4.71%

564 JESUP SPRINGS LANE

Winter Springs, FL

3 beds | 2 baths | 1,668 sq.ft.

$415,000

Airbnb cash on cash: 3.42%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $3361

Traditional Rental Income: $2337

Airbnb ROI: 3.42%

Traditional ROI: 2.71%

355 LANSBROOK LANE

Winter Springs, FL

3 beds | 3 baths | 1,504 sq.ft.

$387,000

Airbnb cash on cash: 3.35%

Traditional cash on cash: 2.11%

Airbnb Rental Income: $3361

Traditional Rental Income: $2165

Airbnb ROI: 3.35%

Traditional ROI: 2.11%

413 DAVID STREET

Winter Springs, FL

3 beds | 2 baths | 1,136 sq.ft.

$329,900

Airbnb cash on cash: 6.12%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $3361

Traditional Rental Income: $2178

Airbnb ROI: 6.12%

Traditional ROI: 4.72%

132 BAYBERRY COURT

Winter Springs, FL

3 beds | 2 baths | 1,458 sq.ft.

$394,000

Airbnb cash on cash: 4.85%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $3356

Traditional Rental Income: $2208

Airbnb ROI: 4.85%