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.

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Springs, FL

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

Showing 117 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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
150 N EDGEMON AVENUE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ch...	3 beds \| 1 baths \| 1,008 sq.ft.	$289,999	Airbnb cash on cash: 2.44% Traditional cash on cash: 6.7% Airbnb Rental Income: $1827 Traditional Rental Income: $2498 Airbnb ROI: 2.44% Traditional ROI: 6.7%
1029 ANTELOPE TRAIL Winter Springs, FL Under contract-accepting backup offers. Located in the highly desirable Tuscawilla communi...	4 beds \| 2 baths \| 1,939 sq.ft.	$481,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 4.29% Airbnb Rental Income: $3833 Traditional Rental Income: $2835 Airbnb ROI: 4.66% Traditional ROI: 4.29%
710 BRIARWOOD DRIVE Winter Springs, FL Welcome to 710 Briarwood Drive in highly desirable Winter Springs! This beautifully mainta...	4 beds \| 2 baths \| 1,769 sq.ft.	$389,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 4.33% Airbnb Rental Income: $3833 Traditional Rental Income: $2505 Airbnb ROI: 5.7% Traditional ROI: 4.33%
1331 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL This beauty is Back on the Market... the previous Buyers were unable to proceed so their l...	3 beds \| 2 baths \| 1,657 sq.ft.	$450,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.23% Airbnb Rental Income: $1827 Traditional Rental Income: $2475 Airbnb ROI: 0.52% Traditional ROI: 3.23%
451 HARBOR WINDS COURT Winter Springs, FL Well maintained! Move-in Ready! Fabulous 2-story, 3 bedroom, 2 full bath and a half bath t...	3 beds \| 3 baths \| 1,914 sq.ft.	$360,900	Airbnb cash on cash: 0.73% Traditional cash on cash: 4.51% Airbnb Rental Income: $1827 Traditional Rental Income: $2614 Airbnb ROI: 0.73% Traditional ROI: 4.51%
337 KIRKCALDY DRIVE Winter Springs, FL Warm and inviting home located in the highly sought-after Highland Village community of Wi...	2 beds \| 2 baths \| 974 sq.ft.	$287,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.52% Airbnb Rental Income: $1652 Traditional Rental Income: $2001 Airbnb ROI: 2.52% Traditional ROI: 5.52%
420 HARBOR WINDS COURT Winter Springs, FL One or more photo(s) has been virtually staged. This stunning 3-bedroom, 2.5-bathroom town...	3 beds \| 3 baths \| 1,914 sq.ft.	$375,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.38% Airbnb Rental Income: $1827 Traditional Rental Income: $2805 Airbnb ROI: 0.2% Traditional ROI: 4.38%
471 HARBOR WINDS COURT Winter Springs, FL Experience the perfect blend of location and low-maintenance living at 471 Harbor Winds Co...	3 beds \| 3 baths \| 1,680 sq.ft.	$335,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 3.91% Airbnb Rental Income: $1827 Traditional Rental Income: $2394 Airbnb ROI: 0.54% Traditional ROI: 3.91%
131 LISA LOOP Winter Springs, FL Check 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% Traditional cash on cash: 4.17% Airbnb Rental Income: $3833 Traditional Rental Income: $3066 Airbnb ROI: 4.04% Traditional ROI: 4.17%
1201 WOLVERINE TRAIL Winter Springs, FL Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighbo...	4 beds \| 2 baths \| 1,979 sq.ft.	$500,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 3.66% Airbnb Rental Income: $3833 Traditional Rental Income: $2802 Airbnb ROI: 4.09% Traditional ROI: 3.66%
1340 DELANEY DRIVE Winter Springs, FL Under contract-accepting backup offers. Welcome to 1340 Delaney Drive, a move-in-ready hom...	3 beds \| 2 baths \| 1,422 sq.ft.	$265,000	Airbnb cash on cash: 2.86% Traditional cash on cash: 7.76% Airbnb Rental Income: $1827 Traditional Rental Income: $2558 Airbnb ROI: 2.86% Traditional ROI: 7.76%
499 CLUB DRIVE Winter Springs, FL Beautiful 2 bedroom 2 bathroom townhome within The Highlands Community. The 20ft high ceil...	2 beds \| 2 baths \| 1,224 sq.ft.	$255,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.4% Airbnb Rental Income: $1652 Traditional Rental Income: $1917 Airbnb ROI: 0.37% Traditional ROI: 3.4%
689 SEVEN OAKS BOULEVARD Winter Springs, FL Under contract-accepting backup offers. This 4 bedroom pool home has an office + a loft, t...	4 beds \| 3 baths \| 2,541 sq.ft.	$600,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 2.81% Airbnb Rental Income: $3833 Traditional Rental Income: $2697 Airbnb ROI: 3.36% Traditional ROI: 2.81%
552 SHADOW GLENN PLACE Winter Springs, FL Welcome to 552 Shadow Glenn Pl, a beautifully maintained 2-bedroom, 2.5-bath END UNIT town...	2 beds \| 3 baths \| 1,359 sq.ft.	$264,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.86% Airbnb Rental Income: $1652 Traditional Rental Income: $2044 Airbnb ROI: 0.43% Traditional ROI: 3.86%
613 BONITA ROAD Winter Springs, FL Back on the market through no fault of the home. The property was previously under contrac...	4 beds \| 4 baths \| 3,281 sq.ft.	$739,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 2.63% Airbnb Rental Income: $3833 Traditional Rental Income: $3368 Airbnb ROI: 2.1% Traditional ROI: 2.63%
429 SHEOAH BOULEVARD #12 Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedr...	3 beds \| 2 baths \| 1,187 sq.ft.	$229,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 4.41% Airbnb Rental Income: $1827 Traditional Rental Income: $1994 Airbnb ROI: 1.36% Traditional ROI: 4.41%
1105 NORTHERN WAY Winter Springs, FL Under contract-accepting backup offers. HIGHEST AND BEST DUE BY 5PM SUNDAY MARCH 1st. Perf...	4 beds \| 2 baths \| 2,142 sq.ft.	$615,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 3.44% Airbnb Rental Income: $3833 Traditional Rental Income: $3246 Airbnb ROI: 3.02% Traditional ROI: 3.44%
1010 TURKEY HOLLOW CIRCLE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 2 baths \| 1,740 sq.ft.	$505,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.91% Airbnb Rental Income: $3833 Traditional Rental Income: $2944 Airbnb ROI: 4.04% Traditional ROI: 3.91%
1163 BALTIC LANE Winter Springs, FL This lovingly maintained 4-bedroom, 2-bath home in a quiet neighborhood of sought-after Wi...	4 beds \| 2 baths \| 2,066 sq.ft.	$510,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.11% Airbnb Rental Income: $3833 Traditional Rental Income: $2630 Airbnb ROI: 3.9% Traditional ROI: 3.11%
622 ANHINGA ROAD Winter Springs, FL NEW ROOF!!! NEW ROOF!!! NEW ROOF!!! The roof is currently being replaced â what you have...	3 beds \| 3 baths \| 1,721 sq.ft.	$399,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 4.75% Airbnb Rental Income: $1827 Traditional Rental Income: $2741 Airbnb ROI: 0.99% Traditional ROI: 4.75%
515 SEASONS COURT Winter Springs, FL One or more photo(s) has been virtually staged.Move-In Ready Home â Fully Updated In...	3 beds \| 2 baths \| 1,101 sq.ft.	$299,900	Airbnb cash on cash: 1.84% Traditional cash on cash: 4.7% Airbnb Rental Income: $1827 Traditional Rental Income: $2140 Airbnb ROI: 1.84% Traditional ROI: 4.7%
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: 0.14% Traditional cash on cash: 2.23% Airbnb Rental Income: $1827 Traditional Rental Income: $2508 Airbnb ROI: 0.14% Traditional ROI: 2.23%
718 LAKESIDE DRIVE Winter Springs, FL Experience comfort and effortless living in this beautifully maintained Winter Springs hom...	2 beds \| 2 baths \| 1,166 sq.ft.	$289,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.86% Airbnb Rental Income: $1652 Traditional Rental Income: $2075 Airbnb ROI: 1.6% Traditional ROI: 4.86%
1254 SPOTTED SANDPIPER LOOP Winter Springs, FL Live luxuriously in almost New Townhouse! Immaculate 3-story townhouse (built 2023) boasts...	4 beds \| 4 baths \| 2,359 sq.ft.	$499,990	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.77% Airbnb Rental Income: $3833 Traditional Rental Income: $3196 Airbnb ROI: 3.36% Traditional ROI: 3.77%
540 PINEBRANCH CIRCLE Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained tow...	3 beds \| 3 baths \| 1,602 sq.ft.	$339,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.06% Airbnb Rental Income: $1827 Traditional Rental Income: $2388 Airbnb ROI: 0.75% Traditional ROI: 4.06%
1075 CONDOR PLACE Winter Springs, FL Charming three bedroom, two full bathroom, two car garage home with large fully fenced bac...	3 beds \| 2 baths \| 1,749 sq.ft.	$414,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.45% Airbnb Rental Income: $1827 Traditional Rental Income: $2545 Airbnb ROI: 1.33% Traditional ROI: 4.45%
31 S EDGEMON AVENUE Winter Springs, FL Under contract-accepting backup offers. This charming home offers a spacious floor plan wi...	4 beds \| 3 baths \| 1,270 sq.ft.	$348,000	Airbnb cash on cash: 7.13% Traditional cash on cash: 4.17% Airbnb Rental Income: $3833 Traditional Rental Income: $2038 Airbnb ROI: 7.13% Traditional ROI: 4.17%
403 MURPHY ROAD Winter Springs, FL Welcome home to this beautiful 3 bedrooms, 2 bathrooms house with a pool. Come and enjoy t...	3 beds \| 2 baths \| 1,520 sq.ft.	$410,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.49% Airbnb Rental Income: $1827 Traditional Rental Income: $2310 Airbnb ROI: 0.95% Traditional ROI: 3.49%
1539 EAGLE NEST CIRCLE Winter Springs, FL Under contract-accepting backup offers. Tucked away in the private, tree-lined streets of ...	4 beds \| 3 baths \| 2,846 sq.ft.	$895,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 2.41% Airbnb Rental Income: $3833 Traditional Rental Income: $3887 Airbnb ROI: 1.35% Traditional ROI: 2.41%
110 MOCKINGBIRD LANE Winter Springs, FL Welcome home! This beautifully updated 4 bed, 2 bath block home sits on over Â¼ acre with ...	4 beds \| 2 baths \| 1,660 sq.ft.	$425,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.68% Airbnb Rental Income: $3833 Traditional Rental Income: $2498 Airbnb ROI: 4.95% Traditional ROI: 3.68%
600 NORTHERN WAY #502 Winter Springs, FL Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offer...	3 beds \| 2 baths \| 1,425 sq.ft.	$279,999	Airbnb cash on cash: 1.75% Traditional cash on cash: 5.13% Airbnb Rental Income: $1827 Traditional Rental Income: $2226 Airbnb ROI: 1.75% Traditional ROI: 5.13%
122 STONE GABLE CIR Winter Springs, FL ELEGANT CONTEMPORARY HOUSE WELCOMES YOU THROUGH A FOYER INTO THE LIVING/DINING AREA. THE H...	3 beds \| 3 baths \| 2,147 sq.ft.	$499,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 3.47% Airbnb Rental Income: $1827 Traditional Rental Income: $2819 Airbnb ROI: 0.29% Traditional ROI: 3.47%
1356 VIA VILLA NOVA Winter Springs, FL Your private oasis awaits on a PREMIUM WATERFRONT LOT. Forget the stress... MOVE-IN READ...	3 beds \| 2 baths \| 1,864 sq.ft.	$499,999	Airbnb cash on cash: 1.51% Traditional cash on cash: 5.01% Airbnb Rental Income: $1827 Traditional Rental Income: $2967 Airbnb ROI: 1.51% Traditional ROI: 5.01%
565 GREEN SPRING CIRCLE Winter Springs, FL Under contract-accepting backup offers. Discover an affordable townhome in Winter Springs,...	2 beds \| 2 baths \| 1,363 sq.ft.	$249,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 4.63% Airbnb Rental Income: $1652 Traditional Rental Income: $1955 Airbnb ROI: 1.38% Traditional ROI: 4.63%
1204 SWAN STREET Winter Springs, FL Great location, No HOA..69 acres , 4 bedrooms,2 bathrooms, one half bathroom out door sho...	4 beds \| 3 baths \| 3,334 sq.ft.	$750,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 3.11% Airbnb Rental Income: $3833 Traditional Rental Income: $3308 Airbnb ROI: 2.68% Traditional ROI: 3.11%
1224 NORTHERN WAY Winter Springs, FL Under contract-accepting backup offers. This stunning 4-bedroom, 3.5-bath custom-built...	4 beds \| 4 baths \| 4,131 sq.ft.	$1,395,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 1.85% Airbnb Rental Income: $3833 Traditional Rental Income: $4585 Airbnb ROI: 0.63% Traditional ROI: 1.85%
930 ARABIAN AVENUE Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 3,522 sq.ft.	$999,900	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.73% Airbnb Rental Income: $3833 Traditional Rental Income: $3576 Airbnb ROI: 2.11% Traditional ROI: 2.73%
30 MOREE LOOP #39 Winter Springs, FL Welcome 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% Traditional cash on cash: 5.25% Airbnb Rental Income: $1827 Traditional Rental Income: $2117 Airbnb ROI: 1.32% Traditional ROI: 5.25%
202 ARROWHEAD COURT Winter Springs, FL BRAND NEW TILE ROOF! Buyer backed out due to personal reasons. Gorgeous custom-built h...	5 beds \| 5 baths \| 4,078 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.06% Airbnb Rental Income: $null Traditional Rental Income: $5131 Airbnb ROI: N/A Traditional ROI: 2.06%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Winter Springs, FL

150 N EDGEMON AVENUE

Winter Springs, FL

3 beds | 1 baths | 1,008 sq.ft.

$289,999

Airbnb cash on cash: 2.44%

Traditional cash on cash: 6.7%

Airbnb Rental Income: $1827

Traditional Rental Income: $2498

Airbnb ROI: 2.44%

Traditional ROI: 6.7%

1029 ANTELOPE TRAIL

Winter Springs, FL

4 beds | 2 baths | 1,939 sq.ft.

$481,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $3833

Traditional Rental Income: $2835

Airbnb ROI: 4.66%

Traditional ROI: 4.29%

710 BRIARWOOD DRIVE

Winter Springs, FL

4 beds | 2 baths | 1,769 sq.ft.

$389,000

Airbnb cash on cash: 5.7%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $3833

Traditional Rental Income: $2505

Airbnb ROI: 5.7%

Traditional ROI: 4.33%

1331 AUGUSTA NATIONAL BOULEVARD

Winter Springs, FL

3 beds | 2 baths | 1,657 sq.ft.

$450,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $1827

Traditional Rental Income: $2475

Airbnb ROI: 0.52%

Traditional ROI: 3.23%

451 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,914 sq.ft.

$360,900

Airbnb cash on cash: 0.73%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $1827

Traditional Rental Income: $2614

Airbnb ROI: 0.73%

Traditional ROI: 4.51%

337 KIRKCALDY DRIVE

Winter Springs, FL

2 beds | 2 baths | 974 sq.ft.

$287,900

Airbnb cash on cash: 2.52%

Traditional cash on cash: 5.52%

Airbnb Rental Income: $1652

Traditional Rental Income: $2001

Airbnb ROI: 2.52%

Traditional ROI: 5.52%

420 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,914 sq.ft.

$375,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $1827

Traditional Rental Income: $2805

Airbnb ROI: 0.2%

Traditional ROI: 4.38%

471 HARBOR WINDS COURT

Winter Springs, FL

3 beds | 3 baths | 1,680 sq.ft.

$335,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 3.91%

Airbnb Rental Income: $1827

Traditional Rental Income: $2394

Airbnb ROI: 0.54%