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

separator

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 this beautifully updated 4-bedroom, 2-bath home in Winter Springs, FL, featurin...	4 beds \| 2 baths \| 1,769 sq.ft.	$375,000	Airbnb cash on cash: 5.92% Traditional cash on cash: 5.12% Airbnb Rental Income: $3833 Traditional Rental Income: $2724 Airbnb ROI: 5.92% Traditional ROI: 5.12%
1331 AUGUSTA NATIONAL BOULEVARD Winter Springs, FL BRAND NEW tile barrel roof just installed Welcome to easy-maintenance living in the hi...	3 beds \| 2 baths \| 1,657 sq.ft.	$450,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 3.94% Airbnb Rental Income: $1827 Traditional Rental Income: $2776 Airbnb ROI: 0.52% Traditional ROI: 3.94%
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: 5.3% Airbnb Rental Income: $1652 Traditional Rental Income: $1943 Airbnb ROI: 2.52% Traditional ROI: 5.3%
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.	$365,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 4.53% Airbnb Rental Income: $1827 Traditional Rental Income: $2805 Airbnb ROI: 0.23% Traditional ROI: 4.53%
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.	$330,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 4.74% Airbnb Rental Income: $1827 Traditional Rental Income: $2627 Airbnb ROI: 0.57% Traditional ROI: 4.74%
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: 4.39% Airbnb Rental Income: $3833 Traditional Rental Income: $3167 Airbnb ROI: 4.04% Traditional ROI: 4.39%
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: 3.93% Airbnb Rental Income: $3833 Traditional Rental Income: $2930 Airbnb ROI: 4.09% Traditional ROI: 3.93%
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%
1250 STONE HARBOUR ROAD Winter Springs, FL IMMACULATE 4 bedroom, 2 bathroom home in the beautiful GATED community of Parkstone! Loca...	4 beds \| 2 baths \| 2,113 sq.ft.	$540,000	Airbnb cash on cash: 3.29% Traditional cash on cash: 2.37% Airbnb Rental Income: $3833 Traditional Rental Income: $2543 Airbnb ROI: 3.29% Traditional ROI: 2.37%
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.	$247,500	Airbnb cash on cash: 0.41% Traditional cash on cash: 4.3% Airbnb Rental Income: $1652 Traditional Rental Income: $2096 Airbnb ROI: 0.41% Traditional ROI: 4.3%
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: 3.68% Airbnb Rental Income: $3833 Traditional Rental Income: $3184 Airbnb ROI: 3.36% Traditional ROI: 3.68%
552 SHADOW GLENN PLACE Winter Springs, FL Under contract-accepting backup offers. Welcome to 552 Shadow Glenn Pl, a beautifully main...	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 Tucked beneath a canopy of mature trees in one of Winter Springsâ most charming ranch-st...	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: 4.78% Airbnb Rental Income: $1827 Traditional Rental Income: $2075 Airbnb ROI: 1.36% Traditional ROI: 4.78%
1106 SUPERIOR COURT Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to the highly sought-after Tuscawi...	4 beds \| 3 baths \| 2,353 sq.ft.	$625,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 2.87% Airbnb Rental Income: $3833 Traditional Rental Income: $3076 Airbnb ROI: 2.75% Traditional ROI: 2.87%
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: 4.66% Airbnb Rental Income: $1827 Traditional Rental Income: $2709 Airbnb ROI: 0.99% Traditional ROI: 4.66%
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: 5.1% Airbnb Rental Income: $1827 Traditional Rental Income: $2253 Airbnb ROI: 1.84% Traditional ROI: 5.1%
572 PINEBRANCH CIRCLE Winter Springs, FL This beautiful 3 bedroom 2.5 bath townhome is located in Winter Springs near 417 plenty of...	3 beds \| 3 baths \| 1,564 sq.ft.	$333,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.19% Airbnb Rental Income: $1827 Traditional Rental Income: $2051 Airbnb ROI: 0.9% Traditional ROI: 3.19%
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%
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.	$495,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 4.72% Airbnb Rental Income: $3833 Traditional Rental Income: $3616 Airbnb ROI: 3.4% Traditional ROI: 4.72%
1300 SWIFT CREEK WAY Winter Springs, FL One or more photo(s) has been virtually staged. Welcome to your new home at 1300 Swift Cre...	4 beds \| 3 baths \| 2,030 sq.ft.	$550,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 3.52% Airbnb Rental Income: $3833 Traditional Rental Income: $3170 Airbnb ROI: 3.2% Traditional ROI: 3.52%
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: 4.28% Airbnb Rental Income: $1827 Traditional Rental Income: $2456 Airbnb ROI: 0.75% Traditional ROI: 4.28%
600 NORTHERN WAY #302 Winter Springs, FL One or more photo(s) has been virtually staged. Seller may consider buyer concessions if m...	3 beds \| 2 baths \| 1,425 sq.ft.	$275,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.1% Airbnb Rental Income: $1827 Traditional Rental Income: $2226 Airbnb ROI: -0.35% Traditional ROI: 3.1%
1075 CONDOR PLACE Winter Springs, FL Under contract-accepting backup offers. Charming three bedroom, two full bathroom, two car...	3 beds \| 2 baths \| 1,749 sq.ft.	$414,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.76% Airbnb Rental Income: $1827 Traditional Rental Income: $2667 Airbnb ROI: 1.33% Traditional ROI: 4.76%
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.	$408,500	Airbnb cash on cash: 0.96% Traditional cash on cash: 5.01% Airbnb Rental Income: $1827 Traditional Rental Income: $2883 Airbnb ROI: 0.96% Traditional ROI: 5.01%
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.	$400,000	Airbnb cash on cash: 5.32% Traditional cash on cash: 4.7% Airbnb Rental Income: $3833 Traditional Rental Income: $2774 Airbnb ROI: 5.32% Traditional ROI: 4.7%
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: 5.16% Airbnb Rental Income: $1827 Traditional Rental Income: $2233 Airbnb ROI: 1.75% Traditional ROI: 5.16%
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: 4.06% Airbnb Rental Income: $1827 Traditional Rental Income: $3095 Airbnb ROI: 0.29% Traditional ROI: 4.06%
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: 0.72% Traditional cash on cash: 4.41% Airbnb Rental Income: $1827 Traditional Rental Income: $3060 Airbnb ROI: 0.72% Traditional ROI: 4.41%
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: 4.24% Airbnb Rental Income: $3833 Traditional Rental Income: $4099 Airbnb ROI: 2.68% Traditional ROI: 4.24%
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.	$779,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3908 Airbnb ROI: N/A Traditional ROI: 3.22%
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: 5.37% Airbnb Rental Income: $1827 Traditional Rental Income: $2141 Airbnb ROI: 1.32% Traditional ROI: 5.37%
202 ARROWHEAD COURT Winter Springs, FL Under contract-accepting backup offers. BRAND NEW TILE ROOF! **Buyer backed out due to per...	5 beds \| 5 baths \| 4,078 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.26% Airbnb Rental Income: $null Traditional Rental Income: $5368 Airbnb ROI: N/A Traditional ROI: 2.26%
600 NORTHERN WAY #1403 Winter Springs, FL A Beautiful, Well-Appointed Condo in Tuscany Place Condominiums ~ Upon Entering this Beaut...	3 beds \| 2 baths \| 1,377 sq.ft.	$325,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 4% Airbnb Rental Income: $1827 Traditional Rental Income: $2343 Airbnb ROI: 0.69% Traditional ROI: 4%
314 SAN GABRIEL STREET Winter Springs, FL Seller 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% Traditional cash on cash: 5.5% Airbnb Rental Income: $1827 Traditional Rental Income: $2157 Airbnb ROI: 2.38% Traditional ROI: 5.5%

Real Estate investment in Winter-springs, FL

There are 131 properties for sale in the city of Winter Springs . The median list price in Winter Springs is $408,500 and the average price per square foot is $210. In April 2026, the average monthly cash on cash return in Winter Springs is 4.00%. The average monthly rental income in Winter Springs is $2,645.

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

There are 131 investment properties available for sale in Winter-springs.

In 2026, the best neighborhood to buy investment property is Winter Springs.

The ROI for Long-Term is higher than the Short-Term in Winter-springs with average rental income of $2,645.

Your search for investment property begins and ends here

Investment Property 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.

$375,000

Airbnb cash on cash: 5.92%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $3833

Traditional Rental Income: $2724

Airbnb ROI: 5.92%

Traditional ROI: 5.12%

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: 3.94%

Airbnb Rental Income: $1827

Traditional Rental Income: $2776

Airbnb ROI: 0.52%

Traditional ROI: 3.94%

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: 5.3%

Airbnb Rental Income: $1652

Traditional Rental Income: $1943

Airbnb ROI: 2.52%

Traditional ROI: 5.3%

420 HARBOR WINDS COURT

Winter Springs, FL

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

$365,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $1827

Traditional Rental Income: $2805

Airbnb ROI: 0.23%

Traditional ROI: 4.53%

471 HARBOR WINDS COURT

Winter Springs, FL

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

$330,000

Airbnb cash on cash: 0.57%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $1827

Traditional Rental Income: $2627

Airbnb ROI: 0.57%

Traditional ROI: 4.74%

131 LISA LOOP

Winter Springs, FL

4 beds | 3 baths | 2,309 sq.ft.

$489,000

Airbnb cash on cash: 4.04%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $3833

Traditional Rental Income: $3167

Airbnb ROI: 4.04%