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.

Golden Highlands Investment Property for Sale in Winter Springs, FL

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

Showing 123 Golden Highlands Investment Property 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
477 GREEN SPRING CIRCLE Winter Springs, FL Conveniently located in Winter Springs, this property is a Charming end-unit townhome offe...	3 beds \| 2 baths \| 1,280 sq.ft.	$234,999	Airbnb cash on cash: 2.88% Traditional cash on cash: 5.73% Airbnb Rental Income: $1827 Traditional Rental Income: $1967 Airbnb ROI: 2.88% Traditional ROI: 5.73%
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 Under 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% 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.	$284,900	Airbnb cash on cash: 2.55% Traditional cash on cash: 5.37% Airbnb Rental Income: $1652 Traditional Rental Income: $1943 Airbnb ROI: 2.55% Traditional ROI: 5.37%
420 HARBOR WINDS COURT Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	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%
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 Under contract-accepting backup offers. IMMACULATE 4 bedroom, 2 bathroom home in the beaut...	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%
299 WOODGREEN LANE Winter Springs, FL Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Gre...	3 beds \| 3 baths \| 1,326 sq.ft.	$290,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 4.04% Airbnb Rental Income: $1827 Traditional Rental Income: $1876 Airbnb ROI: 2.05% Traditional ROI: 4.04%
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.	$198,900	Airbnb cash on cash: 1.71% Traditional cash on cash: 5.64% Airbnb Rental Income: $1827 Traditional Rental Income: $2075 Airbnb ROI: 1.71% Traditional ROI: 5.64%
1106 SUPERIOR COURT Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	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%
622 ANHINGA ROAD Winter Springs, FL NEW ROOF 2026, HVAC 2017â2018, and water heater 2022, giving buyers peace of mind from d...	3 beds \| 3 baths \| 1,721 sq.ft.	$398,500	Airbnb cash on cash: 0.99% Traditional cash on cash: 4.67% Airbnb Rental Income: $1827 Traditional Rental Income: $2709 Airbnb ROI: 0.99% Traditional ROI: 4.67%
515 SEASONS COURT Winter Springs, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged...	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.	$485,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 4.84% Airbnb Rental Income: $3833 Traditional Rental Income: $3616 Airbnb ROI: 3.49% Traditional ROI: 4.84%
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%
276 SAN GABRIEL STREET Winter Springs, FL Don't Wait!! Seller offers $5,000 Towards buyer's closing costs. This 3-bedroom, 2-bathroo...	3 beds \| 2 baths \| 1,089 sq.ft.	$290,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 4.19% Airbnb Rental Income: $1827 Traditional Rental Income: $1998 Airbnb ROI: 1.75% Traditional ROI: 4.19%
201 BURGESS DRIVE Winter Springs, FL Welcome to this TRULY IMPRESSIVE 4-bedroom, 2.5-bath colonial-inspired residence in the hi...	4 beds \| 3 baths \| 3,046 sq.ft.	$675,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.3% Airbnb Rental Income: $3833 Traditional Rental Income: $3124 Airbnb ROI: 2.11% Traditional ROI: 2.3%
110 MOCKINGBIRD LANE Winter Springs, FL Under contract-accepting backup offers. Welcome home! This beautifully updated 4 bed, 2 ba...	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.	$269,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 5.41% Airbnb Rental Income: $1827 Traditional Rental Income: $2233 Airbnb ROI: 1.86% Traditional ROI: 5.41%
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 Under contract-accepting backup offers. Your private oasis awaits on a PREMIUM WATERFRONT ...	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 Under contract-accepting backup offers. Great location, No HOA..69 acres , 4 bedrooms,2 b...	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%
702 GLASGOW COURT Winter Springs, FL Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac ...	4 beds \| 3 baths \| 1,878 sq.ft.	$317,700	Airbnb cash on cash: 6.05% Traditional cash on cash: 5% Airbnb Rental Income: $3833 Traditional Rental Income: $2691 Airbnb ROI: 6.05% Traditional ROI: 5%
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%
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%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Winter Springs, FL

477 GREEN SPRING CIRCLE

Winter Springs, FL

3 beds | 2 baths | 1,280 sq.ft.

$234,999

Airbnb cash on cash: 2.88%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $1827

Traditional Rental Income: $1967

Airbnb ROI: 2.88%

Traditional ROI: 5.73%

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.

$284,900

Airbnb cash on cash: 2.55%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $1652

Traditional Rental Income: $1943

Airbnb ROI: 2.55%

Traditional ROI: 5.37%

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%