Real Estate Investment Properties for Sale in Casselberry, FL

Looking for investment property in Casselberry, FL with high ROI ?

Explore a variety of short-term homes & houses in Casselberry, FL. Invest wisely with VRBO & Casselberry, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Woodlawn Investment Property for Sale in Casselberry, FL

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

Showing 75 Woodlawn Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
254 OAK PARK PLACE Casselberry, FL Located in the desirable South Division of Sunset Oaks, Seminole County, this charming sin...	4 beds \| 2 baths \| 1,966 sq.ft.	$400,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 4.74% Airbnb Rental Income: $2648 Traditional Rental Income: $2828 Airbnb ROI: 2.57% Traditional ROI: 4.74%
481 HIBISCUS ROAD Casselberry, FL Under contract-accepting backup offers. A true garden home in Casselberry Garden District ...	3 beds \| 1 baths \| 1,112 sq.ft.	$284,999	Airbnb cash on cash: 2.7% Traditional cash on cash: 4.64% Airbnb Rental Income: $1793 Traditional Rental Income: $1826 Airbnb ROI: 2.7% Traditional ROI: 4.64%
1663 SPICEWOOD LANE Casselberry, FL COME take a look at this Beautiful Ranch Style Home in the heart of Casselberry. This Sing...	3 beds \| 2 baths \| 1,708 sq.ft.	$415,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.66% Airbnb Rental Income: $1793 Traditional Rental Income: $2270 Airbnb ROI: 1.18% Traditional ROI: 3.66%
612 KENWICK CIRCLE #103 Casselberry, FL Beautifully maintained and thoughtfully updated 2-bedroom, 2-bath condo located in the Oxf...	2 beds \| 2 baths \| 1,126 sq.ft.	$199,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 3.43% Airbnb Rental Income: $1003 Traditional Rental Income: $1642 Airbnb ROI: -1.83% Traditional ROI: 3.43%
526 E FOOTHILL WAY Casselberry, FL Situated on a peaceful, tree-lined street with mature landscaping and a generously sized b...	4 beds \| 2 baths \| 1,556 sq.ft.	$349,900	Airbnb cash on cash: 3.56% Traditional cash on cash: 4.49% Airbnb Rental Income: $2648 Traditional Rental Income: $2322 Airbnb ROI: 3.56% Traditional ROI: 4.49%
351 LILAC ROAD Casselberry, FL Under contract-accepting backup offers. HURRY! Perfect location! NO HOA, NO CDD! Welcome t...	3 beds \| 2 baths \| 1,602 sq.ft.	$408,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 3.38% Airbnb Rental Income: $1793 Traditional Rental Income: $2279 Airbnb ROI: 0.83% Traditional ROI: 3.38%
4226 CLOVERLEAF PLACE Casselberry, FL Welcome to this spacious 4-bedroom, 2-bathroom pool home, perfectly blending comfort, func...	4 beds \| 2 baths \| 1,676 sq.ft.	$394,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 4.29% Airbnb Rental Income: $2648 Traditional Rental Income: $2426 Airbnb ROI: 3.19% Traditional ROI: 4.29%
636 KENWICK CIRCLE #105 Casselberry, FL Welcome to Oxford Square community!! This immaculate 2 bedroom, 2 bath condo situated on t...	2 beds \| 2 baths \| 1,126 sq.ft.	$179,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 4.39% Airbnb Rental Income: $1003 Traditional Rental Income: $1655 Airbnb ROI: -1.53% Traditional ROI: 4.39%
520 GEORGETOWN DRIVE Casselberry, FL Ready for immediate showings, this well-maintained 3BR/1.5BA townhouse in Casselberry offe...	3 beds \| 2 baths \| 1,344 sq.ft.	$222,500	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.36% Airbnb Rental Income: $1793 Traditional Rental Income: $1806 Airbnb ROI: 0.98% Traditional ROI: 3.36%
3965 JOURNEY COURT Casselberry, FL PRICE IMPROVEMENT!! Beautiful move in ready home in a great area of Casselberry. Deer Run ...	3 beds \| 2 baths \| 1,304 sq.ft.	$358,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 3.02% Airbnb Rental Income: $1793 Traditional Rental Income: $2041 Airbnb ROI: 0.83% Traditional ROI: 3.02%
208 DIAMOND CV #104 Casselberry, FL Approved For Renting. MUST GO!!!!!!!!. REDUCED!!!! REDUCED!!! Charming 1 Bedroom, 1 b...	1 beds \| 1 baths \| 722 sq.ft.	$139,999	Airbnb cash on cash: -1.1% Traditional cash on cash: 3.93% Airbnb Rental Income: $969 Traditional Rental Income: $1293 Airbnb ROI: -1.1% Traditional ROI: 3.93%
236 PLAZA OVAL Casselberry, FL Welcome to this beautiful one of kind property in the heart of Casselberry, Fl. This home ...	4 beds \| 2 baths \| 1,793 sq.ft.	$490,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 3.01% Airbnb Rental Income: $2648 Traditional Rental Income: $2431 Airbnb ROI: 2.11% Traditional ROI: 3.01%
1252 ASH TREE COVE Casselberry, FL Welcome to the CARLISLE FLOOR PLAN, a 4 BED / 2 FULL BATH / 1 HALF BATH Single Family Ho...	4 beds \| 3 baths \| 2,412 sq.ft.	$539,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 3.67% Airbnb Rental Income: $2648 Traditional Rental Income: $2741 Airbnb ROI: 2.23% Traditional ROI: 3.67%
5275 Hidden Pines Cir Casselberry, FL Minutes from the beach, this well-appointed 4-bedroom, 2-bath home offers 1,820 sq ft of o...	4 beds \| 2 baths \| 1,820 sq.ft.	$343,238	Airbnb cash on cash: 3.98% Traditional cash on cash: 5.34% Airbnb Rental Income: $2648 Traditional Rental Income: $2454 Airbnb ROI: 3.98% Traditional ROI: 5.34%
5279 Hidden Pines Cir Casselberry, FL TO BE BUILT, Est Completion Fall 2025. Welcome to HIDDEN PINES by Adams Homes. Located jus...	3 beds \| 2 baths \| 1,530 sq.ft.	$317,349	Airbnb cash on cash: 2.06% Traditional cash on cash: 5.36% Airbnb Rental Income: $1793 Traditional Rental Income: $2292 Airbnb ROI: 2.06% Traditional ROI: 5.36%
5291 Hidden Pines Cir Casselberry, FL TO BE BUILT, Est Completion Fall 2025. Welcome to HIDDEN PINES by Adams Homes. Located jus...	5 beds \| 4 baths \| 3,030 sq.ft.	$403,602	Airbnb cash on cash: 3.04% Traditional cash on cash: 7.8% Airbnb Rental Income: $2619 Traditional Rental Income: $3793 Airbnb ROI: 3.04% Traditional ROI: 7.8%
5295 Hidden Pines Cir Casselberry, FL TO BE BUILT, Est Completion Fall 2025. Welcome to HIDDEN PINES by Adams Homes. Located jus...	3 beds \| 2 baths \| 1,530 sq.ft.	$316,349	Airbnb cash on cash: 2.93% Traditional cash on cash: 6.25% Airbnb Rental Income: $1793 Traditional Rental Income: $2292 Airbnb ROI: 2.93% Traditional ROI: 6.25%
5303 Hidden Pines Cir Casselberry, FL TO BE BUILT, Est Completion Fall 2025. Welcome to HIDDEN PINES by Adams Homes. Located jus...	5 beds \| 4 baths \| 3,030 sq.ft.	$403,602	Airbnb cash on cash: 3.04% Traditional cash on cash: 7.8% Airbnb Rental Income: $2619 Traditional Rental Income: $3793 Airbnb ROI: 3.04% Traditional ROI: 7.8%
1057 NODDING PINES WAY Casselberry, FL One or more photo(s) has been virtually staged. Donât miss your chance to own this beaut...	3 beds \| 2 baths \| 1,775 sq.ft.	$465,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 3.19% Airbnb Rental Income: $1793 Traditional Rental Income: $2324 Airbnb ROI: 0.85% Traditional ROI: 3.19%
525 E FOOTHILL WAY Casselberry, FL New Roof at closing! This charming 3-bedroom, 2-bath home in the heart of Casselberry need...	3 beds \| 2 baths \| 1,492 sq.ft.	$294,999	Airbnb cash on cash: 3.13% Traditional cash on cash: 6.48% Airbnb Rental Income: $1793 Traditional Rental Income: $2236 Airbnb ROI: 3.13% Traditional ROI: 6.48%
1402 WAUKON CIRCLE Casselberry, FL Welcome Home to this stunning 5-bedroom, 3.5-bathroom residence located in the sought-afte...	5 beds \| 4 baths \| 2,701 sq.ft.	$660,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 3.57% Airbnb Rental Income: $2619 Traditional Rental Income: $3371 Airbnb ROI: 1.33% Traditional ROI: 3.57%
1251 ASH TREE COVE Casselberry, FL Welcome to the CARLISLE FLOOR PLAN, a 4 BED / 2 FULL BATH / 1 HALF BATH Single Family Ho...	4 beds \| 3 baths \| 2,412 sq.ft.	$529,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.83% Airbnb Rental Income: $2648 Traditional Rental Income: $2777 Airbnb ROI: 2.29% Traditional ROI: 3.83%
107 THRUSH LANE Casselberry, FL PRICE IMPROVEMENT! Welcome to your dream home in the sought-after city of Casselberry! Thi...	3 beds \| 2 baths \| 1,383 sq.ft.	$380,000	Airbnb cash on cash: 1.6% Traditional cash on cash: 3.81% Airbnb Rental Income: $1793 Traditional Rental Income: $2095 Airbnb ROI: 1.6% Traditional ROI: 3.81%
5307 Hidden Pines Cir Casselberry, FL TO BE BUILT, Est Completion late Summer 2025. Welcome to HIDDEN PINES by Adams Homes. Loca...	3 beds \| 2 baths \| 1,530 sq.ft.	$316,349	Airbnb cash on cash: 2.08% Traditional cash on cash: 5.45% Airbnb Rental Income: $1793 Traditional Rental Income: $2309 Airbnb ROI: 2.08% Traditional ROI: 5.45%
5315 Hidden Pines Cir Casselberry, FL TO BE BUILT, Est Completion Fall 2025. Welcome to HIDDEN PINES by Adams Homes. Located jus...	3 beds \| 2 baths \| 1,634 sq.ft.	$318,391	Airbnb cash on cash: 2.06% Traditional cash on cash: 5.5% Airbnb Rental Income: $1793 Traditional Rental Income: $2335 Airbnb ROI: 2.06% Traditional ROI: 5.5%
230 S EMBREY DRIVE Casselberry, FL Situated in the heart of Lake Concord Park, Casselberry, this inviting 3/2 single family h...	3 beds \| 2 baths \| 1,352 sq.ft.	$359,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 4.56% Airbnb Rental Income: $1793 Traditional Rental Income: $2040 Airbnb ROI: 2.38% Traditional ROI: 4.56%
209 TWELVE LEAGUE CIRCLE Casselberry, FL Under contract-accepting backup offers. SELLER OFFERING BUYER $5000 TOWARDS RATE BUY DOWN ...	3 beds \| 2 baths \| 1,446 sq.ft.	$420,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.06% Airbnb Rental Income: $1793 Traditional Rental Income: $2137 Airbnb ROI: 0.95% Traditional ROI: 3.06%
474 C Street Casselberry, FL Excellent investment opportunity in Casselberry. This well-maintained 1-bedroom, 1-bath pr...	1 beds \| 1 baths \| 690 sq.ft.	$147,900	Airbnb cash on cash: -1.07% Traditional cash on cash: 3.49% Airbnb Rental Income: $969 Traditional Rental Income: $1265 Airbnb ROI: -1.07% Traditional ROI: 3.49%
281 SANDPIPER DRIVE Casselberry, FL Under contract-accepting backup offers. Beautifully remodeled from top to bottom, this 4-b...	4 beds \| 2 baths \| 1,793 sq.ft.	$475,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 3.99% Airbnb Rental Income: $2648 Traditional Rental Income: $2786 Airbnb ROI: 2.26% Traditional ROI: 3.99%
3585 JERICHO DRIVE Casselberry, FL Welcome to this RARE FIND and beautifully upgraded split-3 level home, designed for modern...	4 beds \| 3 baths \| 2,413 sq.ft.	$549,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 5.55% Airbnb Rental Income: $2648 Traditional Rental Income: $3784 Airbnb ROI: 2.12% Traditional ROI: 5.55%
5327 Hidden Pines Cir Casselberry, FL Spacious 4-Bedroom Home with Modern Finishes & Ideal Layout - Just 30 Minutes from the Bea...	4 beds \| 2 baths \| 1,820 sq.ft.	$326,707	Airbnb cash on cash: 4.28% Traditional cash on cash: 5.72% Airbnb Rental Income: $2648 Traditional Rental Income: $2460 Airbnb ROI: 4.28% Traditional ROI: 5.72%
5333 Hidden Pines Cir Casselberry, FL TO BE BUILT, Est Completion Fall 2025. Welcome to HIDDEN PINES by Adams Homes. Located jus...	3 beds \| 2 baths \| 1,530 sq.ft.	$316,349	Airbnb cash on cash: 2.07% Traditional cash on cash: 5.48% Airbnb Rental Income: $1793 Traditional Rental Income: $2321 Airbnb ROI: 2.07% Traditional ROI: 5.48%
205 S WILDERNESS POINT Casselberry, FL Under contract-accepting backup offers. Welcome to the quiet community of Deer Run and you...	2 beds \| 3 baths \| 1,166 sq.ft.	$239,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 4.74% Airbnb Rental Income: $1003 Traditional Rental Income: $1889 Airbnb ROI: -0.76% Traditional ROI: 4.74%
1175 PASEO DEL MAR #A Casselberry, FL Under contract-accepting backup offers. Wake up to breathtaking water views at 1175 Paseo ...	1 beds \| 1 baths \| 781 sq.ft.	$164,000	Airbnb cash on cash: -1.65% Traditional cash on cash: 4.1% Airbnb Rental Income: $969 Traditional Rental Income: $1518 Airbnb ROI: -1.65% Traditional ROI: 4.1%
335 SANDPIPER DRIVE Casselberry, FL This beautifully updated 3 bedroom, 2 bathroom home is tucked inside one of Casselberryâ...	3 beds \| 2 baths \| 1,513 sq.ft.	$389,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 4.37% Airbnb Rental Income: $1793 Traditional Rental Income: $2189 Airbnb ROI: 1.95% Traditional ROI: 4.37%
1779 LAUREL BROOK LOOP Casselberry, FL Welcome to 1779 Laurel Brook Loop, a beautifully updated home in a quiet gated Casselberry...	4 beds \| 2 baths \| 1,959 sq.ft.	$450,000	Airbnb cash on cash: 2.09% Traditional cash on cash: 3.7% Airbnb Rental Income: $2648 Traditional Rental Income: $2694 Airbnb ROI: 2.09% Traditional ROI: 3.7%
5363 Hidden Pines Cir Casselberry, FL Spacious 4-Bedroom Home with Modern Finishes & Ideal Layout - Just 30 Minutes from the Bea...	4 beds \| 2 baths \| 2,313 sq.ft.	$364,410	Airbnb cash on cash: 3.65% Traditional cash on cash: 5.31% Airbnb Rental Income: $2648 Traditional Rental Income: $2586 Airbnb ROI: 3.65% Traditional ROI: 5.31%
5369 Hidden Pines Cir Casselberry, FL Welcome to this beautifully maintained single-family home offering 1920 square feet of con...	4 beds \| 2 baths \| 1,920 sq.ft.	$337,231	Airbnb cash on cash: 4.09% Traditional cash on cash: 5.59% Airbnb Rental Income: $2648 Traditional Rental Income: $2493 Airbnb ROI: 4.09% Traditional ROI: 5.59%
5375 Hidden Pines Cir Casselberry, FL Welcome to this beautifully maintained single-family home offering 2100 square feet of con...	4 beds \| 2 baths \| 2,100 sq.ft.	$342,357	Airbnb cash on cash: 4% Traditional cash on cash: 5.74% Airbnb Rental Income: $2648 Traditional Rental Income: $2578 Airbnb ROI: 4% Traditional ROI: 5.74%
5345 Hidden Pines Cir Casselberry, FL Spacious 4-Bedroom Home with Modern Finishes & Ideal Layout - Just 30 Minutes from the Bea...	4 beds \| 2 baths \| 2,313 sq.ft.	$363,410	Airbnb cash on cash: 3.66% Traditional cash on cash: 5.33% Airbnb Rental Income: $2648 Traditional Rental Income: $2586 Airbnb ROI: 3.66% Traditional ROI: 5.33%

Your search for investment property begins and ends here

Woodlawn Investment Property for Sale in Casselberry, FL

254 OAK PARK PLACE

Casselberry, FL

4 beds | 2 baths | 1,966 sq.ft.

$400,000

Airbnb cash on cash: 2.57%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $2648

Traditional Rental Income: $2828

Airbnb ROI: 2.57%

Traditional ROI: 4.74%

481 HIBISCUS ROAD

Casselberry, FL

3 beds | 1 baths | 1,112 sq.ft.

$284,999

Airbnb cash on cash: 2.7%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1793

Traditional Rental Income: $1826

Airbnb ROI: 2.7%

Traditional ROI: 4.64%

1663 SPICEWOOD LANE

Casselberry, FL

3 beds | 2 baths | 1,708 sq.ft.

$415,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $1793

Traditional Rental Income: $2270

Airbnb ROI: 1.18%

Traditional ROI: 3.66%

612 KENWICK CIRCLE #103

Casselberry, FL

2 beds | 2 baths | 1,126 sq.ft.

$199,000

Airbnb cash on cash: -1.83%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $1003

Traditional Rental Income: $1642

Airbnb ROI: -1.83%

Traditional ROI: 3.43%

526 E FOOTHILL WAY

Casselberry, FL

4 beds | 2 baths | 1,556 sq.ft.

$349,900

Airbnb cash on cash: 3.56%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $2648

Traditional Rental Income: $2322

Airbnb ROI: 3.56%

Traditional ROI: 4.49%

351 LILAC ROAD

Casselberry, FL

3 beds | 2 baths | 1,602 sq.ft.

$408,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1793

Traditional Rental Income: $2279

Airbnb ROI: 0.83%

Traditional ROI: 3.38%

4226 CLOVERLEAF PLACE

Casselberry, FL

4 beds | 2 baths | 1,676 sq.ft.

$394,000

Airbnb cash on cash: 3.19%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $2648

Traditional Rental Income: $2426

Airbnb ROI: 3.19%

Traditional ROI: 4.29%

636 KENWICK CIRCLE #105

Casselberry, FL

2 beds | 2 baths | 1,126 sq.ft.

$179,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 4.39%

Airbnb Rental Income: $1003

Traditional Rental Income: $1655

Airbnb ROI: -1.53%