Longwood, FL Investment Property for Sale

Real Estate Investments for Sale in Longwood, FL With High ROI

Are you looking for a vacation rental in Longwood, 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 Longwood, FL. Invest wisely with VRBO & Longwood, 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 Longwood, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
369 BALOGH PLACE Longwood, FL Absolute perfection in an amazing location!!! It really does not get better than this!! Th...	4 beds \| 2 baths \| 1,947 sq.ft.	$507,500	Airbnb cash on cash: 7.31% Traditional cash on cash: 3.96% Airbnb Rental Income: $5557 Traditional Rental Income: $2855 Airbnb ROI: 7.31% Traditional ROI: 3.96%
1960 ALAQUA DRIVE Longwood, FL Welcome to this Stunning ALAQUA DREAM residence where luxury meets functionality! Located...	5 beds \| 6 baths \| 4,581 sq.ft.	$1,719,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.7% Airbnb Rental Income: $null Traditional Rental Income: $6295 Airbnb ROI: N/A Traditional ROI: 1.7%
213 CROWN OAKS WAY #213 Longwood, FL Come fall in love with this tastefully updated and well maintained three bedroom, two full...	3 beds \| 2 baths \| 1,804 sq.ft.	$234,900	Airbnb cash on cash: 7.52% Traditional cash on cash: 7.6% Airbnb Rental Income: $3061 Traditional Rental Income: $2380 Airbnb ROI: 7.52% Traditional ROI: 7.6%
618 FOX HUNT CIRCLE Longwood, FL This stunning POOL home offers over 2000 sqft of living space with 4 spacious bedrooms, 2 ...	4 beds \| 2 baths \| 2,056 sq.ft.	$549,900	Airbnb cash on cash: 6.83% Traditional cash on cash: 3.88% Airbnb Rental Income: $5557 Traditional Rental Income: $2924 Airbnb ROI: 6.83% Traditional ROI: 3.88%
240 NEEDLES TRAIL Longwood, FL PRICE IMPROVEMENT!! SELLERS ARE OFFERING $44K CONCESSIONS TOWARDS SOLAR ASSUMPTION!! We...	3 beds \| 2 baths \| 2,185 sq.ft.	$635,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 2.73% Airbnb Rental Income: $3061 Traditional Rental Income: $2858 Airbnb ROI: 1.89% Traditional ROI: 2.73%
561 SHINING ARMOR LANE Longwood, FL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	N/A beds \| N/A baths \| N/A	$358,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 2.98% Airbnb Rental Income: $1635 Traditional Rental Income: $1742 Airbnb ROI: 1.29% Traditional ROI: 2.98%
150 Sandy Oaks Place Longwood, FL Embark on a transformative journey with this 2.3-acre property at the end of a cul-de-sac,...	3 beds \| 3 baths \| 2,733 sq.ft.	$749,999	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.67% Airbnb Rental Income: $3061 Traditional Rental Income: $3279 Airbnb ROI: 1.36% Traditional ROI: 2.67%
404 Magnolia Oak Drive Longwood, FL This beautiful Sweetwater Oaks Pool Home is a must see! Located on an oversized corner lot...	4 beds \| 3 baths \| 1,965 sq.ft.	$564,900	Airbnb cash on cash: 6.36% Traditional cash on cash: 3.35% Airbnb Rental Income: $5557 Traditional Rental Income: $2856 Airbnb ROI: 6.36% Traditional ROI: 3.35%
186 PARSONS ROAD Longwood, FL Welcome to 186 Parsons Road, concrete block home nestled in the pristine Markham Woods are...	4 beds \| 2 baths \| 2,116 sq.ft.	$499,900	Airbnb cash on cash: 7.85% Traditional cash on cash: 4.19% Airbnb Rental Income: $5557 Traditional Rental Income: $2733 Airbnb ROI: 7.85% Traditional ROI: 4.19%
266 W SABAL PALM PLACE #266 Longwood, FL Welcome Home! Let me introduce you to this beautifully maintained 2 bedroom 2 full bath co...	2 beds \| 2 baths \| 1,202 sq.ft.	$287,900	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.87% Airbnb Rental Income: $1952 Traditional Rental Income: $1838 Airbnb ROI: -0.61% Traditional ROI: 0.87%
1370 N MARCY DR DRIVE Longwood, FL Move in Ready, this 4-bedroom, 2-bathroom home with a split floor plan is perfect for a fa...	4 beds \| 2 baths \| 2,004 sq.ft.	$499,999	Airbnb cash on cash: 7.62% Traditional cash on cash: 4.38% Airbnb Rental Income: $5557 Traditional Rental Income: $2927 Airbnb ROI: 7.62% Traditional ROI: 4.38%
966 N RONALD REAGAN BOULEVARD Longwood, FL This property did not flood from Hurricane Ian, HIGH AND DRY! Located just 1/2 mile from t...	5 beds \| 3 baths \| 2,490 sq.ft.	$795,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $3387 Airbnb ROI: N/A Traditional ROI: 2.79%
109 CROWN OAKS WAY #109 Longwood, FL Welcome to your dream home in the charming neighborhood of "The Springs"! This fully renov...	1 beds \| 1 baths \| 877 sq.ft.	$162,000	Airbnb cash on cash: -2.48% Traditional cash on cash: 0% Airbnb Rental Income: $1569 Traditional Rental Income: $1501 Airbnb ROI: -2.48% Traditional ROI: 0%
3033 TIMPANA POINT Longwood, FL Welcome to 3033 Timpana Point - 4 bedroom,4.5 bath home located in one of Seminole countyâ...	4 beds \| 6 baths \| 5,108 sq.ft.	$1,095,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.66% Airbnb Rental Income: $5557 Traditional Rental Income: $5638 Airbnb ROI: 1.49% Traditional ROI: 2.66%
245 CROWN OAKS WAY #245 Longwood, FL Imagine yourself surrounded by a canopy of trees in your beautiful community of The Spring...	2 beds \| 2 baths \| 1,143 sq.ft.	$192,999	Airbnb cash on cash: 4.17% Traditional cash on cash: 6.09% Airbnb Rental Income: $1952 Traditional Rental Income: $1791 Airbnb ROI: 4.17% Traditional ROI: 6.09%
141 SPRINGWOOD CIRCLE #G Longwood, FL Convenient Location Corner of Interstate I-4 and State Road 434. Close to fabulous sho...	1 beds \| 1 baths \| 666 sq.ft.	$139,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.34% Airbnb Rental Income: $1569 Traditional Rental Income: $1343 Airbnb ROI: -0.33% Traditional ROI: 1.34%
235 TOLLGATE TRAIL Longwood, FL Move in ready home in sought after The Woodlands community. This 4 bed, 2 bath home is fr...	4 beds \| 2 baths \| 2,449 sq.ft.	$479,900	Airbnb cash on cash: 7.57% Traditional cash on cash: 4.87% Airbnb Rental Income: $5557 Traditional Rental Income: $3231 Airbnb ROI: 7.57% Traditional ROI: 4.87%
343 W HORNBEAM DRIVE Longwood, FL Sabal Point! Outstanding 3 BD/ 2 BT PLUS a Bonus Room adjoins the Master Suite, that could...	3 beds \| 2 baths \| 2,279 sq.ft.	$519,900	Airbnb cash on cash: 2.39% Traditional cash on cash: 3.5% Airbnb Rental Income: $3061 Traditional Rental Income: $2901 Airbnb ROI: 2.39% Traditional ROI: 3.5%
613 LONGMEADOW CIRCLE Longwood, FL Great Home in a great community. This spacious 4 bedroom 2 bath home near Sabal Point Elem...	4 beds \| 3 baths \| 2,147 sq.ft.	$498,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 3.65% Airbnb Rental Income: $5557 Traditional Rental Income: $2929 Airbnb ROI: 6.9% Traditional ROI: 3.65%
1150 N RONALD REAGAN BOULEVARD Longwood, FL Absolutely Turn Key fully renovated two-story block standalone building zoned Neighborhood...	1 beds \| 3 baths \| 2,480 sq.ft.	$785,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.3% Airbnb Rental Income: $1569 Traditional Rental Income: $2171 Airbnb ROI: -0.14% Traditional ROI: 1.3%
1787 OAKBROOK DRIVE Longwood, FL Step into the epitome of luxury living in this Charles Clayton custom home where elegance ...	5 beds \| 5 baths \| 4,677 sq.ft.	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.47% Airbnb Rental Income: $null Traditional Rental Income: $5612 Airbnb ROI: N/A Traditional ROI: 1.47%
236 S FOX CHASE POINT Longwood, FL 3 Bedroom 2.5 bath Wekiva single-family residence on a cul-de-sac wooded lot with a spacio...	3 beds \| 3 baths \| 1,919 sq.ft.	$419,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 4.93% Airbnb Rental Income: $3061 Traditional Rental Income: $2835 Airbnb ROI: 3.73% Traditional ROI: 4.93%
569 SHINING ARMOR LANE Longwood, FL Nestled in the highly coveted gated community of Highcroft, this exquisite property offers...	3 beds \| 3 baths \| 1,438 sq.ft.	$399,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 1.18% Airbnb Rental Income: $3061 Traditional Rental Income: $2151 Airbnb ROI: 1.74% Traditional ROI: 1.18%
679 SEMINOLE AVENUE Longwood, FL Opportunity is knocking, will you answer?Â Rarely does a duplex like this hit the market,...	5 beds \| N/A baths \| 2,951 sq.ft.	$648,800	Airbnb cash on cash: N/A Traditional cash on cash: 1.83% Airbnb Rental Income: $null Traditional Rental Income: $2295 Airbnb ROI: N/A Traditional ROI: 1.83%
120 ICHABOD TRAIL Longwood, FL Welcome to your private sanctuary nestled in a coveted Sleepy Hollow neighborhood, offerin...	4 beds \| 3 baths \| 2,010 sq.ft.	$479,000	Airbnb cash on cash: 7.78% Traditional cash on cash: 4.79% Airbnb Rental Income: $5557 Traditional Rental Income: $3105 Airbnb ROI: 7.78% Traditional ROI: 4.79%
790 SILHOUETTE COURT Longwood, FL Auction Property. Looking for a place to call Home. Look no further! This Beautiful 3 Bed...	3 beds \| 2 baths \| 1,820 sq.ft.	$499,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.73% Airbnb Rental Income: $3061 Traditional Rental Income: $2517 Airbnb ROI: 3.39% Traditional ROI: 3.73%
669 N LONGVIEW PLACE Longwood, FL Stunning Waterfront Oasis in Desirable Sabal Point Community Welcome to your dream ...	5 beds \| 4 baths \| 3,376 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $4698 Airbnb ROI: N/A Traditional ROI: 4.73%
311 GREEN OAK COURT Longwood, FL Check out this amazing home on a double cul-de-sac! Sweetwater Oaks is one of the most sou...	4 beds \| 4 baths \| 3,353 sq.ft.	$764,900	Airbnb cash on cash: 4.38% Traditional cash on cash: 3.87% Airbnb Rental Income: $5557 Traditional Rental Income: $4074 Airbnb ROI: 4.38% Traditional ROI: 3.87%
459 SABAL TRAIL CIRCLE Longwood, FL NEW PRICE REDUCTION Located in much sought after Sabal Trail in Sabal Point. This Stunni...	4 beds \| 3 baths \| 2,508 sq.ft.	$685,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 2.68% Airbnb Rental Income: $5557 Traditional Rental Income: $3133 Airbnb ROI: 4.73% Traditional ROI: 2.68%
3108 CLUBSIDE DRIVE Longwood, FL This move-in ready, 2-primary bedrooms with 2 1/2-baths condo is on the first floor offeri...	2 beds \| 3 baths \| 1,365 sq.ft.	$237,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 2% Airbnb Rental Income: $1952 Traditional Rental Income: $2007 Airbnb ROI: -0.54% Traditional ROI: 2%
127 SHERIDAN COURT Longwood, FL Charming 3 Bedroom 2 bathroom home in highly desirable Windsor Manor neighborhood in Longw...	3 beds \| 2 baths \| 1,697 sq.ft.	$425,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 4.63% Airbnb Rental Income: $3061 Traditional Rental Income: $2496 Airbnb ROI: 4.3% Traditional ROI: 4.63%
101 MAGNOLIA OAK DRIVE Longwood, FL Welcome to this stunning property nestled in the desirable Sweetwater Oaks community! This...	4 beds \| 2 baths \| 2,302 sq.ft.	$582,500	Airbnb cash on cash: 6.67% Traditional cash on cash: 3.74% Airbnb Rental Income: $5557 Traditional Rental Income: $2846 Airbnb ROI: 6.67% Traditional ROI: 3.74%
102 AUTUMN DRIVE Longwood, FL Three bedroom Townhome in The Springs with beautiful updates throughout. The remodeled kit...	3 beds \| 3 baths \| 1,746 sq.ft.	$465,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 2.68% Airbnb Rental Income: $3061 Traditional Rental Income: $2382 Airbnb ROI: 2.64% Traditional ROI: 2.68%
307 NEW WATERFORD PLACE Longwood, FL Huge Price Reduction - Seller says let's get this house Sold!!! Beautiful 3/2 one story ho...	3 beds \| 2 baths \| 1,648 sq.ft.	$399,900	Airbnb cash on cash: 3.77% Traditional cash on cash: 4.05% Airbnb Rental Income: $3061 Traditional Rental Income: $2466 Airbnb ROI: 3.77% Traditional ROI: 4.05%
206 BUTTONWOOD DRIVE Longwood, FL Nestled amidst the beauty of Sweetwater, this exquisite home offers a sanctuary of tranqui...	4 beds \| 3 baths \| 2,515 sq.ft.	$675,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.11% Airbnb Rental Income: $5557 Traditional Rental Income: $3100 Airbnb ROI: 5.25% Traditional ROI: 3.11%
602 N SWEETWATER BOULEVARD Longwood, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated POOL h...	4 beds \| 3 baths \| 2,740 sq.ft.	$675,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.47% Airbnb Rental Income: $5557 Traditional Rental Income: $3322 Airbnb ROI: 5.25% Traditional ROI: 3.47%
484 PALM SPRINGS DRIVE Longwood, FL BACK ON THE MARKET!! Welcome to your new home in a central location in Longwood, across th...	4 beds \| 3 baths \| 2,480 sq.ft.	$525,000	Airbnb cash on cash: 7.43% Traditional cash on cash: 5.16% Airbnb Rental Income: $5557 Traditional Rental Income: $3328 Airbnb ROI: 7.43% Traditional ROI: 5.16%
111 RIVERPARK COURT Longwood, FL PRICE REDUCED AGAIN MOTIVATED SELLERS, Bring your OFFERS! Welcome to this exceptional ...	5 beds \| 3 baths \| 2,686 sq.ft.	$709,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $3697 Airbnb ROI: N/A Traditional ROI: 3.56%
259 NEW WATERFORD PLACE Longwood, FL Rare opportunity in Wekiva Cove subdivision with cul-de-sac (Lake Brantley School District...	4 beds \| 3 baths \| 2,684 sq.ft.	$625,900	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.43% Airbnb Rental Income: $5557 Traditional Rental Income: $3201 Airbnb ROI: 5.56% Traditional ROI: 3.43%
314 SAND TRAP COVE #314 Longwood, FL One story unit located in beautiful Wekiva that overlooks a lush wooded area and this coul...	3 beds \| 2 baths \| 1,456 sq.ft.	$285,000	Airbnb cash on cash: 6.97% Traditional cash on cash: 5.74% Airbnb Rental Income: $3061 Traditional Rental Income: $2031 Airbnb ROI: 6.97% Traditional ROI: 5.74%

Real Estate investment in Longwood, FL

There are 114 properties for sale in the city of Longwood . The median list price in Longwood is $502,750 and the average price per square foot is $217. In May 2024, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,841.

Longwood, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 114 investment properties available for sale in Longwood.

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

The ROI for Short-Term is higher than the Long-Term in Longwood with average rental income of $3,061.

Your search for investment property begins and ends here

Investment Property for Sale in Longwood, FL

369 BALOGH PLACE

Longwood, FL

4 beds | 2 baths | 1,947 sq.ft.

$507,500

Airbnb cash on cash: 7.31%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $5557

Traditional Rental Income: $2855

Airbnb ROI: 7.31%

Traditional ROI: 3.96%

1960 ALAQUA DRIVE

Longwood, FL

5 beds | 6 baths | 4,581 sq.ft.

$1,719,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.7%

Airbnb Rental Income: $null

Traditional Rental Income: $6295

Airbnb ROI: N/A

Traditional ROI: 1.7%

213 CROWN OAKS WAY #213

Longwood, FL

3 beds | 2 baths | 1,804 sq.ft.

$234,900

Airbnb cash on cash: 7.52%

Traditional cash on cash: 7.6%

Airbnb Rental Income: $3061

Traditional Rental Income: $2380

Airbnb ROI: 7.52%

Traditional ROI: 7.6%

618 FOX HUNT CIRCLE

Longwood, FL

4 beds | 2 baths | 2,056 sq.ft.

$549,900

Airbnb cash on cash: 6.83%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $5557

Traditional Rental Income: $2924

Airbnb ROI: 6.83%

Traditional ROI: 3.88%

240 NEEDLES TRAIL

Longwood, FL

3 beds | 2 baths | 2,185 sq.ft.

$635,000

Airbnb cash on cash: 1.89%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $3061

Traditional Rental Income: $2858

Airbnb ROI: 1.89%

Traditional ROI: 2.73%

561 SHINING ARMOR LANE

Longwood, FL

N/A beds | N/A baths | N/A

$358,000

Airbnb cash on cash: 1.29%

Traditional cash on cash: 2.98%

Airbnb Rental Income: $1635

Traditional Rental Income: $1742

Airbnb ROI: 1.29%

Traditional ROI: 2.98%

150 Sandy Oaks Place

Longwood, FL

3 beds | 3 baths | 2,733 sq.ft.

$749,999

Airbnb cash on cash: 1.36%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $3061

Traditional Rental Income: $3279

Airbnb ROI: 1.36%

Traditional ROI: 2.67%

404 Magnolia Oak Drive

Longwood, FL

4 beds | 3 baths | 1,965 sq.ft.

$564,900

Airbnb cash on cash: 6.36%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $5557

Traditional Rental Income: $2856

Airbnb ROI: 6.36%