Real Estate Investment Properties for Sale in Longwood, FL

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

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
12 HORSEMAN COVE Longwood, FL Average monthly electric bill is $35.00 Welcome to this incredible opportunity in the ...	4 beds \| 2 baths \| 2,265 sq.ft.	$499,999	Airbnb cash on cash: 7.26% Traditional cash on cash: 4.5% Airbnb Rental Income: $5377 Traditional Rental Income: $3005 Airbnb ROI: 7.26% Traditional ROI: 4.5%
4102 CLUBSIDE DRIVE #4102 Longwood, FL Spacious 2-Bedroom Corner Unit in Clubside at Sabal Point â Private, Updated & Move-In R...	2 beds \| 3 baths \| 1,380 sq.ft.	$235,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 3.9% Airbnb Rental Income: $1115 Traditional Rental Income: $1894 Airbnb ROI: -1.29% Traditional ROI: 3.9%
401 REIDER AVENUE Longwood, FL Under contract-accepting backup offers. Lakefront living in the heart of Longwood! This ch...	3 beds \| 2 baths \| 1,451 sq.ft.	$429,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 4.4% Airbnb Rental Income: $3221 Traditional Rental Income: $2527 Airbnb ROI: 4.32% Traditional ROI: 4.4%
204 BROM BONES LANE Longwood, FL Under contract-accepting backup offers. Charming Pool Home with Expansive Outdoor Living l...	4 beds \| 3 baths \| 2,394 sq.ft.	$550,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 4.34% Airbnb Rental Income: $5377 Traditional Rental Income: $3419 Airbnb ROI: 6.04% Traditional ROI: 4.34%
211 FAIRWAY DRIVE #211 Longwood, FL Welcome to this charming condo located in the highly sought-after, gated community of The ...	3 beds \| 2 baths \| 1,496 sq.ft.	$195,000	Airbnb cash on cash: 7.4% Traditional cash on cash: 5.16% Airbnb Rental Income: $3221 Traditional Rental Income: $2080 Airbnb ROI: 7.4% Traditional ROI: 5.16%
641 E CHURCH AVENUE Longwood, FL Ready to save money on gas, your utility bills and home maintenance ? Welcome home to 641 ...	3 beds \| 2 baths \| 1,537 sq.ft.	$359,900	Airbnb cash on cash: 5.68% Traditional cash on cash: 4.96% Airbnb Rental Income: $3221 Traditional Rental Income: $2253 Airbnb ROI: 5.68% Traditional ROI: 4.96%
112 CROWN OAKS WAY #112 Longwood, FL Huge price reduction . Your gain and owners loss! Owner is very motivated and ready to mov...	2 beds \| 2 baths \| 1,119 sq.ft.	$130,000	Airbnb cash on cash: -3.86% Traditional cash on cash: 4.14% Airbnb Rental Income: $1115 Traditional Rental Income: $1741 Airbnb ROI: -3.86% Traditional ROI: 4.14%
2681 AZALEA DRIVE Longwood, FL Crisp evenings, glowing firelight, and the perfect place to call home. This 3-bedroom, 2-b...	3 beds \| 2 baths \| 1,399 sq.ft.	$370,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 3.42% Airbnb Rental Income: $3221 Traditional Rental Income: $1994 Airbnb ROI: 4.87% Traditional ROI: 3.42%
945 NORFOLK COURT Longwood, FL This is a charming 2 bedroom, 2 bathroom townhouse in the much desired Danbury Mill. A qua...	2 beds \| 2 baths \| 1,402 sq.ft.	$340,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.37% Airbnb Rental Income: $1115 Traditional Rental Income: $1986 Airbnb ROI: -0.53% Traditional ROI: 3.37%
1800 W LAKE BRANTLEY ROAD Longwood, FL Under contract-accepting backup offers. Charming Longwood Home in the Lake Brantley School...	3 beds \| 2 baths \| 1,486 sq.ft.	$384,900	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.35% Airbnb Rental Income: $3221 Traditional Rental Income: $2313 Airbnb ROI: 4.85% Traditional ROI: 4.35%
364 HOWARD BOULEVARD Longwood, FL Welcome to this charming 3-bedroom, 2-bath home tucked away at the end of a quiet dead-end...	3 beds \| 2 baths \| 1,400 sq.ft.	$375,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 4.19% Airbnb Rental Income: $3221 Traditional Rental Income: $2122 Airbnb ROI: 5.25% Traditional ROI: 4.19%
310 VISTA OAK DRIVE Longwood, FL ~MOTIVATED SELLER~ Welcome to your dream home in the highly sought-after gated community...	4 beds \| 5 baths \| 3,286 sq.ft.	$999,500	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.64% Airbnb Rental Income: $5377 Traditional Rental Income: $5513 Airbnb ROI: 2.33% Traditional ROI: 3.64%
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: 2.29% Traditional cash on cash: 2.71% Airbnb Rental Income: $2039 Traditional Rental Income: $1652 Airbnb ROI: 2.29% Traditional ROI: 2.71%
400 BRASSIE DRIVE Longwood, FL Under contract-accepting backup offers. Welcome to 400 Brassie Drive! This custom-built m...	4 beds \| 4 baths \| 4,003 sq.ft.	$889,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 1.71% Airbnb Rental Income: $5377 Traditional Rental Income: $3128 Airbnb ROI: 3.12% Traditional ROI: 1.71%
105 FAIRWAY DRIVE Longwood, FL Stunning 2-Bedroom Condo in Gated Community â Fairway Villas at The Springs! Welcome ...	2 beds \| 1 baths \| 1,140 sq.ft.	$199,999	Airbnb cash on cash: -1.58% Traditional cash on cash: 2.95% Airbnb Rental Income: $1115 Traditional Rental Income: $1600 Airbnb ROI: -1.58% Traditional ROI: 2.95%
449 SPRINGWOOD COURT Longwood, FL This beautifully updated three-bedroom, two-bath home in Longwood offers 1,075 square feet...	3 beds \| 2 baths \| 1,075 sq.ft.	$365,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 3.17% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.1% Traditional ROI: 3.17%
731 CRESTBROOK LOOP Longwood, FL Welcome to 731 Crestbrook Loop in The Landings- one of Longwoodâs most desirable gated ...	3 beds \| 3 baths \| 2,140 sq.ft.	$425,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 5.72% Airbnb Rental Income: $3221 Traditional Rental Income: $3173 Airbnb ROI: 4.02% Traditional ROI: 5.72%
2040 E TRIANGLE DRIVE Longwood, FL NEW PRICE REDUCTION! Now priced below market value. Charming, Updated 3-Bedroom Home ...	3 beds \| 2 baths \| 1,283 sq.ft.	$345,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 3.62% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.42% Traditional ROI: 3.62%
1889 RANCHLAND TRAIL Longwood, FL Exquisite 4-Bedroom Estate with Pool on 2+ Acres in the Coveted LongwoodâLake Mary Area,...	4 beds \| 3 baths \| 2,333 sq.ft.	$989,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 1.83% Airbnb Rental Income: $5377 Traditional Rental Income: $3252 Airbnb ROI: 2.96% Traditional ROI: 1.83%
358 WINCHESTER COURT Longwood, FL $5000 lender credit with seller's preferred lender Renovated 3-bedroom, 2.5-bath townh...	3 beds \| 3 baths \| 1,682 sq.ft.	$335,000	Airbnb cash on cash: 3.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $3221 Traditional Rental Income: $2181 Airbnb ROI: 3.6% Traditional ROI: 2.6%
258 W Sabal Palm Place #22 Longwood, FL Enjoy low-maintenance living & a terrific investment opportunity! This stylish 2-bedroom, ...	2 beds \| 2 baths \| 1,202 sq.ft.	$253,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 2.3% Airbnb Rental Income: $1115 Traditional Rental Income: $1688 Airbnb ROI: -1.66% Traditional ROI: 2.3%
150 ESSEX DRIVE Longwood, FL Step into the warmth and charm of this rare cabin-style retreat nestled in the heart of Lo...	3 beds \| 2 baths \| 1,449 sq.ft.	$445,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 3.04% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.75% Traditional ROI: 3.04%
501 RIVERBEND BOULEVARD Longwood, FL Are you ready to finally add the most important key to your keychain? After scrolling for...	4 beds \| 2 baths \| 2,559 sq.ft.	$639,900	Airbnb cash on cash: 4.84% Traditional cash on cash: 2.39% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 4.84% Traditional ROI: 2.39%
494 N PIN OAK PLACE #302 Longwood, FL Resort-style living or a smart investment opportunityâwelcome to 494 N Pin Oak Place, Un...	2 beds \| 2 baths \| 1,110 sq.ft.	$199,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 6.41% Airbnb Rental Income: $1115 Traditional Rental Income: $1717 Airbnb ROI: 1.24% Traditional ROI: 6.41%
966 N RONALD REAGAN BOULEVARD Longwood, FL HIGH AND DRY! Located just 1/2 mile from the Longwood SunRail Station. Donât miss your o...	5 beds \| 3 baths \| 2,490 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3535 Airbnb ROI: N/A Traditional ROI: 4.32%
4 HUDSON COVE Longwood, FL Itâs your lucky day! Buyers financing fell through day before closing. Fully Renovat...	4 beds \| 3 baths \| 2,263 sq.ft.	$599,999	Airbnb cash on cash: 5.54% Traditional cash on cash: 2.66% Airbnb Rental Income: $5377 Traditional Rental Income: $2678 Airbnb ROI: 5.54% Traditional ROI: 2.66%
674 PINE SHADOW COURT Longwood, FL Discover this beautifully maintained 4-bedroom, 3-bath home in the sought-after Sabal Poin...	4 beds \| 3 baths \| 2,754 sq.ft.	$710,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.41% Airbnb Rental Income: $5377 Traditional Rental Income: $3403 Airbnb ROI: 4.75% Traditional ROI: 3.41%
470 S PIN OAK PLACE #312 Longwood, FL Bright, Updated Condo with Pond Views in A-Rated Seminole County School District! Welcome...	1 beds \| 1 baths \| 823 sq.ft.	$175,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.42% Airbnb Rental Income: $1304 Traditional Rental Income: $1352 Airbnb ROI: 0.69% Traditional ROI: 3.42%
328 ISLAND SOUND COURT Longwood, FL Welcome to this stunning 5-bedroom, 4-bathroom energy-efficient Pulte home located in a de...	5 beds \| 4 baths \| 3,715 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $4310 Airbnb ROI: N/A Traditional ROI: 2.15%
223 ROYAL OAKS CIRCLE Longwood, FL BRING YOUR OFFER! MOTIVATED SELLERS will consider all offers! IMPROVED PRICE! One of the...	4 beds \| 2 baths \| 2,842 sq.ft.	$599,900	Airbnb cash on cash: 6.33% Traditional cash on cash: 3.51% Airbnb Rental Income: $5377 Traditional Rental Income: $2711 Airbnb ROI: 6.33% Traditional ROI: 3.51%
1510 PELICAN STREET Longwood, FL 3-bed, 2-bath residence nestled on a serene, tree-lined street in one of Longwoodâs DESI...	3 beds \| 2 baths \| 1,269 sq.ft.	$298,800	Airbnb cash on cash: 6.03% Traditional cash on cash: 4.17% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 6.03% Traditional ROI: 4.17%
115 MARCY BOULEVARD Longwood, FL Welcome to 115 Marcy Blvd, a charming residence nestled in the heart of Longwood! This bea...	5 beds \| 3 baths \| 2,013 sq.ft.	$499,995	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $3195 Airbnb ROI: N/A Traditional ROI: 4.41%
123 GOLF CLUB DRIVE Longwood, FL Under contract-accepting backup offers. Newly Renovated, move-in-ready villa with new roof...	2 beds \| 2 baths \| 1,539 sq.ft.	$324,900	Airbnb cash on cash: -2.34% Traditional cash on cash: 1.85% Airbnb Rental Income: $1115 Traditional Rental Income: $2018 Airbnb ROI: -2.34% Traditional ROI: 1.85%
722 EAGLE AVENUE Longwood, FL Investor Goldmine in Longwood! Attention flippers, rehabbers, and savvy investors â This...	3 beds \| 2 baths \| 1,548 sq.ft.	$250,000	Airbnb cash on cash: 7.39% Traditional cash on cash: 5.94% Airbnb Rental Income: $3221 Traditional Rental Income: $2153 Airbnb ROI: 7.39% Traditional ROI: 5.94%
556 LAKE WILDMERE COVE Longwood, FL PRICE REDUCTION! PRICED TO SELL! Introducing 556 Lake Wildmere Cove, a stunning Key West s...	3 beds \| 3 baths \| 2,294 sq.ft.	$433,700	Airbnb cash on cash: 3.36% Traditional cash on cash: 3.93% Airbnb Rental Income: $3221 Traditional Rental Income: $2726 Airbnb ROI: 3.36% Traditional ROI: 3.93%
152 SPRINGWOOD CIRCLE #B Longwood, FL Updated and spacious condo on FIRST LEVEL close to community pool and laundry. 2 Bedrooms...	2 beds \| 1 baths \| 1,020 sq.ft.	$172,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 6.56% Airbnb Rental Income: $1115 Traditional Rental Income: $1512 Airbnb ROI: 1.86% Traditional ROI: 6.56%
1821 STANLEY STREET Longwood, FL Seller will consider assisting buyer with closing cost and rate by down or other credits. ...	3 beds \| 2 baths \| 2,567 sq.ft.	$485,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.53% Airbnb Rental Income: $3221 Traditional Rental Income: $2427 Airbnb ROI: 3.68% Traditional ROI: 3.53%
322 N SHADOWBAY BOULEVARD Longwood, FL Welcome to Lake Vista at Shadowbay - No HOA and No Restrictions! This beautiful and well-m...	3 beds \| 2 baths \| 1,599 sq.ft.	$525,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.25% Airbnb Rental Income: $3221 Traditional Rental Income: $2395 Airbnb ROI: 3.45% Traditional ROI: 3.25%
102 TOMOKA TRAIL #102 Longwood, FL New Roof 10/25! This gem of a condo is ready for you to make it your new home in the oasi...	3 beds \| 2 baths \| 1,590 sq.ft.	$275,000	Airbnb cash on cash: 7.03% Traditional cash on cash: 5.69% Airbnb Rental Income: $3221 Traditional Rental Income: $2147 Airbnb ROI: 7.03% Traditional ROI: 5.69%
1651 KENLYN DRIVE Longwood, FL Under contract-accepting backup offers. This beautiful home is ready to be loved by new ow...	3 beds \| 2 baths \| 1,687 sq.ft.	$375,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 3.58% Airbnb Rental Income: $3221 Traditional Rental Income: $2142 Airbnb ROI: 4.58% Traditional ROI: 3.58%

Real Estate investment in Longwood, FL

There are 130 properties for sale in the city of Longwood . The median list price in Longwood is $450,000 and the average price per square foot is $220. In October 2025, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,321.

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

There are 130 investment properties available for sale in Longwood.

In 2025, 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 $3,221.

Your search for investment property begins and ends here

Investment Property for Sale in Longwood, FL

12 HORSEMAN COVE

Longwood, FL

4 beds | 2 baths | 2,265 sq.ft.

$499,999

Airbnb cash on cash: 7.26%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $5377

Traditional Rental Income: $3005

Airbnb ROI: 7.26%

Traditional ROI: 4.5%

4102 CLUBSIDE DRIVE #4102

Longwood, FL

2 beds | 3 baths | 1,380 sq.ft.

$235,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $1115

Traditional Rental Income: $1894

Airbnb ROI: -1.29%

Traditional ROI: 3.9%

401 REIDER AVENUE

Longwood, FL

3 beds | 2 baths | 1,451 sq.ft.

$429,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $3221

Traditional Rental Income: $2527

Airbnb ROI: 4.32%

Traditional ROI: 4.4%

204 BROM BONES LANE

Longwood, FL

4 beds | 3 baths | 2,394 sq.ft.

$550,000

Airbnb cash on cash: 6.04%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $5377

Traditional Rental Income: $3419

Airbnb ROI: 6.04%

Traditional ROI: 4.34%

211 FAIRWAY DRIVE #211

Longwood, FL

3 beds | 2 baths | 1,496 sq.ft.

$195,000

Airbnb cash on cash: 7.4%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $3221

Traditional Rental Income: $2080

Airbnb ROI: 7.4%

Traditional ROI: 5.16%

641 E CHURCH AVENUE

Longwood, FL

3 beds | 2 baths | 1,537 sq.ft.

$359,900

Airbnb cash on cash: 5.68%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $3221

Traditional Rental Income: $2253

Airbnb ROI: 5.68%

Traditional ROI: 4.96%

112 CROWN OAKS WAY #112

Longwood, FL

2 beds | 2 baths | 1,119 sq.ft.

$130,000

Airbnb cash on cash: -3.86%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $1115

Traditional Rental Income: $1741

Airbnb ROI: -3.86%

Traditional ROI: 4.14%

2681 AZALEA DRIVE

Longwood, FL

3 beds | 2 baths | 1,399 sq.ft.

$370,000

Airbnb cash on cash: 4.87%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $3221

Traditional Rental Income: $1994

Airbnb ROI: 4.87%