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
3996 RADLEY COURT #3996 Longwood, FL One or more photo(s) has been virtually staged. MOTIVATED SELLER with an UNBELIEVABLE pric...	2 beds \| 2 baths \| 1,427 sq.ft.	$225,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 5.5% Airbnb Rental Income: $1482 Traditional Rental Income: $2287 Airbnb ROI: -0.32% Traditional ROI: 5.5%
108 KILKENNY COURT Longwood, FL Virtually Staged. Welcome to 108 Kilkenny Court located in the sought-after community in W...	4 beds \| 2 baths \| 1,979 sq.ft.	$538,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.46% Airbnb Rental Income: $2202 Traditional Rental Income: $2833 Airbnb ROI: 1.1% Traditional ROI: 3.46%
374 WINCHESTER PLACE Longwood, FL Virtually Staged. Welcome to 374 Winchester Place, a charming 2-bedroom, 2-bath townhome i...	2 beds \| 2 baths \| 1,303 sq.ft.	$290,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.99% Airbnb Rental Income: $1482 Traditional Rental Income: $1859 Airbnb ROI: 0.02% Traditional ROI: 2.99%
417 SUMMIT RIDGE PLACE #213 Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully updated condo located ...	2 beds \| 2 baths \| 1,274 sq.ft.	$225,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.79% Airbnb Rental Income: $1482 Traditional Rental Income: $1871 Airbnb ROI: -0.08% Traditional ROI: 3.79%
276 W BAY AVENUE Longwood, FL Step into the timeless elegance of this beautifully crafted Victorian Home, newer construc...	3 beds \| 3 baths \| 1,814 sq.ft.	$419,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.8% Airbnb Rental Income: $3176 Traditional Rental Income: $2503 Airbnb ROI: 3.69% Traditional ROI: 3.8%
421 MEADOWRIDGE COVE Longwood, FL Welcome to this beautiful 4 bedroom 2 Â½ bath 2 STORY home in the exclusive gated communit...	4 beds \| 3 baths \| 3,048 sq.ft.	$650,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.88% Airbnb Rental Income: $2202 Traditional Rental Income: $2828 Airbnb ROI: -0.07% Traditional ROI: 1.88%
1566 REBECCA PLACE Longwood, FL Under contract-accepting backup offers. Rare opportunity in Cedar Cove! Homes in this soug...	4 beds \| 4 baths \| 3,365 sq.ft.	$915,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 3.51% Airbnb Rental Income: $2202 Traditional Rental Income: $4658 Airbnb ROI: -0.03% Traditional ROI: 3.51%
148 WISTERIA DRIVE Longwood, FL Pro pics coming but dont wait to see this incredible home...Welcome to The Springs, one of...	4 beds \| 3 baths \| 2,662 sq.ft.	$725,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.63% Airbnb Rental Income: $2202 Traditional Rental Income: $3263 Airbnb ROI: 0.24% Traditional ROI: 2.63%
102 N SILVER CLUSTER COURT Longwood, FL Under contract-accepting backup offers. Welcome to 102 Silver Cluster Ct N in Longwood, a ...	3 beds \| 2 baths \| 1,166 sq.ft.	$383,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 3.2% Airbnb Rental Income: $3176 Traditional Rental Income: $1980 Airbnb ROI: 4.53% Traditional ROI: 3.2%
1870 CROWLEY CIRCLE E Longwood, FL Under contract-accepting backup offers. Short Sale. Approved Short Sale. Welcome to your p...	4 beds \| 4 baths \| 3,258 sq.ft.	$625,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 5.32% Airbnb Rental Income: $2202 Traditional Rental Income: $4618 Airbnb ROI: 0.22% Traditional ROI: 5.32%
278 BLACKWATER PLACE Longwood, FL Virtually Staged. Welcome to your dream home nestled in the charming and tucked-away commu...	3 beds \| 2 baths \| 1,582 sq.ft.	$364,777	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.52% Airbnb Rental Income: $3176 Traditional Rental Income: $2198 Airbnb ROI: 4.28% Traditional ROI: 3.52%
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: -0.86% Traditional cash on cash: 2.75% Airbnb Rental Income: $767 Traditional Rental Income: $1664 Airbnb ROI: -0.86% Traditional ROI: 2.75%
884 CUTLER ROAD Longwood, FL One or more photo(s) has been virtually staged. - Price Improvement - Welcome to this beau...	5 beds \| 3 baths \| 2,601 sq.ft.	$599,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 1.98% Airbnb Rental Income: $4962 Traditional Rental Income: $2235 Airbnb ROI: 5.04% Traditional ROI: 1.98%
106 SPRINGWOOD CIRCLE #B Longwood, FL Virtually Staged. This darling condo is located in the Springwood community and offers won...	2 beds \| 1 baths \| 1,020 sq.ft.	$148,000	Airbnb cash on cash: 5.13% Traditional cash on cash: 8.45% Airbnb Rental Income: $1482 Traditional Rental Income: $1517 Airbnb ROI: 5.13% Traditional ROI: 8.45%
106 HIDDEN OAK DRIVE Longwood, FL Tucked beneath a canopy of towering oaks on a quiet, tucked-away street, this 3-bedroom, 2...	3 beds \| 2 baths \| 2,127 sq.ft.	$460,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.49% Airbnb Rental Income: $3176 Traditional Rental Income: $2525 Airbnb ROI: 3.33% Traditional ROI: 3.49%
478 SABAL TRAIL CIRCLE Longwood, FL NEW PRICE: As Of 6/15 : Welcome to the desirable Sabal Point community! Located at 478 S...	4 beds \| 3 baths \| 2,529 sq.ft.	$599,500	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.83% Airbnb Rental Income: $2202 Traditional Rental Income: $3502 Airbnb ROI: 0.51% Traditional ROI: 3.83%
105 FAIRWAY DRIVE Longwood, FL THE SPRINGS LIFESTYLE AT AN UNBEATABLE VALUE Imagine waking up in the heart of one of Lon...	2 beds \| 1 baths \| 1,140 sq.ft.	$169,999	Airbnb cash on cash: 0.2% Traditional cash on cash: 3.62% Airbnb Rental Income: $1482 Traditional Rental Income: $1600 Airbnb ROI: 0.2% Traditional ROI: 3.62%
300 NEW WATERFORD PLACE #202 Longwood, FL Perfect for First-Time Buyers or Those Ready to Downsize! Donât miss this rare opport...	2 beds \| 2 baths \| 1,176 sq.ft.	$269,900	Airbnb cash on cash: 1.87% Traditional cash on cash: 4.65% Airbnb Rental Income: $1482 Traditional Rental Income: $1754 Airbnb ROI: 1.87% Traditional ROI: 4.65%
114 JUNIPER LANE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Qu...	2 beds \| 2 baths \| 2,049 sq.ft.	$460,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.63% Airbnb Rental Income: $1482 Traditional Rental Income: $2469 Airbnb ROI: 0.32% Traditional ROI: 3.63%
1715 SUNSET DRIVE Longwood, FL Virtually Staged. Welcome to this inviting single-story home in Longwood, offering a brigh...	3 beds \| 2 baths \| 1,344 sq.ft.	$329,900	Airbnb cash on cash: 5.78% Traditional cash on cash: 4.69% Airbnb Rental Income: $3176 Traditional Rental Income: $2119 Airbnb ROI: 5.78% Traditional ROI: 4.69%
2214 Earleaf Court Longwood, FL This stunning 4-bedroom, 3-bathroom home is nestled in a highly sought-after neighborhood,...	4 beds \| 3 baths \| 3,955 sq.ft.	$1,450,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 0.64% Airbnb Rental Income: $2202 Traditional Rental Income: $3572 Airbnb ROI: -0.79% Traditional ROI: 0.64%
860 Charlotte St. Longwood, FL 4-Bed / 3.5-Bath Home Built in 2006. -needs updating, new ac.	4 beds \| 4 baths \| N/A	$449,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 5.25% Airbnb Rental Income: $2202 Traditional Rental Income: $3324 Airbnb ROI: 1.26% Traditional ROI: 5.25%
1025 BUCKSAW PLACE Longwood, FL Short Sale. Short Sale â Opportunity awaits! This home has been winterized and is ready ...	3 beds \| 3 baths \| 2,289 sq.ft.	$419,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 6.1% Airbnb Rental Income: $3176 Traditional Rental Income: $3557 Airbnb ROI: 3.3% Traditional ROI: 6.1%
2040 E TRIANGLE DRIVE Longwood, FL Beautiful opportunity in the highly desirable Longwood area, perfectly located just minute...	3 beds \| 2 baths \| 1,283 sq.ft.	$340,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 3.59% Airbnb Rental Income: $3176 Traditional Rental Income: $1912 Airbnb ROI: 5.3% Traditional ROI: 3.59%
450 E WARREN AVENUE Longwood, FL Under contract-accepting backup offers. Situated on an oversized double lot in the heart o...	2 beds \| 1 baths \| 888 sq.ft.	$265,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 3.51% Airbnb Rental Income: $1482 Traditional Rental Income: $1587 Airbnb ROI: 1.35% Traditional ROI: 3.51%
1889 RANCHLAND TRAIL Longwood, FL Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home, perfectly situated ...	4 beds \| 3 baths \| 2,333 sq.ft.	$998,900	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.18% Airbnb Rental Income: $2202 Traditional Rental Income: $3601 Airbnb ROI: 0.07% Traditional ROI: 2.18%
207 LONESOME PINE DRIVE Longwood, FL Under contract-accepting backup offers. FANTASTIC OPPORTUNITY IN SWEETWATER OAKS! Nestled ...	4 beds \| 2 baths \| 1,908 sq.ft.	$559,900	Airbnb cash on cash: 0.87% Traditional cash on cash: 2.08% Airbnb Rental Income: $2202 Traditional Rental Income: $2281 Airbnb ROI: 0.87% Traditional ROI: 2.08%
1954 ELKHORN COURT Longwood, FL Welcome to this exceptional residence in the prestigious gated community of Hidden Cove, w...	4 beds \| 4 baths \| 3,009 sq.ft.	$789,900	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.39% Airbnb Rental Income: $2202 Traditional Rental Income: $3239 Airbnb ROI: 0.23% Traditional ROI: 2.39%
965 BUCKSAW PLACE Longwood, FL Under contract-accepting backup offers. Welcome to this spacious 4-bedroom, 3-bath home in...	4 beds \| 3 baths \| 2,361 sq.ft.	$530,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.36% Airbnb Rental Income: $2202 Traditional Rental Income: $2919 Airbnb ROI: 0.79% Traditional ROI: 3.36%
210 WEEPING ELM LANE Longwood, FL Rare Opportunity in Shadowood Village at The Springs! Welcome to this spacious 3-bedroom, ...	3 beds \| 2 baths \| 2,076 sq.ft.	$470,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 2.41% Airbnb Rental Income: $3176 Traditional Rental Income: $2022 Airbnb ROI: 3.4% Traditional ROI: 2.41%
305 SWEETWATER CLUB CIRCLE Longwood, FL Welcome home to this stunning, fully renovated home sitting on 1.51 acres in the coveted S...	5 beds \| 6 baths \| 4,975 sq.ft.	$1,400,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 4.03% Airbnb Rental Income: $4962 Traditional Rental Income: $8006 Airbnb ROI: 0.91% Traditional ROI: 4.03%
101 CHERRY HILL CIRCLE Longwood, FL This 4 bedrooms/3 bathrooms home is ideal for families and those who enjoy entertaining. R...	4 beds \| 3 baths \| 2,359 sq.ft.	$699,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.49% Airbnb Rental Income: $2202 Traditional Rental Income: $2973 Airbnb ROI: 0.46% Traditional ROI: 2.49%
470 FREEMAN STREET Longwood, FL Under contract-accepting backup offers. Set on an oversized lot with Water VIEWS in the de...	4 beds \| 2 baths \| 2,261 sq.ft.	$475,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 4.75% Airbnb Rental Income: $2202 Traditional Rental Income: $3094 Airbnb ROI: 1.49% Traditional ROI: 4.75%
1319 SUMMERTREE COURT Longwood, FL Welcome to 1319 Summertree Ct, a move-in ready home tucked away on a cul-de-sac in the des...	4 beds \| 3 baths \| 2,133 sq.ft.	$479,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.82% Airbnb Rental Income: $2202 Traditional Rental Income: $2726 Airbnb ROI: 1.41% Traditional ROI: 3.82%
572 LAKE WILDMERE COVE Longwood, FL Here is your opportunity to own a true Turn Key Investment property.This almost new townho...	4 beds \| 5 baths \| 2,294 sq.ft.	$455,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.79% Airbnb Rental Income: $2202 Traditional Rental Income: $3121 Airbnb ROI: 0.33% Traditional ROI: 3.79%
284 ISLAND SOUND COURT Longwood, FL Step into refined elegance and effortless sophistication in this nearly new Dockside maste...	4 beds \| 3 baths \| 2,692 sq.ft.	$799,999	Airbnb cash on cash: 0.01% Traditional cash on cash: 1.67% Airbnb Rental Income: $2202 Traditional Rental Income: $2884 Airbnb ROI: 0.01% Traditional ROI: 1.67%
486 N PIN OAK PLACE #112 Longwood, FL Virtually Staged. Seller may consider buyer concessions if made in an offerWelcome to ...	2 beds \| 1 baths \| 959 sq.ft.	$187,900	Airbnb cash on cash: 3.15% Traditional cash on cash: 7.19% Airbnb Rental Income: $1482 Traditional Rental Income: $1767 Airbnb ROI: 3.15% Traditional ROI: 7.19%
450 LONGMEADOW LANE Longwood, FL Excellent opportunity in Sabal Point. POOL house with two NEW HVACs. 4 bedrooms, 3.5 bathr...	4 beds \| 4 baths \| 2,623 sq.ft.	$509,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 6.09% Airbnb Rental Income: $2202 Traditional Rental Income: $3873 Airbnb ROI: 1.42% Traditional ROI: 6.09%
556 LAKE WILDMERE COVE Longwood, FL MOTIVATED SELLER â MAJOR PRICE REDUCTION! Priced AGGRESSIVELY BELOW MARKET VALUE for an...	3 beds \| 3 baths \| 2,294 sq.ft.	$419,700	Airbnb cash on cash: 3.41% Traditional cash on cash: 5.09% Airbnb Rental Income: $3176 Traditional Rental Income: $3120 Airbnb ROI: 3.41% Traditional ROI: 5.09%
1310 RIDGE ROAD Longwood, FL Welcome to your own private oasis in the highly desirable Longwood area! This beautifully ...	3 beds \| 2 baths \| 1,520 sq.ft.	$475,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 4.33% Airbnb Rental Income: $3176 Traditional Rental Income: $2881 Airbnb ROI: 3.38% Traditional ROI: 4.33%

Real Estate investment in Longwood, FL

There are 142 properties for sale in the city of Longwood . The median list price in Longwood is $369,779 and the average price per square foot is $171. In July 2026, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,427.

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

There are 142 investment properties available for sale in Longwood.

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

The ROI for Long-Term is higher than the Short-Term in Longwood with average rental income of $2,427.

Your search for investment property begins and ends here

Investment Property for Sale in Longwood, FL

3996 RADLEY COURT #3996

Longwood, FL

2 beds | 2 baths | 1,427 sq.ft.

$225,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 5.5%

Airbnb Rental Income: $1482

Traditional Rental Income: $2287

Airbnb ROI: -0.32%

Traditional ROI: 5.5%

108 KILKENNY COURT

Longwood, FL

4 beds | 2 baths | 1,979 sq.ft.

$538,000

Airbnb cash on cash: 1.1%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $2202

Traditional Rental Income: $2833

Airbnb ROI: 1.1%

Traditional ROI: 3.46%

374 WINCHESTER PLACE

Longwood, FL

2 beds | 2 baths | 1,303 sq.ft.

$290,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $1482

Traditional Rental Income: $1859

Airbnb ROI: 0.02%

Traditional ROI: 2.99%

417 SUMMIT RIDGE PLACE #213

Longwood, FL

2 beds | 2 baths | 1,274 sq.ft.

$225,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $1482

Traditional Rental Income: $1871

Airbnb ROI: -0.08%

Traditional ROI: 3.79%

276 W BAY AVENUE

Longwood, FL

3 beds | 3 baths | 1,814 sq.ft.

$419,000

Airbnb cash on cash: 3.69%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $3176

Traditional Rental Income: $2503

Airbnb ROI: 3.69%

Traditional ROI: 3.8%

421 MEADOWRIDGE COVE

Longwood, FL

4 beds | 3 baths | 3,048 sq.ft.

$650,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $2202

Traditional Rental Income: $2828

Airbnb ROI: -0.07%

Traditional ROI: 1.88%

1566 REBECCA PLACE

Longwood, FL

4 beds | 4 baths | 3,365 sq.ft.

$915,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $2202

Traditional Rental Income: $4658

Airbnb ROI: -0.03%

Traditional ROI: 3.51%

148 WISTERIA DRIVE

Longwood, FL

4 beds | 3 baths | 2,662 sq.ft.

$725,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $2202

Traditional Rental Income: $3263

Airbnb ROI: 0.24%