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.

Single Family Homes for Sale in Longwood, FL

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

Showing 94 Single Family Residential 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
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%
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%
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%
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%
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%
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%
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.	$350,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 3.56% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.33% Traditional ROI: 3.56%
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.	$450,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 2.99% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.69% Traditional ROI: 2.99%
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%
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%
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 Under contract-accepting backup offers. Welcome to 115 Marcy Blvd, a charming residence ne...	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%
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%
1651 KENLYN DRIVE Longwood, FL This beautiful home is ready to be loved by new owners! Featuring 3 bedrooms, 2 bathrooms,...	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%
215 NOB HILL CIRCLE Longwood, FL Under contract-accepting backup offers. This is the one. Owner is looking for a CASH offer...	4 beds \| 3 baths \| 2,538 sq.ft.	$475,000	Airbnb cash on cash: 7.94% Traditional cash on cash: 6.11% Airbnb Rental Income: $5377 Traditional Rental Income: $3475 Airbnb ROI: 7.94% Traditional ROI: 6.11%
1581 MONICA JOY CIRCLE Longwood, FL Located in TOP RATED SEMINOLE COUNTY SCHOOL DISTRICT. Single story ranch home on a cul de ...	4 beds \| 2 baths \| 2,073 sq.ft.	$469,900	Airbnb cash on cash: 7.97% Traditional cash on cash: 4.04% Airbnb Rental Income: $5377 Traditional Rental Income: $2564 Airbnb ROI: 7.97% Traditional ROI: 4.04%
975 CROSS CUT WAY Longwood, FL Beautiful 4 bedroom 2.5 bathroom home Freshly Painted with Luxury Vinyl flooring and Stain...	4 beds \| 3 baths \| 2,289 sq.ft.	$475,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 4.14% Airbnb Rental Income: $5377 Traditional Rental Income: $2982 Airbnb ROI: 7.08% Traditional ROI: 4.14%
218 W MAGNOLIA AVENUE Longwood, FL Back on the market after 2025 TOTAL RENOVATION FULLY COMPLETED - Now this gorgeous propert...	3 beds \| 2 baths \| 1,574 sq.ft.	$386,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 3.67% Airbnb Rental Income: $3221 Traditional Rental Income: $2157 Airbnb ROI: 4.6% Traditional ROI: 3.67%
154 SHADOW TRAIL Longwood, FL Under contract-accepting backup offers. Welcome to 154 Shadow Trail, a beautifully renovat...	3 beds \| 2 baths \| 1,417 sq.ft.	$439,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.19% Airbnb Rental Income: $3221 Traditional Rental Income: $2270 Airbnb ROI: 3.74% Traditional ROI: 3.19%
2330 PLEASANT DRIVE Longwood, FL One or more photo(s) has been virtually staged. Completely renovated and move-in ready, th...	3 beds \| 2 baths \| 1,745 sq.ft.	$425,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 4.61% Airbnb Rental Income: $3221 Traditional Rental Income: $2491 Airbnb ROI: 4.62% Traditional ROI: 4.61%
821 SUTTER LOOP Longwood, FL NEW PRICE IMPROVEMENT SEPT 19!, NEW ROOF April 2025! 1 YEAR HOME WARRANTY! NO HOA FEE! ROO...	4 beds \| 2 baths \| 2,074 sq.ft.	$430,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 4.75% Airbnb Rental Income: $5377 Traditional Rental Income: $2655 Airbnb ROI: 8.82% Traditional ROI: 4.75%
2108 SILVER LEAF COURT Longwood, FL One or more photo(s) has been virtually staged. Captivating and ideally nestled within the...	5 beds \| 4 baths \| 4,200 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $4807 Airbnb ROI: N/A Traditional ROI: 2.9%
1006 HANGING VINE POINT Longwood, FL ** Save Big: lender credit (based on loan amount) toward closing costs or rate buy-down wi...	4 beds \| 3 baths \| 2,540 sq.ft.	$649,900	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.93% Airbnb Rental Income: $5377 Traditional Rental Income: $3488 Airbnb ROI: 5.25% Traditional ROI: 3.93%
335 RUTH BOULEVARD Longwood, FL Brand-New Custom Home in Prime Longwood Location-No HOA! This custom-build 4 bedroom ,3 ba...	4 beds \| 3 baths \| 2,014 sq.ft.	$560,000	Airbnb cash on cash: 6.86% Traditional cash on cash: 3.81% Airbnb Rental Income: $5377 Traditional Rental Income: $2698 Airbnb ROI: 6.86% Traditional ROI: 3.81%
721 ROCK CREEK LOOP Longwood, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	3 beds \| 3 baths \| 1,998 sq.ft.	$411,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 4.5% Airbnb Rental Income: $3221 Traditional Rental Income: $2704 Airbnb ROI: 3.95% Traditional ROI: 4.5%
1204 DUNCAN COURT Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. VE...	4 beds \| 2 baths \| 2,292 sq.ft.	$519,900	Airbnb cash on cash: 6.37% Traditional cash on cash: 3.6% Airbnb Rental Income: $5377 Traditional Rental Income: $2947 Airbnb ROI: 6.37% Traditional ROI: 3.6%
183 PARSONS ROAD Longwood, FL Escape into peace, nature and privacy on 12.3 acres of delightful Old Florida property. Wa...	4 beds \| 3 baths \| 3,731 sq.ft.	$5,800,000	Airbnb cash on cash: -0.49% Traditional cash on cash: -0.68% Airbnb Rental Income: $5377 Traditional Rental Income: $3288 Airbnb ROI: -0.49% Traditional ROI: -0.68%
287 HILLTOP DRIVE Longwood, FL Convenience, Land, Nature, Energy Efficiency. Keep a horse and chickens. It is rare to fin...	4 beds \| 3 baths \| 2,522 sq.ft.	$575,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 3.5% Airbnb Rental Income: $5377 Traditional Rental Income: $2780 Airbnb ROI: 6.32% Traditional ROI: 3.5%

Your search for investment property begins and ends here

Single Family Homes 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%

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%

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%

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%

Traditional ROI: 3.42%

1800 W LAKE BRANTLEY ROAD

Longwood, FL

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

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

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%