Real Estate Investment Properties for Sale in Winter Park, FL
Looking for investment property in Winter Park, FL with high ROI ?
Explore a variety of short-term homes & houses in Winter Park, FL. Invest wisely with VRBO & Winter Park, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Condos for Sale in Winter Park, FL
Search for Condo for Sale in Winter Park, Florida. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 41 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
150 KILLARNEY BAY COURT #5Winter Park, FLTucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfec... |
2 beds | 2 baths | 1,140 sq.ft. |
$362,500 |
Airbnb cash on cash: 4.55%
|
700 MELROSE AVENUE #D21Winter Park, FLLocated in the historic Winter Park Gardens community, this condo has been meticulously ma... |
1 beds | 1 baths | 871 sq.ft. |
$198,800 |
Airbnb cash on cash: 6.51%
|
151 N ORLANDO AVENUE #212Winter Park, FLExperience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom... |
3 beds | 2 baths | 1,875 sq.ft. |
$575,000 |
Airbnb cash on cash: 2.47%
|
311 E MORSE BOULEVARD #7-2Winter Park, FLOne or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from... |
1 beds | 1 baths | 900 sq.ft. |
$399,000 |
Airbnb cash on cash: 0.42%
|
535 N INTERLACHEN AVENUE #106Winter Park, FLCombining luxury living with exceptional value, this immaculate, move-in-ready condo is ju... |
2 beds | 2 baths | 1,000 sq.ft. |
$599,900 |
Airbnb cash on cash: 2.97%
|
151 N ORLANDO AVENUE #118Winter Park, FLInvestment opportunity! Discover this hidden gemâa 2-bed, 1-bath condo nestled in the he... |
2 beds | 1 baths | 710 sq.ft. |
$299,999 |
Airbnb cash on cash: 6.61%
|
2500 LEE ROAD #243Winter Park, FLReasons you'll love this condo: convenient, cozy and quiet, you can't beat this community ... |
1 beds | 1 baths | 645 sq.ft. |
$200,000 |
Airbnb cash on cash: 5.71%
|
101 S INTERLACHEN AVENUE #104Winter Park, FLFIRST TIME ON THE MARKET! SUPER RARE, GROUND FLOOR, DOWNTOWN WINTER PARK CONDO AT LACHEN H... |
2 beds | 2 baths | 949 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.35%
|
2500 LEE ROAD #208Winter Park, FLThis charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfor... |
2 beds | 2 baths | 956 sq.ft. |
$200,000 |
Airbnb cash on cash: 8.82%
|
640 KILLARNEY BAY COURT #4Winter Park, FLOne or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake... |
2 beds | 3 baths | 1,718 sq.ft. |
$620,000 |
Airbnb cash on cash: 1.57%
|
151 N ORLANDO AVENUE #204Winter Park, FLOne or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restric... |
2 beds | 1 baths | 710 sq.ft. |
$236,000 |
Airbnb cash on cash: 6.59%
|
184 SANDLEWOOD TRAIL #2Winter Park, FLFHA, VA, and DPA approved. Nestled just minutes from the charming boutiques and award-winn... |
2 beds | 3 baths | 1,133 sq.ft. |
$315,000 |
Airbnb cash on cash: 6.3%
|
240 KILLARNEY BAY COURT #4Winter Park, FLWelcome to Killarney BayâWinter Parkâs best-kept secret for tranquil lakeside living, ... |
2 beds | 3 baths | 1,536 sq.ft. |
$410,000 |
Airbnb cash on cash: 3.73%
|
311 E MORSE BOULEVARD #7-5Winter Park, FLMajor Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio ... |
1 beds | 1 baths | 482 sq.ft. |
$359,000 |
Airbnb cash on cash: 3.19%
|
151 N ORLANDO AVENUE #101Winter Park, FLWelcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled ... |
2 beds | 1 baths | 804 sq.ft. |
$265,000 |
Airbnb cash on cash: 7.45%
|
640 PARK AVENUE N #26Winter Park, FLA gem in the heart of the city -was completely renovated in 2024, downtown Winter Park -wa... |
2 beds | 2 baths | 858 sq.ft. |
$598,400 |
Airbnb cash on cash: 2.47%
|
265 E CANTON AVENUE #GEWinter Park, FLRARE CORNER TOP-FLOOR CONDO WITH AMAZING VIEWS â FULLY FURNISHED AND IN THE HEART OF WIN... |
2 beds | 2 baths | 1,057 sq.ft. |
$631,400 |
Airbnb cash on cash: 0.28%
|
1308 S PENNSYLVANIA AVENUE #3Winter Park, FLThis beautifully updated 1-bedroom, 1-bath condo offers 823 sq. ft. of stylish living spac... |
1 beds | 1 baths | 823 sq.ft. |
$325,000 |
Airbnb cash on cash: 3.63%
|
225 E CANTON AVENUE #225Winter Park, FLUnder contract-accepting backup offers. This beautifully updated 2-bedroom, 2-bathroom cor... |
2 beds | 2 baths | 1,057 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.18%
|
1602 ALABAMA DRIVE #PH404Winter Park, FLUnder contract-accepting backup offers. A Jewel Box: Curated for a Life Well Lived. Pentho... |
3 beds | 4 baths | 2,709 sq.ft. |
$2,490,000 |
Airbnb cash on cash: -0.62%
|
130 KILLARNEY BAY COURT #5-3Winter Park, FLUnder contract-accepting backup offers. SUPERB LOCATION! Donât miss out on this beautif... |
2 beds | 3 baths | 1,536 sq.ft. |
$479,000 |
Airbnb cash on cash: 3.58%
|
2238 HAWICK LANE #2238Winter Park, FLWelcome to 2238 Hawick Lane, where modern living meets timeless charm in Winter Park, FL! ... |
3 beds | 3 baths | 1,775 sq.ft. |
$519,000 |
Airbnb cash on cash: 4.12%
|
3019 ANTIQUE OAKS CIRCLE #124Winter Park, FLPRICE IMPROVEMENT!! Prime Location and Zip Code are key! Low HOA! Welcome home to 3019 Ant... |
1 beds | 1 baths | 749 sq.ft. |
$163,500 |
Airbnb cash on cash: 6.71%
|
3651 N GOLDENROD ROAD E #102Winter Park, FLWelcome to this beautifully updated 2 bedroom/ 2 bath first floor condo. This open flo... |
2 beds | 2 baths | 840 sq.ft. |
$188,000 |
Airbnb cash on cash: 9.33%
|
334 SCOTTSDALE SQUARE #334Winter Park, FLCASH ONLY. Desirable Winter Park Location with highly rated schools! Down the street Full ... |
3 beds | 2 baths | 1,250 sq.ft. |
$130,000 |
Airbnb cash on cash: -5.74%
|
7466 CANFORD COURT #25Winter Park, FLMOTIVATED SELLER. Welcome to this cozy and well-maintained condo with a townhome feel nest... |
2 beds | 2 baths | 1,393 sq.ft. |
$197,990 |
Airbnb cash on cash: 7.31%
|
200 SAINT ANDREWS BOULEVARD #2306Winter Park, FLExcellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-b... |
2 beds | 2 baths | 1,015 sq.ft. |
$219,000 |
Airbnb cash on cash: 7.28%
|
296 LEWFIELD CIRCLEWinter Park, FL1 bed, 1 bath condo in Winter Park |
1 beds | 1 baths | 678 sq.ft. |
$157,000 |
Airbnb cash on cash: 7.31%
|
225 LEWFIELD CIRCLE #225Winter Park, FLOne or more photo(s) has been virtually staged. **This property qualifies for a closing co... |
2 beds | 2 baths | 953 sq.ft. |
$200,000 |
Airbnb cash on cash: 8.6%
|
7707 COUNTRY PLACE #4Winter Park, FLBeautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. ... |
2 beds | 2 baths | 1,068 sq.ft. |
$259,900 |
Airbnb cash on cash: 6.93%
|
4960 TANGERINE AVE. UNIT Unit 4960 Unit N/AWinter Park, FLVery well maintained cozy condo in Winter Park. This condo has one bedroom, and one bathro... |
1 beds | 1 baths | 763 sq.ft. |
$150,000 |
Airbnb cash on cash: 8.45%
|
2458 GRAND TETON CIRCLE #2458Winter Park, FLWelcome to your dream home in Winter Park! This beautifully updated, spacious two-bedroom ... |
2 beds | 2 baths | 1,457 sq.ft. |
$310,000 |
Airbnb cash on cash: 6.29%
|
5122 LAZY OAKS DRIVE #5122Winter Park, FLWelcome to Lazy Oaks, a beautifully maintained condominium community tucked away in the de... |
2 beds | 2 baths | 1,008 sq.ft. |
$279,000 |
Airbnb cash on cash: 8.01%
|
182 SCOTTSDALE SQUARE #182Winter Park, FLDon't miss this exceptional opportunity to invest in a 1-bedroom, 1-bathroom condo in the ... |
1 beds | 1 baths | 756 sq.ft. |
$80,000 |
Airbnb cash on cash: -9.17%
|
200 SAINT ANDREWS BOULEVARD #101Winter Park, FLOne or more photo(s) has been virtually staged. Welcome to this inviting first-floor 1 bed... |
1 beds | 1 baths | 727 sq.ft. |
$150,000 |
Airbnb cash on cash: 9.72%
|
226 SCOTTSDALE SQUARE #226Winter Park, FLGreat investment property. Convenient to major roads, Full Sail and UCF. |
2 beds | 2 baths | 1,020 sq.ft. |
$95,000 |
Airbnb cash on cash: -7.82%
|
200 SAINT ANDREWS BOULEVARD #601Winter Park, FLUnder contract-accepting backup offers. Welcome to this spacious and beautifully updated f... |
1 beds | 1 baths | 727 sq.ft. |
$169,900 |
Airbnb cash on cash: 8.19%
|
337 SCOTTSDALE SQUARE #337Winter Park, FLUnder contract-accepting backup offers. Just Reduced!! Great opportunity. This well-mainta... |
1 beds | 1 baths | 785 sq.ft. |
$80,000 |
Airbnb cash on cash: -9.79%
|
200 ST ANDREWS BOULEVARD #512Winter Park, FL**This property qualifies for a closing cost credit up to $2,700 through the Sellerâs pr... |
1 beds | 1 baths | 835 sq.ft. |
$165,500 |
Airbnb cash on cash: 6.19%
|
200 SAINT ANDREWS BOULEVARD #2206Winter Park, FLUnder contract-accepting backup offers. Welcome to the beautiful community of Four Seasons... |
2 beds | 2 baths | 987 sq.ft. |
$179,000 |
Airbnb cash on cash: 9%
|