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.
San Rafael Hill Investment Property for Sale in Winter Park, FL
Search for San Rafael Hill Investment Property for Sale in Winter Park, Florida. Browse all of Mashvisor’s San Rafael Hill Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 179 San Rafael Hill Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1221 RICHMOND ROADWinter Park, FLAn Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. ... |
5 beds | 6 baths | 5,164 sq.ft. |
$5,450,000 |
Airbnb cash on cash: N/A
|
132 BURKS CIRCLEWinter Park, FLExperience refined living in this completely remodeled single story residence located in t... |
4 beds | 5 baths | 3,022 sq.ft. |
$1,675,000 |
Airbnb cash on cash: 0.95%
|
2211 Azalea PlWinter Park, FLLuxurious waterfront estate in one of Winter Parkâs most prestigious neighborhoods, offe... |
5 beds | 7 baths | 7,278 sq.ft. |
$5,495,000 |
Airbnb cash on cash: N/A
|
2607 Lafayette AveWinter Park, FLWelcome to 2607 Lafayette Avenueâa stunning custom home in one of Winter Parkâs most d... |
4 beds | 4 baths | 2,770 sq.ft. |
$1,095,000 |
Airbnb cash on cash: 2.17%
|
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. |
$260,000 |
Airbnb cash on cash: 7.61%
|
3018 NORTHWOOD BOULEVARDWinter Park, FLOne or more photo(s) has been virtually staged. "MOVE-IN READY", 3-BED, 2-FULL BATHS, SING... |
3 beds | 2 baths | 1,761 sq.ft. |
$734,000 |
Airbnb cash on cash: 2.97%
|
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%
|
2550 VENETIAN WAYWinter Park, FL"The richness of an artist is the fusion of influences that have shaped his life and work"... |
4 beds | 5 baths | 4,875 sq.ft. |
$2,499,000 |
Airbnb cash on cash: 0.3%
|
1608 BOMI CIRCLEWinter Park, FLYour beautifully upgraded home in Winter Park with NO HOA is waiting for you! Centrally lo... |
3 beds | 2 baths | 1,807 sq.ft. |
$475,000 |
Airbnb cash on cash: 6.12%
|
2774 BRIGHT BIRD LANEWinter Park, FLMotivated seller! Brand new townhouse professionally decorated, and available today! Built... |
3 beds | 3 baths | 1,907 sq.ft. |
$465,000 |
Airbnb cash on cash: 5.48%
|
1660 WALNUT AVENUEWinter Park, FLUnder Construction. Elegant and modern new construction home perfectly situated in beautif... |
4 beds | 4 baths | 2,172 sq.ft. |
$1,759,000 |
Airbnb cash on cash: 1.35%
|
2033 CANNY COVEWinter Park, FLStep into this stunning townhome and be greeted by an open-concept kitchen, dining, and li... |
3 beds | 3 baths | 1,907 sq.ft. |
$432,000 |
Airbnb cash on cash: 4.79%
|
625 BRECHIN DRIVEWinter Park, FLPICTURE PERFECT HOME IN WINTER PARKâS KENILWORTH SHORES! Homes of this quality and prese... |
3 beds | 2 baths | 1,827 sq.ft. |
$765,000 |
Airbnb cash on cash: 3.32%
|
720 N PENNSYLVANIA AVENUEWinter Park, FLNestled in one of Winter Parkâs most sought-after locations, this 3-bedroom, 2-bathroom ... |
3 beds | 2 baths | 1,115 sq.ft. |
$550,000 |
Airbnb cash on cash: 4.56%
|
726 N PENNSYLVANIA AVENUEWinter Park, FLWelcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of moder... |
3 beds | 2 baths | 1,167 sq.ft. |
$695,000 |
Airbnb cash on cash: 3.43%
|
726 And 720 N PENNSYLVANIA AVENUEWinter Park, FLWelcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibili... |
6 beds | N/A baths | 2,284 sq.ft. |
$1,215,000 |
Airbnb cash on cash: 0.33%
|
5325 CYPRESS RESERVE PLACEWinter Park, FLATTENTION BUYERS!! Price adjusted to $918,000 and $15K SELLER CONCESSION TOWARDS BUYERS C... |
5 beds | 4 baths | 3,598 sq.ft. |
$918,000 |
Airbnb cash on cash: N/A
|
1400 ALABAMA DRIVEWinter Park, FLExtraordinary Waterfront Neoclassical Italian Estate situated on a prime .71-acre corner l... |
5 beds | 9 baths | 7,916 sq.ft. |
$5,895,000 |
Airbnb cash on cash: N/A
|
607 DUNBLANE DRIVEWinter Park, FLWelcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park... |
4 beds | 3 baths | 2,046 sq.ft. |
$675,000 |
Airbnb cash on cash: 4.98%
|
101 S INTERLACHEN AVENUE #104Winter Park, FLFIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN H... |
2 beds | 2 baths | 949 sq.ft. |
$635,000 |
Airbnb cash on cash: 2.43%
|
1360 FORMOSA AVENUEWinter Park, FLDiscover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the... |
3 beds | N/A baths | 1,890 sq.ft. |
$625,000 |
Airbnb cash on cash: 3.39%
|
1564 CAVENDISH ROADWinter Park, FLCharming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potenti... |
3 beds | 1 baths | 1,140 sq.ft. |
$450,000 |
Airbnb cash on cash: 5.72%
|
701 DENTON ROADWinter Park, FLMotivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Pa... |
3 beds | 2 baths | 2,268 sq.ft. |
$565,000 |
Airbnb cash on cash: 4.22%
|
1910 GLENCOE ROADWinter Park, FLUnder Construction. Stunning architectural masterpiece built by LUIH homes nestled in the ... |
4 beds | 6 baths | 4,205 sq.ft. |
$3,490,000 |
Airbnb cash on cash: 0.21%
|
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. |
$195,000 |
Airbnb cash on cash: 9.06%
|
3601 MIDIRON DRIVEWinter Park, FLBUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread... |
2 beds | 1 baths | 954 sq.ft. |
$459,000 |
Airbnb cash on cash: 3.36%
|
2487 HARBOUR WAYWinter Park, FLUnmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 ... |
3 beds | 3 baths | 1,803 sq.ft. |
$319,900 |
Airbnb cash on cash: 8.38%
|
1399 ALOMA AVENUEWinter Park, FL***Price Adjustment *** Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is ... |
3 beds | 2 baths | 1,804 sq.ft. |
$665,000 |
Airbnb cash on cash: 4.06%
|
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. |
$229,000 |
Airbnb cash on cash: 6.81%
|
541 W CANTON AVENUEWinter Park, FLTimeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new... |
4 beds | 4 baths | 3,553 sq.ft. |
$2,935,000 |
Airbnb cash on cash: 0.5%
|
311 E MORSE BOULEVARD #7-5Winter Park, FLMajor Price Improvement! Here is your rare opportunity to own a studio apartment in Whispe... |
1 beds | 1 baths | 482 sq.ft. |
$359,000 |
Airbnb cash on cash: 3.19%
|
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%
|
1112 PRESERVE POINT DRIVEWinter Park, FLPresenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rar... |
5 beds | 6 baths | 6,502 sq.ft. |
$8,500,000 |
Airbnb cash on cash: N/A
|
1018 TURNER ROADWinter Park, FLSeller may consider buyer concessions if made in an offer | Lakefront charm meets quiet lu... |
3 beds | 2 baths | 2,237 sq.ft. |
$835,000 |
Airbnb cash on cash: 2.27%
|
2835 BONGART ROADWinter Park, FLSeller is Motivated, must sell NOW! - Welcome to your spectacular pool home in Winter Park... |
3 beds | 3 baths | 1,880 sq.ft. |
$449,900 |
Airbnb cash on cash: 6.4%
|
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%
|
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. |
$570,000 |
Airbnb cash on cash: 2.5%
|
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. |
$145,000 |
Airbnb cash on cash: 8.17%
|
2922 REEF KNOT PLACEWinter Park, FLOne or more photo(s) has been virtually staged. Stunning Lakefront Living in an Exclusive ... |
4 beds | 4 baths | 3,153 sq.ft. |
$1,295,000 |
Airbnb cash on cash: 1.76%
|
446 ALBERTA DRIVEWinter Park, FLCharming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t... |
4 beds | 3 baths | 3,263 sq.ft. |
$1,750,000 |
Airbnb cash on cash: 1.39%
|