271 Orlando Avenue
Winter Park, FL 32789 · Orange County
$1,550,000
0
Beds
0
Baths
3,430
Sq ft
1949
Year built
Location
About this home
Rare hospitality-yield opportunity in Winter Park's Class A core, directly in the Hillstone trade area on South Orlando Avenue. The offering consists of 12 short-term rental units — 8 studios and 4 one-bedroom/one-bath — plus a street-facing office suite fronting S. Orlando Ave. The thesis is straightforward: Winter Park generates year-round, non-theme-park demand — Rollins, Park Avenue, AdventHealth Winter Park, and the corporate and event traffic that fills the surrounding hotels at rates a 12-unit boutique operation can match without a hotel's cost structure.
Facts & features
Interior
- Living area
- 3,430 sq ft
- Stories
- 1
- Appliances
- Dryer, Microwave, Refrigerator, Washer
- Cooling
- Central Air
- Heating
- Central
Exterior & lot
- Lot size
- 0.18 acres
- Construction
- Block, Stucco
- Roof
- Concrete
Financial
- Price / sqft
- $452/sqft
- Annual tax
- $11,445.21
- Tax year
- 2026
Utilities
- Utilities
- Electricity Available, Public, Water Connected
- Water
- Public
- Sewer
- Public Sewer
Property
- Property type
- Commercial
- Year built
- 1949
- Subdivision
- Killarney Estates
- Days on market
- 3 days
Estimate your monthly cost
Twenty percent down over thirty years at 6.5%. Insurance is not included.
- Principal & interest
- $7,838
- Property tax
- $954
- Estimated monthly
- $8,792
Ask about this property
Answered from this listing’s own figures and the sales around it.
Similar homes nearby
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Oct 16, 2026 | Listed | $1,550,000 | — |
Neighbourhood
The schools below come from the MLS record for this home. Walking, transit and cycling figures for Winter Park, FL are not connected yet, so this page does not show them.
About this area
WINTER PARK, FL sits in Orange County.
Written from this listing’s own record and the homes we hold nearby.
- Elementary school
- Not listed
- Not named in the MLS record for this home
- Middle school
- Not listed
- Not named in the MLS record for this home
- High school
- Not listed
- Not named in the MLS record for this home
Frequently asked questions
What would 271 ORLANDO AVENUE, WINTER PARK cost per month?
About $8,792 a month: $7,838 principal and interest, $954 property tax. That assumes 20% down at 6.5% over 30 years, and leaves out insurance.
Is 271 ORLANDO AVENUE, WINTER PARK priced fairly?
It is listed at $1,550,000. There are not enough comparable homes close by to put a range around that yet, so the asking price is the honest answer.
How long has 271 ORLANDO AVENUE, WINTER PARK been on the market?
It came on the market today.
Has the price of 271 ORLANDO AVENUE, WINTER PARK changed?
The price has not moved since it was listed.
How big is 271 ORLANDO AVENUE, WINTER PARK?
3,430 square feet. That is $452 a square foot.
What year was 271 ORLANDO AVENUE, WINTER PARK built?
Built in 1949.
What is the HOA fee at 271 ORLANDO AVENUE, WINTER PARK?
The feed lists no association fee for this property.
What are the property taxes at 271 ORLANDO AVENUE, WINTER PARK?
Property tax works out to about $954 a month, $11,445 a year, on the 2026 assessment.
Is 271 ORLANDO AVENUE, WINTER PARK still available?
It is still on the market.
Listing
- Listed by
- Robert Arnold, Jr
- Brokerage
- SAND DOLLAR REALTY GROUP INC
- MLS number
- MFR814332864
Listing information is deemed reliable but is not guaranteed.