220 Overlook Rd

$3,600
Price
2
Beds
1,393 Sq. Ft.
$31 / Sq. Ft.
1,393
Sq. Ft.
$31
per Sq. Ft.

Description

Charming Cape Cod–style home available for lease in the heart of Winter Park. Ideally located just one block from Lake Mizell and moments from Park Avenue and Rollins College, this residence offers an exceptional lifestyle surrounded by premier shops, dining, and local amenities. The home features a spacious and inviting floor plan with a large living room, sunroom or dining area, and two generously sized bedroom suites. Interior highlights include beautiful hardwood floors, quartz countertops, walk-in...Charming Cape Cod–style home available for lease in the heart of Winter Park. Ideally located just one block from Lake Mizell and moments from Park Avenue and Rollins College, this residence offers an exceptional lifestyle surrounded by premier shops, dining, and local amenities. The home features a spacious and inviting floor plan with a large living room, sunroom or dining area, and two generously sized bedroom suites. Interior highlights include beautiful hardwood floors, quartz countertops, walk-in closets, custom built-ins, and a private screened-in porch, perfect for relaxing or entertaining. Additional features include a one-car saltbox detached garage equipped with a utility sink, washer, and dryer. If you’re seeking a character-rich home in an unbeatable location, this is truly a special opportunity.
  1. Listed by Julie Bombardo • Brokerage DRE #2034958 • PREMIER SOTHEBY'S INTL. REALTY
    P: (407)-230-6696 C: (407)-230-6696 JulieBombardo@gmail.com

Property Details for 220 Overlook Road

Subdivision Name
SYLVAN LAKE SHORES
Garage Spaces
1
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 12/10/2025 10:51 AM

Property Details for 220 Overlook Road

StatusActive
MLS #O6365244
Days on Market14
Rental Incentives-
Available Date09/22/2023
Lease Term12 Months
Furnished-
Compass TypeRental
MLS TypeResidential Lease / Single Family Residence
Year Built1938
Lot Size0.14 AC / 6,196 SF
CountyOrange County

Location

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY, Julie Bombardo
Add your commute

Building Information for 220 Overlook Road

Building/Complex220 Overlook RdFloor-Stories-Pet Policy-Pet Policy DetailsNoYear Built1938Building Size-Lot Size0.14 AC / 6,196 SF

Property Information for 220 Overlook Road

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 1855.0
  • Building Area Units: Square Feet
  • Directions: West Fairbanks Ave, continue onto E Osceola Ave, continue on Brewer Ave, Brewer Ave turns slightly right and becomes Aloma Ave. Right on Sylvan Blv and straight to Overlook Rd. Home is on the left.
  • Elementary School: Brookshire Elem
  • Middle Or Junior School: Glenridge Middle
  • High School: Winter Park High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Long Term YN: true
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 220
  • Street Name: OVERLOOK
  • Street Suffix: ROAD
  • State: FL
  • City: WINTER PARK
Parking
  • Attached Garage: No
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Additional Applicant Fee: $75
  • Association Name: None
  • Association: No
  • Management: Full Time
Virtual Tour
Property
Lot Information
  • Parcel Number: 052230850608031
  • Water Access: No
  • Water Extras: No
  • Living Area: 1393
Property and Assessments
  • Year Built Numeric: 1938
  • New Construction: No
  • Owner Pays: Grounds Care
  • Dock YN: No
Utilities
  • Sewer: Public Sewer
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Exterior Features: French Doors
  • Levels: One
  • Patio And Porch Features: Deck, Screened, Side Porch
  • Pool Private: No
  • Pool: None
  • Pool Private: No
  • Security Deposit: $3,600
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 2
  • Bathrooms Full: 2
  • Additional Rooms: Den/Library/Office, Family Room
  • Appliances: Dishwasher, Dryer, Range, Range Hood, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Family Room
  • Fireplace: Yes
  • Flooring: Hardwood
  • Heating: Central
  • Interior Features: Eating Space In Kitchen, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
  • Laundry Features: In Garage
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 9.0
  • Primary Bed Size: King
  • Water View: No
  • Window Features: Shades, Shutters
  • Bathrooms Half: 0
Rental
Rental Information
  • Pets Allowed: No

Property History for 220 Overlook Road

DateEvent & SourcePriceAppreciation
Dec 9, 2025

Listed (Active)

MFRMLS #O6365244

$3,600—
Nov 14, 2023

Rented

MFRMLS #O6139540

$3,450—
Nov 2, 2023

Pending

MFRMLS #O6139540

—
Sep 6, 2023

Listed (Active)

MFRMLS #O6139540

$3,500—
DateEvent & SourcePrice
12/09/2025

Listed (Active)

MFRMLS #O6365244

$3,600
11/14/2023

Rented

MFRMLS #O6139540

$3,450
11/02/2023

Pending

MFRMLS #O6139540

—
09/06/2023

Listed (Active)

MFRMLS #O6139540

$3,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 220 Overlook Road

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 5
Charter - K to 8
Public - 6 to 8
Charter - 9 to 12
Rating
School
Distance
Brookshire Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Glenridge Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

220 Overlook Road is available for rent in Winter Park, FL 32789. This property was listed on December 9, 2025 by PREMIER SOTHEBY'S INTL. REALTY, it's currently listed at $3,600. It has been on the market for a total of 14 days and was last rented on November 14, 2023. This listing's school district is Orange County Public Schools. Nearby schools include Brookshire Elementary School, Cornerstone Academy Charter and Glenridge Middle School. 220 Overlook Road is a 2-bed, 2-bath, 1,393 sqft a property built in 1938.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY, Julie Bombardo

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 12/10/2025 10:51 AM