Winter Park

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1691 Chestnut Ave, Winter Park, Florida 32789

Residential For Sale

COMPASS FLORIDA LLC
Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park.  Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft.
$4,799,900
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
4,582Sqft

1913 N Park Ave, Winter Park, Florida 32789

Residential Lease For Rent

FLATFEE.COM
Rent a spacious home on Park Ave and walk to shops and restaurants! Lots of Light, Split floor plan, Garage, Inner courtyard, Screened Porch, Lawn Service Split floor plan with ceramic tile throughout, granite kitchen countertops, and spacious kitchen with stainless still appliances. French doors from the kitchen and living rooms open to a private courtyard.
$2,750
3Bedroom(s)
2Bathroom(s)
1,324Sqft

1823 Sunset Dr, Winter Park, Florida 32789

Residential For Sale

COMPASS FLORIDA LLC
Fantastic Lake Knowles Terrace community close to The Via's, Downtown Winter Park and I-4 road access. Lots of possibilities to restore this 1940 classic home or create your own brand new structure . This property offers so much potential in Winter Park's premier and sought after location.
$779,000
2Bedroom(s)
3Bathroom(s)
2,414Sqft

301 Rippling Ln, Winter Park, Florida 32789

Residential For Sale

XCLUSIVE HOMES LLC
Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winter Park's largest freshwater spring-fed lakes (240 acres) this stunning lakefront home offers breathtaking views and direct water access.
$2,349,900
4Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
3,694Sqft

1040 Aloma Ave, Winter Park, Florida 32789

Residential Lease For Rent

FLATFEE.COM
Charming Single-Family Home in Winter Park! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Cortland Park neighborhood. Built in 1987, this property combines timeless architecture with modern comforts, offering 2,112 sq. ft. of living space on a spacious 9,745 sq. ft. lot.
$1,750
3Bedroom(s)
2Bathroom(s)
DrivewayParking(s)
2,112Sqft

2923 Antique Oaks Cir #37, Winter Park, Florida 32792

Residential For Sale

FLATFEE.COM
Condo in Winter Park, FL. 2923 Antique Oaks Cir, Unit 37. Updated 1,105 sq. ft. first-floor, North West corner condo. 2 bedrooms, 2 bathrooms. Located in the Winter Park School District: Updated Interiors: Recently remodeled with modern finishes, including brand-new appliances (convection oven, refrigerator, dishwasher), and a new LG stackable washer/dryer in the interior laundry room.
$196,400
2Bedroom(s)
2Bathroom(s)
AssignedParking(s)
1,105Sqft

184 Sandlewood Trl #2, Winter Park, Florida 32789

Residential For Sale

SAVVY AVENUE, LLC
Presenting a gorgeous, completely renovated condo with a townhome feel, available in highly desirable Winter Park. This two-story home boasts new everything...
$350,000
2Bedroom(s)
3Bathroom(s)
1,133Sqft

4957 Old Lucerne Park Rd, Winter Haven, Florida 33881

Residential For Sale

JOSEPH WALTER REALTY LLC
Welcome to this charming 3-bedroom, 2-bathroom home, offering 1,216 sq. ft. of well-designed living space in a quiet, friendly neighborhood. Perfectly suited for first-time homebuyers or anyone looking for a peaceful retreat, this home features an open layout with spacious living areas and plenty of room to grow.
$50,000
3Bedroom(s)
2Bathroom(s)
1,216Sqft

1250 S Pennsylvania Ave #8, Winter Park, Florida 32789

Residential For Sale

MINK REALTY
Quiet Virginia Heights Neighborhood with Stunning: private lake access park, walk to town around lake Virginia, directly across street from Mead Gardens, 2 short blocks to WP Tennis Center, Azalea Playground Park, New 7 Oaks Park, And less than a 1/2 mile stroll to New Orange Avenue Shops & Dinning. Easy in / out access via private drive; QUIET side with private drive, easy entry exit.
$839,999
3Bedroom(s)
3Bathroom(s)
1,957Sqft

690 Osceola Ave #405, Winter Park, Florida 32789

Residential For Sale

SAVVY AVENUE, LLC
Beautiful Lakefront unit with Lake Virginia ViewFrom the moment you open the door you will be drawn into this South facing lakefront condo on the Winter Park Chain of Lakes offering panoramic views of Lake Virginia (Rollins College) and Downtown Orlando -a most unique and calming oasis in the City. this lake front unit feels like your on a island retreat.
$525,000
1Bedroom(s)
2Bathroom(s)
Under BuildingParking(s)
850Sqft

113 S Winter Cir, Avon Park, Florida 33825

Residential For Sale

JOSEPH WALTER REALTY LLC
Great Double-Wide Mobile Home in Excellent Condition - Priced to Sell! Don't miss this opportunity at 113 S Winter Cir, Avon Park, FL 33825 - a spacious 3-bedroom, 2-bathroom double-wide mobile home, perfect for everyone. This well-maintained home features central AC, sleek hard surface countertops, a relaxing hot tub, and a convenient shed for extra storage.
$179,900
3Bedroom(s)
2Bathroom(s)
1,620Sqft

1368 Blue Stem Ln, Winter Park, Florida 32792

Residential Lease For Rent

ECO LUXE REALTY
Available November 8th, 2025 - Distinctive, private, unique and full of character is what sets this estate apart from all other properties on the market. Welcome home to your freshly built and highly updated Anastasia plan in the fabulous newer Winter Park community of Hawk's Crest.
$4,750
4Bedroom(s)
4Bathroom(s)
2,589Sqft
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August 19, 2022