421 Lakewood Drive, WINTER PARK, FL 32789
Local realty services provided by:Better Homes and Gardens Real Estate Synergy



Listed by:mick night
Office:premier sotheby's intl. realty
MLS#:O6153641
Source:MFRMLS
Price summary
- Price:$4,500,000
- Price per sq. ft.:$556.72
About this home
This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and meticulous, landscaped grounds, combined with elevated panoramic views from a spacious 3/4 acre lot, with approx. 140 feet on the street and approx.. 110 feet of prime lake frontage. This property offers a sense of privacy, tranquility and breathtaking views capturing both northern sunrises & sunsets… Inside, you'll find extensive renovations, over the years, that have elevated the space enhanced with Wolfe-Rizor Interior Design elements… There is plenty of natural light throughout, with extensive windows, numerous French doors and a thoughtful layout that seamlessly blends indoor and outdoor living spaces. The primary level includes a defined foyer entry, secluded library/home office, kitchen, gathering room, formal living and dining rooms. The chef's kitchen is thoughtfully designed and enhanced by an expansive island, commercial grade range, lake side breakfast room, and catering area for creating culinary experiences in hosting family and friends. The lavish living room includes room for a grand piano and has its own fireplace open to an expansive 30' long dining room with direct lake views… along with a screened lanai... The primary suite is conveniently located on the ground floor, offering a private expansive retreat with a sitting area and serene, picturesque lake views. The luxurious primary bathroom provides a spa-like experience including modern fixtures, his/her separate baths, and a generous walk-in closet/dressing room. The main level also includes a potential 6th bedroom used previously for a caretaker's quarters tucked away by the garage entry... The upstairs living areas, include 4 additional bedroom suites (generous sizes) located on the second floor with a couple of bonus/flex rooms and sitting area... When you're not savoring the indoor elegance, step outside to enjoy the lakefront living with entertaining terrace, tropical pool, sprawling lawn with retaining walls, boathouse and majestic cypress, oak & palm trees to enhance the lakefront lifestyle... Located on private, quiet street with oversized 3-car garage… Note: roof replaced in 2021. All within walking distance to downtown Winter Park and famed Park Avenue…
Contact an agent
Home facts
- Year built:1957
- Listing Id #:O6153641
- Added:652 day(s) ago
- Updated:August 14, 2025 at 07:40 AM
Rooms and interior
- Bedrooms:5
- Total bathrooms:9
- Full bathrooms:7
- Half bathrooms:2
- Living area:5,847 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central, Electric
Structure and exterior
- Roof:Shingle
- Year built:1957
- Building area:5,847 sq. ft.
- Lot area:0.72 Acres
Schools
- High school:Winter Park High
- Middle school:Maitland Middle
- Elementary school:Lakemont Elem
Utilities
- Water:Public, Water Connected
- Sewer:Public, Public Sewer, Sewer Connected
Finances and disclosures
- Price:$4,500,000
- Price per sq. ft.:$556.72
- Tax amount:$24,481 (2023)
New listings near 421 Lakewood Drive
- New$135,000Active2 beds 1 baths881 sq. ft.
1695 Lee Road #C206, WINTER PARK, FL 32789
MLS# O6335646Listed by: EXP REALTY LLC - Open Fri, 4 to 6pmNew$250,000Active2 beds 2 baths1,217 sq. ft.
7642 Glenmoor Lane, WINTER PARK, FL 32792
MLS# O6335789Listed by: THE WILKINS WAY LLC - New$377,500Active3 beds 2 baths1,461 sq. ft.
3490 Bougainvillea Drive, WINTER PARK, FL 32792
MLS# S5132615Listed by: KELLER WILLIAMS ADVANTAGE III - New$2,895,000Active4 beds 3 baths3,258 sq. ft.
1074 Mckean Circle, WINTER PARK, FL 32789
MLS# O6334017Listed by: PREMIER SOTHEBY'S INTL. REALTY - New$529,990Active4 beds 4 baths2,163 sq. ft.
1938 Risby Alley, ORLANDO, FL 32803
MLS# O6335555Listed by: K HOVNANIAN FLORIDA REALTY - New$119,000Active2 beds 3 baths1,085 sq. ft.
3002 George Mason Avenue #3, WINTER PARK, FL 32792
MLS# O6335335Listed by: KELLER WILLIAMS ADVANTAGE REALTY - New$2,800,000Active5 beds 6 baths4,469 sq. ft.
1341 Place Picardy, WINTER PARK, FL 32789
MLS# O6319556Listed by: STOCKWORTH REALTY GROUP - $1,799,000Pending3 beds 4 baths3,121 sq. ft.
690 Williams Drive, WINTER PARK, FL 32789
MLS# O6334889Listed by: KELLY PRICE & COMPANY LLC - New$425,000Active2 beds 2 baths1,148 sq. ft.
690 Osceola Avenue #209, WINTER PARK, FL 32789
MLS# O6334757Listed by: LOKATION - New$195,000Active2 beds 3 baths1,031 sq. ft.
7444 Woodburn Court #29, WINTER PARK, FL 32792
MLS# S5131940Listed by: LPT REALTY, LLC