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$1,894,400
Parklando 03 SubDv. 32789 Zip Code
Welcome to 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Step Inside Modern Elegance. Completely remodeled in 2022, this home radiates warmth and sophistication. Solid white oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Resort Living, Every Day. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape. Retreat in Comfort. The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. Why Wait? This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge. Opportunities like this in Winter Park are scarce. Don’t miss it.

2614 Parkland Drive, Winter Park

$425,000
Eastgate Sub SubDv. 32792 Zip Code
A great opportunity to own land in one of Winter Park's most sought-after pockets. This property's true value lies in its prime homesite. You can build your dream home or renovate to suit, all while capturing the location that can't be replicated. Tucked in an established, tree-lined neighborhood minutes from Park Avenue's boutiques and dining, Winter Park's chain of lakes, and easy access to I-4, this address puts you at the center of it all. Zoned for top-rated Winter Park schools, this is the kind of location families compete for. Whether you're an investor, builder, or buyer looking to create something custom, this is a foundation worth building on. Land + location + schools — the trifecta that makes Winter Park real estate hold its value.

1909 Taylor Avenue, Winter Park

$2,200,000
Lake Sylvan Shores SubDv. 32789 Zip Code
Exceptional opportunity to build your dream home in one of Winter Park’s most sought-after neighborhoods! This cleared, vacant homesite is ready for construction and offers the perfect canvas to create a custom residence tailored to your vision. Nestled on a quiet street, the property is surrounded by beautiful homes while providing convenient access to Park Avenue’s renowned shopping and dining, Rollins College, top-rated schools, parks, golf courses, and major roadways. Whether you’re a builder, investor, or future homeowner, this is a rare chance to secure a prime piece of land in an established community where new construction opportunities are increasingly limited. Don’t miss the chance to bring your vision to life in the heart of Winter Park!

1415 Grove Terrace, Winter Park

$695,000
Conwill Estates SubDv. 32789 Zip Code
Exceptional opportunity to build new or renovate and expand on this desirable lot in Winter Park. Situated on a charming tree lined street and in a neighborhood that is experiencing a great deal of new development. The existing 1950s residence features parquet wood flooring and open living and dining spaces, which overlooks the backyard and open wooden deck. With generous space to work with, there are great possibilities to create your own custom residence. The property is zoned for long-established schools - Lakemont Elementary, which is just down the street from the property, as well as Maitland Middle and Winter Park High. Plus, ideally located within a short stroll to the Winter Park Y, Phelps Park, and minutes to downtown Park Ave's shopping and dining! Property is being sold AS IS.

1622 Arbor Park Drive, Winter Park

$649,000
Tantum Add SubDv. 32789 Zip Code
Under contract-accepting backup offers. THE best kept secret in WP! 6500sq/ft buildable lot located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street with million $$ neighbors! Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. Rent or live in until you expand or build new in the renovated charming bungalow, w/ refinished hardwood floors, brand new kitchen with stainless appliances, 3 generous bedrooms, bonus Florida Room, PLUS single car garage! Cozy firepit seating area with twinkle lights overlooking the golf course. Don’t miss this “one of kind – live your best Winter Park life” opportunity!

1037 N Virginia Avenue, Winter Park

$449,000
32789 Zip Code
Some opportunities don't announce themselves. They show up quietly in Winter Park's most sought-after zip code, waiting for someone who knows exactly what to do with them. This vacant lot inside Waterbridge sits in the 32789 zip code, a rare chance to build the home you've always had in mind, in a neighborhood that has already decided who it is. Waterbridge is a tight-knit, tree-lined enclave where the homes are custom and the neighbors stay. Lots like this do not come available often. The address puts you minutes from Park Avenue's galleries and weekend farmers market, AdventHealth Winter Park, and the employers and services that make this corridor one of Winter Park's most connected. The schools zoned here, Glenridge Middle and Winter Park High, are among the most respected in Orange County and part of why buyers seek out this zip code specifically. Build the primary suite you've never been able to find. Design the kitchen around how you actually cook. Choose the ceiling heights, the materials, the layout. Every decision a resale home will never let you make is yours to make here. A lot in Waterbridge represents something that rarely surfaces: the convergence of a blank canvas and a proven address.

Jessica Court, Winter Park

$1,595,000
Tuscany Terrace SubDv. 32789 Zip Code
Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue's renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted "Vias" of Winter Park, a collection of streets long regarded as one of the city's most established and desirable residential enclaves. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end users alike - a rare chance to secure one of winter Park's most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park

$850,000
Lakeview Terrace SubDv. 32789 Zip Code
Build your dream home in one of Winter Park’s most desirable locations. This 66.6’ x 127’ homesite at 1780 Bryan Avenue offers a rare opportunity to secure the last remaining lot of three consecutive new construction parcels. Surrounded by newly built luxury residences, the property provides a clean slate for custom design while maintaining strong future value. The lot’s generous dimensions allow for a spacious floor plan, outdoor living areas, and a private backyard retreat. Situated on a quiet, tree-lined street, yet just minutes from Park Avenue, top-rated schools, dining, and shopping, the location strikes the perfect balance between convenience and neighborhood charm. Opportunities like this are increasingly rare in Winter Park—don’t miss your chance to be part of a growing enclave of new construction homes in a highly sought-after area.

1780 Bryan Avenue, Winter Park

$899,900
Lake Forest Park SubDv. 32789 Zip Code
**BUILD YOUR DREAM HOME** A rare opportunity to secure over half an acre of lakefront land in one of Winter Park’s most coveted residential corridors. NO HOA. Situated directly on Lake Forest, this 0.54-acre parcel offers the kind of lot that simply doesn’t come available in this market - expansive, private, and adorned with mature tree canopy that frames sweeping water views. The homesite carries an R-1A zoning designation and is tucked on a quiet street, yet sits just minutes from the dining, shopping, and culture of downtown Winter Park and Baldwin Park. The generous lot dimensions provide ample room for a custom estate build, a pool, and meaningful setbacks. Served by top-rated Audubon Park K-8 and Winter Park High School, and positioned within one of Central Florida’s most desirable zip codes.

2823 Wright Avenue, Winter Park

$2,690,000
Sicilian Shores SubDv. 32789 Zip Code
One of the last remaining opportunities to build on a truly exceptional street in the Winter Park Via’s, this .48-acre homesite offers a fantastic combination of a prime location, a large lot, and surrounded but gorgeous homes. The lot is cleared and ready to build! The current owners have thoughtfully commissioned architectural plans by renowned Winter Park architect Gary Hancock. With the Seller's impeccable taste and luxurious finishes, every detail was meticulous designed. The architectural and interior design plans could provide a jump start on your new stunning custom home. While plans are available, buyers also have the flexibility to bring their own vision to life. Ideally located just minutes from Park Avenue and surrounded by some of Winter Park’s most beautiful lakefront homes, this homesite also enjoys close proximity to the Winter Park Racquet Club, Kraft Azalea Garden, Phelps Park, and the Winter Park YMCA. Zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High. A truly special opportunity to create a custom residence in one of Winter Park’s most coveted settings.

620 Pinetree Road, Winter Park

$4,500,000
Winter Park SubDv. 32789 Zip Code
JUST LISTED - RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,999,000!!! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses. Future residents will enjoy picturesque walks along Winter Park's famous brick streets just off the shores of the chain of lakes. Nearby attractions like the Winter Park Farmer's Market, the Winter Park Golf Course, a highly rated 9-hole gem in the center of town, Casa Feliz, Central Park, and more are all within just a few minutes stroll.

503 N Interlachen Avenue, Winter Park