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$450,000
2 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. NESTLED IN THE HEART OF HISTORIC WINTER PARK, THIS CHARMING RESIDENCE AT 518 SHOREVIEW AVE OFFERS TIMELESS CHARCTER. JUST STEPS FROM BEAUTIFUL LAKE KILARNEY. INSIDE, YOU WILL FIND STUNNING HARDWOOD FLOORS THAT ADD WARMTH AND ELEGANCE THROUGHOUT, ALONG WITH AN UPDATED PRIMARY BATHROOM FEATURING A RELAXING GARDEN TUB.THE INVITING FLORIDA ROOM PROVIDES THE PERFECT SPACE TO UNWIND OR ENTERTAIN WHILE ENJOYING THE NATURAL SURROUNDINGS. THE KITCHEN FEATURES A REVERSE OSMOSIS SYSTEM TO FILTER THE DRINKING WATER. THIS PROPERTY IS A RARE OPPORTUNITY TO OWN A PIECE OF WINTER PARK HISTORY IN AN UNBEATABLE LOCATION NEXT TO FABULOUS SHOPPING AND DINING EXPERIENCES. ** SELLER HAS PLANS FOR ATTIC EXPANSION AVAILABLE.

518 Shoreview Avenue, Winter Park
$1,780,000
4 Beds ⋅ 4 Baths ⋅ Green Terrace V/140 Lot 3 Blk B SubDv. ⋅ 32789 Zip Code
Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.

1750 Carollee Lane, Winter Park
$640,000
5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code
This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in front porch adds to the home’s classic charm and provides the perfect space to relax and unwind. Tucked away in the rear of the property there is both flexibility and income potential: a stylish studio office and a spacious one-bedroom unit complete with its own living area and separate loft. This property is ideal for investors, multi-generational living, or owner-occupants seeking strong rental returns. Located closely to beautiful Lake Killarney and conveniently situated near highways, restaurants, and shopping, this property combines charm, location, and income potential in one exceptional offering.

352 Cambridge Boulevard, Winter Park
$956,809
4 Beds ⋅ 4 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. Experience a life where timeless craftsmanship meets modern convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath, 2,662 sq. ft. home is situated on a 6,748 sq. ft. lot and is a meticulously designed modern Craftsman, blending rich architectural details with functional, contemporary living. One of three consecutive custom builds — each with its own distinctive architecture and character — this residence offers a rare combination of individuality and neighborhood harmony. Perfectly located just 6 minutes from Park Avenue’s boutique shopping and dining, and within close reach of top-rated hospitals, it places you at the center of Winter Park’s most sought-after amenities. This property is ideal for designing your forever home. Pricing reflects the starting point, with a variety of upgrade options available to further personalize finishes and features. The adjacent homes, including 1835 Karolina Ave and parcel 21, are also available in the desirable 32789 zip code.

Lot #20 Karolina Ave, Winter Park
$1,175,000
3 Beds ⋅ 2 Baths ⋅ College Place Rep SubDv. ⋅ 32789 Zip Code
Charming 1925 Craftsman with Spanish-Style Guest Apartment in Winter Park's College Quarter. Nestled in the heart of the historic College Quarter, this beautifully preserved 1925 Craftsman home offers timeless character, modern livability, and a rare bonus: a separate Spanish/Moorish-style garage apartment with its own unique architectural flair. The main house features 3 bedrooms, 2 bathrooms, and 1,867 square feet of inviting living space. Classic elements like original heart of pine floors and period finishes can easily blend in well with additional interior updating. Although the house has the history, the flow of the layout works well with today’s modern living and entertaining style. Additionally, just behind the main home, is a 504-square-foot garage apartment which offers a living space, kitchenette, bedroom and bathroom. It has striking interior details, such as hand-hewn pecky cypress beams, heavy plaster work, keyhole shaped doors and hand-wrought ironwork and a cozy fireplace. The apartment space is —a perfect guest retreat, income-producing rental, or private home office. The property also comes with deeded lake access to scenic Lake Virginia, part of the coveted Winter Park Chain of Lakes. The proximity to downtown Winter Park is just a short stroll, through tree-lined brick streets to Park Avenue’s shops and restaurants, as well as Rollins College, which is just a street away. Whether you're seeking historic character, walkable charm, or lakeside living, this unique Winter Park property delivers it all! 4-Point inspection was completed, please see attachments for survey and for home details.

835 Antonette Avenue, Winter Park
$1,050,000
3 Beds ⋅ 4 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code
Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and Winter Park Village, this stunning modern Craftsman by David Weekley Homes perfectly blends luxury, comfort, and convenience. The thoughtfully designed floor plan features a downstairs primary suite, rich hardwood flooring, and sliding barn doors opening to a versatile dining room or home office. The heart of the home is the gourmet all-white kitchen, showcasing Cambria quartz countertops, a large center island, and top-of-the-line JennAir appliances—ideal for both everyday living and entertaining. Perfect Lock & Leave Living! Enjoy effortless living in this beautifully maintained neighborhood, ideal for those seeking a low-maintenance lifestyle. With all lawn care included, you can spend more time doing what you love—whether that's traveling, entertaining, or simply relaxing. Just lock the door and go—peace of mind comes standard. Located in the vibrant community of Winter Park—home to Rollins College, Michelin-starred restaurants, charming local boutiques, parks, and a lively farmers market—you’ll also love being just minutes from Winter Park Village for shopping, dining, and entertainment. Don't miss this rare opportunity to own a modern gem in one of Central Florida’s most sought-after neighborhoods!

795 W Canton Avenue, Winter Park
$1,025,000
4 Beds ⋅ 3 Baths ⋅ Dubsdread Heights SubDv. ⋅ 32789 Zip Code
Welcome to your Winter Park dream home—a modern farmhouse masterpiece blending timeless design with contemporary comforts. Built in 2019, this single-family home offers four spacious bedrooms, two and a half baths, and luxurious finishes you'll cherish for years. Nestled between the highly coveted areas and school zones of College Park and Winter Park, this property is an opportunity you can't miss. Step into the foyer, leading to a bright, open-concept living space and a kitchen that’s designed to impress. Featuring quartz countertops, sleek stainless appliances, shaker cabinetry, and a wine fridge, this kitchen is perfect for both everyday living and entertaining. The living area transitions smoothly into the expansive fenced backyard, complete with ample space for a future pool. Upstairs, you'll find all four bedrooms, including the stunning primary suite with hardwood floors, a custom walk-in closet, and a spa-like bathroom with dual sinks. A versatile loft, laundry room, and additional full bathroom complete the second floor. Enhancing its charm are plantation shutters throughout and proximity to the serene Dubsdread Golf Course—a perfect spot for morning jogs or evening strolls. Enjoy the ease of accessing all that College Park and Winter Park have to offer, as well as convenient commuting via Interstate-4. There is no HOA in this community. This home is available immediately.

2680 Oglesby Avenue, Winter Park
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Osceola Court SubDv. ⋅ 32789 Zip Code
Walk to beautiful downtown Winter Park for fabulous shopping, restaurants, SunRail/Amtrak station and just steps to Rollins College campus. Make yourself at home in this beautifully restored historic 4 bedroom 3 ½ bath home with award winning finishes. Quality features include beautiful hardwood floors, intricate crown moldings, high ceilings and an expansive wraparound front porch. The open living area has a spacious dining room/living room combo with fireplace and is great for entertaining. Large windows make the kitchen and home light and bright with custom cabinetry, recessed under plus inner cabinet lighting and marble countertops. An expansive primary suite includes a large sitting area with a fireplace, luxurious bath and large walk-in closet. The 2020 renovation added new AC, insulation, new impact and triple pane windows for efficiency. Parking is easy with a circular driveway, carport and a 2-car garage with plenty of storage. Call today for an appointment!

567 Osceola Avenue, Winter Park
$1,425,000
3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
FEATURED ON HOUSE HUNTERS LAKEFRONT EDITION! Indulge in the epitome of LAKEFRONT luxury living on the shores of stunning Lake Killarney. Nestled within the vibrant heart of Winter Park, this exceptional residence offers a serene retreat on the largest private lake in Winter Park. Lake Killarney, a cherished gem, spans 259 acres of pristine, ski-able waters, ensuring exclusive tranquility for residents, with no access for non-residents. Convenience meets sophistication with this prime location, mere minutes from premier amenities including Whole Foods, Trader Joe's, REI, and the charming boutiques of Park Avenue Winter Park. Downtown Orlando, Maitland, Lake Mary, and the upscale shopping paradise of the Mall at Millenia are all within effortless reach, promising a lifestyle of unparalleled convenience. Step inside this bespoke custom home and be captivated by its distinctive features. With 10-foot ceilings, designer finishes throughout, and a meticulously crafted kitchen and baths, every detail exudes elegance. Boasting 3 bedrooms and a versatile loft that can easily transition into a fourth bedroom, along with 2.5 baths, this residence caters to every need. Embrace outdoor bliss with a dark bottom swimming pool, a private BOAT DOCK complete with a cradle, and lifts for both jet skis and paddle boards, ensuring effortless access to the water. Lavish low maintenance backyard landscaping with luxury turf surrounds the pool & lake, creating a picturesque oasis for relaxation and entertainment. Additional highlights include an upstairs balcony offering panoramic lake views, a secluded private courtyard, a spacious 2-car garage, and deluxe amenities such as a wine cooler, mini-fridge, and wet bar in the master suite. Granite and marble adorn the countertops and showers, while an oversized tub in the master bath provides the ultimate in indulgence. With an unrivalled level of craftsmanship and attention to detail, this home offers a lifestyle of unparalleled luxury. The value of this exquisite property surpasses its asking price, making it a wise investment in a rapidly appreciating area. Envision a life spent lounging by the pool, paddle boarding on the lake, or cruising to Hillstone for a waterfront dining experience. Create lasting memories with family and friends in your own slice of paradise at 580 Ololu Drive. Experience the epitome of lakeside living and make this dream home yours today.

580 Ololu Drive, Winter Park
$1,430,000
4 Beds ⋅ 4 Baths ⋅ Green Terrace SubDv. ⋅ 32789 Zip Code
Beautiful custom 4 bedroom 3.5 bath family home in the heart of Winter Park. Indulge your inner chef in the gourmet kitchen, featuring an expansive Island Bar with counter top seating, custom wood cabinetry, granite countertops, and a walk-in pantry, perfect for culinary enthusiasts. Enjoy formal meals in the separate dining room or more casual dining in the kitchenette. The kitchen’s open layout and spacious island overlook the inviting family room, ideal for entertaining guests. The primary bedroom, located on the first floor, features a walk-in closet, while its spacious ensuite has dual sinks, granite countertops, a separate tub and walk-in shower. French doors beckon you to the expansive backyard, creating seamless indoor-outdoor living. Work from home in the separate office space and unwind in the additional large bonus room, offering versatility for various lifestyles. Retreat to generously sized bedrooms for ultimate comfort and relaxation. With a great flow throughout the home, every space is thoughtfully connected for effortless living. Conveniently located near Winter Park hospital and surrounded by excellent schools, this home offers both luxury and practicality. Plus, indulge in fantastic shopping and dining options just minutes away in Historic Park Avenue. Schedule to see this home today!

1750 Carollee Lane, Winter Park
$1,875,000
5 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Welcome to your dream home! This exquisite 5-bedroom, 4-bathroom residence is a true masterpiece, perfectly blending luxurious living with traditional design. Boasting a spacious 3,703 square feet. Upon entering, you are greeted by a beautifully appointed foyer, dining room, formal living room and office, ideal for those who work from home. Primary bedroom suite located on the first floor. The home features a thoughtfully designed layout with wood floors that have been meticulously refinished to add warmth and elegance. The heart of the home is the brand-new kitchen, a chef's delight, modern cabinetry, and exquisite countertops. The open-concept design seamlessly connects the kitchen to the living spaces, creating an inviting atmosphere for entertaining friends and family. Upstairs spaces include 3 bedrooms and two bathrooms, storage room and a charming playroom, perfect for family enjoyment. This property offers not only comfortable living spaces but also a touch of luxury with a heated pool and spa, providing the perfect setting for relaxation and recreation. The professionally landscaped yard, surrounded by a new fence, ensures both privacy and a picturesque setting for outdoor activities, this stunning home sits on a generous 90'x125' lot, providing an expansive and private oasis. A unique feature of this property is the 2-car garage with an additional apartment above, perfect for guests or an active family. The entire property has been thoughtfully upgraded, including a new roof, new interior and exterior paint, and meticulous landscaping to enhance curb appeal. Located in a great neighborhood, this home is not just a residence; it's a lifestyle. With its prime location, impeccable upgrades, and thoughtful design, representing a rare opportunity to own a truly exceptional home. Don't miss the chance to make this your forever home!

1331 Wooddale Avenue, Winter Park
$1,260,000
5 Beds ⋅ 3 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
This custom 5-bedroom, 3-bath home just steps from Winter Park's exclusive Vias neighborhood features interior architectural accents throughout, including hardwood floors, architectural ceilings, and custom closets and shelving in each bedroom. Enjoy the 2,577 sq. ft. home's professionally designed lush landscaping, trees and backyard privacy from a heated saltwater pool and spa and covered lanai with stained tongue and groove ceiling. A gourmet kitchen with quartz counter tops includes an oversized island with seating for four, Miele and subzero appliances, white shaker style cabinets and a kitchen tile backsplash. The elegant master suite includes spacious closets, a soaking tub, large European sport showers, designer porcelain tile, and Moen faucets. Designed as a smart home perfect for entertainment and working from home, it includes high-speed WIFI with professional CAT 6 wiring, an upgraded alarm system with five cameras, and programmable Nest thermostats controlling the zoned air conditioning system. Other interior features include upgraded crown molding throughout, motorized blinds, 4-panel shaker solid core doors, 6-inch baseboards, and a tankless water heater. A covered front porch includes Old Chicago brick pavers, a tongue and groove ceiling, and metal roof. Other exterior accents include sand finish smooth stucco, Shaker siding on the front, a front covered porch , a sand set paver driveway and walkway, low voltage landscape lighting and a privacy fence. The garage was upgraded with epoxy flooring. This great location is zoned for top-rated schools including Dommerich Elementary, Maitland Middle, and Winter Park High School.

1320 Bessmor Road, Winter Park
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Mid Century Modern home with Craftsman style finishes perfect for the car enthusiast minutes from downtown Park Avenue. Single story ranch features soaring ceilings, large windows, slate looking porcelain tile floors throughout and custom Arts & Crafts style details throughout. Updated kitchen features Thermador appliances, Sub Zero refrigerator, custom cabinetry, cooking island and cozy seating area overlooking private walled gardens. Large primary suite with gas burning fireplace, individual sink areas, separate shower and tub area. Two separate 2 car garages have large rollup doors for recreational vehicles, cars and additional space for workshop and hobbies. One garage features 15' ceilings, air conditioning and rooftop terrace accessible by outdoor spiral staircase. Inside separate laundry room with lots of natural light.

1921 Englewood Road, Winter Park