Homes for Sale Between $800,000 to $900,000 in Winter Park, FL

4 Beds ⋅ 3 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to Waters Edge at Hawks Crest, one of Winter Park’s premier gated communities! This beautifully appointed 4-bedroom, 3-bath home offers nearly 3,000 square feet of thoughtfully designed living space, exceptional curb appeal, and an outdoor entertaining area that truly sets it apart. Step inside to a welcoming foyer flanked by a formal dining area and a versatile formal living room with double doors—perfect for a home office, den, or flex space. At the heart of the home is an impressive gourmet kitchen featuring quartz countertops, a large center island with stainless undermount sink, wall oven/microwave combination, cooktop with stainless steel range hood, metallic hexagon tile backsplash, modern pendant lighting, and a technology-equipped refrigerator. The kitchen flows seamlessly into the casual dining and family room, creating an open-concept gathering space filled with natural light from oversized triple sliding glass doors. An electric shade provides added privacy and makes movie nights a breeze. The spacious primary suite offers a striking stacked-stone entry and a separate flex area ideal for a sitting room, office, nursery, or workout space, with direct access to the lanai. The ensuite bath features dual quartz vanities, a soaking tub, large tiled shower, private water closet, and an impressive custom-designed walk-in closet with abundant storage. The split-bedroom floor plan provides three additional bedrooms, two full baths—including a convenient pool bath—and a dedicated laundry room. The garage offers additional storage racks, while solar-powered Tesla panels and two Powerwalls add another notable feature to the home. The showstopper is the expansive screened lanai, designed for year-round Florida living and entertaining. Multiple conversation and dining areas, an outdoor kitchen, TV area, oversized premium spa with additional jets, and app-controlled lighting create the perfect setting for everything from intimate evenings to large gatherings. A 6-foot privacy fence completes this private backyard retreat. Residents of Hawks Crest enjoy an impressive collection of community amenities, including a clubhouse with indoor and outdoor entertaining spaces and grills, resort-style pool, splash pad, playgrounds, fitness center, putting green, outdoor games, dog park, neighborhood parks, and access to a community dock on Lake Howell.

2052 Wood Thrush Lane, Winter Park

$899,900

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 2nd Add SubDv. ⋅ 32792 Zip Code

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021 and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020 and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024. The garage is air-cooled. Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional, conveniently situated in a wonderful community with Cady Way pool and Cady Way trail, which spans 7.2 miles and connects to the Seminole Trail outdoor recreation. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park

$899,000

4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

3006 Northwood Boulevard, Winter Park

$899,000

Fairbanks Park SubDv. ⋅ 32789 Zip Code

Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and entertainment. Lots like this are seldom available. Whether you’re envisioning a custom residence or an investment in one of Central Florida’s most desirable neighborhoods, this is a truly rare opportunity in the heart of Winter Park.

731 Midget Drive, Winter Park

$879,000

3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $879,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape. Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests. At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.

1621 Chestnut Avenue, Winter Park

$875,000

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 4th Add SubDv. ⋅ 32792 Zip Code

Virtually Staged. FULLY RENOVATED 4-BEDROOM, 3-BATH POOL HOME IN THE HEART OF WINTER PARK! this beautifully updated home sits on a spacious 9,915-square-foot lot surrounded by mature trees and charming streets. Thoughtfully renovated from top to bottom, this move-in-ready property offers modern finishes, major system upgrades, and the Florida lifestyle you've been looking for! Step inside to discover a bright, inviting interior featuring NEW FLOORING THROUGHOUT, NEW WINDOWS, AND FRESH INTERIOR AND EXTERIOR PAINT. The completely remodeled kitchen showcases NEW CABINETRY, NEW APPLIANCES, AND UPDATED FINISHES, creating a stylish and functional space for everyday living and entertaining. Enjoy added peace of mind with a NEW ROOF (2025), NEW AC SYSTEM (2025), AND NEW WATER HEATER.Step outside to your private backyard retreat featuring a FULLY RESURFACED POOL and a spacious, fenced yard perfect for relaxing, entertaining, and enjoying Florida's beautiful weather year-round. The property also features a 2-CAR GARAGE AND AN OVERSIZED DRIVEWAY, providing plenty of additional parking. Washer and dryer are included! Ideally located just minutes from **CADY WAY TRAIL, PARK AVENUE, ROLLINS COLLEGE, AND WINTER PARK PINES GOLF CLUB, with convenient access to shopping, dining, parks, and major roadways. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School. Enjoy the charm of an established Winter Park neighborhood with the convenience of a fully updated home. ALL THE MAJOR UPDATES HAVE BEEN DONE—JUST MOVE IN AND ENJOY! Some photos have been virtually staged.

618 Blairshire Circle, Winter Park

$860,000

5 Beds ⋅ 4 Baths ⋅ Lake Ann Estates Unit 3 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet of elegant living space. A dramatic two-story foyer with a sweeping staircase welcomes you into light-filled formal and casual living areas, including a spacious great room anchored by a fireplace. The gourmet island kitchen features rich cabinetry, stainless steel appliances, and generous counter space, flowing effortlessly to the surrounding living and dining spaces finished with wood-look flooring. The expansive primary suite provides a spa-like bath with a soaking tub and a separate glass-enclosed shower, while four additional bedrooms offer ample room for rest or a home office. Outside, a screened, in-ground pool and spa are framed by a paver deck and a large fully fenced yard, complemented by a covered patio and an oversized three-car garage. A rare offering of space and comfort on a generous, secluded lot. Included 100-Day Home Warranty with buyer activation

120 Longbranch Road, Winter Park

100 S Interlachen Avenue Unit 401, Winter Park

$850,000

3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park

$850,000

Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code

Bring your vision to life in Winter Park. Situated on N Phelps Avenue, this approximately .24-acre property offers a rare opportunity to build new in an area surrounded by custom homes, luxury residences, and ongoing redevelopment. Offered for its land value, this property is well suited for builders, investors, developers, or anyone ready to create a home designed around their own style and needs. The 75-foot frontage with 140-foot depth provides flexibility for a variety of architectural designs and potential for outdoor living, a pool, and backyard space. With new construction continuing to reshape the surrounding area, 870 N Phelps presents an exciting opportunity to secure a sizable homesite and build from the ground up.

870 N Phelps Avenue, Winter Park

$849,000

3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code

Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

437 N Capen Avenue, Winter Park

$849,000

2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

$836,000

3 Beds ⋅ 3 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code

Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Now offering $10,000 Seller Credit! Call to schedule your showing today!

338 Blue Heron Drive, Winter Park

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