Winter Park Homes For Sale & Real Estate - 404 homes

Remarks: Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect space to start your morning or end your day. To the left of the entry, you will find the large formal living room with 1 of 2 gas fires places located in this home. The bay window lets you take in views of your lush landscaped front yard and fills the space with tons of sunlight. Stepping off the entry you are greeted with a large formal dining room space. Sliders lead to the patio and the unique courtyard patio gives you views of your pool from not only the dining but the primary and family room all with sliders making this the perfect patio for parties, social gatherings and events. Just off the dining room you will find the great room including the breakfast area with built in cabinetry, the family room and the kitchen. The heart of the home is your kitchen, and this space has been designed for the chef of the home. White cabinetry, island, solid surface counter tops, lighting, and a huge walk-in pantry are just a few of the special touches you will find. Stainless steel appliances: Sub-Zero refrigerator, Bosh dishwasher, double oven, and microwave all the tools needs to create amazing meals. The family room's jewelry is the barrel ceiling a special touch you won't find often. Gas fireplace, spacious, Sliders leading to the patio as well as a screened patio area. The family room also includes a wet bar with ice market and wine frig. Just off the living room is the half bath. A separate area off the living could be a mother-in-law suite, she or he cave or the options are endless. a large bonus room includes a full bath which also doubles as the pool bath, sliders leading to a private yard space and a sink area. Upstairs in this area you will also find a full bedroom with vaulted ceilings and a full bath. To the right of the dining room, you will find 2 additional rooms and 2 full baths. The primary suite includes a sitting room with double doors leading to the bedroom, massive suite with bay window and views of the pool. not 1 but 2 full baths and 2 walk in closet because why share when you can have your own. This home also includes 2 tankless heaters, newer roof, well for sprinklers, home generator, skylights, dog run circular driveway custom drapes, auto blinds, freshly painted, artificial turf and so much more. So what are you waiting for?

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Steven Looper (321-662-3582)

Remarks: Under contract-accepting backup offers. Priced BELOW appraised value for a quick sale! Welcome to this stunning newer-construction townhome offering modern design, spacious living, and unbeatable value in one of Orlando’s most convenient locations. Featuring 3 bedrooms, 3 bathrooms, and nearly 2,000 sq ft of living space, this home boasts an open-concept layout, contemporary finishes, and abundant natural light throughout. The kitchen flows seamlessly into the main living area—perfect for entertaining—while the generously sized bedrooms provide comfort and flexibility for any lifestyle. Built in 2024, this home offers the peace of mind of newer construction with stylish, move-in-ready appeal.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Irene Navarro (786-224-8499)

Remarks: Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Drew Henner (407-406-0662)

Remarks: 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.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Nick Mckee (407-913-0171)

Remarks: One or more photo(s) has been virtually staged. Limited-time incentive: Seller offering a $20,000 buyer credit for qualified buyers. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers the perfect blend of timeless architecture and contemporary design, offering 5 bedrooms, 4 bathrooms, and nearly 2,900 sqft of refined living space. Step inside to discover: • 10-ft ceilings & 8-ft solid-core doors • Wide-plank luxury vinyl flooring throughout • Gourmet kitchen with quartz countertops, custom cabinetry, stainless steel appliances & oversized island • Elegant electric fireplace and expansive great room • Built-in wine cellar discreetly tucked under the stairs • Downstairs guest suite for added privacy Upstairs, the primary suite impresses with pool views and a spa-style bath: dual vanities, soaking tub, walk-in shower, and a generous closet. Three additional bedrooms include a Jack & Jill layout plus one with a private en-suite. A large upstairs laundry room adds convenience. Outside, your private backyard oasis awaits: • In-ground pool, fully landscaped • Summer kitchen with built-in grill • Covered patio for year-round entertaining Located just minutes from Park Avenue, this home offers walkability, top-rated schools, cultural landmarks, boutique shops, and dining. A rare opportunity to own new construction in one of Central Florida’s most iconic neighborhoods. Schedule your private tour today — this home defines the Winter Park lifestyle.

Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)

Listing Agent: Milena Fernandes (407-990-5905)

Remarks: Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.

Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)

Listing Agent: Adam Eisen (407-808-6967)

Remarks: One or more photo(s) has been virtually staged. Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect for modern living. Enjoy the freedom of no HOA, along with a layout ideal for families or entertaining. Midcentury modern-inspired design meets an open-concept layout with a spacious kitchen offering a large island, stainless steel appliances, pantry, granite countertops, full-height granite backsplash, and extensive cabinetry. The primary bath includes dual sinks and a frameless glass shower. Enjoy a large indoor laundry room and a private, oversized fully fenced backyard with a new paver deck and no rear neighbors. Ideal for outdoor living and entertaining. Additional highlights include a newly painted block shed with tin roof (2025) Zoysia grass installed in backyard, pavers installed in back, vinyl fence installed in backyard, GE refrigerator, washer and dryer, (2021) French doors in dining room and primary bath showerhead, (2020) Bosch dishwasher and (2018) Mitsubishi split air conditioner installed in primary bedroom and Mitsubishi split air conditioner installed in second bedroom. Just a short distance to the Winter Park YMCA, and minutes from vibrant Park Avenue, where you’ll find boutique shopping, the popular Winter Park Farmers' Market and a variety of top-rated dining options. In a sought-after school district, Lakemont Elementary, Maitland Middle and Winter Park High. This home combines location, lifestyle and convenience, making it a rare opportunity in one of Central Florida’s desirable communities.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Maryanne Branner (321-377-3909)

Remarks: Your pool home in Winter Park just became one of the best opportunities under $450K. Now priced at $449,900, this home offers 3 bedrooms plus a versatile bonus room, approximately 1,770 sq ft, a 2-car garage, and extended driveway — all in the established Eastbrook community with NO HOA. Major systems are already taken care of: roof 2018, solar panels 2020 (fully paid off), water heater 2019, and AC replaced in July 2013. A home warranty through First American Home Warranty is included, giving extra confidence on major components. Inside, the layout is bright and functional, with comfortable living and dining areas that flow naturally. The kitchen has been updated with granite countertops and modern cabinetry, and both bathrooms feature clean, updated finishes. The bonus room adds real flexibility — ideal for a home office, gym, playroom, or even a 4th bedroom setup depending on your needs. Outside, you have a fully fenced backyard with a private pool — the kind of feature buyers are actively looking for in this price range. There’s a good balance between pool deck and green space, making it usable and not just visual. Location is another strong point — just minutes to Park Avenue, Rollins College, Full Sail University, and University of Central Florida, with easy access to major highways and top-rated Seminole County schools. At this new price point, this is where buyers that were waiting start moving — especially for a pool home with no HOA in Winter Park.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Alexa Monasterio Flores (786-915-9294)

Remarks: This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer stainless steel appliances, and a closet pantry. There is a separate dining room that opens onto a very private brick paver patio with a new privacy fence. This unique condo features a flexible layout, an inside utility, and includes the washer & dryer. Modern-design porcelain tile flooring. The home has a large screen porch, which is considered by many in Florida, to be extra living space. There is also a front courtyard that is perfect for a raised bed garden or ???. Highly desired Winter Park schools. A 2-car carport with an ample lockable storage closet. New roof in 2020 and an updated electric system. The complex has a private community pool

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Greg Harrison (407-276-6141)

Remarks: Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features laminate flooring throughout, creating a modern and cohesive living space. The unit is ideally located close to shopping, dining, and everyday conveniences, making daily living easy and enjoyable. With lake access just steps away, you can take in the serene waterfront setting while still being minutes from everything Winter Park has to offer. Lawn care is included, ensuring a well-maintained and picturesque community year-round. Don’t miss this opportunity to enjoy lakefront living with resort-style amenities in one of Central Florida’s most desirable areas.

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This low-maintenance Winter Park one-story condo just became even more affordable ... 4.99% FIXED Interest Rate for 7 years!! This is NOT a buydown... savings of $200/mo or more! This one-story corner unit is Move-in Ready offers privacy, a screened patio overlooking a serene and well-manicured courtyard, and beautiful updates. Inside you will love the updated kitchen with added storage solutions, beautiful updated bathrooms, AND all major mechanical updates already taken care of. With a New Roof, Updated Electrical, Newer A/C, Replaced Water Heater and so much more... plus the community amenities include a pool, sidewalks, pet stations, and an unbeatable Winter Park location - and this 2-bedroom, 2-bath condo offers the ideal combination of comfort, convenience, privacy, and value. Inside, you’ll find a functional split-bedroom floor plan, spacious living and dining areas, indoor laundry, and a screened patio that adds valuable outdoor living space. The one-story layout offers easy everyday living, while the corner-unit location provides added privacy and a more desirable setting within the community. The flexible floor plan works well for everyday living, guests, roommates, or even a home office setup. Located in a community with a pool and situated near shopping, dining, major roadways, and daily conveniences, this property offers easy access to University of Central Florida, Full Sail University, SR-417, FL-436, Downtown Winter Park, and Downtown Orlando. Whether you are searching for a primary residence, a first home, or a low-maintenance property in a central location, this home checks all the boxes. The special financing rate equates to a savings of approximately $213 per month. Now more than ever, if you’ve been searching for an affordable, easy-maintenance, Move-in Ready property in Winter Park ... this is your sign! Seller offering an incredible savings to help you on your path to homeownership. Terms and conditions apply. Call for details.

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Allison Day (407-617-2881)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character while offering the lifestyle people move here for. This 3-bedroom, 2-bathroom home contains 1,356 square feet of thoughtfully updated living space designed for both comfort and style. From the moment you step inside, you'll notice the clean, modern feel created by zero carpet throughout the entire home, giving every room a fresh, cohesive look while making maintenance simple and practical. At the center of the home is the fully updated kitchen, featuring beautiful granite countertops, ample cabinetry, and a functional layout perfect for everyday living or entertaining guests. The kitchen serves as the heart of the home, separating the spacious living room from the formal dining room, creating a natural flow between gathering spaces while maintaining distinct areas for relaxing and hosting. Both bathrooms have been fully renovated, showcasing modern finishes that complement the home's updated aesthetic. Each bedroom offers comfortable space, natural light, and flexibility for a primary suite, guest room, or home office. Convenience continues with the laundry closet featuring a newer stackable washer and dryer, maximizing space while keeping everyday tasks simple and efficient. Step outside and you'll find a fully fenced backyard, providing privacy and plenty of room for pets, outdoor gatherings, or simply enjoying Florida’s beautiful weather. The property also includes an oversized covered carport, offering generous parking and protection from the elements. For electric vehicle owners, the carport is already equipped with a Tesla charger, making daily charging effortless and future-ready. What truly sets this property apart is its unbeatable location. Situated in historic Carver Town, you're just minutes from the charm and vibrancy of downtown Winter Park. Enjoy easy access to Park Avenue’s award-winning restaurants, boutique shopping, art galleries, and cultural attractions. Spend weekends exploring the Winter Park Farmers Market, taking a scenic boat tour on the Winter Park Chain of Lakes, or strolling through Central Park’s shaded oak-lined paths. Whether you're looking for a primary residence, a stylish Winter Park retreat, or a home close to everything that makes this city special, 720 W Webster Avenue delivers the perfect combination of location, updates, and lifestyle. Opportunities to own a fully renovated home this close to downtown Winter Park are rare. Schedule your private showing today and experience everything this exceptional property and location can provide!

Listing is courtesy of: SERHANT (646-480-7665)

Listing Agent: Vincent Cordaro (631-834-0816)

Remarks: Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping.  Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool.  Spacious layouts, refined detailing, and quality construction create a elevated yet livable environment, all set within a beautifully landscaped and private setting. Please inquire for details and customization options.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Matthew Burks (407-257-5347)

Remarks: In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Padgett Mccormick (407-645-4321)

Remarks: Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C, and water heater. Step inside to a Sun-filled sanctuary featuring new luxury vinyl plank flooring and gorgeous tile. The heart of the home is the brand-new chef’s kitchen, featuring custom white oak wood cabinetry, rare Taj Mahal quartzite countertops, and elegant champagne bronze finishes throughout. The kitchen flows seamlessly into the living areas, where new tile work elevates the wet areas for a cohesive, upscale feel. Work from home in style in the dedicated bonus room, an ideal footprint for a private office or creative studio. This home features true functionally for a family to live in everyday. This one of a kind home features a custom in home laundry room, custom vanities, a fireplace made to enhance the homes aesthetic & custom doors through the entire home. Beyond the interior, your private Florida lifestyle awaits. Retreat to the expansive screened-in pool, patio and large backyard. Located just steps from the Winter Park Pines Golf Course and the scenic Cady Way Trail, this home offers more than just a renovation—it offers a lifestyle. Enjoy easy access to the clubhouse for dining, top-rated schools, and the vibrant culture of downtown Winter Park. With every detail thoughtfully curated and major systems already updated, this is the turnkey masterpiece you’ve been waiting for.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Rene Droz, Iii (407-484-8786)

Remarks: Canal Front Oasis on the Winter Park Chain of Lakes! (Seller Financing Available for Qualified Buyers) Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4-bedroom, 3-bath residence offers 3,142 square feet of inspired living space set amid lush, tropical landscaping — all within the best of Winter Park and Maitland. *The canal allows for full Lake Maitland and Winter Park Chain of Lakes access by powerboat. (Current owners have a 19' outboard they use to pull tubes, ski, wakeboard, quick trips to dog island and entertaining via scenic tours through the Winter Park Chain of Lakes.) Originally built in 1959 and completely renovated in 2022, this two-story retreat combines rustic charm with modern luxury. Step inside to discover an open floor plan anchored by a gas fireplace, open kitchen and dining room, warm custom woodwork, and thoughtful built-ins throughout. The renovation includes new electrical, plumbing, new kitchen and baths, engineered hardwood flooring throughout, amongst many more upgrades. The redesigned layout adds over 1,000 square feet, featuring a spacious first-floor laundry room and an all-new second story with a luxurious primary suite, a guest bedroom (currently used as an office), and a full bathroom. Outdoors, enjoy a new boathouse on a canal and an inviting outdoor living area — perfect for entertaining or unwinding along the peaceful canal that connects directly to Lake Maitland and the renowned Winter Park Chain of Lakes. The rear of the property backs up to a wooded conservation area that provides privacy and tranquility. The current owner received a variance for a future pool, and Orange County previously had no objections to pool installation (new owner would need to reapply). The property sits in one of Central Florida’s most sought-after school zones: Dommerich Elementary, Maitland Middle, and Winter Park High. Families here often bike or walk to school. Enjoy regular walks through scenic streets lined with mature cypress trees, palms, vibrant native vegetation and beautiful homes that line Lake Maitland. With no HOA, residents may optionally join the neighborhood association (approx. $120/year) for access to two lakefront parks and a private boat ramp. From the modern amenities and artful landscaping to the serene waterfront setting, this is truly a one-of-a-kind property that blends nature, comfort, and sophistication in the heart of Winter Park. *Canal boat tour video that showcases the trip from the canal to Lake Maitland is available via the virtual tour link in the listing.

Listing is courtesy of: PLAID PROPERTIES, LLC (407-702-0864)

Listing Agent: Andrew Birr (407-702-0864)

Remarks: **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and charm in one of Orlando’s most sought-after communities. Designed for both everyday comfort and effortless entertaining, the first floor features an open-concept kitchen and living area filled with abundant natural light, along with a convenient half bath—ideal for hosting guests. Upstairs, the spacious primary suite boasts a private ensuite bathroom, walk-in closet, and a newly refinished balcony—perfect for morning coffee or evening cocktails. Two additional bedrooms provide generous space and share access to a second balcony, creating a seamless indoor-outdoor living experience. Recent upgrades include a new dishwasher and smart refrigerator (2022), new water heater (2025), refinished front balcony (2025), new roof, and new carpet upstairs (2026). Updated light fixtures and primary bedroom flooring within the last five years add a modern touch throughout. The $400 monthly HOA fee includes landscaping and insurance, offering low-maintenance living and added peace of mind. Zoned for some of Orlando’s top-rated schools and walking distance from the new Audubon Park K-8 School, this home presents a rare opportunity to enjoy the very best of Winter Park living. Don’t miss your chance to call this exceptional property home.

Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)

Listing Agent: Courtney Dietch (407-952-3779)

Remarks: This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have tile flooring. The Primary Bedroom has Luxury Vinyl Flooring. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently being used for storage. The Roof was replaced in 2022 and the yard has a sprinkler system. Make an appointment to see today!!

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Diane Gerry Pa (407-405-5550)

Remarks: One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, Fresh New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with dark wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Cable & Internet, Lake Access & Dock, Pool & Clubhouse, and Designated Parking.

Listing is courtesy of: THE ANDERSON GROUP & CO PL (407-960-5657)

Listing Agent: Alison Maltby (407-325-1483)

Remarks: Under contract-accepting backup offers. Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers unique architectural appeal paired with thoughtful modern enhancements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers excellent curb appeal and outdoor functionality. Inside, the home has seen numerous recent updates, including new quartz kitchen countertops (2025), updated bathrooms, and updated walls and flooring throughout. The bonus room provides flexibility for use as an additional bedroom, home office, or secondary living area. Major system improvements include PEX plumbing, a newly installed 17 SEER AC system, a new water heater, electrical updates completed in 2008, and a metal roof installed in 2013 over 1x12 tongue-and-groove decking, offering exceptional strength and longevity. The home is protected by an active termite bond, with Sentricon installed in 2025. The backyard is highlighted by a 15’ x 30’ in-ground pool, a new vinyl fence (2023), and a five-zone in-ground sprinkler system with a programmable timer. The property is located in Flood Zone X (no flood insurance required) and has no HOA. Enjoy an excellent location known for top-rated schools, just minutes from AdventHealth, Full Sail University, FL-436, and an abundance of shopping and dining options. Do not miss the opportunity to purchase a well-maintained home with proven rental income and long-term investment potential.

Listing is courtesy of: SOUTHERN LAND & HOMES (850-973-2200)

Listing Agent: Benjamin Jones (850-673-7888)