Homes For Sale in Winter Park 32789 - 218 homes

Remarks: Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

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

Listing Agent: Ellen Bessette (407-496-0076)

Remarks: Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Thomas Bonner (407-401-3748)

Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor corner residence in Whispering Waters—one of Winter Park's most sought-after 55+ communities. Perfectly positioned adjacent to Lake Osceola and just steps from iconic Park Avenue, this rare offering places award-winning dining, boutique shopping, the Winter Park Farmers' Market, Rollins College, Central Park, museums, and scenic lakeside strolls all within easy walking distance. Inside, the bright and open floor plan is thoughtfully designed to maximize both space and natural light. The kitchen, dining, and living areas flow seamlessly together, creating a comfortable setting for everyday living or entertaining. Multiple storage closets greet you upon entry, while a separate hallway provides additional storage and convenient access to the full bathroom—an uncommon feature for a studio-style residence that enhances both functionality and privacy. One of the home's standout features is the generously sized private screened balcony, offering a true extension of the living space. Overlooking the beautifully landscaped interior courtyard with peaceful views of the community pool and Lake Osceola beyond, this inviting outdoor retreat is the perfect place to enjoy your morning coffee, unwind with a glass of wine, dine al fresco, or simply relax while enjoying the fresh Florida air. It's also a wonderful setting to wave hello and visit with neighbors, reflecting the warm sense of community Whispering Waters is known for. Residents enjoy an exceptionally low-maintenance lifestyle, with electric, gas, water, sewer, and trash all included in the condominium fee. Additional amenities include elevator access, on-site management, a community laundry facility, beautifully maintained common areas, expansive lakefront patios overlooking Lake Osceola, a resident club room, and a sparkling community pool. Whether you're searching for a full-time residence, a seasonal escape, or an elegant home for a family member, this exceptional property offers an affordable opportunity to enjoy the coveted Winter Park lifestyle in one of Central Florida's most desirable locations.

Listing is courtesy of: TURN-KEY MOVES REALTY (407-796-2221)

Listing Agent: Mathew Kelly (407-796-2221)

Remarks: Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Jennifer Sloan (407-810-8333)

Remarks: Under contract-accepting backup offers. Virtually Staged. *** JUST REDUCED TO $625,000 | 1830 Edwin Blvd, Winter Park, FL 32789*** This is your moment. One of Winter Park's most beautifully RENOVATED and MOVE-IN READY homes has just been repriced, and at $625,000, it will not last long. From the moment you step inside, you are welcomed by an open, airy layout with soaring VAULTED CEILINGS that make the home feel expansive and inviting. Gorgeous TILE FLOORING flows seamlessly throughout every room, while natural light floods the space through DOUBLE-PANED WINDOWS (2018) and remote-controlled German Velux SKYLIGHTS (2021), creating an atmosphere that simply feels good to be in. The thoughtfully designed floor plan connects the living, dining, and kitchen areas in a way that is as functional as it is beautiful, making it ideal for everyday living and effortless entertaining. At the heart of the home, the stunning CUSTOM EUROPEAN-STYLE KITCHEN is a true showpiece, featuring premium Cambria quartz countertops (2025) and top-of-the-line appliances including a NEW refrigerator (2025), BOSCH dishwasher (2024), and Maytag microwave (2022). This kitchen was designed to impress and built to perform. Both bathrooms have been FULLY REMODELED with sleek modern finishes and NEW VANITIES (2025). All interior doors were replaced (2017), and every detail has been carefully considered to deliver a home that feels truly turnkey from top to bottom. For peace of mind, major systems have all been upgraded. A high-efficiency Amana AC with smart thermostat (2024), a tankless water heater (2025), a complete PEX plumbing upgrade to the city connection (2025), modernized PVC drain lines in the bathrooms, laundry and kitchen (2025), new sinks and faucets (2025), and updated kitchen electrical wiring to current code (2025) mean you can move in with complete confidence. NEW ROOF (2021). Step outside to your own private retreat. A fenced backyard (2018) and screened patio (2022) create the perfect space for relaxing or entertaining year-round. Driveway pavers (2024), a carport (2024), and an OVERSIZED Tuff Shed (2024) round out an exterior that is just as polished as the interior. Smart home features including electronic front door locks (2023), a smart ceiling fan (2023), and smart kitchen lighting (2025) add a layer of modern convenience that ties it all together beautifully. And the location? Simply unbeatable. Just minutes from the legendary Park Avenue, and within walking distance to premier shopping, dining, parks, and everyday conveniences, this home places you right in the heart of everything Winter Park has to offer. Location. Layout. Quality. This home has it all, and now at a price that reflects real value in today's market. Opportunities like this do not come around often. *** SCHEDULE YOUR SHOWING TODAY BEFORE IT IS GONE! ***

Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)

Listing Agent: Nydia Marrero (407-620-6221)

Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredible location come together on a quiet tree-lined street. Ideally positioned just a short golf cart ride from Park Avenue, the YMCA, and Interlachen Country Club, this home offers the perfect combination of privacy, convenience, and refined Winter Park living. From the moment you step inside, an impressive foyer greets you, showcasing intricate marble mosaic tile that sets the tone for the craftsmanship found throughout. The open-concept floor plan flows effortlessly into the main living spaces, where the spacious living room serves as the centerpiece of the home with elegant archways, custom shelving with LED underlighting, warm wood beam accents, and a stunning stone-wrapped fireplace creating the perfect balance of sophistication and comfort. Designed for both everyday living and entertaining, the dining room features a beautiful dry bar complete with a wine refrigerator, while the chef’s kitchen is truly the heart of the home. Outfitted with Calacatta quartz countertops, a paneled built-in refrigerator, a full suite of Thermador appliances, and a spacious walk-in pantry, every detail has been thoughtfully selected to deliver both style and functionality. The first-floor primary suite provides a private retreat with generous proportions and a spa-inspired bathroom featuring marble mosaic tile, dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large walk-in closet. A rare additional first-floor guest suite adds incredible flexibility for family and visitors. Upstairs, the home continues to impress with a spacious loft, a conveniently located laundry room, and three additional bedrooms, offering plenty of room for everyone. Step outside and experience your personal outdoor oasis with a spacious covered lanai featuring a full summer kitchen overlooking the sparkling pool and spa. The oversized backyard provides an abundance of green space, creating the perfect setting for relaxing, entertaining, or enjoying time with family. Additional highlights include impact-rated windows and doors, premium finishes throughout, and an unbeatable location surrounded by some of Winter Park’s most desirable amenities. This is a rare opportunity to own a brand-new home combining thoughtful design, exceptional craftsmanship, and one of Central Florida’s most sought-after lifestyles.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!

Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)

Listing Agent: Andrew Musashe (407-645-5700)

Remarks: Under contract-accepting backup offers. Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: LOCATION! LOCATION! LOCATION! Welcome to Knowles Manor...a charming 11 unit condo perched on quiet brick street in the heart of Olde Winter Park...just steps from the Winter Park 9 golf course, Casa Feliz, and the boutiques, restaurants, and vibrant lifestyle of Park Avenue, this location is hard to beat. This delightful first-floor residence is the perfect place to call home or an ideal pied-a'-terre for seasonal living. Inside you'll find easy maintenance tile flooring throughout, a full kitchen and bath, abundant closet space, and an adorable screened rear porch-perfect for relaxing with your morning coffee or unwinding at the end of the day. Additional highlights include a quaint community patio, one assigned parking space steps from your front door, a new HVAC system installed in 2021, and a new roof 2025. Whether you are looking for a full time residence, a weekend retreat, or a low maintenance Winter Park getaway, this charming condo is ready to welcome you home. Welcome Home!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Catherine D'Amico (407-252-3210)

Remarks: Welcome to this beautifully updated one-bedroom, one-bath condo in the heart of Winter Park. Thoughtfully maintained and move-in ready, this inviting home offers a bright, clean interior with tasteful finishes and a functional layout designed for comfortable, low-maintenance living. A spacious screened porch overlooks a serene courtyard, creating the perfect spot to enjoy your morning coffee or unwind at the end of the day. Perfectly situated, this home is nestled between two beautiful parks—Mead Botanical Garden, just steps away, and Seven Oaks Park—offering easy access to nature, walking paths, and green space. You're also just minutes from Rollins College, the boutiques and restaurants of Park Avenue, AdventHealth Winter Park, and the vibrant Mills 50 District. Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Orlando Urban Trail, Dinky Line Trail, and Baldwin Park, all just a short bike ride away. With convenient access to Orlando Avenue (US-17/92), I-4, and both the Winter Park and AdventHealth SunRail stations, commuting throughout Central Florida is effortless. Located in the desirable Mead Garden Condominiums community with a sparkling pool and beautifully maintained grounds, this charming condo offers an exceptional blend of comfort, convenience, and the best of the Winter Park lifestyle.

Listing is courtesy of: FAIRBANKS REALTY (407-758-1323)

Listing Agent: Randy Wilson (407-758-1323)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake Killarney views, and a peaceful setting on a quiet private lakefront street. From the moment you enter, pride of ownership shines through, with custom built-ins throughout creating stylish and functional living spaces. The heart of the home is the updated kitchen and dining area, featuring high-end bamboo floors, stainless steel appliances, real wood custom cabinetry, and a large island overlooking a versatile flex space perfect for a formal living room, den, or office. The spacious great room is warm and inviting with a wood-burning fireplace and a dramatic wall of four French doors that fill the space with natural light. The elegant primary suite offers a walk-in closet and a spacious bath with dual vanities, a soaking tub, and separate shower. Step outside to a covered patio and expansive backyard with plenty of room to entertain, garden, or unwind. Just minutes from Park Avenue, premier shopping, dining, and Winter Park’s beloved parks and amenities, this is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods on .33 acres. Brand new roof and newer AC for total peace of mind. Schedule a private tour today.

Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)

Listing Agent: Jacob Johnson (407-353-0106)

Remarks: Under contract-accepting backup offers. Virtually Staged. Located in the heart of Orwin Manor, one of Winter Park’s most beloved historic neighborhoods, 1521 Cavendish Road is a beautifully renovated 2-bedroom, 1-bath home offering 1,042 square feet of thoughtfully updated living space. Positioned between Winter Park, College Park, and Downtown Orlando, residents enjoy convenient access to AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, Park Avenue, Ivanhoe Village, and some of the area's most celebrated dining, shopping, and cultural destinations. Surrounded by mature landscaping, manicured hedges, colorful garden beds, and stately palms, the home's curb appeal reflects the character and pride of ownership found throughout the neighborhood. French front doors open to a spacious foyer that leads into a bright family and dining room combination, where new pine laminate flooring, crown molding, plantation shutters, and updated lighting blend historic character with modern comfort. The renovated kitchen features shaker cabinetry, Silestone countertops, stainless steel appliances, abundant storage, and natural light. Both bedrooms have been thoughtfully updated with new flooring, LED recessed lighting, ceiling fans, and plantation shutters, while the recently renovated bathroom pairs basketweave tile flooring, subway tile, quartz countertops, and classic finishes that honor the home's original style. Outside, the large backyard has been transformed into a private retreat featuring a composite deck, new fencing, mature palms, raised garden beds, steel-edged landscaping, and a paver walkway. Thoughtfully updated while preserving its architectural charm, this home offers a rare opportunity to enjoy historic character in a neighborhood that continues to benefit from the growth, investment, and enduring appeal of Winter Park and Downtown Orlando. Schedule your private tour today.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: John Goggin (321-332-3000)

Remarks: Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: Rare lakefront opportunity on the beautiful pristine Lake Killarney in the heart of Winter Park! Build your dream home on this coveted corner lot graced by original brick streets. Lake Killarney is a crystal-clear, spring-fed private lake — motorized boats welcome, yet no public boat ramp ensures a peaceful, exclusive experience. Enjoy sweeping 1-mile sunset views from one of only three homes on a quiet dead-end street. Walk to Hillstone, Trader Joe's, and 20+ world-class restaurants. An additional 40 X 65 ft from rear lot line is available to purchase to extend the footprint of your dream home. This extended lot size will create approx 10,000 sf lot. This is Florida lakefront living at its finest — don't miss it!

Listing is courtesy of: PROMAX PROPERTY SOLUTIONS (407-647-3377)

Listing Agent: David Murray (407-647-3377)

Remarks: This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.

Listing is courtesy of: GM SUNSHINE REALTY LLC (407-376-1261)

Listing Agent: Giuseppina Moriconi (407-376-1261)

Remarks: Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Stephanie Baldner (407-419-0629)

Remarks: Under contract-accepting backup offers. Virtually Staged. Set apart from the ordinary, this historic Winter Park residence offers a rare opportunity to own a home rich in character and authenticity. Homes like this, with timeless architectural detail and enduring charm, rarely come to market, especially in such a premier location just steps from the shores of Lake Virginia. Surrounded by multi million dollar estates, this 4 bedroom, 2 bath home blends classic warmth with everyday livability. Original wood floors, a wood burning fireplace, and thoughtfully designed living spaces reflect a level of craftsmanship and character that simply cannot be replicated. The spacious dining room is perfect for hosting memorable family gatherings, while the updated kitchen with wood cabinetry offers both function and charm. Upstairs, a versatile loft space provides flexibility for a media room, office, or play area, complete with peekaboo views of Lake Virginia that create a subtle connection to the surrounding landscape. Adding to the home’s appeal is a detached 20 x 20 studio flooded with natural light and offering endless possibilities, ideal for an artist’s retreat, home office, gym, or guest space.This is more than a home, it is an opportunity to own a piece of Winter Park’s character and history. Set among some of Winter Park’s most distinguished homes, this property delivers an unbeatable lifestyle, walkable to all that Park Avenue has to offer, surrounded by luxury, and full of potential to enjoy, enhance, or reimagine.

Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)

Listing Agent: Elizabeth Nordquist (407-694-0996)

Remarks: Under contract-accepting backup offers. Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noir is a custom-built statement home located within one of Winter Park's most desirable pockets and zoned for Audubon Park K-8. From the moment of arrival, the home's striking blend of natural stone, warm white oak, rich textures, and beautifully composed architectural lines creates an unforgettable first impression. Step inside and you're immediately greeted by soaring ceilings, exposed oak beams, wide-plank white oak flooring, and expansive walls of glass that fill the home with natural light. The great room serves as the heart of the residence, anchored by a floor-to-ceiling natural stone fireplace with illuminated built-ins and expansive sliders that seamlessly connect indoor and outdoor living. At the center of the home, you'll find a beautifully executed kitchen designed for both entertaining and everyday living, featuring floor-to-ceiling custom white oak cabinetry, designer stone surfaces, a substantial center island, illuminated wine display, a 48-inch gas range, and abundant storage. Nearby, a walk-in pantry, fully built-out laundry room, and mudroom enhance functionality while maintaining the home's refined design language. Privately positioned on the main level, the dedicated office provides an inspiring setting for work, study, or creativity, while the primary suite serves as a true retreat. The spa-inspired bath is finished with floating oak vanities, rich stone surfaces, a freestanding soaking tub, and an expansive wet room that feels more like a luxurious resort. It's the kind of retreat you'll appreciate every morning and look forward to returning to at the end of each day. Upstairs, a versatile loft creates the perfect setting for a media room, playroom, study space, or secondary gathering area. One bedroom enjoys the privacy of its own ensuite bath and walk-in closet, while two additional bedrooms are connected by a beautifully appointed Jack-and-Jill bath. Step outside and you'll find yourself lingering a little longer than planned. A custom PebbleTec pool, covered tongue-and-groove lanai, fully integrated outdoor kitchen, and private backyard setting create an environment designed for effortless entertaining and low-maintenance enjoyment. Built by Structure Redevelopment, a boutique builder known for delivering thoughtfully crafted custom residences throughout Central Florida. Just minutes from Park Avenue, Rollins College, East End Market, Audubon Park, and Downtown Orlando, Casa Noir brings together exceptional architecture, thoughtful design, and everyday livability in one of Winter Park's most desirable locations - Schedule your tour today.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Ahmad Hassan, Pa (718-641-9358)

Remarks: Under contract-accepting backup offers. Welcome to one of Orlando's most beloved neighborhoods, where tree-lined streets, golf course views, and a true sense of community create the lifestyle buyers are searching for. Perfectly positioned across from the 5th tee of historic Dubsdread Golf Course, this beautifully renovated home places you in the heart of the Dubsdread bubble—just minutes from the dining, shopping, and charm of both College Park and Winter Park. Set on an oversized .22-acre lot, this move-in-ready residence offers over 1,500 square feet of thoughtfully updated living space, blending classic character with today's most desired upgrades. Inside, you'll find refinished original hardwood floors, a fully renovated kitchen featuring stunning quartz countertops, new cabinetry, and new stainless steel appliances, plus two completely renovated bathrooms with fresh, timeless finishes. A 2023 rear addition adds valuable living space, while the inviting Florida room and screened porch provide the perfect spots to enjoy morning coffee, entertain friends, or unwind after a round of golf. Beyond the cosmetic improvements, the heavy lifting has already been done. Enjoy peace of mind with updated plumbing (2026) including removal of cast iron piping, updated electrical (2026), roof (2020), tankless water heater (2023), and energy-efficient windows (2023). Homes in the Dubsdread District rarely offer this combination of location, charm, lot size, and major renovations. Whether you're drawn to the golf course views, the walkable neighborhood feel, or the proximity to Orlando's best restaurants, parks, and entertainment, this home delivers the lifestyle that makes this area one of Orlando's most desirable places to call home. Move-in ready, extensively updated, and perfectly located—schedule your private showing today!

Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)

Listing Agent: Emily Nickley (407-448-0556)