Homes For Sale in Winter Park 32789 - 233 homes

Remarks: Welcome to 147 Interlachen Place, Enjoy Winter Park's most desirable location! One block from Historic Park Avenue/Central Park. Spacious, bright and all on ONE FLOOR. The buildings second floor offers privacy and easy access. The Southwest corner provides direct natural light throughout the day. Private elevator access with secured underground parking. This beautiful home offers a short walk to everything Winter Park, a pedestrian village of delight! Natural light fills the central courtyard which features an iron water fountain. Private pool with heated spa and outdoor grilling and entertaining area. Interior features include fireplaces in living room, 2 Southwest facing covered outdoor walkout balconies, accessed by living room, den, master bedroom and one directly over looking the pool. Master bathroom includes separate tub and shower, dual closets, split vanities and plenty of storage space. 4 full bath- 1 half bath (5). Two specified parking spaces also have large storage closets with security gate and elevator access to your floor. K-8 Audubon School district! Unit / building “horseshoe” configuration provides no neighbors on any of the 4 sides, courtyard interior, Private Luxury Living all on ONE floor!

Listing is courtesy of: HELLOSOLD LLC (954-778-5300)

Listing Agent: Dan Farber (954-778-5300)

Remarks: Highly coveted Winter Park! 40+ Pictures! 2026 Updates include New Roof Feb 2026, New Paint and Carpet New main DBL pane windows. This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is effortless in the expansive kitchen featuring granite countertops, premium wood cabinetry, stainless steel appliances, and a generously sized pantry. A half bathroom and utility closet complete the ground floor, where ceilings soar to a height of 9'3". Ascend to the upper level to discover the luxurious master bedroom suite, boasting French doors leading to a balcony, a spacious walk-in closet, and a lavish ensuite bath featuring dual sinks, a glass-enclosed shower, and a relaxing garden tub. Two additional bedrooms await upstairs, both sharing access to a covered porch perfect for savoring your morning coffee. The second full bathroom and laundry closet round out the upstairs layout, with one of the bedrooms boasting its own walk-in closet. New 2026 Updates to include New Roof Feb 2026, Carpet, New main DBL pane windows, complete interior paint, light fixtures/fans. You will appreciate the convenience of an attached 2-car garage designed for SUVs, two covered entries, adorned with mature trees. Solid build quality utilizing concrete block construction on both floors. Located just a short stroll from the vibrant East End Market and various shopping, this residence also offers easy access to upscale Park Avenue, Rollins College, Baldwin Park, Florida Hospital, and the serene beauty of Leu Gardens. Zoned for Audubon and Winter Park HS, this home truly has it all!

Listing is courtesy of: NICOLE-HUDSON REALTY CORP (407-491-5488)

Listing Agent: Edward Rice, Jr (407-353-0331)

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: Under contract-accepting backup offers. Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.

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

Listing Agent: Marystuart Day (407-620-8683)

Remarks: Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!

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: This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas, setting a warm and elegant tone. The open-concept floor plan is designed for everyday living and effortless entertaining, with expansive windows allowing natural sunlight to pour into every space. At the heart of the home is a beautifully designed kitchen that blends classic style with modern functionality. A stunning quartz waterfall island anchors the space, complemented by custom cabinetry and a suite of high-end appliances including an ILVE induction range with six elements and Café French door refrigerator, dishwasher and microwave. Designer-grade lighting and refined finishes elevate the kitchen into a centerpiece of the home. The dining room is filled with light and character, featuring three sets of French doors that open to a charming private front and side courtyard, an ideal setting for morning coffee or intimate outdoor dining. In the living room, a dramatic wall of sliding glass doors connects the interior to the brick patio and backyard, creating a seamless indoor-outdoor lifestyle. The first-floor primary suite offers a peaceful retreat, complete with a spacious walk-in closet and a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub and dual vanities. Additional conveniences on the main level include a beautifully appointed powder bath, a dedicated laundry room and a generous storage room tucked neatly beneath the staircase. Upstairs, a versatile loft provides additional living space ideal for a media area, office or lounge. Two additional bedrooms are also on the second floor, each featuring custom built-in closets, beautiful designer lighting and abundant natural light. Built with quality and efficiency in mind, the home includes numerous upgrades such as a slate roof, Trane air-conditioning system, Rheem tankless water heater and a two-car attached garage. Ideally just minutes from the renowned shopping and dining of Park Avenue and charm of downtown Winter Park, this exceptional home also offers convenient access to major roadways, Orlando International Airport, leading hospitals, and top-rated public and private schools, bringing together style, comfort and location in one remarkable new construction opportunity.

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

Listing Agent: Mick Night (407-629-4446)

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: Under contract-accepting backup offers. Virtually Staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric fireplace and wine refrigerator. The sleek, updated kitchen offers a gas range, stylish finishes and a functional layout perfect for everyday living and entertaining.  Retreat to the spacious primary bedroom with a fabulous ensuite bath, complete with a soaking tub, dual vanities, a large separate shower, and a generous walk-in closet. A split-bedroom floor plan provides added privacy and comfort. The fully fenced backyard offers plenty of room for a pool and includes private parking for a boat on the side of the home. Whether you enjoy the home as it is or choose to build your dream residence, the possibilities are endless. New roof installed in 2022.

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

Listing Agent: Cindy Kuykendall (407-718-3235)

Remarks: MOVE IN READY - FENCED IN YARD - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to offer. Fully renovated in 2021—including new roof, electrical, plumbing, fixtures, finishes, and appliances—this home is truly move-in ready. The spacious primary suite is thoughtfully separated from the other bedrooms in a desirable split floor plan, ideal for privacy. Three additional bedrooms provide flexibility for family, guests, or dedicated work-from-home spaces. Enjoy a meticulously maintained yard, a welcoming neighborhood with no HOA, and the charm of one of Winter Park’s most sought-after areas. Don’t miss this gem!

Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)

Listing Agent: Susan Pinnock (407-435-9125)

Remarks: A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled in the highly sought-after and peaceful neighborhood of Orwin Manor in Winter Park. Rich in character and thoughtfully updated throughout, this exceptional residence seamlessly combines the elegance of its original architecture with the comfort and sophistication of modern living. Upon entering, you are welcomed by an inviting foyer featuring new tile flooring and refined vertical shiplap detailing, setting the tone for the home’s timeless design. Custom transitions lead into the spacious living room, where original hardwood floors, a cozy fireplace, and smart lighting create a warm and inviting atmosphere ideal for both entertaining and everyday living. The formal dining room comfortably accommodates gatherings of eight and is highlighted by a stunning Serena & Lily chandelier, creating the perfect setting for memorable dinners and celebrations. Just beyond, the fully renovated chef’s kitchen serves as the heart of the home. Updated in 2020, it features elegant Calacatta countertops, an oversized island, premium Samsung appliances, and stylish West Elm lighting. An adjacent eat-in dining space offers a more casual setting and opens directly to the beautifully paved backyard, perfect for outdoor dining and entertaining. The home’s accommodations are equally impressive, including a serene primary suite complete with dual closets and a beautifully appointed bathroom featuring sleek matte finishes. Additional living spaces include a versatile recreation room and a well-appointed guest bedroom, each designed with both comfort and functionality in mind. A private attic provides valuable additional storage space. Every detail of the home has been carefully considered to enhance both aesthetics and practicality, including smart exterior lighting, a durable vinyl privacy fence, low-maintenance landscaping tailored to Florida living, and an updated Carrier HVAC system with a smart thermostat for year-round comfort. Preserving the integrity of the home’s historic character, original woodwork, including baseboards and casings, has been thoughtfully maintained, while curated paint selections and Trex exterior staircases add lasting beauty and durability. Ideally located just minutes from Park Avenue, College Park, and major thoroughfares, this remarkable property offers an exceptional combination of tranquility, convenience, and community. More than just a home, it is a rare opportunity to own a beautifully preserved piece of Winter Park history where timeless charm and contemporary elegance exist in perfect harmony. New roof 2026***

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

Listing Agent: Nicole Howell (321-217-7918)

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: Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the property offers a setting that few locations can rival. The existing residence features approximately three bedrooms, two-and-a-half bathrooms, and generously proportioned living spaces filled with warmth and character. Lovingly maintained over the years, the home provides a comfortable foundation for renovation, restoration, or reimagination. Outdoors, a screened pool creates a private retreat for year-round enjoyment, while a detached two-car garage and separate studio shed offer exceptional flexibility for hobbies, creative pursuits, a home office, fitness space, or guest accommodations. What truly distinguishes this offering is the double lot itself. Opportunities of this scale within the heart of Winter Park are increasingly rare, providing the space and flexibility to construct a custom estate tailored to your vision while preserving ample room for outdoor living, gardens, and recreation. Life here extends far beyond the property lines. Enjoy morning walks beneath majestic oak canopies, afternoons on the Chain of Lakes, outdoor concerts, art festivals, sidewalk cafés, and some of Florida's most picturesque streetscapes. Whether renovating the existing residence or creating the home of your dreams, this exceptional property represents a rare chance to secure a legacy homesite in one of the most desirable addresses in Central Florida.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)

Listing Agent: Mel Bernstein (407-810-4726)

Remarks: Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.

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

Listing Agent: Cara Edwards (407-616-3204)

Remarks: Discover a unique opportunity in the heart of Winter Park, just moments from Lake Killarney. This versatile property offers exceptional potential for multigenerational living, a primary residence with additional income, or a strategic investment. The home features a flexible layout designed to adapt to a variety of needs, with bright living spaces, natural light throughout, and comfortable areas ideal for both everyday living and entertaining. Its design allows for privacy and functionality, making it an attractive option for homeowners and investors alike. Enjoy a spacious outdoor setting surrounded by mature landscaping, perfect for relaxing or hosting gatherings. Recent upgrades add even more value and peace of mind, including solar panels that will be fully paid off at closing, as well as a newer roof and updated air conditioning system, offering efficiency and long-term savings. Ideally located just minutes from Park Avenue, Rollins College, and a wide variety of shopping, dining, and entertainment options. With easy access to major roadways, commuting throughout Central Florida is both quick and convenient. A rare opportunity to own a property with flexibility, location, and strong long-term value in one of the area’s most desirable communities. Schedule your private showing today.

Listing is courtesy of: AROD PARTNERS REALTY (407-627-7621)

Listing Agent: Suheil Flores (407-693-3060)

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)