Refine Search
Map
Sort by
$960,000
Ethel Park SubDv. ⋅ 32789 Zip Code
An outstanding opportunity to acquire a generously sized homesite in the highly desirable Winter Park area. Measuring approximately 75' x 154', this 11,555-square-foot lot offers excellent potential for a custom luxury residence. This property is being offered for its land value, presenting an ideal opportunity for a builder, developer, investor, or buyer looking to create a custom home tailored to today's luxury lifestyle. The Winter Park area hosts a remarkable collection of luxury homes, custom estates, and continued new development, making this an attractive location for those seeking to build in an established and highly desirable market. With its generous lot dimensions and surrounding luxury development, this property provides an excellent canvas for your next custom-home project.

447 N Phelps Avenue, Winter Park
$960,000
2 Beds ⋅ 1 Baths ⋅ Ethel Park SubDv. ⋅ 32789 Zip Code
An outstanding opportunity to acquire a generously sized homesite in the highly desirable City of Winter Park area. Measuring approximately 75' x 154', this 11,555-square-foot lot offers excellent potential for a custom luxury residence. This property is being offered for its land value, presenting an ideal opportunity for a builder, developer, investor, or buyer looking to create a custom home tailored to today's luxury lifestyle. The Winter Park area hosts a remarkable collection of luxury homes, custom estates, and continued new development, making this an attractive location for those seeking to build in an established and highly desirable market. With its generous lot dimensions and surrounding luxury development, this property provides an excellent canvas for your next custom-home project.

447 N Phelps Avenue, Winter Park
$950,000
3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park
$825,000
Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Welcome to this beautiful lot located in one of Winter Park’s most desirable neighborhoods. This exceptional location presents the perfect opportunity to build your dream home in one of the most sought after school zones Winter Park has to offer. Set along picturesque brick streets shaded by mature trees, the location is hard to beat. It is within walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. Enjoy the chance to create a home tailored to your lifestyle with a perfect blend of classic Winter Park character, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park
$975,000
4 Beds ⋅ 3 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite, home office, or potential rental income. For homeowners, the additional living space provides the freedom to accommodate family members or guests while maintaining privacy and separation. For investors, the configuration creates the potential to generate supplemental income, subject to applicable local regulations and requirements. The property’s location adds to its appeal, placing you near Winter Park’s renowned dining, shopping, parks, cultural attractions, and vibrant community amenities. Also, just a short distance to Rollins College! Whether you’re looking to offset your mortgage, create an additional income stream, or simply secure a property with adaptable living options, this home offers a compelling combination of lifestyle and investment potential. Opportunities with this level of flexibility are hard to find. Live in the main residence, utilize the suite for family or guests, or explore its income-producing potential. 471 Holt Ave. offers the versatility today’s buyers are looking for and the potential long-term value investors appreciate. Don’t miss the opportunity to make this flexible Winter Park property your next home or investment.

471 Holt Avenue, Winter Park
$999,500
3 Beds ⋅ 2 Baths ⋅ Lake Maitland SubDv. ⋅ 32789 Zip Code
A RARE WINTER PARK RENOVATION OPPORTUNITY DIRECTLY ACROSS FROM HOWELL BRANCH PRESERVE! Situated on an approximately 0.23-acre lot, this distinctive 3-bedroom, 2-bath home offers an exceptional opportunity for an investor, renovator, or buyer seeking to complete and personalize a property in one of Central Florida’s most desirable communities. Renovations have already begun, providing the next owner with a valuable head start. The home features a spacious open-concept living, dining, and kitchen area; original hardwood flooring in several bedrooms; updated flooring in other areas; renovated bathroom elements; a large walk-in shower; generous flex and storage space; and an expansive driveway and garage area. Some improvements and finish work remain, allowing the buyer to complete the renovation according to their own vision. The approximately 10,219-square-foot lot is directly across from the 10.38-acre Howell Branch Preserve, which offers a playground, fitness trail with exercise stations, picnic pavilion, boardwalk, observation deck, restrooms, open lawn, and protected natural surroundings. Property is offered strictly AS IS. Public records reflect approximately 1,487 square feet of heated living area. Additional areas, measurements, permitted improvements, and intended uses must be independently verified by the buyer. The seller will not complete repairs. Bring your contractor and imagination to explore the possibilities offered by this unique Winter Park property.

1220 Howell Branch Road, Winter Park
$899,000
3 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $899,000, this single-story block home sits on a generous 50x150' lot and offers 2,022 square feet of living space with 3 bedrooms and 2.5 baths. Whether you envision a thoughtful remodel or a ground-up new build, this property presents outstanding potential in one of Winter Park's most desirable pockets, where similar transformations are already reshaping the streetscape. Inside, tile flooring flows through the main living areas, complementing a versatile layout that includes a formal living room, a combined kitchen and dining area, and a separate den with pocket doors perfect for a home office or media room. The oversized bedrooms offer generous space throughout, including a primary suite with a private en suite bath. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, ideal for family or guests. At the rear of the home, an enclosed sunroom provides a peaceful retreat overlooking the well-manicured backyard, a tranquil spot to relax and unwind. With its prime location, solid bones, and abundant possibilities, 1621 Chestnut Avenue is ready for its next owner to make it their own.

1621 Chestnut Avenue, Winter Park
$799,000
3 Beds ⋅ 3 Baths ⋅ Casa Jardin Condo SubDv. ⋅ 32789 Zip Code
In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms, two-and-a-half baths and a thoughtfully designed floor plan that lives like a private home. Bathed in natural light, the interiors are framed by expansive window walls and floor-to-ceiling glass doors that create a bright, airy ambiance throughout. Architectural details including graceful arched passageways, column-lined hallways, and a custom wrought-iron spiral staircase add timeless character and sophistication. Beautifully updated and meticulously maintained, every room reflects a sense of warmth and refinement. The spacious primary retreat is a sanctuary, featuring soaring cathedral ceilings, dual walk-in closets and a spa-inspired bath designed for relaxation. Two additional bedrooms offer versatility for guests, family or a home office. The open-concept living and dining areas are enhanced by travertine and luxury vinyl plank flooring, coffered ceilings, designer lighting, and a beautifully appointed chef’s kitchen complete with solid wood cabinetry, granite countertops, a center island and generous walk-in pantry. French doors open to a freshly painted screened courtyard, creating a private outdoor escape ideal for entertaining or quiet evenings at home. Above, the freshly painted rooftop terrace provides a spectacular setting for alfresco dining, sunset gatherings or simply enjoying Florida’s year-round sunshine. Additional features include a powder bath, plantation shutters, ceiling fans throughout, an oversized two-car garage, and a third-floor walk-in attic offering abundant storage and exciting future expansion possibilities. Residents of Casa Jardin enjoy a beautifully refreshed community, recently enhanced with a new roof, exterior paint and professional landscaping. Ownership also includes exclusive access to Lake Virginia and renowned Winter Park Chain of Lakes through College Point, featuring a private lakefront gathering area along with kayak and paddleboard storage. Ideally near Azalea Lane Recreation Center, the Winter Park Tennis Center, Orange Avenue’s popular restaurants and shops, and top-rated schools, this remarkable residence offers a rare opportunity to enjoy one of Central Florida’s desirable lifestyles.

1278 S Pennsylvania Avenue Unit 13, Winter Park
$975,000
2 Beds ⋅ 2 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated along the shores of Lake Osceola & just a short stroll from Park Avenue. Priced below appraised value, this rare third-floor mid-century modern condo offers exceptional value and a truly turnkey lifestyle. Filled with natural light, the thoughtfully designed floor plan features spacious living and dining areas overlooking tranquil waterfall ponds and lush, beautifully maintained grounds. A versatile bonus space provides the perfect setting for a home office, den, or creative retreat. The expansive owners suite is designed for relaxation, featuring a private sitting area, dual closets, direct access to the pool, and a spa-inspired bath complete with a jetted tub. The generously sized secondary bedroom offers a cozy reading nook and dual closets, providing comfort and flexibility for guests. Enjoy effortless, worry-free living with secure underground parking, a deeded parking space, and convenient elevator access. Even better, monthly association dues include electricity, air conditioning, heat, water, sewer, and trash—making everyday living remarkably simple. Step outside your door and enjoy everything that makes Winter Park so special, from the acclaimed shops and restaurants of Park Avenue to Rollins College and Winter Parks historic golf course. With its prime lakefront setting, exceptional location, and low-maintenance lifestyle, this is a rare opportunity to own a piece of one of Central Florida’s most desirable communities. Discover the best of Winter Park living at Whispering Waters—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park
$825,000
2 Beds ⋅ 2 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along picturesque brick streets shaded by mature trees, this inviting home offers a warm, light-filled interior and a private backyard oasis. From the moment you enter, you’ll notice the abundance of natural light and the large windows that frame the living spaces. The spacious living room flows seamlessly into a bright, functional kitchen featuring newer appliances and a large window overlooking the front yard. Just off the kitchen, an indoor laundry room adds everyday convenience. A beautiful sunroom overlooks the private, landscaped backyard and offers a versatile space that could easily serve as a home office, reading room, or additional sitting area. Down the hallway, the spacious primary suite features an en-suite bathroom, ample closet space, and abundant natural light with peaceful views of the backyard. The second bedroom is generously sized and includes a walk-in closet. Step outside to discover a true gardener’s paradise. The lush, private backyard features a beautiful paved patio, winding paved pathway, mature landscaping, and plenty of space to relax, entertain, or enjoy the outdoors. The location is hard to beat, walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. The home also offers access to top-rated Orange County schools. Important updates include a complete remodel and added square footage (2009), a newer roof (2022), regularly maintained HVAC system (2020), hot water heater (2024), updated bathrooms (2025), kitchen appliance updates (2026), and a regularly maintained irrigation system. This special home offers the perfect blend of classic Winter Park character, modern updates, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park
$985,000
4 Beds ⋅ 3 Baths ⋅ Park Pointe Rep SubDv. ⋅ 32789 Zip Code
A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN but THERE ARE MANY FEATURES TO POINT OUT - THIS 2868 SQFT HOME has a 3-WAY SPLIT with 4 BEDROOMS, 3 FULL BATHROOMS, plus BONUS ROOM & OFFICE. YOU WILL NOT BELIEVE ALL THE STORAGE, STORAGE, STORAGE UNDER AIR! The BONUS ROOM (12.4 X 11.7) OFF PRIMARY BEDROOM COULD BE a NURSERY, OFFICE, EXERCISE ROOM, or OWNERS RETREAT. There is an ADDITIONAL OFFICE (13.6 X 11.6 ) with BUILT N DESK & STORAGE CABINETS MAKING a GREAT HOMESCHOOL ROOM, CRAFT AREA, or HOME OFFICE WHERE a PRIVATE EXTERIOR ENTRY DOOR is NEEDED. ONE BEDROOM could be USED as an IN-LAW SUITE with IT’S ENSUITE BATHROOM with SHOWER. The SPACIOUS GARAGE has NEW SHARK FLOORING (7/26), NEW PAINT, NEW ELECTRIC CAR CHARGING OUTLET (6/26), NEW INSULATED GARAGE DOOR & A MINI SPLIT AC – LOTS OF POSSIBILITIES! MANY FUN MEMORIES can be ENJOYED with FAMILY & FRIENDS AROUND the BEAUTIFUL SCREENED POOL & LARGE COVERED LANAI & DECK ( RESURFACED 9/25 ) The NEW OWNER of this LOVELY HOME will APPRECIATE all the UPDATES that have BEEN DONE over LAST FEW YEARS – NEW $29K LENOX UPGRADED AC (3/26), NEW FRONT DOOR (4/26), NEW GOOGLE NEST DOORBELL (3/26), NEW INSULATION in ATTIC & ON GARAGE DOOR (6/26), NEW PAVER DRIVEWAY (5/26 ) NEW UPGRADED FLASHING AROUND CHIMNEY (5/26), GAS TANKLESS WATER HEATER W RECIRCULATING FEATURE(2023), NEW DUCT WORK (2019) NEW WINDOWS (2020), WHOLE HOUSE REPLUMBED (2020), ROOF (2016), STAINLESS APPLIANCES (2019), WHOLE HOUSE WATER SOFTNER & DOUBLE OSMOSIS SYSTEM for DRINKING WATER, SELLER WILL CONSIDER CARPET ALLOWANCE WITH ACCEPTABLE OFFER. ****** THIS HOME IS WORTH SEEING ******

2667 Cochise Trail, Winter Park
$775,000
4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central Florida’s most desirable communities. At the center of the home is a completely redesigned kitchen that is both stylish and highly functional. New cabinetry, quartz countertops, stainless steel appliances, generous storage, and an oversized island with bar seating create an inviting setting for everyday meals and entertaining. A beautiful picture window frames views of the lush backyard and fills the kitchen with natural light. The open living spaces flow seamlessly together over wood-look tile flooring, while fresh interior paint, updated fixtures, and an electric fireplace add warmth and a polished contemporary feel. Privately positioned on one side of the home, the expansive primary suite feels like a retreat of its own. The suite includes a custom designed walk-in closet and a beautifully designed bathroom with separate vanities, a freestanding soaking tub, an oversized walk-in shower, and a private water closet. Three additional bedrooms are located on the opposite side of the home, providing separation and flexibility for family members or overnight guests. The outdoor setting is equally impressive. The enormous, fully fenced backyard has been lovingly maintained and features mature greenery, privacy, and plenty of room for entertaining, recreation, gardening, pets, or a future outdoor living retreat. Bonus: there is additional parking on the west side of the home that is accessible from the backyard - perfect for hosting or entertaining! A cobblestone driveway enhances the home’s curb appeal, while notable improvements include replacement of the HVAC system and ductwork in 2016, numerous plumbing updates, and extensive interior renovations. Enjoy a location that places the best of Winter Park within easy reach. The home is conveniently located near the Winter Park YMCA, Lakemont Elementary School, Phelps Park, Rollins College, and the Winter Park Chain of Lakes -  not to mention all of the boutiques, restaurants, museums, & cafés, and community events of historic Park Avenue. Baldwin Park, Winter Park Village, and Audubon Park are also just minutes away, offering even more options for dining, shopping, entertainment, and outdoor recreation. This is an exceptional opportunity to enjoy a gorgeous, fully updated home in the highly desirable in-town Winter Park address. Schedule your private showing and experience the lifestyle, location, and thoughtful design of 1562 Arbor Park Drive.

1562 Arbor Park Drive, Winter Park
$999,000
3 Beds ⋅ 3 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! Just FRESHLY PAINTED interior in 'Alabaster' tones! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops, plus natural gas, great for cooking! An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. Updated TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting.

1138 S Pennsylvania Avenue, Winter Park
$950,000
4 Beds ⋅ 3 Baths ⋅ Northwood Terrace SubDv. ⋅ 32789 Zip Code
Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite counters and KitchenAid stainless appliances. Out back, an expanded patio overlooks a private, fenced yard built for gathering. Everything is new: roof, windows, 200-amp electrical, plumbing with new water heater, HVAC ductwork, and Nest thermostat. Best of all, you can live it on foot: walk to East End Market, Kelly's Homemade Ice Cream, Redlight Redlight, Sushi Lola's, and top-rated Audubon Park K-8. Zoned for Winter Park High, and minutes to Park Avenue and Rollins College. A turnkey classic in one of Winter Park's most established, walkable neighborhoods.

3006 Northwood Boulevard, Winter Park
$849,000
3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code
Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

437 N Capen Avenue, Winter Park
$810,000
3 Beds ⋅ 4 Baths ⋅ Virginia Hgts Rep SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!

1265 Arlington Pl, Winter Park
$836,000
3 Beds ⋅ 3 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code
Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Now offering $10,000 Seller Credit! Call to schedule your showing today!

338 Blue Heron Drive, Winter Park
$989,500
1 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

269 E Canton Avenue Unit 269, Winter Park
$918,000
4 Beds ⋅ 3 Baths ⋅ Karolina On Killarney SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and intentional design create a home that feels both elevated and livable. What makes this opportunity truly unique: this is the last remaining homesite within a curated collection of three custom builds—each thoughtfully designed with its own architectural identity, yet unified in creating a refined, cohesive streetscape. The other two homes are already underway, making this your only chance to secure a position in this limited offering. Located just 6 minutes from Park Avenue, you’re moments from Winter Park’s best—boutique shopping, award-winning dining, and everyday conveniences—while also being close to top-rated hospitals and major thoroughfares. Offered as a custom build, this home allows you to tailor finishes, selections, and details to match your vision. Pricing reflects the base build, with upgrade options available to create a fully personalized end product. With new construction opportunities in 32789 at this price point becoming increasingly scarce, offerings like this are few and far between—especially with the ability to fully customize your home from the ground up.

Lot #21 Karolina Ave, Winter Park
$820,000
5 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code
*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

1927 Eland Avenue, Winter Park
$899,000
Fairbanks Park SubDv. ⋅ 32789 Zip Code
Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and entertainment. Lots like this are seldom available. Whether you’re envisioning a custom residence or an investment in one of Central Florida’s most desirable neighborhoods, this is a truly rare opportunity in the heart of Winter Park.

731 Midget Drive, Winter Park
$899,000
2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code
Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park