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$5,125,000
5 Beds 6 Baths J Kronenberger Sub SubDv. 32789 Zip Code
This stunning private residence is on an oversized lot featuring a private sports pad, kids playground and sparkling pool. Encompassing over 6,700 square feet of expansive .55-acre lot, this home boast five spacious bedrooms, one office, 5.5 baths and a dedicated movie room, recording studio and a fully equipped gym with a private sauna. Ideally just moments from serene Lake Maitland and the charming Azalea Park, this home offers natural beauty and prime location. The chef's kitchen is designed for function and style with dual oversized islands, ideal for entertaining and everyday living. Spacious, inviting and thoughtfully designed, this oversized family room is the heart of the home-ideal for everything from cozy movie nights to lively holiday parties featuring expansive square footage, the room comfortably accommodates large groups, with plenty of space for multiple seating areas and a bar area. Oversized windows flood the space with natural light while the high ceilings and an open layout enhance the airy welcoming feel. Whether you are hosting extended family or entertaining friends, this room is built for connection, comfort and lasting memories. The private recording studio can be turned into a private mother-in-law suite or a kids playroom. The luxurious primary suite retreat to your own private oasis featuring a cozy fireplace, direct access to a serene private porch and a one-of-a-kind walk-in closet designed for style and functionality. The oversized en-suite bath boasts a steam shower, creating a spa-like experience right at home. Two additional en-suite bedrooms upstairs, each with walk in closets. Thoughtfully designed for convenience, this home features a spacious mud room off the garage which is ideal for busy households. Enjoy the ultimate convenience with two separate laundry rooms, one’s downstairs for easy access and a second upstairs near the bedrooms, making laundry day effortless and efficient. Ideally near Winter Park Racquet Club, Interlachen Country Club and accessible to Park Avenue, this exceptional residence also offers an extraordinary residence with a luxurious functionality and a premier location.

1240 Harding Street, Winter Park

$837,500
2 Beds 2 Baths Park West Condo SubDv. 32789 Zip Code
A unique opportunity to own this Winter Park luxury corner condominium unit in the gated Park West community. Resting on the corner of New York Avenue and Carolina, with direct second-floor balcony views of Central Park and Park Avenue, and proximity to the quintessential Winter Park experience. Designed by nationally renowned Soco Interiors, a turnkey opportunity that adds ease to the lock-and-go lifestyle. Designer touches and quiet elegance blend to create this California casual interior that was meticulously designed and appointed with function and comfort at the forefront. Open dining and living spaces with balconies on each side make hosting a breeze. A marble-framed fireplace and beautiful wide-plank white oak floors add warmth and charm to this special place. The modern gourmet kitchen is highly functioning for family dinner or entertaining guests. White clean-lined custom cabinetry, gold accent hardware, quartz surfaces and solid quartz backsplash add to the seamless design. A fabulously designed scullery with designer tile floor includes a dedicated laundry/pantry, ample storage and additional counter space for a morning bar. The primary bedroom has ample space and beautiful light with access to one of the two balconies, custom-organized closet and a bath that is appointed with modern finishes such as marble floors/shower and fantastic tropical palm wallpaper that is so chic and fun. An additional large private bedroom suite is inviting and makes it easy to entertain guests for the weekend. Fresh striped wallpaper and organic selections finish out the custom second bath. This pristine unit is in a great building in Park West overlooking Central Park. On a prime corner, with one balcony facing the park and the other overlooking the tennis courts and pool. Elevators throughout and meticulously maintained, all in security of a gated community, Park West has always delivered for decades. Call us for a private showing.

200 Carolina Avenue Unit 201, Winter Park

$1,100,000
3 Beds 3 Baths Fairbanks Park SubDv. 32789 Zip Code
Welcome home! Nestled in the heart of Winter Park this 3-bedroom, 2.5 bathroom residence offers a perfect blend of convenience, energy efficiency, and refined comfort. From the moment you enter, you'll be captivated by high ceilings and crown molding for a spacious and refined feel. The kitchen is a chef's dream featuring granite countertops, stainless steel appliances, a gas range and upgraded plumbing fixtures. Enjoy cozy evenings in the living room by the new gas fireplace or relax outside by the cocktail pool, perfect for entertaining and enjoying the Florida sunshine in a tropical setting. The primary suite includes a private balcony with serene views of Lake Midget park. The spacious master bathroom is a true oasis with a soaking tub and rainfall shower. Powered blackout roller shades in the primary suite and downstairs living area ensure restful sleep and complete privacy. Closet systems throughout the home add a layer of organization and luxury. Recent upgrades to the home include a new roof with architectural shingles (2023), energy efficient Pella Impervia windows (2024), an updated air conditioning/heat pump system (2022) and full flake epoxy garage floors with ultra quiet garage door openers. Enjoy low utility bills and energy efficiency with dual-zone A/C, tankless hot water system, R40 attic insulation & foamed block walls. Easy access to I-4 and just minutes from iconic Park Avenue, Downtown Orlando, Rollins College and Baldwin Park. Shopping, numerous restaurants and bars, tennis facilities, multiple parks and city facilities are just a short walk or drive away. Whether you're looking for the perfect place to call home or a stunning Winter Park retreat, this home delivers unmatched quality, location, and lifestyle.

930 S Kentucky Avenue, Winter Park

$2,700,000
5 Beds 5 Baths Windsong Lakeside SubDv. 32789 Zip Code
Experience Mediterranean charm in this fabulous five-bedroom, five-bath pool home built by Cahill Builders. On the north side of Windsong, this home features an open floor plan with spacious living areas that flow seamlessly and provide warm natural light. The living room with cozy gas fireplace overlooks the spacious and open dining room while the light-filled family room with French doors has wonderful views of the covered lanai and pool. You will love entertaining in the chef’s eat-in kitchen with many updates and upgrades completed in 2024. Kitchen features include stainless appliances, natural gas cooktop, double ovens, large center prep island and large walk-in pantry. The first-floor luxurious owner’s retreat features vaulted and hand-crafted wood beam ceilings, wide plank wood floors and bath with dual vanities, walk-in shower and spa tub. Bedroom Suite 2, which is also on the main level is ideal for guests, home office or nursery. As you go upstairs, the second floor offers a thoughtfully designed retreat for both relaxation and entertainment. There are three spacious bedrooms each with their private baths. This layout offers comfort and privacy for family or guests. The media room provides the ideal setting for movie nights or immersive gaming and includes an additional room for a playroom, library or large air-conditioned storage space. Whether you are entertaining or unwinding, this upper-level layout delivers functionality and privacy. Go outside to enjoy the covered lanai which overlooks the private and expansive yard filled with a vibrant mix of citrus trees, tropical plants and year-round flowering garden. The fabulous landscape was designed by a landscape architect with the concept to provide continuous blooms and inviting sitting areas under the sun. The sparkling pool and spa, large surrounding patio and firepit area invite year-round enjoyment. Additional amenities include custom molding and trim work, an entry fountain and three-car garage (one with split air conditioning). Windsong, one of Winter Park's sought-after neighborhoods, offers exclusive amenities to their residents including a pontoon boat to enjoy Winter Park Chain of Lakes, two community pools, a splash park, playground, a lakefront clubhouse and a scenic pier for fishing. Ideal location is minutes from hospitals, schools, golf courses, and Park Avenue’s amazing dining and shopping.

1445 Holts Grove, Winter Park

$1,079,000
3 Beds 3 Baths Winter Park Residential SubDv. 32789 Zip Code
Experience the best of Winter Park living in this distinguished three-bedroom, three-bathroom condominium, located in the secure and sought-after Douglas Grand development—just one block from vibrant Park Avenue. Spanning an impressive 2,649 sq ft on a single level, this third-floor residence blends timeless architectural charm, quality construction, and everyday function. Step inside to an expansive living space enhanced by tall ceilings, extensive millwork, and natural light filtered through custom shutters. The open chef’s kitchen features premium Thermador stainless steel appliances, real wood cabinetry with under-cabinet lighting, granite countertops, travertine flooring, and a pantry. An oversized central island with seating for four provides eat-in convenience. The floor plan offers a seamless flow from the kitchen to dining to the family room, creating flexible and efficient space. Located off the general living space, there are two additional bedrooms and bathrooms. One bedroom includes an en suite bathroom, while the other is adjacent to a full hallway bath. The bathrooms include stone flooring, real wood vanities, granite countertops, large mirrors with quality light fixtures, and a mix of walk-in shower with glass enclosure and tub-shower combination. Relax and recharge in the luxurious primary suite with two walk-in custom-cabinetry closets and a spa-like bathroom offering an extended vanity with two sinks and an adjacent makeup vanity—all with granite countertops. A deep soaking tub, a sizable glass-enclosed shower, linen closet, and private water closet complete the primary bathroom features. The laundry room includes a Samsung front-loading washer and dryer, utility sink, and ample built-in storage. The current owner invested over $100,000 in all-new impact-rated windows, providing peace of mind, energy efficiency, and enhanced comfort. Additional building highlights include two deeded garage parking spaces in a secure garage and two secure lobbies with private elevator entry. The HOA provides on-site management, care for community grounds, a pet-friendly policy, proactive maintenance, and comprehensive coverage including building insurance, water, sewer, and trash—affording owners the convenience of a true lock-and-leave lifestyle. Don’t miss the rare opportunity to own a secure and spacious single-level condo that allows you to embrace the walkable lifestyle of Winter Park in a location steps from the restaurants and shops of Park Avenue or Hannibal Square, the SunRail, Farmers’ Market, and more.

100 S Virginia Avenue Unit 319, Winter Park

$130,000
2 Beds 1 Baths Waterfall Cove SubDv. 32789 Zip Code
Welcome to a delightfully bright and inviting 2-bedroom, 1-bathroom condo nestled in the peaceful Waterfall Cove community at 1695 Lee Rd, Unit C206, Winter Park, FL 32789. Thoughtfully designed, this home features a covered balcony that invites relaxing mornings or cozy evenings outdoors, while the spacious primary bedroom offers the convenience of a walk-in closet—perfectly blending comfort and efficient use of space. Waterfall Cove elevates everyday living with community amenities including a pool, playground, and covered picnic area, making it ideal for both relaxation and active enjoyment. Plus, high-speed internet and cable are included in the HOA fees, offering modern convenience and simplified budgeting. The location is outstanding. You’re minutes from Rollins College—a short 2½-mile drive—making it perfect for students, faculty, renters, or families alike  . Stroll or drive to Park Avenue for galleries, boutiques, and cafes. Winter Park Village, recently refreshed by a major renovation, offers a vibrant array of tenants and experiences—from Arhaus and Brighton Collectibles to coworking at Spaces and upscale dining under one beautifully redesigned streetscape—now fully leased and thriving. With downtown Winter Park just minutes away and I-4 under one mile from your doorstep, getting around town is effortless and efficient  . This condo is perfectly balanced for homeowners seeking cozy elegance as well as investors looking for a turnkey residence in a high-demand location of Winter Park. Whether you seek a relaxed retreat or a smart, energy-efficient investment anchored by community and convenience, this property captures it all. Schedule your private showing today—the next chapter of refined Winter Park living starts here.

1695 Lee Road Unit C206, Winter Park

$1,640,000
3 Beds 4 Baths Winter Park Residential SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. This signature corner unit in the exclusive Douglas Grand, is perched on the top two floors, with panoramic views of downtown Winter Park, Hannibal’s Square and Rollins College all steps away. This spacious luxury unit includes a three-bedroom split plan and three-and-a-half en-suite baths, with two private balconies from bedrooms overlooking Central Park. Every convenience of the desirable Winter Park lifestyle is at your doorstep. A gated parking garage provides security for you and your guests. Step inside to discover the 3,174-square-foot perfectly renovated residence with gorgeous new blonde wood floors throughout the living room and bedrooms, and surrounded by windows that invite beautiful light in. Entertain with ease in the expansive gourmet kitchen, recently renovated with added cabinetry including a pantry, new quartz counters, custom back splash and top-of-the-line appliances. Bar seating at the counter peninsula still leaves room for an additional dine-in table if you desire. What makes this unit unique is the open-air two-story center atrium that connects all the living spaces together and adds secluded outdoor living for privacy with views to the stars. The primary bedroom enjoys treetop views, private balcony just recently tiled and generous space and closet. The primary bath suite includes updated dual vanities, separate shower and an indulgent jetted tub. Secondary bedrooms are private with one upstairs and the third bedroom suite, or office, offers versatility and function. Elevate your lifestyle with a host of modern amenities, including updated designer fixtures, recessed lighting and fans, some new Pella doors and windows, fresh paint, spacious walk-in closets that provide ample storage in every bedroom and a freshly painted interior and private laundry. Enjoy the added convenience of two deeded parking spaces in the gated-attached garage, with direct access to your floor and access door right next to your front door, so convenient. Every aspect of luxury living has been meticulously curated for your enjoyment. Indulge in the unparalleled convenience of strolling to nearby restaurants, coffee shops and boutiques. Rollins College is nearby, as well as fabulous events in Central Park and the bustling farmers market. Don’t miss your chance to experience the pinnacle of urban sophistication at The Douglas Grand.

101 S New York Avenue Unit 313, Winter Park

$1,110,000
5 Beds 3 Baths Virginia Heights SubDv. 32789 Zip Code
Vintage original 5-Bed, 3-Bath pool home with new roof on an estate-size lot adorned with mature landscaping and breathtaking views that overlook a natural wooded area in desirable Virginia Heights. This fabulous property could have a full renovation to make best use of the existing home, or the 16,000+ square foot lot offers the perfect opportunity to build the new home of your dreams and maximize the value of the property. Whether updating or building new, you will revel in the ambiance and privacy of this sought after neighborhood among an eclectic blend of classical and modern homes built by premier custom homebuilders. Walk or bicycle to Rollins College and downtown Winter Park's fine restaurants, boutique shops, and farmers market, or enjoy exclusive deeded lake access to the beautiful Winter Park Chain of Lakes, Lake Virginia with kayaks, paddle boards, canoes and fishing from College Point, a private lakefront park. This property could be your ideal family retreat for generations to come.

233 Hampden Place, Winter Park

$465,000
2 Beds 3 Baths Killarney Bay Condo SubDv. 32789 Zip Code
SUPERB LOCATION! Don’t miss out on this beautifully updated 2 bedroom 2.5 bath 2-story condo in Killarney Bay. Upon entering, you immediately notice the charm and character of this impeccably maintained condo. Recent updates include a fully renovated screened porch including floor, screen enclosure and roof, new sliding doors and windows, new refrigerator, new dishwasher, newly painted interior and recently installed closet organization systems. The kitchen with solid wood cabinets, stainless steel appliances, granite countertops and counter seating is open to the dining/family room combo featuring a cozy corner fireplace. The flex space in the front of the condo can serve as a formal dining room, home office or art studio with generous shelves that span an entire wall of the room. Convenient downstairs laundry room with storage and half bath with access to additional storage under the stairs. Wood tile floors, plantation shutters, ceiling fans and vaulted ceilings in the upstairs bedrooms. Wood plank flooring on the staircase. Generous upstairs hall closet! Two master suites both with spacious walk-in closets and en suite bathrooms. The front bedroom features a balcony with a sitting area and alcove for a tv or desk and the back bedroom presents as a quiet, private retreat with extra closet space. The recently renovated screened porch overlooking the manicured landscape is the perfect place to relax and unwind. Two assigned parking spaces, one covered and located in front of the condo. Outdoor closet located on screened porch. Community pool and dock and view of Lake Killarney. Kayaks and paddleboard storage available. Walkable to Winter Park Village, Trader Joes and a variety of restaurants and shopping along the 17-92 corridor. Easy access to I.4 via Fairbanks or Lee Rds. You simply cannot beat this location! Call today to schedule your showing!

130 Killarney Bay Court Unit 5-3, Winter Park

$580,000
3 Beds 3 Baths Arbors/Aragon SubDv. 32789 Zip Code
Nestled in a peaceful enclave near Park Avenue in Winter Park, this inviting 3 bedroom, 3 bathroom, 1,701 SF townhome offers classic Florida living with modern comforts. A welcoming entry opens to bamboo wood flooring that flows through the main living areas. The living room and adjacent dining space connect seamlessly to the gorgeous kitchen, featuring 42" wood cabinets, stainless appliances, granite countertops, and a breakfast bar, ideal for casual mornings or entertaining guests. Upstairs, the light-filled primary suite offers a peaceful retreat with double-vanity sinks, a garden tub with separate shower, a generous walk-in closet, and a private balcony. Two additional well-sized bedrooms and a hall bathroom provide space for family, guests, or a home office. The home rests on a corner lot with lush landscaping, a cozy front porch, and a 2 car garage. Step outside to discover a fully fenced backyard, perfectly sized for al fresco dining, gardening, or to enjoy a morning coffee in the Florida sunshine. Located just minutes from A-rated Winter Park schools, and close to Winter Park’s shops, restaurants, golf courses, and cultural attractions, this home offers an exceptional blend of convenience and community.

915 Aragon Avenue, Winter Park

$2,650,000
6 Beds 5 Baths Palmer Park SubDv. 32789 Zip Code
Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated, high-end finishes. From the rounded stone entry feature and custom iron double doors to the soaring ceilings and designer lighting, this home instantly impresses. The spacious great room opens to a wall of glass folding doors that reveal a private backyard retreat—featuring a heated pool and spa, lush landscaping, and an expansive lanai with summer kitchen. The home is serviced by natural gas, seamlessly supporting modern comfort and efficiency. The kitchen is truly the heart of the home, boasting dual oversized islands, WOLF appliances, fully custom cabinetry, two dishwashers, a double oven and a massive walk-in pantry. A nearby sunken bar offers the perfect spot for entertaining. Downstairs includes two well-appointed bedrooms, one with its own en suite—ideal for guests or multigenerational living. The detached casita includes a full bath and is pre-plumbed for a kitchenette and washer/dryer, offering endless potential as a guest suite, gym, or studio. Upstairs, the primary suite is a sanctuary: a double-sided fireplace, private balcony overlooking the pool, two generous walk-in closets (one with a secondary laundry hookup), and a spa-worthy bath complete with a sauna and a massive multi-head shower. A bonus loft with wet bar and two additional bedrooms round out the second floor. Located just minutes from Park Avenue and zoned for top-rated public schools including Winter Park High, a community known for both academic and extracurricular excellence (some say there’s championship energy in the air), this home offers a rare blend of luxury, lifestyle, and location.

575 Palmer Avenue, Winter Park

$775,000
2 Beds 2 Baths Cloisters Condo SubDv. 32789 Zip Code
Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious, designer-selected finishes throughout. Step inside to discover a beautifully appointed interior featuring high-end touches. The kitchen is a true showpiece, boasting custom wood cabinetry with artistic wood detailing, granite countertops, full counter-to-cabinet backsplashes, and top-tier appliances including a Wolf cooktop and oven, Fisher & Paykel dishwasher, Liebherr wine cooler, and Sub-Zero refrigerator. The expansive kitchen island comfortably seats four, with a sleek, integrated extension that effortlessly accommodates up to seven—perfect for entertaining in style. The open-concept living area flows seamlessly to a spacious private balcony, offering tranquil views of the heated pool, putting green, lush landscaping, and the shimmering waters of Lake Osceola—ideal for a morning coffee or year-round entertaining. The primary suite is a serene retreat, featuring blackout blinds, a Sleep Number smart bed with dual temperature controls, and custom floor-to-ceiling built-ins with integrated lighting, display shelving, and a dedicated vanity area. Additional built-in cabinetry lines the hallway leading to the en-suite bathroom, providing ample space for jewelry, shoes, and wardrobe essentials. The second bedroom is designed for versatility, with a wall-to-wall built-in home office setup overlooking a beautiful resort-style view, along with its own matching floor-to-ceiling built-ins for display and storage. Both bathrooms have been tastefully reimagined with new vanities, granite countertops, upgraded shower enclosures and hardware, and stylish lighting and mirrors. The primary bath includes additional custom built-ins for optimal storage and organization. Throughout the home, fresh paint and luxury vinyl flooring create a clean, modern aesthetic. Additional features include an in-unit washer and dryer tucked behind a custom wood door, a built-in safe, and a new A/C unit installed in 2024. The residence also includes a deeded covered-parking space and a private storage unit. The Cloisters community offers a wealth of amenities, including an onsite property manager, ample guest parking, elevators, a heated pool, onsite laundry facilities, a putting green, private lake access, a dock, and boat slips available via resident lottery. Residents also enjoy two fitness centers with one dry sauna and a recently updated clubhouse with a full kitchen and bath—ideal for private gatherings. Just a short stroll from the boutiques, restaurants, and cultural attractions of Park Avenue, and Rollins College, this fully renovated, turnkey residence presents a rare opportunity to enjoy the ultimate blend of location, luxury, and lifestyle. Realtor/owner is a licensed Florida real estate broker.

100 S Interlachen Avenue Unit 204D, Winter Park

$2,125,000
2 Beds 3 Baths Landmark Winter Park SubDv. 32789 Zip Code
When you enter through the secure and elegant wrought iron gates and walk into in the private central courtyard, you'll feel the sophistication of The Landmark Winter Park. Take the elevator to the second floor and your private entrance balcony overlooking the courtyard. Inside, this spacious corner unit you'll find 2 bedrooms, 3 full bathrooms and a spacious media room/office. From the foyer look through the large dining and living room space to windows overlooking shady Morse Boulevard. This unit lives large with the floor plan nicely splitting the primary suite, second bedroom and media room/office for maximum comfort and privacy. And perhaps most impressive of all is the large, bright kitchen with huge center island, loads of counter space and storage, Sub Zero refrigerator, KitchenAid 6-burner gas range and wine cooler. Twelve-foot ceilings and large windows throughout add to to the spacious, luxurious feeling. The massive primary suite is truly a retreat, with French doors opening onto the private balcony from the bedroom, large spa-inspired bathroom and fully built-out walk-in closet. Bedroom two, on the other side of the condo also has a walk-in closet and a generous bathroom with step-in shower. The office/media room is large and private, completely separate from the bedrooms, with direct access to the third bathroom. Laundry/utility room with rear exit door is away from the living space and has lots of storage. Two dedicated parking spaces in the secure underground garage, and each unit has its own climate controlled storage space for bicycles and other large items. The Landmark Building is Winter Park's premiere address. Luxury, privacy and proximity to all Park Avenue is known for, including boutique shopping, cafes and fine dining, as well as Central Park and Rollins College with many events and programs throughout the year. Easy access to Central Florida's highways, and SunRail station just steps away. Luxury living in Winter Park, it is here in The Landmark.

140 E Morse Boulevard Unit C, Winter Park

$2,037,500
5 Beds 5 Baths Conwill Estates SubDv. 32789 Zip Code
Price Reduced to sell. An exceptional custom home by award-winning Davila Homes, perfectly blending modern design and functionality. Located in sought-after Conwill Estates, just minutes from Park Avenue, this 5-bed, 4.5-bath residence features volume ceilings, floor-to-ceiling bronze sliding doors, and a seamless indoor-outdoor living experience. The chef’s kitchen showcases waterfall quartz countertops, Sub-Zero & Wolf appliances, a large island, walk-in pantry, and opens to the living area with phantom screens and views of the resort-style gas-heated pool, fire pit, and a brand-new outdoor kitchen, perfect for entertaining. A first-floor owner’s suite offers pool views, private terrace, motorized shades, spa bath with soaking tub, and expansive shower. Upstairs you'll find 4 en-suite bedrooms, a bonus room with wet bar, wine fridge, 2nd laundry, and balcony overlooking the backyard. Additional upgrades include Summer Kitchen, surround sound, gas fireplace, upstairs & downstairs laundry, private well for irrigation, generator, new HVAC system for downstairs (2025), new water heater (2025), and air-conditioned garage with tiled floors (not included in living SF). This home has been impeccably maintained and is in pristine condition, aluminum roof is a plus. — it truly feels like new. From the moment you step inside, you’ll fall in love with its elegance and charm.

1781 Pine Avenue, Winter Park

$145,000
1 Beds 1 Baths Lakeside Manor Apts Condo SubDv. 32789 Zip Code
Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living room with dining space. The tidy kitchen with matching all white appliances is clean as a whistle. You'll love the large utility is where you'll find the air conditioner, hot water heater and plenty of shelving. The bathroom has new vanity (2025), mirror and light fixture (2025), and newer toilet. You'll find the bedroom spacious with a large double closet. Ceiling fans in living and bedroom. Location in the community is handy, with assigned parking space just steps away and easy access to the quiet courtyard. You'll love the lakefront outdoor space including pool, club house, tons of manicured green space, over-water covered seating on the new dock, boat launch and slips. Close to shopping and dining in Winter Park, easy access to highways. This community is everything people come to Florida to find!

2500 Lee Road Unit 243, Winter Park

$2,288,215
3 Beds 4 Baths Alabama Condo SubDv. 32789 Zip Code
A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

1602 Alabama Drive Unit PH404, Winter Park

$1,000,000
4 Beds 4 Baths Winter Park Village SubDv. 32789 Zip Code
Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining. Step inside to discover an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The kitchen features brand-new appliances, quartz countertops, shaker-style cabinetry, a classic subway tile backsplash, and a large island ideal for gathering. Elegant new light fixtures and a built-in wet bar elevate the space with a touch of sophistication. The first-floor primary suite is a serene retreat, offering two closets and a well-appointed en-suite bathroom complete with a soaking tub and separate walk-in shower. Upstairs, a spacious loft opens to a walk-out balcony and is accompanied by three additional bedrooms and two full bathrooms – perfect for family and guests. Storage is abundant with three walk-in closets, a double closet, and a convenient under-stair space. Additional highlights include a two-car garage with an epoxy floor, a screened patio for year-round enjoyment, and a fenced backyard oasis ideal for relaxation or entertaining. Freshly painted and surrounded by all-new professional landscaping with an irrigation system, this home offers exceptional curb appeal. Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle.

2607 Lafayette Avenue, Winter Park

$1,825,000
4 Beds 4 Baths Woodmere Terrace Rep SubDv. 32789 Zip Code
A rare gem in the heart of the Vias – Nestled in one of Winter Park’s most sought-after neighborhoods, this beautifully designed home is the epitome of comfort, luxury, and convenience. Located just minutes from Park Avenue, top-rated schools, and the best dining and shopping in Central Florida, this property offers an unbeatable lifestyle in a truly prime location. Inside, the home impresses with an open-concept first floor that’s tailor-made for entertaining. The seamless flow between the spacious living room, dining area, and chef’s kitchen makes it easy to host gatherings of any size—from intimate dinners to lively celebrations. Natural light pours in through large windows, highlighting designer finishes and a thoughtful floor plan that blends elegance with everyday functionality. With four oversized bedrooms and four full bathrooms, there's ample space for everyone to spread out comfortably. The private office on the main level is perfect for working from home, while upstairs, a versatile loft offers flex space that can be used as a playroom, reading nook, or creative studio. The true showstopper is the expansive theater room, offering endless possibilities—use it as a media lounge, game room, fitness center, or whatever your lifestyle demands. Step outside to your resort-inspired backyard oasis, featuring a sparkling pool and spa, lush, professionally landscaped grounds, and a covered patio that’s perfect for summer BBQs and year-round outdoor living. Whether you're relaxing with family or entertaining guests, this outdoor space delivers the feel of a luxury getaway right at home. Don’t miss your chance to own a home that offers exceptional space, stylish design, and one of the most desirable locations in Winter Park.

1665 Temple Drive, Winter Park

$2,100,000
4 Beds 3 Baths Cortland Park SubDv. 32789 Zip Code
Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame the formal entry, setting a tone of architectural distinction. Inside, a gallery-style foyer showcases designer wallpaper and salvaged pew rail detailing from a New York City church. The formal living room offers a stately gas fireplace, bespoke built-ins, and a large fixed window framing the lake, ideally suited for a quiet reading nook. The adjacent sunroom, encased in fixed glass, captures the surrounding canopy and lake vistas in all seasons. A generous dining room with custom dry bar, underlit floating shelving, and beverage refrigeration provides an ideal setting for elegant entertaining. The gourmet kitchen is thoughtfully appointed with paneled appliances including refrigerator and freezer columns, refrigerator drawers and a microwave drawer. Additional features include natural gas cooking, double ovens, and a sun-drenched breakfast room opening to the rear terrace and lap pool. A Dutch door entry offers functional access for daily living, while the basement below presents an opportunity for climate-controlled wine storage. The upstairs primary suite exudes comfort and sophistication with its gas fireplace, walk-in closet illuminated by a lake-facing window, a private covered balcony, and a spa-inspired bath with dual vanities, soaking tub, steam shower and private water closet. Two additional guest rooms with a Jack and Jill bath complete the upper level. Extensive renovations include a newer roof, Andersen windows and doors, two HVAC systems, full re-piping and rewiring, fresh paint, lighting, a newly installed pool heater and Hardie board siding—all executed within the last five years. The walk-up attic and pristine basement offer rare additional storage. Refinished hardwood floors throughout provide a consistent, elegant backdrop. This residence is a compelling blend of character, craftsmanship and contemporary living.

104 Cortland Avenue, Winter Park

$2,495,000
4 Beds 5 Baths Robert Dhu Macdonald Park SubDv. 32789 Zip Code
Now offered at $2,495,000—an outstanding value for a thoughtfully designed pool home on a spacious lot in Winter Park’s most sought after neighborhoods. Located in the heart of the “Golden Triangle”—the core residential district just a short walk from Park Avenue’s world-class shopping and dining—940 Lincoln Circle is a beautifully renovated West Indies/Key West-style home that blends architectural charm, comfortable elegance, and thoughtful functionality on an oversized .33-acre lot. With 4 bedrooms and 4.5 bathrooms across 3,551 square feet, this home lives primarily as a one-story layout, enhanced by a private upstairs suite with bedroom, full bath, and bonus room—accessible from both inside and a separate outdoor entry. Ideal for multigenerational living, guests, or private work/living quarters, this flexible plan is rarely available in such a prime location. A gated front porch and covered entry open into the foyer and an expansive formal living room with vaulted wood-paneled ceilings and gas fireplace. The space flows easily into the dining area and kitchen, which overlook the screened porch and backyard oasis. The kitchen is appointed with marble countertops, custom cabinetry, gas cooktop, cabinet-paneled Sub-Zero refrigerator/freezer, double ovens, and a walk-in pantry. A custom wine room—perfect for entertaining—sits just off the main living space. A nearby den (or optional fourth bedroom with closet) is paired with a bright enclosed Florida room currently used as a home office with rose garden views. This wing connects to a full bath and a secondary bedroom at the front of the home. A stylish powder bath is conveniently tucked away for guests. The private primary suite is positioned at the rear of the property and features a soft entry, dual custom closets, outdoor access, and a beautifully appointed bathroom with dual vanities, glass-enclosed shower, soaking tub, and private water closet. Upstairs, a second guest suite with bonus/flex room and full bath is ideal for visitors, a gym, or studio. At the rear of the home, a welcoming family room with fireplace opens to the covered lanai and kitchen, offering ideal indoor-outdoor flow. The backyard is a fully fenced retreat with lush landscaping, renovated saltwater pool with new equipment, and mature trees surrounding multiple hardscape patios and garden paths. A well-appointed full bathroom with exterior access off the screened patio offers convenient functionality for pool use, gardening, or even dog washing—enhancing the home’s seamless indoor-outdoor lifestyle. The outdoor kitchen includes a Blaze grill, Fire Magic refrigerator, Blackstone griddle, stainless sink, storage cabinetry, and vent hood—creating a true resort-style environment. The oversized two-car garage features epoxy floors, built-in storage, and space for larger vehicles. Additional highlights include two Rinnai tankless water heaters, 2024 Trane condenser, 2019 Mitsubishi mini-split, full-house Generac generator with transfer switch, motorized shades by The Shade Store, and a well-appointed laundry room with built-in cabinetry, utility sink, and yard access. A rare opportunity in Winter Park’s most walkable and desirable neighborhood.

940 Lincoln Circle, Winter Park

$4,599,000
5 Beds 7 Baths Robert Dhu Macdonald Park SubDv. 32789 Zip Code
Welcome to Lincoln! This new construction single family home has been meticulously crafted and constructed by Wooten Built, a locally established, award-winning developer and luxury home Builder. Location! Location! Location! Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to Winter Park shops, restaurants, and the Winter Park Golf Course. This bespoke home includes premium features, appliances, fixtures and finishes as follows: Elevator, Wolf/Sub-Zero appliances, wine cooler tower, built-in coffee maker, Lutron RA3 Automation, wired for security with plenty of camera drops, whole-house audio pre-wire featuring Sonos speakers and 5.1 surround, first floor primary bedroom with ensuite washer/dryer, additional guest suite first floor, 11’4” first floor ceilings and custom 10’ solid core DOORS, wet bar, large vaulted upstairs living room, large flex-space upstairs bonus room, trey ceilings, huge front entry window and door system, two 10’x10’ full-view garage doors, circular driveway, full-house natural gas generator, heated pool with spa and fire & water bowls, plenty of pool deck space, and exquisite landscaping. Smart glass covers the large ~14’ x 10’ front entry system… Choose frosted for privacy or transparent/thru-view at the press of a button! A 6’ masonry-stucco wall encompasses the property. The rear cabana/pergola houses the summer kitchen, pool bar, pool-bath and outdoor shower. Enjoy two fireplaces!: a 100” linear electric fireplace in living room and a 60” linear natural gas fireplace by the pool deck. Inquire with agent for more information.

985 Lincoln Circle, Winter Park

$718,500
3 Beds 3 Baths Quarters At Winter Park Condo Ph 2 SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. A rare (and low-maintenance!) gem, this 3 bed/2.5 bath home is located just around the corner from Park Avenue and Rollins College. Tucked away in the most perfect location, this 2-story Winter Park condo was stripped down to the studs and completely remodeled in 2007 with all new plumbing, electrical, ductwork, flooring, appliances, and natural gas line, plus (2) newer HVAC systems installed in Nov. 2022. The gated front courtyard was designed by a landscape architect, where foliage, a potted herb garden, wooden bench, and fountain create a tranquil welcome for your guests. Enter to a spacious dining room flooded with natural light through the bank of French doors that open to the courtyard. A built-in dry bar, complete with 2 wine refrigerators, makes this a perfect space for entertaining, while oak wood flooring throughout the home adds warmth and charm. The stylish chef’s kitchen has cool concrete counters, custom cabinetry, and dual-fuel 6-burner Wolf range, plus a cozy dinette with a built-in terrazzo-topped table and banquette. A breakfast bar provides extra seating, and the living room beyond includes a clean-burning bioethanol fireplace and soaring windows with views of the interior screened 2-story courtyard. Upstairs, the private primary retreat offers multiple closets, a balcony overlooking the interior courtyard, and an en-suite bath featuring a large walk-in shower with body sprays, a towel warmer, and a laundry room with built-in storage. At the opposite end, the front-facing bedroom can double as an office, with a custom built-in desk and shelving along one wall, plus a screened balcony that overlooks the front courtyard, perfect for sipping your morning coffee or tea. A 3rd bedroom, 2nd full bathroom, linen closet, and quaint sitting area/nook complete the second floor. A private alleyway behind the building provides access to the oversized 2-car garage with a custom built-in workbench and sink, and 2 dedicated storage units. Walk to the Rollins, Park Avenue, the Winter Park Tennis Center, Azalea Lane Playground, or through the brand new Seven Oaks Park on your way to the shops and eateries along Orange Avenue. The ideal blend of sophistication and practicality, this condo is simply perfect for those seeking an effortless lifestyle in the heart of Winter Park.

1130 Washington Avenue Unit 11-C, Winter Park

$780,000
2 Beds 2 Baths Cloisters Condo SubDv. 32789 Zip Code
Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

106 S Interlachen Avenue Unit 317, Winter Park

$535,000
2 Beds 1 Baths Cloisters Condo SubDv. 32789 Zip Code
The Cloisters, one of Winter Park's established and sought-after communities features an ornate architectural design complemented by lush landscaping and an inviting entryway. This fourth-floor two-bedroom, one-bathroom condominium offers approximately 901 square feet with a spacious and modern living experience. Upon entering this residence, you are greeted with a bright and open living area accentuated by abundant wide-plank oak hardwood flooring and complete with features such as crown molding, a Nest thermostat, recessed lighting, and plantation shutters. The primary bedroom provides ample space and natural lighting, while the updated kitchen boasts modern finishes, including new quartz countertops & backsplash, stainless steel appliances, and an induction oven. The bathroom has been upgraded with Kohler fixtures and porcelain tile. For added convenience, the home includes an in-unit washer and dryer, as well as a balcony providing access to the scenic views and spacious grounds. The electrical panel box has been updated, along with new electrical outlets throughout. Residents can enjoy the community's numerous amenities, including a heated pool, hosting events in the renovated social room with a full kitchen, boat dock, and putting green, all set against the tranquil backdrop of Lake Osceola. The association dues include cable TV, building insurance, internet, maintenance (grounds, exterior, pool), on-site management, sewer, trash collection and water, providing a maintenance-free lifestyle. Additional highlights include an assigned covered parking space, storage room and a lakefront seating area. This sophisticated condominium creates a welcoming and refined atmosphere, making this an ideal residence. The location is conveniently located within walking distance to the vibrant Park Avenue, offering access to boutique shopping, dining, Rollins College and the renowned Morse Museum.

100 S Interlachen Avenue Unit 410F, Winter Park

$217,500
2 Beds 2 Baths Mead Garden SubDv. 32789 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floor unit offers the ease of single-level living once inside, featuring an open-concept layout filled with natural light. The updated kitchen (2016) boasts stylish tile flooring that mimics hardwood, granite countertops, a farmhouse sink, and stainless-steel appliances, all overlooking the spacious great room. One of the property's standout features is the spacious private balcony overlooking the lush beauty Mead Gardens. The balcony offers privacy and tranquility as there are no rear neighbors. The primary suite offers a peaceful garden view, an ensuite bath with walk-in shower and a single vanity. The second bedroom features sliding doors to the front entry and has easy access to a full guest bathroom with a tub/shower combo. Residents enjoy access to a sparkling community pool, laundry facilities, and mailboxes just steps away. Enjoy this prime Winter Park location, located just minutes from Park Avenue and Rollins College.

1250 S Denning Drive Unit 230, Winter Park

$1,042,500
4 Beds 3 Baths Dixie Terrace SubDv. 32789 Zip Code
Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park Village, this beautifully renovated 4-bedroom, 3-bath home offers the ultimate in walkable luxury living. Nestled on a charming brick street lined with sidewalks, this residence combines timeless elegance with unbeatable convenience. Inside, enjoy 10’ ceilings, rich wood, custom tray ceilings, and detailed crown molding. The home has been thoughtfully renovated, delivering a fresh, timeless aesthetic throughout. The flexible downstairs bedroom makes a great guest suite, home office, or den. Upstairs, the stunning primary suite is a true retreat, complete with French doors to a private covered patio, a walk-in closet, and a newly renovated spa-like bath featuring dual vanities, an oversized soaking tub, and a luxurious steam shower. Two additional upstairs bedrooms share a modern, well-appointed bathroom, and a conveniently located laundry room adds to the home’s functional appeal. Step outside and enjoy Florida living at its best with a second covered patio that opens to a spacious, private backyard—a rare find this close to Park Avenue. A paver driveway with extra parking pad leads to a one-car garage. Located in a top-rated school district and are the corner from shops, restaurants, parks, and more, this home offers a lifestyle of comfort, charm, and convenience in one of Winter Park’s most sought-after neighborhoods.

1341 Lyndale Boulevard, Winter Park

$570,000
2 Beds 3 Baths Killarney Bay Condo SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opportunity to enjoy waterfront living with unmatched convenience. Just steps from Hillstone, Trader Joe’s, and Winter Park Village, this 2-bedroom, 2.5-bathroom home is the perfect blend of modern sophistication and timeless charm. Inside, you’ll find a beautifully designed open-concept kitchen ideal for entertaining, two spacious primary suites—each with its own spa-inspired en-suite bathroom—and a bonus office space with sweeping lake views that make working from home feel like a retreat. From top to bottom, every detail has been thoughtfully curated for both comfort and style. Step outside to your private covered patio and soak in postcard-worthy sunsets, or head down to the dock for a quiet moment by the water. The community offers a serene lakeside pool, very low HOA fees, and a laid-back lifestyle just minutes from some of Winter Park’s best shopping and dining. Come discover a one-of-a-kind home where lakefront tranquility meets urban convenience—this is Winter Park's best kept secret.

640 Killarney Bay Court Unit 4, Winter Park

$2,440,000
4 Beds 5 Baths Winter Park Heights SubDv. 32789 Zip Code
One lucky Buyer's gain is this Seller's bittersweet goodbye. A job relocation has these homeowners leaving behind a home they absolutely love, and now, you can make 1700 Palm Ave. yours! Modern sophistication and everyday functionality come together seamlessly in this exceptional Winter Park residence. With 3,770 square feet of thoughtfully designed living space, this 4-bedroom, 4.1-bath home offers a fantastic floorplan featuring a first-floor primary suite, private office, and a striking two-story great room filled with soft natural light from the south-facing backyard. Upstairs, a generous loft/bonus room accompanies three en-suite bedrooms, including a second suite designed as an alternate primary, complete with a private balcony, dual walk-in closets, and a dedicated water closet. The smart three-way split bedroom configuration enhances privacy and flexibility, while the first-floor primary suite features two large walk-in closets and a stackable washer and dryer for added convenience. The open-concept layout flows effortlessly to the covered lanai, complete with electronic roll-down screens, two beverage refrigerators, and a gas grill—overlooking a sleek saltwater pool framed by gray and white marble pavers. Tall sliding glass doors stack to create a seamless indoor-outdoor living experience, perfect for entertaining. Lush, mature podocarpus hedges and Japanese blueberry trees line the perimeter, offering a private and polished backdrop. The chef’s kitchen is outfitted with top-of-the-line Viking appliances, a gas cooktop, quartz countertops, and a walk-in pantry. A spacious island with a beverage fridge and generous storage complements the adjacent dining area, which comfortably seats eight, with room to expand for larger gatherings. Custom electronic roller shades add privacy and a clean, modern aesthetic, electronic/rechargeable blinds throughout the first floor and matching manual blinds upstairs. Wide-plank oak floors extend throughout the main level and up the architectural floating staircase. The oversized garage is equally well-appointed, featuring two storage closets and a built-in rack system. Ideally located just minutes from Winter Park’s renowned shops and dining on Park Avenue. The home is zoned for top-rated WP schools, including Winter Park High, Maitland Middle, and Lakemont Elementary. Looking to join a tennis league or spend afternoons on the golf course? This home is surrounded by both public and private clubs for social and athletic enjoyment. 1700 Palm Ave. delivers fabulous living in one of Central Florida’s most coveted neighborhoods.

1700 Palm Avenue, Winter Park