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1140 Washington Avenue Unit 16C, Winter Park
$739,000
3 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Renovated in 2022, this 3-bedroom, 2.5-bath home offers 2,069 square feet of bright, modern living space. The open main level connects the living area, dining space, and kitchen, which has stainless steel appliances and sleek contemporary cabinetry. A fireplace anchors the living room, and large windows bring in natural light throughout. Upstairs, the oversized primary suite gives you room to spread out, with two more bedrooms for guests, a home office, or flexible space. Step outside to a private courtyard with a outdoor kitchen, a quiet place for morning coffee or evening dinners . A 2-car garage with electric car charger and large driveway complete the package. Roof replacement Jan 2027. 5-minute walk to Rollins College and 10 minutes on foot to Park Avenue’s shops, restaurants, and Saturday farmers market. You can leave the car in the garage.

1140 Washington Avenue Unit 16C, Winter Park

700 Melrose Avenue Unit B23, Winter Park
$295,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Enjoy beautiful pond and garden views from this tastefully updated two-bedroom, two-bath upstairs condominium in Winter Park Gardens. The kitchen features solid-surface countertops and wood cabinetry, while both bathrooms offer updated vanities and elegant finishes. Plantation shutters, laminate and tile flooring complement the inviting interior. A bright Florida room with floor-to-ceiling windows provides the perfect setting to relax and take in the breathtaking pond and garden views. The unit is also plumbed for convenient in-unit washer and dryer installation. Set on more than eight acres of lush, meticulously maintained grounds, Winter Park Gardens features landscaped gardens, a tranquil pond, and a community pool. Located next door to the Winter Park Tennis Center and within walking distance of Rollins College and Park Avenue, this beautifully maintained and managed community places you minutes from Winter Park’s finest restaurants, gardens, and parks.*Click on Virtual Tour for video overview of this exceptional community!

700 Melrose Avenue Unit B23, Winter Park

1118 Washington Avenue Unit 5C, Winter Park
$895,000
3 Beds ⋅ 3 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Welcome to 1118 Washington Ave, a spacious 3-bedroom, 2.5-bath townhome in one of Winter Park's most walkable and sought-after locations. 2,100 square feet of light-filled living space, plus a 300+ square foot glass atrium, puts the best of the city right outside your door. The showstopper is the one-of-a-kind glass atrium / covered patio. Sunlight pours in, and it's great for morning coffee, dinner with friends, or a quiet evening with a book. You won't find another like it! Inside, the open, airy layout flows easily from living areas to bedrooms. Updated flooring gives the home a clean, move-in-ready feel, and the A/C was replaced in 2024. A brand-new roof is being installed, so you can buy with confidence. The spacious two-car garage gives you plenty of room for vehicles, storage, and hobbies. The location is what makes this home special. Park Avenue's boutiques, cafés, and restaurants are just steps away, and Rollins College is nearby. Walk to the Winter Park Tennis Center, or spend afternoons at Seven Oaks Park and Mead Botanical Garden. A stroll down to the lake is part of your everyday routine. Few homes put so much of what makes Winter Park special within a few minutes' walk. Come see why this one is a rare find.

1118 Washington Avenue Unit 5C, Winter Park

1261 Michigan Avenue, Winter Park
$650,000
3 Beds ⋅ 3 Baths ⋅ Park Shore SubDv. ⋅ 32789 Zip Code
Exceptional Winter Park Living! Discover this newer, two-story SMART corner townhome, ideally situated in a highly desirable Winter Park location. Showcasing attractive architectural details, a welcoming covered entry, and meticulously maintained tropical landscaping, this residence offers the perfect blend of modern sophistication, comfort, and convenience. Step inside to a spacious, light-filled open-concept living and dining area highlighted by soaring ceilings, attractive wood-look flooring, contemporary finishes, and an effortless transition into the stunning kitchen. Designed for both everyday living and entertaining, the kitchen showcases crisp white cabinetry, stainless steel appliances, an expansive quartz waterfall island with seating for four, designer pendant lighting, and sliding glass doors opening to the private courtyard. A versatile built-in serving area, ideal for a coffee bar or dry bar, adds both style and functionality. The inviting courtyard provides a seamless extension of the interior living space, creating an intimate setting for alfresco dining, entertaining, or simply unwinding. Accented by elegant travertine flooring, this charming outdoor retreat also offers covered access to the detached two-car garage. Upstairs, you will find three generously sized bedrooms, two tastefully updated baths, and a spacious laundry room. The serene primary suite offers a relaxing escape with sophisticated accent walls, oversized windows, and elegant trim details. The luxurious en-suite bath features dual vanities, sleek quartz countertops, modern lighting, and an oversized walk-in shower with a frameless glass enclosure and exquisite floor-to-ceiling tile. Two additional bedrooms are filled with natural light and offer flexible living arrangements, including the possibility of a home office or study. Connecting these bedrooms is a beautifully designed Jack-and-Jill bath featuring a double-sink vanity, quartz countertops, stylish lighting, and a tub/shower combination enhanced by floor-to-ceiling tile. Remote-controlled window shades throughout provide added privacy and convenience, while a central vacuum system offers another thoughtful feature. Completing the second floor is an oversized laundry room equipped with a full-size washer and dryer, extensive custom cabinetry, ample countertop space, and attractive wood-look flooring. Perfectly positioned near the exciting new Minnesota Row development, this residence enjoys convenient access to shopping, dining, and major roadways. Just minutes from the heart of downtown Winter Park and its renowned Park Avenue shopping district, residents can enjoy an exceptional selection of sidewalk cafés, fine dining, upscale boutiques, museums, and the picturesque beauty of Central Park. Combining sophisticated finishes, thoughtfully designed interiors, exceptional outdoor living, and the convenience of SMART home technology, this impressive corner townhome offers an outstanding opportunity to enjoy the very best of the Winter Park lifestyle. A must-see residence! Call today to schedule your private showing!

1261 Michigan Avenue, Winter Park

1350 Lyndale Boulevard, Winter Park
$1,499,000
4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
Photos coming soon. Experience timeless elegance and exceptional living in the heart of Winter Park! Nestled along a charming, quiet brick-lined street just moments from iconic Park Avenue, this beautifully designed custom residence offers the perfect combination of sophistication, comfort, and Florida indoor-outdoor living. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and 3,478 square feet of living space, this impressive home welcomes you with soaring 10-foot ceilings, rich Brazilian cherry hardwood floors, elegant architectural details, and an abundance of natural light. At the heart of the home, the gourmet kitchen is designed for both everyday living and effortless entertaining, featuring a spacious center island, natural wood cabinetry, premium cooking appliances, built-in refrigerator, and wine refrigerator. The kitchen flows seamlessly into the inviting family room, complete with a beautiful gas fireplace. The luxurious first-floor primary suite offers a peaceful retreat with generous walk-in closets, a spa-inspired bathroom, and French doors opening to the private screened pool and patio. Upstairs, additional bedrooms and a spacious bonus room provide flexibility for a home office, fitness studio, media room, or guest accommodations. Step outside to your own private oasis, where a sparkling pool, relaxing spa, mature landscaping, and inviting outdoor living spaces create an ideal setting for entertaining or unwinding year-round. Additional highlights include formal living and dining spaces, an attached two-car garage, abundant storage, and a desirable location with no HOA. Enjoy the best of the Winter Park lifestyle, with convenient access to Park Avenue's celebrated restaurants, boutique shopping, cafés, cultural attractions, parks, and nearby lakes. An exceptional opportunity to own a distinctive residence in one of Central Florida's most desirable communities. Schedule your private showing and discover everything this Winter Park home has!

1350 Lyndale Boulevard, Winter Park

700 Melrose Avenue Unit A22, Winter Park
$310,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Discover the charm of Winter Park Gardens, a sought-after 55+ community nestled among more than 8 acres of lush landscaping, majestic live oak trees, winding walking paths, and tranquil pond views. This inviting 2-bedroom, 2-bathroom condo offers approximately 1,074 square feet of comfortable living space. One of its most special features is the enclosed, air-conditioned Florida room, where dramatic floor-to-ceiling windows frame beautiful pond and garden views, creating the perfect setting to enjoy your morning coffee, unwind with a good book, or simply take in the peaceful surroundings. Thoughtfully updated by the current owner within the past year, improvements include a new tankless water heater, new toilets, upgraded electrical panel, new primary bedroom window, new primary bathroom vanity, and new closet doors throughout the hallway and bedrooms. The kitchen features updated appliances, including a newer refrigerator, and washer/dryer hookups add everyday convenience. One assigned parking space is also included. Enjoy the community swimming pool and beautifully maintained grounds. Conveniently located within in a few short minutes of downtown Winter Park, Park Avenue, Rollins College, and Mead Botanical Garden, this residence offers the perfect blend of comfortable living, natural beauty, and the sought-after Winter Park lifestyle. Experience the convenience, peaceful surroundings, and unique appeal that make Winter Park Gardens such a special place to call home!

700 Melrose Avenue Unit A22, Winter Park

1500 Harris Circle, Winter Park
$1,175,000
3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set among distinguished residences and substantial lakefront estates, the home occupies a corner lot along a charming brick street and offers three bedrooms, three full bathrooms and approximately 2,096 square feet of living space. Extensive improvements in recent years bring together exceptional finishes, thoughtful craftsmanship and substantial updates behind the walls. With interior design by New York City–based Paulette Pascarella, traditional architectural details find fresh expression through sophisticated materials and beautifully considered modern appointments. Expansive windows welcome natural light, while polished marble flooring in warm ivory tones extends throughout much of both levels. The kitchen features solid wood cabinetry, quartz countertops and a full-height backsplash, complemented by a Bertazzoni refrigerator, Bosch 800 Series gas range and Miele dishwasher. A separate study and sitting room has wood flooring and custom built-ins. With a full bathroom immediately adjacent, this versatile space presents potential for conversion into a fourth bedroom with an en-suite bath. Carefully selected details include Visual Comfort and Currey lighting, Buster + Punch and Baldwin hardware, and custom window treatments incorporating designer textiles and motorized shades from The Shade Store. Nine Marvin Ultimate windows with wood interiors, a VELUX skylight and a mahogany Craftsman front door further distinguish the renovation. A custom stair railing by Boris Petkoff Iron Works and millwork by Dunning Custom Carpentry add distinctive craftsmanship. All three bedrooms are upstairs, where the primary suite features soaring ceilings, treetop outlooks and an extensively fitted California Closets walk-in dressing room with custom cabinetry and soft-close dovetail drawers. Its beautifully appointed bathroom features Perrin + Rowe Georgian Era vanity and shower fixtures, reflecting the caliber of fittings selected throughout the home. Two additional bedrooms, one with an en-suite bathroom, provide flexibility for guests or a home office. Upstairs views of Lake Sylvan connect the interiors to their picturesque surroundings. Substantial improvements include whole-house repiping, electrical upgrades, a Rinnai tankless water heater and a whole-house water treatment system. The roof was replaced in August 2023. Outside, cottage gardens frame a welcoming entrance, while an intimate brick patio nestled within the garden and a quiet garden corner offer peaceful places for morning coffee or an afternoon outdoors. A private parking pad adds convenience. Beyond the garden, oak-shaded brick streets invite leisurely walks past beautiful homes and scenic views of Lakes Sylvan and Osceola. A small lakeside green space lies just down Harris Circle, with Crosby Wellness Center, AdventHealth and Park Avenue’s dining, boutiques and cultural attractions conveniently nearby. An inviting choice for a primary residence or Winter Park retreat.

1500 Harris Circle, Winter Park

2718 Eastern Parkway, Winter Park
$2,450,000
4 Beds ⋅ 5 Baths ⋅ Parklando SubDv. ⋅ 32789 Zip Code
Exceptional craftsmanship, bespoke finishes, and impeccably appointed interiors define 2718 Eastern Parkway, a newly constructed residence by Barefoot Brothers Construction in Winter Park. Offering 3,308 square feet of thoughtfully designed living space, this four-bedroom home with four full baths and one half bath seamlessly blends timeless architecture with modern luxury. A gated front courtyard creates a gracious arrival experience, setting the tone for the exceptional attention to detail found throughout. Inside, detailed ceilings, and wainscotting, rich engineered hardwood flooring, custom millwork, and artisanal built-ins create a sophisticated yet welcoming atmosphere. Influenced by British Colonial design, the interiors showcase layered textures, refined architectural details, and carefully curated finishes that elevate everyday living. The expansive great room flows effortlessly into the dining area and chef's kitchen, providing an elegant setting for both intimate gatherings and grand entertaining. Designed as the heart of the home, the kitchen features striking quartzite countertops, custom tailored cabinetry, a walnut island, and luxurious appliances. A separate walk-in pantry and refined scullery provide discreet preparation and storage spaces, while a dedicated mudroom enhances functionality without compromising style. Privately situated on the main level, the primary suite serves as an opulent retreat, complete with an artfully crafted walk-in wardrobe and a spa-inspired bath featuring dual vanities, a freestanding soaking tub, an oversized walk-in shower, a private water closet, and linen storage. Upstairs, a second primary suite offers equally impressive accommodations with its own walk-in closet and well-appointed en-suite bath. Two additional bedrooms, each featuring private en-suite baths, provide exceptional comfort and flexibility for family and guests. The home's outdoor living experience is equally compelling. A covered lanai overlooks a private resort-style pool, while the summer kitchen with built-in grilling station creates the perfect backdrop for year-round alfresco dining and entertaining. Additional highlights include a two-car garage, natural gas service, two tankless water heaters, and abundant storage solutions throughout. Located in the heart of Winter Park, the home enjoys convenient access to the area's most coveted destinations, including Park Avenue's renowned boutiques, fine dining, sidewalk cafés, Central Park, museums, galleries, the farmers market, and Winter Park Village. Defined by bespoke craftsmanship, luxurious millwork, and thoughtfully curated design, the well appointed 2718 Eastern Parkway home presents a rare opportunity to experience elevated living in one of Central Florida's most desirable communities.

2718 Eastern Parkway, Winter Park

1611 Chestnut Avenue, Winter Park
$985,000
4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code
Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.

1611 Chestnut Avenue, Winter Park

700 Melrose Avenue Unit M23, Winter Park
$289,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park

2823 Parkland Circle, Winter Park
$3,250,000
5 Beds ⋅ 6 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, this nearly 4,500 square-foot home pairs thoughtful design with exceptional indoor-outdoor living. An impressive entry foyer sets the tone for a residence filled with designer details and and a floor plan featuring five en-suite bedrooms, six full baths, and the convenience of two laundry rooms to serve each floor. At the heart of the home, the chef's kitchen is appointed with Thermador appliances and designed for every day living and entertaining. Expansive living spaces are anchored by an indoor fireplace, and flow seamlessly to the covered lanai, where a second fireplace, fully equipped outdoor kitchen and private pool create an exceptional setting for year-round Florida living. Outdoor lush tropical landscaping and striking gas lanterns give the home a distinctive sense of arrival and timeless curb appeal. An oversized garage provides generous space for vehicles and storage, while integrated smart-home features including cameras, alarm, smart switches, and speakers with Sonos, bring modern convenience throughout. Zoned for sought-after Audubon Park School and Winter Park High School.

2823 Parkland Circle, Winter Park

1742 Temple Drive, Winter Park
$3,395,995
4 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
The Art of Living Well: A New Chapter at Moon Haus, Winter Park, Florida Moon Haus is a ground-up, virtually new modern luxury home in Winter Park, Florida, minutes from Park Avenue, Interlachen Country Club, and Phelps Park. This is not a renovation. It was designed and built as a true architectural revival, with the engineering and finish of brand-new luxury construction. From the moment the custom 10-foot glass pivot door swings open, you realize this is not just a house — it is the life you have been envisioning. You step into a light-flooded foyer, and the outside world instantly quiets. Sleek Italian wood floors run underfoot, drawing you into a main living room anchored by a dramatic statement fireplace — a space made for slow espresso mornings and evenings full of friends. The home runs on Control4 smart-home automation. With a tap, lighting shifts to an evening mood, and the climate adjusts. One system runs the whole experience — lighting, and climate — an invisible concierge for the entire home. The kitchen is built for people who love to cook and host. Light-toned European cabinetry conceals clever storage, Neolith surfaces frame professional-grade Sub-Zero and Wolf appliances, and the space works just as well for a multi-course dinner party as for a slow, sun-drenched Sunday morning. Outside, the home becomes a private resort. Glass doors slide open to a rich Brazilian IPE wood deck and a heated French gray mini-pebble pool. At dusk, the sintered-stone summer kitchen fires up under the Florida stars, with soft exterior lighting across the manicured grounds. A generator keeps the essentials running, so the calm does not depend on the weather. Each bedroom is its own en-suite retreat, and the primary suite feels like a boutique hotel. The spa-inspired bath has custom vanities, Neolith surfaces, and gentle ambient lighting, with a custom closet made for a real wardrobe. At the end of the day, it is a profound sense of calm. Set in one of Winter Park's most coveted enclaves, just moments from the energy of Park Avenue, the prestigious Interlachen Country Club, and Phelps Park — and zoned for Dommerich Elementary, Maitland Middle, and Winter Park High, top-rated schools all within about a mile and a half — this is a rare chance to own a virtually new masterpiece in an established, iconic location. Experience the art of living well — connect with us today for an exclusive private tour.

1742 Temple Drive, Winter Park

200 S Interlachen Avenue Unit 350, Winter Park
$2,350,000
3 Beds ⋅ 4 Baths ⋅ Versailles Winter Park Condo SubDv. ⋅ 32789 Zip Code
Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

1250 S Denning Drive Unit 127, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code
Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to a screened-in porch overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park

151 N Orlando Avenue Unit 242, Winter Park
$269,000
2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

151 N Orlando Avenue Unit 242, Winter Park

623 Grenadine Court Unit 623, Winter Park
$189,900
2 Beds ⋅ 2 Baths ⋅ Winter Park Villas Condo SubDv. ⋅ 32792 Zip Code
PRICE IMPROVEMENT! Welcome to this Desirable Winter Park Villas Condo FIRST FLOOR 2 BEDROOM, 2 FULL BATH, 1037 square feet, featuring NEW AIR CONDITIONING SYSTEM and BRAND NEW CARPET freshly installed! EXCELLENT LOCATION walking or bike riding distance to FULL SAIL UNIVERSITY and easy access to UCF! Ideally located in rear of community with ample open parking. Your spacious Kitchen features ample counter space and abundant cabinetry, kitchen sink window with view of front door entry and parking area. Kitchen has a closet pantry and there is an opening to Dining Room with Bar Seating area. Dining Room has views to backyard and a Wet Bar with unique Sink Closet feature. Family Room has a fireplace and views of outside greenery. In hallway off entry is your Washer/Dryer closet and they are both included in the sale. The Primary Bedroom is large with walk in closet, full bathroom with tub shower combo and two vanities. The Secondary Bedroom features back yard views and built in closet and easy access to hallway full second bath. Outside you'll love the covered patio and lawn area for lounging or gardening outside. Off the patio is a storage closet for the Water Heater. Winter Park Villas amenities include community pool, fitness center and tennis courts. Seller is offering a One Year Assurant Home Warranty covering all the appliances included. Located in Winter Park School District and easy access to Orlando International Airport! Call for to see it today, priced under $200,000 location can't be beat! Property may be under audio/visual surveillance.

623 Grenadine Court Unit 623, Winter Park

857 Brock Street, Winter Park
$4,350,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences. Renderings are artistic interpretations. Features and finishes may vary from final construction.

857 Brock Street, Winter Park

1500 Gay Road Unit 3C, Winter Park
$235,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
NEW PRICE/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park

101 S New York Avenue Unit 311, Winter Park
$1,775,000
3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park

1927 Eland Avenue, Winter Park
$799,000
5 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code
A rare single family home with a HUGE guest house, 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. 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. 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. 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

205 Lewfield Circle Unit 205, Winter Park
$182,900
2 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. NEW PRICE! Motivated seller! Move-in ready! Exceptional value in the heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath ground-floor condominium, where comfort, convenience, and an unbeatable location come together. The thoughtfully designed floor plan features an open-concept living and dining area, a screened patio overlooking peaceful landscaped gardens, and recent upgrades and maintenance, including a new electrical panel (2024), washer & dryer (2024), dishwasher (2023), refrigerator (2020), and a complete A/C system service (2025). Enjoy resort-style amenities at Stratford at Winter Park, including two swimming pools, two lighted tennis courts, a fitness center, clubhouse, and car care facilities, all within a beautifully maintained community. Perfectly located just minutes from Park Avenue, Baldwin Park, Full Sail University, Rollins College, AdventHealth Winter Park, shopping, dining, cafés, golf courses, and major highways, this home offers the ideal balance of everyday convenience and the sought-after Winter Park lifestyle. Competitively priced and offering exceptional value in today's market, this move-in-ready home presents the perfect, investor-friendly environment with high rental potential, while also serving as an ideal primary residence or seasonal getaway. Schedule your showing today! Note: Some photos have been virtually staged for illustrative purposes.

205 Lewfield Circle Unit 205, Winter Park

2500 Lee Rd. Unit 222, Winter Park
$184,400
1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
Rent-to-own or lease option available with negotiable terms—Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil lakefront gazebo. Perfectly located just minutes from the world-class shopping and dining of Winter Park Village, this home provides the ultimate balance of peaceful lakeside serenity and city convenience. The interior is just as impressive as the location. This charming, sun-drenched unit features an open-concept layout with gorgeous engineered wood flooring and a sleek kitchen upgraded with granite countertops. It’s a smart, stylish, and incredibly rare find that’s perfectly priced to sell. Whether you are looking for a low-maintenance home or a serene weekend getaway, this property delivers. Don't let this opportunity slip away—schedule your private showing today!

2500 Lee Rd. Unit 222, Winter Park

311 E Morse Boulevard Unit 7-11, Winter Park
$279,000
1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, Winter Park

3370 Cedar Springs Place Unit 156, Winter Park
$179,990
2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 09 SubDv. ⋅ 32792 Zip Code
Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own private bathroom. Step outside to a fenced-in patio that overlooks a serene water canal and conservation area—perfect for relaxing or entertaining. Additional features include an outdoor storage room and extra storage space under the stairs. The Hidden Oaks community offers residents access to a beautiful pool and playground. Whether you're a first-time homebuyer, an investor, or simply looking for a cozy place to call home, this property presents a standout opportunity close to major highways, universities, and popular dining spots in Central Florida.

3370 Cedar Springs Place Unit 156, Winter Park

311 E Morse Boulevard Unit 7-5, Winter Park
$299,000
1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park!  This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and  Structural Integrity Reserve Study with flying colors. Enjoy all of these activities nearby including the award winning restaurants, boutique shops and museums.  There is walkability to the Alfond Inn, Rollins College, the Sunrail / Amtrak Station, Farmer's Market and all things the Park Avenue area has offers including beautiful parks and lakes to explore.  Just outside your door and on the shore of Lake Osceola you will find the historic Winter Park Boat Tour.  At Whispering Waters the lush community grounds and shared patios are a tropical oasis of flowering plants and charming decorative ponds.  This highly sought after ground floor corner unit comes with an abundance of natural light and has just been freshly painted as well as new energy efficient windows installed.  It features neutral colors, easy care ceramic tile in the kitchenette & bathroom, with laminate flooring in the main living area.  The low monthly HOA fee includes electricity, gas, heat, water, sewer, trash, grounds care, pool service and all building exterior maintenance. The owner pays for Cable & Internet. Association approval is required for all new owners.  One assigned & deeded exterior parking space comes with this unit. Drop your groceries off in the covered and gated parking garage in the basement, with a short elevator ride to the ground floor.  Amenities include an onsite manager, pool, clubroom, covered boathouse with boat slips (Docks may become available for lease or purchase). Whether you are seeking a full-time residence, a winter retreat or mother/father in-law suite, this home offers effortless, low-maintenance living-just lock and leave!l Schedule your showing soon as this gem is sure to go quickly! Professional photographs coming soon!

311 E Morse Boulevard Unit 7-5, Winter Park

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