Winter Park, FL Real Estate Search

Winter Park, FL Properties for Sale

 Winter Park Homes for Sale  Winter Park Condos for Sale

Winter Park is a city located in Orange County, Florida, a city of about 25,000 residents. Famous for its stately trees, brick lined roads, spectacular homes, museums, shops along Park Avenue and it breathtaking parks.

Chartered in 1887 the city was originally used as a winter resort for the wealthy Northerners seeking refuge from the cold winters and looking for a warm tranquil place to relax, its main attractions to tourist were its lakes, warm temperatures and natural habitat.

Rollins College the oldest college on Florida and the nations premiere Liberal Arts College was founded ion Winter Haven in 1885 by New England Congregationalists who sought to bring their style to Florida liberal arts education. Rollins has been praised by magazines such as Time and U.S. New and World report has named it one of "America's Best Colleges".

With several lakes adjoining each other and home to Orlando´s many Lake Front Homes, Winter Park is now considered one of the most sought after residential areas a few minutes drive North of Downtown Orlando. Private Schools, Boutique Shops, Luxury Condos, Fine Dining Restaurants, Law Firms and Private Health Clinics are commonly associated with Winter Park.

Welcome to Winter Park, FL, a city that embodies historic elegance, cultural richness, and timeless charm. Nestled just outside of Orlando, Winter Park offers residents a unique living experience characterized by beautiful homes, tree-lined streets, and a vibrant arts and cultural scene. If you're seeking a home that combines history and sophistication, Winter Park is the perfect destination to find your dream residence.

Elegant Homes with Historic Character:

Winter Park features elegant homes that showcase historic character, featuring architectural details and design elements that reflect the city's rich heritage.

Arts and Cultural Scene:

Living in Winter Park means immersing yourself in a thriving arts and cultural scene, with galleries, museums, theaters, and events that celebrate creativity.

Tree-Lined Streets and Scenic Beauty:

Residents of Winter Park enjoy the picturesque beauty of tree-lined streets, lush landscapes, and charming neighborhoods that create a tranquil and inviting atmosphere.

Boutique Shopping and Culinary Delights:

Winter Park offers boutique shopping districts and a culinary scene that caters to diverse tastes, providing residents with a range of unique experiences.

Expert Guidance from Local Realtors:

Navigating the Winter Park, FL real estate market is made easier with the help of local realtors. Their in-depth knowledge of the area and housing market will guide you in finding the perfect home that aligns with your vision of historic elegance and cultural richness.

Conclusion:

Winter Park, FL, offers a living experience where history, culture, and charm harmonize beautifully. Explore Winter Park real estate and discover homes that epitomize the beauty of elegant living. Whether you're seeking a historic home with timeless appeal or a modern residence nestled in a quaint neighborhood, Winter Park provides the perfect opportunity to embrace the city's rich heritage and immerse yourself in its vibrant cultural scene.

Our website features the best Winter Park, FL real estate search for homes, and land properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Winter Park, FL Properties for Sale

Avg. No of Beds
Avg. No of Baths
Avg. Living Ft2
Avg. Listing Price
Cost per ft2
Days on Market

Curious about what’s happening in the Winter Park, FL real estate market? Sign up for a  Winter Park, FL Real Estate Market Report to see what’s active, under contract, and sold!

Newest Winter Park, FL Properties for Sale

$4,250,000
5 Beds 5.5 Baths Robert Dhu Macdonald Park SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Pre-Construction. To be built. Customize the finishes-to-suit on your new home located on one of the most sought-after streets in Winter Park. Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to your favorite shops, restaurants, and the Winter Park Golf Course. Presented by an established, award winning luxury home builder, this bespoke home includes premium features, appliances, fixtures and finishes as follows: ELEVATOR, WOLF/SUB ZERO appliances, wine cooler tower, built-in coffee maker, trash compactor, AUTOMATED LIGHTING and window treatments, full house SOUND SYSTEM, first floor primary bedroom with ensuite washer/dryer and two-person shower, additional GUEST SUITE FIRST FLOOR, 11’4” FIRST FLOOR CEILINGS with 10’ DOORS, wet bar, large vaulted loft, bonus room, three full suites upstairs, trey ceilings, master-carpentry detail throughout, “store-front” window and door system in front, two 10’x10’ full-view garage doors, circular driveway, heated pool with spa and wet sun deck, plenty of pool deck space, and exquisite landscaping. A 6’ masonry-stucco wall encompasses the rear perimeter. The rear cabana houses the summer kitchen, a pool bar, pool-bath and outdoor shower. Enjoy two fireplaces: a linear electric fireplace in living room and natural gas fireplace on rear lanai. Life-like virtual renderings show sample finishes only. You may select your own finishes and colors upon pre-construction purchase. Call now to schedule your meeting with the Builder and get started on your new home!

985 Lincoln Circle, Winter Park

$775,000
Lake Forest Park SubDv. 32789 Zip Code
Back on market. Buyer's financing fell thru. Located 2 miles from historic downtown Winter Park, this 3 bedroom/ 2 bath, 2,220 sq ft mid-century modern is a unique gem. The parcel is a great opportunity to build new or renovate. Perched on a knoll overlooking spring fed Lake Forest, this property is surrounded by the beauty and tranquility of Nature. Cozy and charming, the floor plan is functional, open, and bright. The main living areas and bedrooms have beautiful, mint-condition paraquet floors. The kitchen, located off the carport, has a new range, stainless sink, built-in pantry and room for a washer and dryer. Formal dining room overlooks the library. With 2 walls flanked with floor to ceiling bookcases, the library could make a great home office or additional living space. The family room and Florida room have a bank of windows that overlook the terraced back yard and have views of the lake. With a wood-burning fireplace, built-ins, concrete floors and beamed ceiling, the Florida room would make a great artist’s studio. The spacious bedrooms are located on the right side of the property with 2 bedrooms sharing a Jack ‘N’ Jill bath. The backyard is an oasis with ample grassy space framed with a concrete block wall with 2 more terraced levels down to the lake. The front yard has citrus trees, Brazilian grape vine, lychee and loquat trees and an abundance of camellias and azaleas. Improvements include AC in 2017, roof in 2015 and some windows in 2001. Central location close to Corrine Dr. shops and restaurants, Baldwin Park and downtown Orlando. Top-rated school district with zoning for Audubon K-8 and Winter Park High. Lots of new construction in the area. Peaceful and private make this a paradise. Welcome home!

2837 Wright Avenue, Winter Park

$1,800,000
4 Beds 3.5 Baths Lugano Terrace SubDv. 32789 Zip Code
Don’t miss out on this stunning 4-bedroom, 3 full and 2 half bath, corner lot home in the heart of Winter Park’s sought-after Via’s neighborhood. Fully updated with high-end finishes, hardwood flooring, crown molding, stainless steel appliances, granite countertops and much more. The first floor features a library/den with a gas fireplace, a formal dining room with coffered ceiling, and 2 large bedrooms that share a full bathroom. The gourmet kitchen includes an induction top, stainless appliances, a large closet pantry and spacious eat in area. The cozy family room and kitchen overlook a lush, private fenced back yard and beautiful pool. A large private primary suite is upstairs and showcases 2 walk-in closets with organizers and a large master bath with a walk-in shower, soaking tub and dual sinks with beautiful cabinetry. French doors in the primary suite open to a huge deck overlooking the backyard, a serene spot to relax and enjoy your morning coffee or evening glass of wine. Also upstairs is an en suite bedroom. Offering ample closets and storage space throughout, the home includes a large, 2-car attached garage with a side entrance and workbench, a natural gas-fired whole house generator, and new tiled roof. Just a short stroll to the Winter Park Park Racquet Club, this beautiful home is in the top-rated Dommerich Elementary, Maitland Middle, and Winter Park High School district.

1205 Via Lugano, Winter Park

$1,895,000
4 Beds 3.5 Baths Osceola Shores Sec 01 SubDv. 32789 Zip Code
Welcome to 160 Trismen Terrace. This brilliant home has much to offer. Spotlighting an inviting formal living room, formal dining room with built in cabinetry and side board, a luminous family room with french doors to the pool deck, expansive kitchen with stainless steel appliances, prep sink, numerous cabinets, and vaulted ceilings complete with breakfast area. The generous primary en-suite bedroom features his and hers custom closets, newly remodeled primary contemporary bath with a stand alone tub, walk-in shower, dual vanities and water closet. Guest en-suite bedroom with new modern updated bath, 3rd bedroom can be used for the perfect office featuring views of the pool, and 4th bedroom with new Jack and Jill bathroom. This vibrant home also features a circular drive way with a considerable two car garage, crown moldings, recessed lighting through the entire home, built in bookshelves in the main hall, pristine polished terrazzo and high gloss snowwhite floors, ample inside laundry room with storage, dual HVAC systems with added air purification system, ADT security system, heated immense pool with travertine pool decking, and an abundant half acre lot with vinyl fencing for privacy. Termite bond conveys with the property. Roof replaced in 2019, Pex plumbing 2023, HVAC 2019, Pool 2018, Pella sliding and french doors 2024. This alluring Winter Park home is conveniently located just minutes from all the shops and restaurants of Historic Park Avenue, Trismen Park and so much more. 160 Trismen Terrace is truly a home for those who appreciate entertaining.

160 Trismen Terrace, Winter Park

$397,000
3 Beds 2 Baths Eastbrook Sub SubDv. 32792 Zip Code
Step through the door, take a deep breath, and know that you are finally where you are supposed to be in this delightful Winter Park home! This 3 bedroom, 2 bath with open-concept floor plan is situated in the desired EASTBROOK community. The open family/kitchen/dinette exudes a sense of spaciousness as you enter through the front door. The kitchen features GRANITE countertops, STAINLESS STEEL APPLIANCES and a kitchen island offering additional cabinet space. When you prefer a more private place to relax, the separate living room with BRICK FIREPLACE and additional mini split offers that tranquillity year-round with a door leading to your own large PATIO with an outdoor shower. As you walk down the hall to the primary bedroom featuring an EN-SUITE BATHROOM with GRANITE countertops and a large WALK-IN CLOSET with bifold doors, you pass 2 additional bedrooms and an upgraded guest bathroom. The covered one-car CARPORT also boasts an exterior LAUNDRY ROOM with washer/dryer hook up and additional storage area with shelving, convenient for all your outdoor gear. The EXPANSIVE back yard is surrounded by privacy fencing and mature landscaping with a storage shed as well. Zoned for high-rated Winter Park schools, this home is also conveniently located to all Orlando and its surrounding areas have to offer: Downtown Orlando, Downtown Winter Park, theme parks, golf courses, Rollins College, University of Central Florida and numerous retail shops and restaurants. Come see this home today and make it yours!

3676 Hedgewood Drive, Winter Park

$3,095,000
5 Beds 5.5 Baths Comstock Park SubDv. 32789 Zip Code
Welcome to 1563 Lakehurst, a stunning 5-bedroom, 5-and-a-half-bathroom pool home that epitomizes luxury living and has been meticulously remodeled to perfection. This residence won the prestigious Orlando Parade of Homes 2021 First Place and Grand Award and is a masterpiece of design and craftsmanship.Initially conceived by the local architect Gary Hancock, this home was reimagined by the renowned Ted Maines and Hardwick General Contractors, resulting in a comfortably elegant living space deserving of accolades and awards. Located on an oversized lot on a charming brick-lined street in one of the most desirable neighborhoods of Central Florida, this home boasts an enviable address just moments away from the shops and restaurants of Winter Park and Park Ave. Spanning over 4,300 square feet, the main house offers spacious and inviting living areas flooded with natural light. Every detail was considered throughout the renovation: top-of-the-line Anderson windows, custom inset cabinetry, luxury bi-fold Origin door, designer lighting, engineered oak floors, solid core interior doors, custom mahogany front door, and many more finishes that discerning buyers will recognize and appreciate. The kitchen is the heart of the home, featuring Wolf and Sub-Zero appliances, extensive custom inset cabinetry, Cambria luxury quartz, and a center island spanning almost 20 feet. The separate breakfast bar allows quick and easy coffee, tea, and breakfast prep without disturbing the clean aesthetics of the kitchen. The open living space has an Origin Luxury bi-fold door for indoor-outdoor living, and a vaulted cathedral ceiling finished with designer lighting. The lounge and bar offer a pre-dinner retreat before using the artfully designed formal dining room, with smoked glass, dramatic navy wood paneling, and custom herringbone wood floor. The light-filled primary bedroom is also located on the ground floor. Updated in 2022, this bedroom has Phillip Jeffries wall covering and Flos pendants. The bathroom has two independent vanities and separate closets. A full pool bathroom with shower, additional powder room and large office or flexible space complete the first story. Three additional bedrooms provide ample space for family or guests. The largest bedroom has an ensuite bathroom, and two additional bedrooms are connected by a large bathroom with a double vanity. For those needing additional accommodations, the in-law suite over the garage offers an additional 400+ square feet of living space, perfect for guests or multigenerational living. The extensive back patio has multiple areas for dining, entertaining, and enjoying Florida living. The summer kitchen was installed in 2021, and there is additional wine and refrigeration space. The front parking pad and landscaping were completed in spring 2024.All of the systems are from 2020 or newer. The roof was installed in 2020, 2 tankless water heaters were added in 2020, upstairs and downstairs Carrier air conditioners are from 2023, the guest house a/c is from 2021, and the guest house water heater is from 2024. All drywall, ceilings and tongue and groove was replaced, home was taken down to the studs, and has an effective date for build as 2020. With its unparalleled location, luxury, and craftsmanship, this home is a rare find. Don't miss your opportunity to own a piece of Winter Park's finest—schedule your private showing today!

1563 Lakehurst Avenue, Winter Park

$625,000
4 Beds 3 Baths Glencoe Sub SubDv. 32789 Zip Code
Welcome to your dream home in the heart of Winter Park's Glencoe subdivision, where luxury meets convenience with NO HOA fees! This meticulously renovated and updated 4-bedroom, 3-bathroom residence sits majestically on over a quarter-acre lot, offering a sanctuary of modern comfort and style. From the moment you arrive, the curb appeal beckons with its custom pavers driveway and a detached 1-car garage, providing both parking convenience and additional storage space. Step inside to discover a harmonious blend of contemporary design and functionality, highlighted by brand-new AC, roof, water heater, appliances & septic tank. The interior welcomes you with matching vinyl flooring that flows seamlessly throughout the open floor plan, encompassing the living room, dining area, and kitchen. Natural light floods the space, accentuated by large windows and a back double sliding glass door leading to the expansive backyard. The kitchen is a chef's paradise, boasting brand new stainless steel appliances, elegant white cabinetry with gold accents, luxurious marble countertops, and a stunning tile backsplash. A massive center island serves as the focal point, ideal for effortless meal preparation and entertaining guests. Retreat to the master bedroom, where tranquility awaits with an attached master bathroom and a spacious walk-in closet. The master bathroom exudes opulence with a double sink vanity and a massive walk-in shower, complemented by matching white cabinetry, countertops, and chic black and gold accents echoing the home's sophisticated theme. Additional bedrooms offer ample space, natural light, and versatility, providing ideal accommodations for family members or guests. Step outside through the kitchen to the oversized backyard, a sprawling oasis perfect for hosting family gatherings, celebrating holidays, or simply unwinding in solitude. This exceptional property not only offers unparalleled comfort and style but also boasts an unbeatable location close to major roads, highways, restaurants, entertainment, and more. Don't miss your chance to make this unique residence your own! <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=o8FGEvVwB7G&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

2710 Euston Road, Winter Park

$639,900
3 Beds 2.5 Baths Villas Of Aragon Condo SubDv. 32789 Zip Code
Welcome to easy living in Winter Park! Step into this charming townhouse nestled in the Villas of Aragon. With just 4 townhouses in the neighborhood, connected solely by the garage, you'll enjoy a secluded setting. On the first floor, discover a delightful kitchen boasting timeless white cabinets, granite countertops, stainless-steel appliances, a large breakfast bar, and a charming tongue and groove ceiling which adds a touch of character to this heart of the home. Enjoy meals in the spacious dining room, illuminated by natural light streaming through French doors leading to the courtyard. The dining room seamlessly flows into the inviting living room, adorned with a stunning white brick wood-burning fireplace and elegant plantation shutters. Throughout the home, you'll find gorgeous bamboo flooring adding warmth and sophistication. The first floor is complete with a chic powder bath for guests and a cozy desk nook tucked under the stairs. Upstairs, the large primary bedroom awaits with ample natural light, pitched ceilings, and a rustic barn door leading to the ensuite bathroom. Pamper yourself in the primary bathroom boasting double vanities, a large shower, and two walk-in closets. Two additional generously sized bedrooms share a beautifully renovated secondary bathroom. Step outside to the back patio and bask in the beauty that surrounds you. A pergola adorned with stunning jasmine vines creates a picturesque scene, while fern pine trees offer both elegance and privacy. With an oversized two-car garage, a parking pad for guests, and a low HOA fee of only $400/month, this townhouse offers both convenience and exceptional value. Other highlights include a new roof installed in 2021, a new AC unit in 2022, and fresh exterior and interior paint. Located centrally in Winter Park, this property provides easy access to all major roads and highways. Plus, it's just minutes away from Downtown Winter Park's renowned Park Avenue shopping and dining. Don't miss out on this fabulous opportunity to call this townhouse your home sweet home!

1051 Aragon Avenue Unit 1051, Winter Park

$635,000
3 Beds 2 Baths Orangewood Park SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Welcome home to this well maintained 3-bedroom 2-bathroom home right in the heart of Winter Park. The location is phenomenal - walking distance to East End Market, a short bike ride to Baldwin Park, Ivanhoe Village, or esteemed Park Avenue. While the area boasts an endless list of places to visit you will also enjoy the quiet, oak tree lined streets of his highly sought after Eastern Parkway address as you are welcomed with lush landscaping surrounding the bungalow style home. This home boasts a separate dining area off the living room, with a breakfast nook located off the kitchen. The stunning wood floors lead you back to a primary suite that includes a spacious walk-in closet with custom built-ins and an entry room perfect for an office, sitting area, baby’s room, or anything in between. You will also find 2 bedrooms and a fully renovated bathroom as you continue down the hallway. Florida living at its finest is found on the newly installed patio located in the oversized backyard. Enjoy a completely fenced in backyard with room for BBQ, games, and the perfect place for hosting. The backyard also includes a shed for extra storage. Extra features and updates include: new HVAC 2018, re-piped interior, no cast iron (rare), Roof 2017, replaced well pump for irrigation (low waste water and sewer bills), renovated patio, updated landscape, and renovated guest bathroom.

2817 Eastern Parkway, Winter Park

$1,550,000
3 Beds 3.5 Baths Winter Park Residential SubDv. 32789 Zip Code
Step into luxury living at its finest in this exquisite two-story condominium in the Douglas Grand of downtown Winter Park. Boasting sophistication and elegance, and offering unparalleled comfort and convenience. Spanning across two levels on the north side of the building which is more energy efficient, this residence features three bedrooms, two owner suites one on the main level and one up, 3.5 baths, and a private interior elevator, ensuring effortless access and seamless transitions between spaces. The bright open floor plan is ideal for entertaining and everyday living, highlighted by a spacious kitchen equipped with top-of-the-line Sub-Zero, Bosch and Wolf appliances, complemented by custom cabinetry for a touch of refinement. Indulge in the serenity of the interior atrium, creating a tranquil oasis of natural light in the comfort of your home. Each bedroom is accompanied by its own en-suite bath and walk-in closet, providing ultimate privacy and convenience. The primary suite is a sanctuary of relaxation, offering a generous 25-by-13-foot layout, a large walk-in closet, and access to the outdoor terrace with a treetop view overlooking Morse Boulevard ideal for a morning coffee or evening wine. Convenience meets luxury with two deeded parking spaces in the secured parking garage, ensuring peace of mind and ease of access. There is plenty of additional common area parking as well separate from the gated-off owner’s parking area. In the heart of downtown Winter Park, Douglas Grand offers unrivaled access to renowned Park Avenue, Winter Park Farmer's Market, Central Park, Winter Park Village and Rollins College, placing an array of dining, shopping and entertainment options only a short distance away. Embrace the lock-and-leave lifestyle with the SunRail station just a short stroll away, providing convenient access to downtown Orlando for sporting events or the Dr. Phillips Performing Arts Center. Whether you're seeking a serene retreat or a vibrant urban experience, this sophisticated condominium offers the ideal blend of luxury, convenience and elegance, promising a lifestyle of unparalleled comfort and style.

101 S New York Avenue Unit 304, Winter Park

$749,900
2 Beds 2 Baths Tax Equities Inc Rep SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Welcome to your dream home in this IDEAL Winter Park location! Every aspect of this home has been completely renovated all new mechanical, electrical, plumbing, electrical, doors, and fixtures. New sod and a freshly landscaped front yard boast stunning curb appeal. This gem showcases a spacious layout with a modern farmhouse style, nestled in a classic, sought-after Central Florida neighborhood. As you step onto the covered front porch, you'll immediately feel the inviting atmosphere, perfect for unwinding and soaking in the tranquil neighborhood vibe. Inside, the open floorplan offers versatility to configure living spaces to your heart's desire. The kitchen is a chef's delight, boasting beautiful butcher block counters, a farmhouse sink, and a stylish tile backsplash. Equipped with stainless steel appliances, including a professional Z-Line 36” 6 burner gas range SGR36, a Z-Line dishwasher and KitchenAid refrigerator, you’re ready for culinary adventures. Retreat to the master bedroom, a peaceful haven at the end of the day. The master ensuite bath features a dramatic design with a partial wet room, wrap around, floor to ceiling porcelain tile walls, stunning quartz top vanity and touch-free LED mirror. Contrasting knotty pine barn doors add a down to earth rustic touch. The secondary bedroom is equally inviting, with a vaulted ceiling and easy access to a beautiful full bath just outside its entrance. Step outside to the open patio overlooking the fenced backyard, offering a serene space to relax and enjoy the outdoors. Luxury vinyl plank floors flow seamlessly throughout the entire home, complementing the modern aesthetic. Plus, plumbing is already in place for a future tankless hot water heater installation. This home is located at the heart of the newly designed Winter Park Village and is under a five minute walk to the movies, Publix and restaurants. The beautiful new Winter Park Library, MLK Park and Hannibal Square are all just a few steps away - and let's not forget Trader Joe's! Get the best of both worlds and walk east, just minutes from the famous Park Avenue shops, farmers market at Central Park, dining, arts and entertainment. You’ll also enjoy easy access to I-4 and just a short drive to downtown Orlando. Don't miss the opportunity to make this your forever home! Schedule a showing today and experience the epitome of Winter Park living. <iframe width='853' height='480' src='https://my.matterport.com/show/?m=dG1uYAKsj8u' frameborder='0' allowfullscreen allow='xr-spatial-tracking'></iframe>

840 W Canton Avenue, Winter Park

$320,000
2 Beds 2.5 Baths Vistas At Lake Howell SubDv. 32792 Zip Code
Discover the perfect blend of luxury and convenience in this beautifully updated two-bedroom townhouse located in the gated Vistas at Lake Howell community in desirable Winter Park. This property stands out with its modern amenities and strategic location, offering a lifestyle most can only dream of. The townhouse features a newly updated kitchen complete with new appliances and countertops, a master bath freshly painted, and updated outlet and switch covers, ensuring a contemporary feel throughout. Each bedroom boasts expansive walk-in closets, with the primary suite connected to a versatile loft area and an ensuite bathroom, enhancing both space and privacy. Enjoy the essence of open-concept living with a layout designed for both entertaining and relaxation. The spacious living area extends through large sliding doors to a screened and covered lanai, perfect for alfresco dining or quiet evenings enjoying the breeze. Positioned for ultimate convenience, this home is just minutes from Downtown Winter Park, UCF, Full Sail University, Rollins College, and Advent Health facilities. With an abundance of shopping, dining, and entertainment options nearby, everything you need is within easy reach. Residents benefit from thoughtful community features including extra guest parking, peaceful walkways, and professional lawn maintenance, which contribute to a carefree and low-maintenance lifestyle. Ready for immediate move-in, this townhouse combines comfort, style, and practicality, making it an ideal choice for discerning buyers or investors seeking a prime property in Winter Park.

2645 Galliano Circle, Winter Park

$215,000
32792 Zip Code
Welcome to a thriving business opportunity in the heart of Winter Park, Orlando – a prime location renowned for its upscale ambiance and vibrant community. Presenting an exceptional chance for savvy investors, this established barber shop promises not only a profitable venture but also a pathway to securing the coveted E2 visa. Situated in one of Orlando's greatest neighborhoods, this barber shop enjoys unparalleled visibility and foot traffic. Its strategic location within Winter Park ensures a steady stream of clientele comprising locals and tourists alike, drawn to the area's charm and sophistication. The business's solid financial performance, coupled with its strategic location in an affluent area, positions it as an ideal candidate for visa qualification. With the potential for job creation and contribution to the local economy, this venture aligns perfectly with the requirements for E2 visa approval. Key highlights of this barber shop business include: Prime Location Established Reputation: 5 years of operation. The owner just renew for another 5 years. Profitable Operation: Demonstrated financial performance, with steady revenue streams and growth potential. E2 Visa Eligibility: Meets the criteria for E2 visa approval, offering investors a clear pathway to residency and business ownership in the United States. Don't miss out on this exceptional opportunity to acquire a successful barber shop business in Winter Park, Orlando – an investment sure to yield both financial returns and the fulfillment of E2 visa aspirations. Act now to seize this lucrative venture and embark on a rewarding journey in the thriving Orlando market. Price: $215,000

Winter Park

$1,792,000
4 Beds 4.5 Baths Kenilworth Shoes Sec 03 SubDv. 32792 Zip Code
Introducing a stunning, spacious four bedroom /four bathroom sanctuary boasting hardwood flooring in all main areas, complemented by designer porcelain tile in bathrooms and laundry. Custom by Native Homes. Expansive kitchen showcases beautiful exotic, neutral granite island, large breakfast room overlooking pool and tiled backsplash. There is a separate dining room on the first floor, as well as a second bedroom or private study with a bathroom and closet. Primary suite plus another bedroom suite conveniently located on first floor. Master suite is a dream! The dual sinks in the oversized bathroom offer convenience, while the 66-inch Jacuzzi brand stand-alone soaking tub adds a touch of luxury. The separate massive walk-in shower with dual showerheads perfect for spa-like experience and spacious walk-in closet completes the retreat. Bonus room, two bedrooms and two bathrooms up the wood stairs. All bedrooms showcase huge closets and custom organizers. Custom cabinetry and shoe storage, sitting bench in mudroom before entering garage. Home has been pressure washed and interiors all recently repainted. Tile and carpet professionally cleaned. Shows like a 2024 custom home! Enter your backyard sanctuary. Entertaining lanai including outdoor kitchen counters, fridge and big screen TV. Very private backyard. Green (Zoysia grass) space is perfect for birthday parties, trampolines, bounce houses and more. 2017-2018 added gorgeous saltwater pool with sun shelf surrounded by brick pavers. Fully fenced for pets and kids. Epitome of relaxation and comfort! Full house generator runs off gas. TVs may convey some furniture available. This lot is 10-15% larger than most lots in the neighborhood. Long brick pavered driveway and two car garage with plenty of parking. You will love the very large walk-in storage off the bonus room for rugs, fixtures, décor, and memorabilia. Most desirable Winter Park Schools! Walk to Brookshire Elementary. Close to shopping and restaurants along Park Avenue. Walk to the YMCA and Phelps Park. Golf and tennis neighborhood Racquet Club, Interlachen Country Club, and Winter Park 9 Golf Course.<div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=NtUwQd5NPJY&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

425 Selkirk Drive, Winter Park

$1,175,000
3 Beds 2 Baths Waterbridge SubDv. 32789 Zip Code
Welcome to your dream home in the coveted Waterbridge neighborhood! This stunning one-story pool home boasts everything you've been searching for and more, including a three-car garage. Situated on a spacious corner lot, this residence offers both elegance and comfort. Step inside to discover a welcoming ambiance, highlighted by a gathering living room featuring a double-sided gas fireplace, perfect for cozy evenings or entertaining guests. The dining room is conveniently located off the kitchen, complete with double built-in ovens and overlooking the inviting family room. A sunny Florida room extends off the family room, offering picturesque views of the lush backyard oasis and sparkling pool—a true haven for relaxation and enjoyment. Retreat to the primary suite, featuring a spacious walk-in closet for all your wardrobe needs. Two additional bedrooms, each boasting generous walk-in closets, ensure ample space for family or guests. Plantation shutters throughout add a touch of sophistication, while the large laundry room with cabinetry provides convenience and storage. Step outside to your own private paradise, where a gorgeous pool awaits, complete with a heated spa, sun shelf, and seating bench—all within the confines of a large privacy fenced backyard. Waterbridge residents enjoy access to community amenities including a park and tennis courts, fostering a sense of community and recreation. Conveniently located near shopping, restaurants, and minutes from Park Avenue, this home offers easy access to all the best Winter Park has to offer. Plus, with sought-after Winter Park schools just a stone's throw away, you'll enjoy peace of mind knowing your family is in a top-notch educational environment.

1203 Germaine Drive, Winter Park

$750,000
3 Beds 2 Baths Lawndale SubDv. 32789 Zip Code
A Testament to Timeless Elegance: Your Dream Home Awaits in Winter Park. Step into a piece of history with this beautifully restored 1927 Florida Bungalow, situated in the cherished and serene neighborhood of Orwin Manor. This exquisite home seamlessly blends the charm of its original architecture with modern luxury and conveniences, offering a unique sanctuary for those who value both tradition and contemporary living. As you enter through the inviting foyer, you are welcomed by new tile flooring and vertical shiplap walls, creating an atmosphere of fresh sophistication. Custom transitions draw you into a living room where the warmth of original hardwood floors meets the convenience of smart lighting and a cozy fireplace, perfect for both lively gatherings and quiet evenings at home. The dining room, capable of hosting eight, dazzles under a stylish Serena and Lilly chandelier, setting the scene for memorable dinners. Adjacent lies the heart of the home: a chef’s paradise kitchen. Renovated in 2020, this culinary haven boasts striking Calacatta countertops, a grand island, top-of-the-line Samsung appliances, and chic West Elm lighting. The adjoining eat-in area offers a relaxed dining experience and opens to a beautifully paved backyard, ideal for alfresco dining and entertainment. Accommodation is generous and refined, featuring a lovely master suite with dual closets and a sleek bathroom equipped with matte finishes. Additional rooms include a versatile rec room and a guest bedroom, each meticulously designed for comfort and style. The home also includes a secluded attic for extra storage. Special attention has been given to both aesthetics and functionality, from smart exterior lighting and a durable new vinyl fence to minimal maintenance landscaping designed to flourish in Florida's climate. The updated HVAC system features a Carrier unit and smart thermostat, ensuring year-round comfort. This home is not just a place to live but a piece of history to cherish. Original woodwork, including baseboards and casings, pay homage to the home’s heritage, while the curated paint choices and Trex exterior staircases ensure its beauty endures. Located just minutes from Park Ave, College Park, and major thoroughfares, this home offers an unparalleled blend of tranquility, community, and convenience. Do not miss the chance to own a legacy of luxury in Orwin Man. Every corner of this home tells a story, and every detail invites you to make it your own. Welcome to your dream home, where history and modernity live in perfect harmony.

1707 Harmon Avenue, Winter Park

$6,995,000
5 Beds 5.5 Baths Sicilian Shores SubDv. 32789 Zip Code
Luxurious lakefront living with unparalleled view of Lake Maitland, part of the famed Winter Park chain of lakes with 180 feet of water frontage. Enjoy tranquil views from the lake from almost every room. This custom home is located in the Via's of Winter Park and is close distance to downtown Park Ave and the Winter Park Racquet Club. This home was built by Gallimore and features five bedroom, five & one half bath. As you enter the foyer, you are immediately greeted by high ceilings, open floor plan and panoramic views of the lake. The family room is a fantastic place for entertaining, featuring a gas fireplace, wet bar with refrigerator and opens to the screened pool and gorgeous lakefront. The gourmet kitchen is a chef’s dream featuring a large center island, custom cabinetry, quartz surfaces, top of the line Thermador appliances, and walk-in pantry. The spacious master bedroom is a retreat of its own with amazing views of the lake and a sitting area. The master bathroom has custom cabinets with dual sinks, makeup vanity, modern stand alone tub, walk-in shower and a large walk around closet. There is a guest suite on the first floor with en suite bathroom and walk in closet. Two additional bedrooms upstairs with en suite bathrooms and a huge bonus room or fifth bedroom. This home also features a 3 car garage, a home office, laundry room and walk-in storage room with a large wine refrigerator. Step outside to the backyard paradise, where the pool, heated spa and sun shelf beckons you to relax and unwind. The large covered boat dock is a perfect place to watch the colorful sunset at night and has a separate enclosed storage room. Bring your boat and all your toys and enjoy lakefront living at its best! Roof and boathouse roof updated 2022.

1761 Pinetree Road, Winter Park

$750,000
4 Beds 3.5 Baths Lake Waunatta Woods SubDv. 32792 Zip Code
This home is a work of art ready to be enjoyed by those who appreciate attention to detail. It was completely renovated in 2011/2012 including all walls, kitchen, bathrooms, roof, electrical and plumbing - with the most elegant and timeless of modern touches. From the moment you arrive you will notice the double french doors that welcomes you into the home! The foyer is grand and draws you into the formal living and formal dining rooms. Floor to ceiling windows throughout this home provide lots of natural light. The floors throughout the home are either elegant marble or wood. The formal living room and the great room share a double sided fireplace with elegant touches of marble. The vaulted ceilings provide plenty of space to showcase your art collection or photos of your family. As you enter the heart of this home the kitchen draws your attention to the large entertaining island with classic pendant lighting. The kitchen features stainless steel appliances, Quartz counters, built in pantry, double oven/microwave oven, warming drawer, and beautiful glass tile making this a chef's delight and a wonderful space to enjoy making many gourmet meals. The kitchen opens to the Florida Room and the office - and provides unobstructed views of the pool and patio area. This home features 2 master bedrooms each with its own en-suite. All of the bathrooms have been meticulously updated featuring modern touches with a classic use of marble and glass tile. Finally the backyard is an Oasis - the pool is surrounded by a glass enclosure providing an elegant way to secure the area. The pergola is covered giving you a wonderful space to enjoy dining al fresco - even during a light summer shower. You will love enjoying and entertaining your friends and loved ones in this one of a kind masterpiece. (Foyer, Dining Room and Great Room Chandeliers along with Washer and Dryer do not convey.)

4046 Quenita Drive, Winter Park

$1,445,000
5 Beds 4 Baths V H Musselwhites Sub SubDv. 32789 Zip Code
Presenting a distinguished European Modern residence, the "Ponte Vedra" home epitomizes refined living with its meticulous upkeep and sophisticated design. Boasting 5 bedrooms, 4 baths, and encompassing 3,067 square feet of impeccably maintained open living space. Upon entry, a grand foyer sets the tone, leading seamlessly into the combined living room and dining room, characterized by clean lines and an abundance of natural light. To the left, the gourmet kitchen beckons with its array of upscale features, including Stainless Steel appliances, Stone tile backsplash, and Quartz Counters adorning a spacious breakfast island. A Butler's pantry and Walk-in pantry provide ample storage, ensuring both functionality and style. The gathering room beckons with triple sliders opening onto a captivating covered patio, complete with a roll-away screen and a stunning Tongue and Groove ceiling. Outside, an impressive 47' long market light, paver walkway, and Custom Water Fountain feature create an enchanting outdoor oasis, ideal for entertainment and relaxation. The first floor hosts a generously sized bedroom and full bathroom, catering to guests or multi-generational living needs. Upstairs, a versatile bonus loft space awaits, while the Owner's suite offers luxurious touches such as elegant tray ceilings, recessed lighting, and crown molding. The en-suite bathroom features walk-in closets, split vanities, and an oversized Floor to Ceiling tiled frameless shower with both a rain head and hand-held, accompanied by an iconic floating tub. Additional accommodations include three bedrooms, two full bathrooms, and a well-appointed laundry room with a sink and ample storage. This residence has been meticulously maintained, freshly painted inside and out, and boasts the added convenience of plantation shutters and custom drapery, ensuring a move-in ready experience. Ideally situated near Lakemont Elementary, Publix, Advent Health, and mere minutes from Park Avenue.

1880 Windsor Drive, Winter Park

$1,070,000
4 Beds 3 Baths Lakeside Estates SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this luxurious 4-bedroom, 3-bathroom home nestled in the upscale neighborhood of Lakeside Estates. Built in 2015, this meticulously designed home spans 3,057 square feet of exquisite living space, boasting a perfect blend of elegance and functionality. Upon entering, you are greeted by a grand foyer leading to an expansive living room and dining room adorned with high ceilings and abundant natural light. The heart of the home is the gourmet kitchen, featuring a butler's pantry, granite countertops, stainless steel appliances, double oven, and a walk-in pantry, making it a chef's delight and an entertainer's dream. Adjacent to the kitchen is the family room featuring an accent wall and views of the outside patio. The master suite is a sanctuary unto itself, boasting a luxurious ensuite bathroom with soothing soaking tub, separate shower, his and hers vanities and a spacious walk-in closet. The additional bedrooms, split from the master, are generously sized and offer walk-in closets. Step outside to the resort style oasis, where a sun soaked salt water pool with a captivating waterfall and heated spa awaits. The pool, controlled by a Pentair automation system, adds an element of tranquility and elegance to the outdoor space. The residence also offers a dedicated office space, ideal for remote work or study. This energy-efficient home boast a solar panel system for electricity, ensuring sustainability and cost savings. Additional features include a three car garage with a Gladiator storage system for ample storage space, along with a 12 camera security system for added peace of mind. Lakeside is a beautiful gated community featuring a lake and boat dock and it is located close to Seminole County parks. Don't miss the opportunity to own this extraordinary property. Schedule a showing today and experience the beauty of this remarkable home!

1473 Via Sangro Place, Winter Park

$1,695,000
4 Beds 3.5 Baths Charmont SubDv. 32789 Zip Code
Welcome to your new Winter Park retreat! This custom home boasts exquisite craftsmanship, from its intricate custom woodworking to its elegant crown moldings and hardwood floors. As you step onto the beautiful brick walkway and through the front door, you're greeted by a sense of warmth and luxury. The main floor features a formal living room/den and a dining room which leads to a butler's pantry and a spacious kitchen with a 6 burner gas range with exterior exhaust hood, making this a Chef's Dream Kitchen. Natural light floods the home through numerous windows, creating a bright and inviting atmosphere. The primary bedroom, located on the main floor, offers a peaceful sanctuary with its luxurious ensuite bathroom, complete with dual sinks, a soaking tub, and a stand-up shower. A huge walk-in closet provides ample storage space. Upstairs, you'll find a grand loft, an office with built-in desk and cabinetry, and three additional bedrooms with two bathrooms. The home has been meticulously maintained and features a new roof, new HVAC system, whole house water filtration system, and a new tankless on-demand hot water heater. Outside, a sparkling pool awaits, surrounded by a beautifully landscaped yard. A 2-car detached garage with new flooring in the attic provides additional storage space, along with a shed. Located just outside of Baldwin Park, this home is situated on one of Winter Park's most desirable streets. Enjoy the beauty of Lake Virginia just a short stroll away. With its fantastic location and proximity to excellent Winter Park schools, this home is sure to be in high demand. Schedule your private showing today before it's SOLD!

1931 Laurel Road, Winter Park

$1,995,000
4 Beds 4 Baths Woodmere Terrace Rep SubDv. 32789 Zip Code
Located within the heart of the Vias, this premier property boasts an expansive, almost half-acre lot spanning 19,800 square feet, with dimensions of 120 by 165 feet, all set along a picturesque brick street. Representing a rare find in an "A location" lot, its over 100-foot width opens up a realm of design possibilities, making it an ideal canvas for your dream home. At the heart of this property stands a spacious four-bedroom home, offering over 4,700 square feet of living space. This dwelling is currently vacant and impeccably maintained, presenting a "move-in condition" option for those seeking immediate occupancy or rental income while planning their custom residence. Alternatively, delve into the meticulously crafted proposed remodel plans, designed by Ashley Martin Home and brought to life by M Lahr Homes. These plans, with an investment of approximately $50,000 by the seller, outline a renovation encompassing around 5,400 square feet, promising a blend of modern luxury and timeless charm. While the value lies predominantly in the land and its generous proportions, the existing home exudes a blend of elegance and functionality. Primarily one-level living, it features an owner's suite along with two additional spacious bedrooms, each with en suite facilities, offering the utmost comfort and privacy. A private office, discreetly positioned behind the garage with a separate entrance, adds versatility to the space, catering to various needs from work to creative pursuits. The interior unfolds with an array of captivating features, including soaring ceilings, plantation shutters, crown molding, and solid oak floors throughout. The primary retreat boasts a luxurious en suite and a large walk-in closet, ensuring indulgent relaxation. A gourmet kitchen, adorned with expansive cabinetry and stainless steel appliances, adjoins a charming eat-in area, offering the perfect setting for culinary endeavors. Entertainment options abound with a formal dining room, a living room adorned with a wood-burning fireplace, and a den complete with a wet bar, ideal for hosting guests or unwinding in style. The enclosed Florida room adds a touch of serenity, overlooking the lush backyard oasis. Upstairs, a second potential owner's suite awaits, boasting its own entrance, vaulted ceilings, and a spacious closet. French doors lead to a private covered balcony, offering scenic views of the meticulously landscaped grounds below. Outside, the allure continues with a park-like setting, characterized by mature landscaping, majestic trees, and an expansive brick patio, covered porch, and pergola. This outdoor haven provides the perfect backdrop for al fresco dining, relaxation, and gatherings with loved ones. Situated in the highly sought-after Vias neighborhood of Old Winter Park, this property offers unparalleled convenience and ambiance, with proximity to WPRC, ICC, and downtown Park Avenue. Embrace the opportunity to create your own haven of luxury and sophistication in this coveted locale. Experience the essence of timeless elegance and modern comfort at this remarkable address.

1251 Woodmere Drive, Winter Park

Start Your Search