Courtesy: TURN-KEY MOVES REALTY
407-796-2221
Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you within effortless reach of the Winter Park Farmers’ Market, acclaimed dining, boutique shopping, cultural venues, and a picturesque network of lakes and parks. The residence features a bright and open floor plan where the kitchen, dining, and living spaces flow seamlessly, creating an inviting atmosphere ideal for both everyday living and entertaining. Upon entry, you are welcomed by multiple storage closets and a discreet hallway that provides additional storage and convenient access to the full bathroom—an uncommon luxury for a studio-style layout. Sliding glass doors lead to a generously sized, private covered and enclosed balcony overlooking the tranquil interior courtyard, with peaceful views of the community pool and Lake Osceola beyond. This serene outdoor retreat is the perfect setting for morning coffee, evening relaxation, or quiet reflection amid lush surroundings. Residents enjoy a truly low-maintenance lifestyle, with electric, gas, water, sewer, and trash all included in the condominium fee. Building amenities include elevator access to the third floor, on-site management, a community laundry facility, and beautifully appointed common areas. The property also features expansive outdoor patios overlooking Lake Osceola, a resident club room, and immediate access to the community pool. Located within Whispering Waters, a highly desirable 55+ community, this residence is ideally suited as a primary home, seasonal retreat, or elegant in-law suite—offering timeless Winter Park living with unmatched convenience and charm.
Courtesy: LPT REALTY, LLC
877-366-2213
Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Conveniently location close to healthy centers, excellent schools, restaurants and shopping with easy access to Costco, Walmart, and various dining options. Only 4 miles from Winter Park SunRail Train Station and 20 minutes from Orlando International Airport. This unit offers a cozy living/dining area with sliding doors leading to a private balcony that includes extra storage.
Courtesy: LPT REALTY, LLC
877-366-2213
Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready. As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to maintain. The heart of the home, the kitchen, has been completely reimagined with sleek granite countertops, fresh cabinetry, and contemporary finishes that make cooking and entertaining a joy. The bathroom has also received a full renovation, featuring granite countertops and updated fixtures that enhance both style and function. With thoughtful design at every turn, this condo feels fresh, bright, and uniquely yours. Situated on the second floor for added privacy and natural light, this unit provides a peaceful retreat while still being close to all that Winter Park has to offer. Enjoy being minutes from Park Avenue, with its array of boutique shopping, acclaimed restaurants, art galleries, and outdoor markets. Explore scenic parks, lakeside boat tours, cultural attractions, and community events that make Winter Park one of Central Florida’s most desirable places to live. Whether you’re searching for your next home or an exceptional investment opportunity, 851 Miles Ave #13 showcases stylish updates, quality finishes, and a location you’ll love. Don’t miss your chance — schedule a showing today!
Courtesy: PARK TOWN REAL ESTATE LLC
561-801-9199
Location, Location, Location! Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz. Enjoy a large walk-in closet, one assigned carport space, and a private storage room. The community offers a sparkling saltwater pool, two third-floor outdoor patios, laundry facility, elevator, and a guest-quarters efficiency available to owners for a nominal fee. Just steps from Park Avenue shopping and dining, cafes, churches, Winter Park Golf Club, Rollins College and more. No pets.
Courtesy: ONE LUXURY INTERNATIONAL LLC
407-312-8003
Under Construction. An architectural statement in the heart of Winter Park, this remarkable residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking façade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chef’s kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry with integrated LED under-lighting, sleek quartz countertops, a paneled refrigerator, and a premium induction range are complemented by a full suite of high-end stainless steel appliances, reflecting the builder’s uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
Welcome to 2350 Cady Way! Ideally located within walking distance to Brookshire Elementary and directly across from Showalter Field, this home offers easy access to the Cady Way Trail, Baldwin Park’s downtown area and dog park, Winter Park AdventHealth Hospital, and the Crosby Wellness Center, and is just a 5 to 10 minute drive to Park Avenue’s shopping, dining, and entertainment. Step inside to a bright and inviting living room with sliding doors to the backyard and a shared fireplace with the adjacent family room. The family room offers built-in shelving, cabinet storage, and sliding doors leading to a screened-in porch. The kitchen connects to a spacious laundry room with built-in cabinetry and floating shelves, with direct access to an oversized two-car garage featuring built-in shelving and storage cabinets. On the opposite side of the laundry room is a functional mudroom with an additional door to the backyard. The primary bedroom features a walk-in closet with excellent natural light. The primary bathroom includes a walk-in shower, granite countertops, and built-in storage. The secondary bathroom also offers granite countertops, built-in storage, and a bathtub. Throughout the home you will find abundant storage, exceptional natural light, and new remote-controlled ceiling fans. Major updates include a new HVAC system, full plumbing re-pipe, updated electrical panel, exterior flood lighting, new flooring, new fence, new dishwasher, and chimney repairs completed in 2021. Additional improvements include new garage doors and openers in 2024, and in 2025 a new refrigerator, new roof with a 10-year warranty, fresh interior paint, a landscape refresh, and brand new windows.
Courtesy: COMPASS FLORIDA LLC
407-203-9441
Under Construction. Signature new construction currently under way, thoughtfully designed for modern living with a refined balance of warmth, scale, and functionality. This two-story residence close to 3,200 square feet under air with a 4-bedroom, 4-full-bath layout plus a dedicated office and second-floor media room, delivering flexibility without compromise. The main level is anchored by a private primary suite featuring a generous walk-in closet, alongside a dedicated office with walk-in closet that can easily function as a guest bedroom. A main-level full pool bath, accessible directly from the lanai, enhances everyday livability and seamless indoor-outdoor flow. At the heart of the home, the kitchen is both elevated and inviting—appointed with custom oak cabinetry, a 48-inch gas range, walk-in pantry, and oak flooring. Wood-beam ceilings and a fireplace with custom built-ins frame the living and dining areas, creating a natural, cohesive flow ideal for both daily living and entertaining. Upstairs, additional bedrooms are thoughtfully arranged along with a spacious open media room, providing a flexible retreat for relaxation or gathering while maintaining privacy from the main living spaces. The backyard is designed as an extension of the home, featuring a resort-style pool and built-in BBQ area—perfect for year-round Florida living. Two-car garage. Architectural plans and floorplans available. Designed with care. Built with purpose. Inquire today
Enjoy the best of what luxurious lakefront living has to offer in this stylish, modern, smart new home in Winter Park's exclusive Via's neighbourhood. This spectacular, 5-bedroom, 6.5-bath, multi-level masterpiece combines innovative contemporary design with brilliant architectural artistry, blending the latest in modern living with superior craftsmanship. Tucked away on Lake Maitland adjacent to the Isle of Sicily, this exquisite home features state-of-the-art technology throughout, accented by classic, elegant finishes such as custom Walnut floors, staircase, landing and interior doors, and porcelain tile work. Designed for lakefront living and entertaining inside and out, a large designer chefs kitchen includes custom cabinetry, dual dishwashers, double ovens, warming drawers, a large walk in pantry and wet bar with wine cooler. Step outside to enjoy gorgeous views of the largest lake in Winter Park's chain, and outdoor lanai including a sparkling pool, an outdoor kitchen, a gas fire pit and outdoor shower. The first floor includes a large master suite, 2 additional bedrooms, and a formal dining room. glass-enclosed office, and gas fireplace. The second floor includes a den and two bedrooms with full baths. This modern Smart Home is iPad & Touch Panel integrated, including surround audio, lighting control, video doorbell with off-site answering, garage door control, voice control, retractable phantom lanai and patio screens
Courtesy: LUXE HUNTER REAL ESTATE
407-984-4888
NEW ROOF, NEW HVAC installed before closing along with NEW WATER HEATER and NEW BUILT IN MICROWAVE! Welcome to 2634 Exuma Way, a well-maintained 3-bedroom, 2-bathroom home located in the heart of Winter Park, where comfort meets convenience. This property stands out as the only home in the area featuring a wrought iron privacy fence, offering a unique sense of character and added seclusion. Enjoy morning coffee or evening gatherings on the oversized front patio, while the backyard space provides room to relax, garden, or entertain. Inside, the kitchen features granite countertops and flows seamlessly into the living areas, creating a warm and functional layout. Additional highlights include: Oversized front patio Granite countertops Private backyard space Carport included Ring doorbell included Two separate storage closets for added convenience Located just minutes from Park Avenue, dining, boutique shopping, parks, cultural attractions, and top-rated schools, this home offers the best of Winter Park living—a charming neighborhood feel with easy access to everything Central Florida has to show you. Community is also amenity rich featuring a pool, clubhouse, tennis courts and a small golf area. Perfect for those seeking privacy, functionality, and a prime location. Schedule your showing today and experience the lifestyle this Winter Park gem provides.
Courtesy: RE/MAX TOWN & COUNTRY REALTY
407-695-2066
Mid-Century Modern architecture meets modern comfort in this beautifully updated Winter Park home. Clean lines, open sightlines, and warm architectural details create a timeless aesthetic that feels both stylish and inviting from the moment you arrive. Inside, the home features an open-concept layout with multiple living areas—ideal for entertaining or everyday living. The renovated kitchen is the heart of the home, showcasing sleek cabinetry, stainless steel appliances, modern lighting, generous counter space, and a large island that flows seamlessly into the dining and living areas. Natural light fills each room, highlighting the home’s thoughtful design and functional layout. Step outside from the large, cozy family room into your private backyard oasis—an entertainer’s dream. The resurfaced pool (Dec 2025) and updated pool equipment (Dec 2025) provide worry-free enjoyment, while expansive patio areas, string lighting, and multiple seating areas create the perfect setting for relaxing or hosting gatherings. The outdoor space is both private and versatile, delivering true Florida living year-round. Garden enthusiasts will love the raised garden beds, established landscaping, and fruit trees, including mango, peach, fig, and Meyer lemon—perfect for anyone who enjoys homegrown produce and sustainable living. A charming garden pathway adds character and connects the outdoor spaces beautifully with a garden shed for your tools. Additional highlights include modern flooring throughout, updated bathrooms, flexible living spaces, and a layout that balances comfort with architectural character. Centrally located just minutes from Park Avenue, Rollins College, dining, shopping, downtown, and major roadways, this home offers the perfect blend of style, location, and lifestyle. A rare opportunity to own a Mid-Century Modern home with a private backyard setting and a gardener’s paradise in one of Winter Park’s most desirable areas. This is a welcoming, connected community where neighbors know one another and come together for festive street events throughout the holidays, creating a warm and inviting atmosphere.
Courtesy: KELLY PRICE & COMPANY LLC
407-645-4321
Welcome to 2665 Tierra Circle, a captivating Mediterranean-inspired residence nestled in the desirable Casa Aloma neighborhood of Winter Park. This thoughtfully maintained 4-bedroom, 2-bath home spans 1,885 square feet and has been lovingly cared for by a single owner for the past 23 years, evident in every detail throughout. Step inside to discover a flowing floor plan featuring distinct living, dining, and family rooms, all bathed in abundant natural light, particularly during the afternoon hours. The home's signature feature is its numerous French doors that seamlessly connect the interior spaces to enchanting garden islander styled courtyard areas, creating an indoor-outdoor living experience reminiscent of classic Mediterranean architecture. Elegant tile flooring flows throughout the home, complemented by crown molding that adds a refined touch to each room. The primary bedroom serves as a private retreat with its en suite bathroom featuring a walk-in shower, while three additional guest bedrooms share a well-appointed hall bath. Notably, the dividing wall between the third and fourth bedrooms has been removed to create a generous suite, offering flexibility to reinstate a fourth private bedroom with simple drywall installation if desired. The true showpiece of this property is the mature landscaping and garden spaces that surround the home, offering multiple courtyard areas perfect for entertaining or peaceful relaxation. The private pool provides a refreshing escape, while block walls throughout ensure complete privacy on the spacious 0.24-acre corner lot. Practical updates include a 2021 HVAC system and 2019 roof, natural gas utilities, and a large laundry and storage room. The two-car garage completes this exceptional offering, presenting a rare opportunity to own a meticulously maintained retreat in one of Winter Park's most sought-after neighborhoods.
Welcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter Park, FL. This well-maintained residence features 3 bedrooms and 3 full bathrooms across approximately 1,958 square feet of living space — perfect for comfortable daily living and entertaining. Set on a generous lot of nearly 0.30 acres, the property includes a private fenced-in backyard with an in-ground pool, offering your own tranquil oasis for relaxing, play, and summer gatherings. Inside, the home offers a naturally welcoming layout with a neutral palette throughout and flexible living spaces that allow for personalization. The primary suite boasts a walk-in closet. Located close to a variety of shops, dining, and everyday conveniences.
Courtesy: LPT REALTY, LLC
877-366-2213
Discover comfortable Winter Park living in this bright and stylish 3-bedroom, 2.5-bathroom corner-unit townhome located in the gated Grayson Square community. Abundant natural light fills the open-concept living area, which flows seamlessly to a covered lanai that’s perfect for relaxing mornings or quiet evenings. The modern kitchen includes stainless steel appliances, quartz countertops, and generous storage, offering both convenience and contemporary appeal. The owner’s suite features a spacious walk-in closet and an elegant ensuite bathroom with a glass-door shower and dual quartz vanities. Additional highlights include a two-car garage with epoxy flooring, and a washer and dryer for added ease. The community offers a peaceful pool with a cabana, along with 1GB high-speed fiber optic internet and 75 streaming cable and music channels. Ideally located just minutes from downtown Winter Park, the home provides easy access to major highways (436, 434, 417), as well as nearby conveniences such as Starbucks, Publix, and Walmart. Top-rated Seminole County Schools and the shopping and dining of Park Avenue are also close by. This thoughtfully designed home blends natural light, modern finishes, and a fantastic location to create a welcoming and refined place to call your own. ¡Hablo español!
Courtesy: KELLER WILLIAMS ADVANTAGE REALTY
407-977-7600
Tucked peacefully at the top of a cul-de-sac in the sought-after Garden Lake Estates community, this lakefront residence offers a rare blend of serenity, timeless character, and effortless Florida living. From the first approach, the home feels warm and welcoming, mature landscaping frames the paver drive, and a charming front porch sets the tone for the relaxed, inviting style carried throughout. Inside, the home’s thoughtful split-bedroom layout and multiple gathering spaces create a natural flow for both everyday comfort and entertaining. The formal living and dining areas lead seamlessly into the heart of the home, where a cozy wood-burning fireplace anchors the family room. The kitchen lives warm and inviting, with rich wood cabinetry, granite countertops, stainless steel appliances, and thoughtfully designed glass-front display cabinets. A convenient pass-through connects the kitchen to the sunroom, keeping the cook part of the conversation and offering glimpses of the lake. Combined with the adjacent dining areas, this space supports both casual meals and memorable gatherings with ease. Just beyond, a light-filled sunroom becomes a true showcase space, expanded with tongue-and-groove ceilings, skylights, and panoramic views that draw the outdoors in. This room lives beautifully as a lounge, reading retreat, or entertaining extension, opening directly to the home’s outdoor living areas. Designed for connection to nature, the rear of the home opens to a large screened lanai and an extended lakeside deck, capturing wide sparkling views of Garden Lake. Morning sunrises, evening reflections, and gentle breezes set the backdrop for daily living. Step down to the flagstone patio or the beautifully landscaped yard for even closer access to the shoreline, perfect for launching a kayak or savoring the peaceful setting. Every detail has been tastefully appointed, from updated baths to well-maintained finishes that reflect pride of ownership. The primary suite enjoys privacy and garden views, while two additional bedrooms create versatility for guests, office space, or multigenerational living. This neighborhood is a quiet, established enclave offering a uniquely calm, tucked-away feel while remaining close to everything. A short drive brings you to Winter Park’s signature lifestyle, shopping on Park Avenue, an exceptional dining scene, medical centers including AdventHealth Winter Park, and convenient access to major roadways for commuting or travel. Nearby higher education anchors such as Rollins College and Full Sail University, along with major regional employers, add to the area’s vitality. Schedule your private tour today!
Experience the best value in Winter Park. Beautifully maintained corner-unit townhome in the desirable Four Seasons community, offering a perfect blend of comfort, privacy and style. This bright and inviting residence features modern laminated floors, new carpet in the bedroom areas, granite kitchen countertops, updated lighting, and recently painted interiors. Enjoy the convenience of a private front entrance and a second entrance from the spacious patio- ideal for added flexibility and seamless indoor=outdoor living. Abundant natural light enhances the the open layout and inviting living areas. Four Seasons community delivers top tear amenities: 3 swimming pools, tennis courts, a fitness center, clubhouse, laundry facilities and beautifully maintained green spaces . Ideally located near Full Sail University , shopping, dining, and major roadways. A turnkey home you won't want to miss.
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.
Courtesy: KELLER WILLIAMS WINTER PARK
407-545-6430
Discover a truly unique offering in the heart of Winter Park! This property, located at 1780 Bryan Avenue, is being offered along with the adjoining lots at 1760 and 1770 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to purchase one, two, or all three. Together, these lots provide remarkable options for future use: Combine all three to create a spacious 200' x 127' estate lot Split into two 100' x 127' lots Or develop three individual 66.6' x 127' lots Use this premium property to build an estate-like home, design a family compound, or develop all three lots as spec homes—the possibilities are endless. Whether you’re envisioning a dream residence or an investment project, this is a rare chance in one of Winter Park’s most desirable neighborhoods. Ideally located just minutes from Phelps Park, Park Avenue’s shopping and dining, and top-rated schools, this offering combines convenience with exclusivity. Don’t miss the chance to secure one or more of these exceptional parcels in the heart of Winter Park.
Courtesy: COMPASS FLORIDA LLC
407-203-9441
Beautifully updated and offered for the first time, this 2015 David Weekley home sits on a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. This 5-bedroom, 5-bath home features an office, large bonus room, covered lanai with full summer kitchen, and a backyard putting green. Additional highlights include a 3-car garage, a gated parking pad ideal for extra vehicles, a boat, or jet skis, a tankless gas water heater, and a new roof installed in 2021. Thoughtful improvements include custom built-ins in the living room, office, flex space, and dining room; upgraded closet systems throughout; a customized pantry with pull-out shelving; under-stairs storage with a “secret door”; added attic flooring and garage overhead racks; wood shutters downstairs and blinds upstairs; exterior paint in 2018; custom barn doors; a LaCantina slider conversion; and a 2021 dining room renovation featuring a custom bar and raw-edge floating shelves. With its prime location, curated upgrades, and move-in-ready condition, this exceptional Winter Park home will not last long.
Courtesy: LOKATION
954-545-5583
Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony — perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area with lots of nearby shopping, restaurants, and amenities
Courtesy: KELLER WILLIAMS REALTY AT THE PARKS
407-629-4420
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout with high ceilings, modern finishes, and tile and carpet flooring all throughout. The well-appointed kitchen flows effortlessly into the main living and dining areas, creating a seamless environment for entertaining or everyday living. All three bedrooms include generous walk-in closets, while the primary suite offers a peaceful retreat with its own private bathroom and serene ambiance. A versatile loft on the second floor adds valuable flex space that is ideal for a home office, media area, or playroom. Outside, the home offers a cozy enclosed rear patio perfect for relaxing, dining outdoors, or enjoying your morning coffee in privacy. A spacious two-car garage provides convenience and additional storage. The community surrounding Shadowland Loop is quiet, welcoming, and beautifully maintained, with tree-lined streets and easy access to the best of Winter Park. Residents enjoy proximity to top-rated schools, charming parks, boutique shopping, vibrant dining spots, and the area’s beloved lakes and recreation. With its thoughtful design, modern amenities, and exceptional location, this townhouse delivers the ideal Winter Park lifestyle.
Courtesy: FUTURE HOME REALTY INC
800-921-1330
Winter Park gem! This tastefully updated 2-bedroom, 2-bath corner unit with a spacious patio offers a rare opportunity in a boutique community of only 11 residences, surrounded by million-dollar homes. The unit was repiped in October 2025 and features high-quality enhancements including plantation shutters, built-in closets, a hurricane-rated sliding glass door, smart recessed lighting throughout, a smart fan with light kit in the primary bedroom, and a Nest thermostat. The airy kitchen boasts granite counters with backsplash, soft-close cabinetry, and stainless steel appliances. An open floor plan connects the living and dining areas—ideal for entertaining. The owner’s suite includes a large walk-in closet, custom built-in storage, and a spa-like bathroom. Enjoy a large private balcony overlooking the community pool—perfect for morning coffee or hosting friends. Centrally located, this home is within walking distance to Glenridge Middle School and minutes from grocery stores, AdventHealth, Baldwin Park’s shops and scenic trails, and the dining and boutiques of Park Avenue. Just 15 minutes to Downtown Orlando and under 30 minutes to Orlando International Airport. Zoned for the highly regarded Winter Park school district. HOA fee includes water, pest control, and exterior insurance, and the community is pet-friendly. Excellent option for first-time buyers, downsizers, investors, or students attending Rollins or Full Sail. Call for your private tour today!
Courtesy: HOMEVEST REALTY
407-897-5400
Aloma Trails is a gated townhome community, built by Ryan Homes, located in Winter Park. Conveniently you'll find it's location between UCF and Rollins College. Seminole County is known for its highly rated public schools. Only minutes from Park Avenue shopping and restaurants. This END UNIT townhome features 3 bedrooms, 2 1/2 bathrooms, and a TWO car garage. Granite countertops, 42” upper cabinets, GE appliance package including the microwave, oven, dishwasher, and smooth stop range. The living room is very large and wide open to the kitchen and dining. Collapsible 3 panel sliding glass doors allow easy access to back patio. The primary bedroom features 2 walk-in closets, raised dual vanity sinks in the bathroom with Silestone quartz countertops, and walk-in shower.
Courtesy: KELLER WILLIAMS REALTY AT THE PARKS
407-629-4420
Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new sliding glass door, new bathroom vanity. Updated wiring and electrical panel. Enjoy all your community amenities including a two pools, tennis courts, clubhouse and 24/7 fitness center. The HOA covers water, trash removal, Internet, common area pest control, grounds maintenance, and exterior maintenance while the pool is maintained for your enjoyment. A convenient on-site laundry room features two washers and two dryers free of charge, and the clubhouse is available for rental for gatherings or events. Situated in a prime Winter Park location, this condo is close to grocery stores, shopping centers, and major routes like the 408, Semoran Blvd and St. Rd. 50 for quick access across the area. This condo is just 20 minutes from UCF, 10 minutes from Full Sail, Rollins College, and the vibrant Park Avenue in Winter Park. Quick access to major highways (417 and I-4), everything you need is within reach. Welcome Home!
Courtesy: KELLY PRICE & COMPANY LLC
407-645-4321
Discover refined elegance in this meticulously updated 3-bedroom, 2.5-bath two-story residence in sought-after Winter Park. Offered at $1,200,000, this stunning home seamlessly blends modern luxury with thoughtful design. The heart of this home features a customized chef's kitchen with top-of-the-line Signature Kitchen Suite appliances, including both induction and electric ranges plus natural gas cooking. Sophisticated touches include in-cabinet and drawer lighting, a dedicated coffee station, and wine cooler—perfect for the culinary enthusiast. Enjoy main-floor living with a spacious primary bedroom suite featuring a spa-inspired ensuite bath with jetted tub and separate shower. Throughout this beautifully appointed home, you'll find 11-foot ceilings, fresh paint inside and out, new porcelain flooring on the main level, and designer light fixtures. A gas fireplace adds warmth and ambiance, while plantation shutters and custom draperies provide elegant window treatments. The second floor offers two generous bedrooms with charming Juliet balconies, connected by a convenient Jack and Jill bath. The versatile loft/bonus room features a built-in entertainment center with surrounding bookcases and beverage center—ideal as a media room, home office, or recreation space. A detached two-car garage opens to a private patio and backyard—perfect for entertaining. The unbeatable location offers walkability to the YMCA and Phelps Park. This turnkey residence represents the perfect blend of luxury, location, and lifestyle in Winter Park's vibrant community.
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Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.
The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.
