Location: Winter Park, Winter Park
Do Not Show Listings
528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792
$535,0007 Days on yellowkey MLS ID: O6414677
0 Days Off yellowkey (back on 6/16/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1656 Built: 1964 Tax: $6,000 (2025)Community: Winter Park PinesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,000
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. MULTIPLE OFFERS RECEIVED! Please provide highest and best offers by Tuesday, June 16th at 12:00pm. Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jonathan Cole (407-928-9516)
3651 N GOLDENROD RD #D102, WINTER PARK, FL 32792
$158,00057 Days on yellowkey MLS ID: O6401114
REDUCED by $1,000 (0.6%) on 06/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 840 Built: 1990Monthly Fee: $370 Tax: $2,461 (2025)Community: Lancelot/Winter ParkCondo
Taxes:$2,461
Elementary School: Aloma Elem
Remarks: Virtually Staged. Welcome to this inviting 2-bedroom, 2-bathroom condo located in the desirable Lancelot at Winter Park community, offering the perfect blend of comfort and convenience for investors, first-time buyers, or anyone seeking low-maintenance living. This well-appointed unit features an open and airy layout with abundant natural light, seamlessly connecting the living and dining areas to create an ideal space for both relaxing and entertaining. The modern kitchen provides a functional workspace designed for everyday ease. Residents will also enjoy access to a community pool, perfect for unwinding or hosting guests, along with professionally maintained common areas that enhance the overall appeal of the neighborhood. Ideally situated, this condo offers close proximity to UCF and Full Sail University, making it an excellent option for rental potential, as well as convenient access to major shopping centers, dining options, and key highways including I-4 for easy commuting. Whether you're searching for a primary residence, a second home, or a strong investment opportunity, this property delivers exceptional value in a prime location. The property was previously leased at $1,625/month. The interior of condo was just completely repainted, and all closet doors were fixed!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Christina Munkberg Bianca (407-340-1308)
1404 BORDER DR, WINTER PARK, FL 32789
$1,175,00019 Days on yellowkey MLS ID: O6412140
REDUCED by $25,000 (2.1%) on 06/16/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2469 Built: 2023 Tax: $16,220 (2025)Community: Winter Park VillageSingle Family
Taxes:$16,220
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Remarks: Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
639 SAINT JOHNS CT #639, WINTER PARK, FL 32792
$194,90052 Days on yellowkey MLS ID: O6402025
REDUCED by $5,000 (2.5%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1981 Tax: $3,077 (2025)Community: Winter Park VillasCondo
Taxes:$3,077
Remarks: Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.
Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)
Listing Agent: Adam Eisen (407-808-6967)
205 LEWFIELD CIR #205, WINTER PARK, FL 32792
$220,000156 Days on yellowkey MLS ID: S5141588
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973 Tax: $796 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$796
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: MOTIVATED SELLER! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a BBQ with family and friends at the community clubhouse or enjoy shopping at the many neighborhood retail and grocery outlets nearby. The quaint restaurants, coffee houses, golf courses, and farmers markets of Winter Park and Baldwin Park are within biking distance. There is always something to see and do at this prime location. Recent upgrades include: new electric panel (2024), new washer/dryer in unit (2024), new dishwasher (2023), refrigerator (2020).
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eimi Moreno Carrera (321-945-6195)
700 MELROSE AVE #H4, WINTER PARK, FL 32789
$290,00026 Days on yellowkey MLS ID: O6409318
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1074 Built: 1964Monthly Fee: $699 Tax: $851 (2025)Community: Winter Park Gardens CondoCondo
Taxes:$851
Remarks: Welcome to this charming ground-floor condo, nestled in the highly sought-after 55+ community of Winter Park Gardens. This TWO-bedroom, TWO-bathroom condo offers a perfect blend of comfort, and stunning picturesque views. The open layout seamlessly connects the kitchen to the living area, and into to the sunroom/Florida room. This space is perfect for enjoying the tranquil views, offering a peaceful ambiance year-round. The spacious bedroom is filled with natural light, creating a bright and inviting atmosphere. This condo is located in a vibrant 55+ community that offers beautifully landscaped grounds with lush landscaping, lighted paths, and scenic pond, a sparkling community pool, and a clubhouse where residents can gather and enjoy social activities. The prime location provides easy access to a variety of amenities and attractions. Just minutes away, you'll find the historic Winter Park district, home to the renowned Park Avenue with its boutique shops, restaurants, and cultural events. The nearby Azalea Tennis Center, Mead Botanical Gardens, and Rollins College offer further enriching experiences. Embrace the serene and active lifestyle this community provides, with the added convenience of being close to Downtown Orlando, Baldwin Park, major highways like 408 and I-4, and the MCO Airport. The assigned parking space is just steps away from your front door with plenty of additional parking for guests. Don't miss the chance to make this delightful condo your own.
Listing is courtesy of: TAL BUSIDAN PA (407-227-3001)
Listing Agent: Rob Rallo (407-448-2427)
2708 LION HEART RD, WINTER PARK, FL 32792
$617,500105 Days on yellowkey MLS ID: O6387685
REDUCED by $2,400 (0.4%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1785 Built: 1963 Tax: $7,007 (2024)Community: Winter Park Pines RepSpa: NoSingle Family
Taxes:$7,007
Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
641 NORTHWOOD CIRCLE, WINTER PARK, FL 32789
$1,795,00016 Days on yellowkey MLS ID: O6412554
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2756 Built: 2023 Tax: $18,393 (2025)Community: Winter Park OasisSingle Family
Taxes:$18,393
Elementary School: Lakemont Elem
Remarks: Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private courtyard entrance sets the tone, creating a serene arrival and sense of retreat from the moment you step onto the property. Inside, polished concrete floors and an open, light-filled layout define the home's contemporary aesthetic, with clean lines and seamless flow designed for everyday living and effortless entertaining. Step outside to your own private oasis- complete with a pool and tranquil outdoor spaces- perfect for enjoying Florida living year-round. The home's prime location allows for an exceptional lifestyle- just a short stroll to Park Avenue's renowned shops and dining and an even shorter stroll to the golf course. Offering a unique combination of modern design and in-town convenience, this is Winter Park living at its most elevated.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Sandra Cuba (305-878-0167)
2974 CHANTILLY AVE, WINTER PARK, FL 32789
$499,00011 Days on yellowkey MLS ID: O6412851
REDUCED by $51,000 (9.3%) on 06/15/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1433 Built: 1960 Tax: $1,178 (2025)Community: Winter Park ManorSingle Family
Taxes:$1,178
Remarks: Virtually Staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the oversized 76x133 lot, inviting front porch, and clean curb appeal set the tone. Inside, original terrazzo floors, vaulted ceilings, and a bright open great room create warmth, charm, and livability. French doors open to a screened porch overlooking the spacious backyard. The split-bedroom floor plan features two renovated bathrooms, while the redesigned kitchen offers brand-new appliances, cabinetry, and quartz countertops. A spacious 19x12 family room with tile flooring connects to a large inside laundry room with abundant storage and flexible workspace options. Beyond the visible updates, this home stands apart because so many of the expensive and often-overlooked improvements have already been done, including roof, plumbing re-pipe, septic/drainfield improvements, electrical updates and full-house rewire, hurricane-impact windows, impact front and rear doors, new mini-split HVAC systems, cast iron drain replacement, interior and exterior paint, and more. A rare opportunity to own a thoughtfully improved home in one of Winter Park’s most desirable locations — with no HOA. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
700 MELROSE AVE #F 21, WINTER PARK, FL 32789
$235,90012 Days on yellowkey MLS ID: O6413612
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 787 Built: 1964 Tax: $1,123 (2025)Community: Winter Park Gdns CondoCondo
Taxes:$1,123
Remarks: Floor-to-ceiling dazzling views, of sparkling pond, sweepiing oaks, towering cypress trees, and lush gardens — in the center of esteemed Winter Park. This beautifully updated upstairs unit sits within the serene Winter Park Gardens complex, where your views of the shimmering pond and pool anchor a lush sprawling landscape of live oaks draped in Spanish moss, mature manicured gardens, and lighted walkways- perfect for evening strolls. The unit itself has been thoughtfully renovated with brand-new luxury vinyl plank flooring, an open kitchen, updated granite countertops, and a fully renovated bathroom — all combining to deliver exceptional value in one of Central Florida's most coveted zip codes. This is a 55+ community with room for younger owners.
Listing Agent: Olivia Maxwell (407-222-4440)
2803 BANCHORY RD, WINTER PARK, FL 32792
$495,00019 Days on yellowkey MLS ID: O6404011
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1596 Built: 1965Monthly Fee: $5 Tax: $2,458 (2025)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$2,458
Remarks: Located in Winter Park Pines, this 4-bedroom, 2-bath home offers a warm, flexible layout with comfortable living spaces and everyday functionality throughout. With 1,596 square feet, the home provides room to gather, relax, entertain, and adapt to changing needs over time. Inside, the floor plan includes both a living room and a separate family room, creating useful separation for daily life. One of the bedrooms has been converted into a large closet and dressing room, offering generous storage while still allowing the option to easily convert the space back into a traditional fourth bedroom if desired. The backyard extends the home outdoors with a patio and cobblestone brick area that is well suited for entertaining, outdoor dining, or quiet evenings at home. Set within the established Winter Park Pines community, the home offers sidewalks for excellent walkability, with Cady Way Trail just steps from your door for morning runs, bike rides, and everything in between. Nearby, Cady Way Park adds even more to the neighborhood lifestyle with its pool, tennis and pickleball courts, playground, and beach volleyball, while Park Avenue offers boutique shopping and exceptional dining just minutes away. UCF, Rollins College, and Full Sail University are all within easy reach, along with AdventHealth Winter Park and Orlando International Airport. Zoned for top-rated Winter Park schools, this home combines comfort, convenience, and the everyday appeal that continues to make Winter Park Pines one of Winter Park’s most established neighborhoods.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Melissa Johnson (407-681-4393)
333 CORNWALL RD, WINTER PARK, FL 32792
$579,00026 Days on yellowkey MLS ID: O6409379
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1660 Built: 1963Monthly Fee: $5 Tax: $2,654 (2025)Community: Winter Park PinesSingle Family
Taxes:$2,654
Remarks: Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, making this location a consistent choice for buyers prioritizing long-term value. In addition to the location, the home benefits from key updates already completed, including a 2022 roof, 2021 HVAC system, updated windows installed in 2017, along with an updated kitchen and bathrooms, offering peace of mind and modern functionality for the next owner. Ideally positioned to enjoy the Winter Park lifestyle. Close proximity to Park Avenue’s boutique shopping and exceptional dining, while the University of Central Florida, Rollins College, and Full Sail University are all within easy reach. AdventHealth Winter Park and Orlando International Airport are also close by, making both daily routines and travel simple. This is a home that delivers on every level, location, lifestyle, and lasting quality.
2700 CADY WAY, WINTER PARK, FL 32792
$649,000260 Days on yellowkey MLS ID: O6347690
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1876 Built: 1965 Tax: $8,335 (2024)Community: Winter Park Pines Unit 4Single Family
Taxes:$8,335
Remarks: Welcome to this charming, renovated 4-bedroom, 2-bath home in the highly desirable Winter Park Pines neighborhood, with the Cady Way Trail just steps from your front door. Move-in ready and thoughtfully maintained, this home offers the perfect blend of comfort, style, and an unbeatable location. Inside, the updated kitchen features stainless steel appliances and opens to a cozy sitting area with direct access to the outdoor patio, while a separate dining and family room provide comfortable, functional spaces for everyday living and entertaining. The well-designed layout offers four bedrooms providing flexibility for guests, a home office, or changing lifestyle needs. Step outside to a screened-in lanai overlooking the spacious backyard, creating the perfect setting to relax, entertain, or enjoy Florida living year-round. Situated on a .22-acre lot, the property offers plenty of outdoor space to enjoy, while the spacious two-car garage provides added convenience and storage. Enjoy an active lifestyle with immediate access to the Cady Way Trail and nearby community amenities, including soccer and baseball fields, tennis courts, a playground, and an Olympic-sized pool—all just moments away. Zoned for top-rated schools and located just minutes from Park Avenue’s renowned dining, shopping, and entertainment, this home offers an exceptional Winter Park lifestyle. Why not have it all? This Cady Way Charmer is ready for you to move in and start making memories.
Listing Agent: Megan Byers (407-457-7131)
731 BONGART ROAD, WINTER PARK, FL 32792
$499,00041 Days on yellowkey MLS ID: O6406004
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1526 Built: 1961 Tax: $5,910 (2025)Community: Winter Park EstatesSpa: NoSingle Family
Taxes:$5,910
Remarks: Virtually Staged. Completely renovated pool home on a large corner lot, tucked away on a quiet dead-end street in Winter Park. Solid block construction adds peace of mind, and this one has been updated top to bottom—new laminate flooring throughout, recessed lighting, popcorn ceilings removed, and a fresh, clean feel the moment you walk in. The main living area is bright and open, with natural light pouring into the living room that flows right into the dining space. The kitchen sits just off the dining area and was fully redone with soft-close cabinetry, stainless steel appliances, quartz counters, and a matching quartz backsplash. Off the dining area you’ll find a bonus family room that works perfectly as a media room, playroom, second living space—whatever fits your needs. Sliding doors open straight out to the pool, making indoor-outdoor living easy. This space also connects to a separate wing of the home featuring its own bedroom, full bathroom, and sitting area. It can be closed off from the main house and even has private access through the two-car garage, giving you flexibility for guests, extended family, or potential rental use. On the opposite side of the home are three additional generously sized bedrooms and two full bathrooms, including a bedroom with its own en-suite that can easily function as a primary depending on how you want to use the layout. Out back, you’ve got a large yard with plenty of room to make it your own, a big sparkling pool, and a covered porch area. There’s also a side gate with space to bring in a boat, trailer, or work truck straight to the backyard. A dedicated laundry setup is located off the back porch area, adding convenience for pool days and the separate suite. No HOA, roof from 2019, and a location that’s hard to beat—just minutes to 436, Downtown Winter Park, Full Sail, and UCF. Two-car garage, top rated schools, flexible floor plan, and a ton of usable space inside and out. Call today to set up a private showing!
Listing Agent: Ed Klein (321-377-4018)
914 ENCLAVE PL, WINTER PARK, FL 32792
$1,895,00089 Days on yellowkey MLS ID: O6391825
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3617 Built: 2026Monthly Fee: $372 Tax: $10,000 (2025)Community: The Enclave Winter ParkSingle Family
Taxes:$10,000
Remarks: Pre-Construction. To be built. 914 Enclave Place is a beautiful Alys Beach inspired design. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create a elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matthew Burks (407-257-5347)
641 W LYMAN AVE, WINTER PARK, FL 32789
$509,00015 Days on yellowkey MLS ID: O6408078
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 2003 Tax: $6,342 (2025)Community: Town/Winter ParkSingle Family
Taxes:$6,342
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: LOCATION. LOCATION. LOCATION. Heres the thing; in Winter Park, that's not a cliché. It's everything. There are homes in Central Florida that require a car for everything. This is not one of them. 641 West Lyman Avenue doesn't sit near Hannibal Square. It sits on it. This corner lot property is literally at the edge of one of Winter Park's most beloved and walkable districts — a place that draws residents and visitors alike with its brick-lined streets, acclaimed restaurants, wine bars, local boutiques, and genuine sense of community. Step outside your front door and within minutes you're at The Ravenous Pig, Prato, Chez Vincent, Park Avenue Tavern, Vinia Wine Bar, or CFS Coffee. The Saturday Farmers Market, the Hannibal Square Heritage Center, and the energy of one of Central Florida's most distinctive neighborhoods are all right here. And Park Avenue — Winter Park's crown jewel — is just a quick walk beyond that. Then there's Rollins College. Florida's oldest private university, founded in 1885, is an easy walk from your front door. Whether that matters to you as a parent, a professional, a culture enthusiast, or simply someone who values the intellectual and artistic energy a college campus brings to a neighborhood, this proximity is rare. You don't get Rollins-adjacent addresses very often — and when you do, they hold their value. And speaking of things that hold their value — the schools. This home is zoned for Winter Park High School, consistently rated one of the best public high schools in the state of Florida. Niche ranks it an A overall and among the top 5 public high schools in the entire Orlando metro area. It offers International Baccalaureate, Advanced Placement, and a college prep track that outperforms district and state averages across the board. For families, the school zone alone makes this address worth the conversation. The home itself is a clean, updated three-bedroom, two-bath bungalow — 1,120 square feet built in 2003, sitting on a corner lot enclosed by a white vinyl privacy fence. Inside, the sellers have done the work: new flooring throughout, new lighting, and all new appliances. There's nothing to fix, nothing to update, and nothing to negotiate around. You move in and you start living. That's the thing about this property. It's a turnkey home on the corner of one of Central Florida's most desirable walkable neighborhoods, in a school zone that parents actively relocate for, steps from a historic college campus and some of the best restaurants in the region. That combination, at this price point, inside the Winter Park city limits, simply does not come around often. Come see it before someone else does.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ted Moseley (352-729-1019)
2430 CHANTILLY AVE, WINTER PARK, FL 32789
$1,665,00034 Days on yellowkey MLS ID: O6401352
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2916 Built: 2026 Tax: $4,730 (2025)Community: Winter Park VillageSpa: NoSingle Family
Taxes:$4,730
Remarks: Positioned as one of the best values currently available in Winter Park, this exceptional 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 facade 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 chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders 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.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
350 CORNWALL RD, WINTER PARK, FL 32792
$765,00080 Days on yellowkey MLS ID: O6394524
REDUCED by $10,000 (1.3%) on 05/28/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2038 Built: 1963 Tax: $2,127 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$2,127
Remarks: Fully reimagined and COMPLETELY RENOVATED AND DESIGNED BY HGTV DESIGNER, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases ALL-NEW CABINETRY and QUARTZ COUNTERTOPS, highlighted by a dramatic WATERFALL KITCHEN ISLAND, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked. Seller Motivated!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kelly Butterfield (407-463-1289)
700 MELROSE AVE #K25, WINTER PARK, FL 32789
$245,0008 Days on yellowkey MLS ID: O6414821
0 Days Off yellowkey (back on 6/13/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 787 Built: 1964 Tax: $3,196 (2025)Community: Winter Park Gardens CondoCondo
Taxes:$3,196
Remarks: Under contract-accepting backup offers. Bright, beautifully updated 1-bed/1-bath condo with floor-to-ceiling views and a prime walkable location in the heart of Winter Park. The renovated kitchen and bath shine with modern finishes, while expansive windows frame serene, ever-changing views of the lushly landscaped grounds. Set within the sought-after Winter Park Gardens, residents enjoy 8 acres of private tropical gardens, peaceful walking paths, and a resort-style pool — all just steps from Park Avenue's dining, boutiques, and culture. A rare combination of tranquil garden living and unbeatable urban convenience. This is a 55+ community with room for younger owners. Call list agents for details.
700 MELROSE AVE #J24, WINTER PARK, FL 32789
$390,00026 Days on yellowkey MLS ID: R4911307
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 987 Built: 1964 Tax: $3,874 (2025)Community: Winter Park Gardens CondoCondo
Taxes:$3,874
Remarks: Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally updated one bedroom unit has just been completed. All new paint, porcelain flooring, all new fixtures, bathroom, appliances, new wood cabinets, new stone counters. All NEW The desirable condo community of Winter Park Gardens is nestled between Mead Gardens, Azalea Tennis Center and upcoming Winter Park's Progress Point. Unit is located on the second floor but there is an elevator and stairs to help to the location. Spacious 2 bedroom , 2 bath unit has large open floor plan. Main living area has an additional glass sunroom which provides additional space and breath-taking views of the beautifully landscaped and private courtyard. With its prime location in Winter Park, you'll have easy access to a many of the dining opportunities, shopping, and entertainment options. This is a 55+ community Whether you're strolling through the charming downtown area of Park Avenue or Hannibal Square or immersing yourself in the thriving arts and culture scene, with the Orlando Museum of Art right around the corner This property is centrally located to Downtown Orlando and Downtown Winter Park… no need to use the expressways! !THIS UNIT DOES NOT REQUIRE OWNER TO BE OVER 55+ furniture can convey with purchase.
Listing is courtesy of: KIMBRIDGE REALTY, LLC (407-755-7367)
Listing Agent: Scott Butts (321-239-8509)
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