Location: Winter Park
Do Not Show Listings
2973 SANBINA ST, WINTER PARK, FL 32789
$377,88076 Days on yellowkey MLS ID: O6407521
1 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1965 Tax: $5,253 (2025)Community: Howell HeightsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,253
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!
Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)
Listing Agent: Andrew Musashe (407-645-5700)
426 WORTHINGTON DR, WINTER PARK, FL 32789
$2,499,00036 Days on yellowkey MLS ID: O6418049
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3520 Built: 2026 Tax: $9,459 (2025)Community: Kenilworth Shores Sec 01Spa: YesSingle Family
Taxes:$9,459
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Nestled within the highly sought-after Kenilworth Shores neighborhood, this extraordinary new construction home represents a rare opportunity to own one of Winter Park's finest new builds. Thoughtfully designed with an exceptional floor plan and uncompromising level of craftsmanship, detail, and finishes. This home is located just minutes from everything Winter Park has to offer. Step through the front doors into a breathtaking two-story foyer where soaring ceilings, and a statement chandelier create an unforgettable first impression. Designed for both everyday living and effortless entertaining, the floor plan is one of the home's most desirable features. Rare for Winter Park, the residence offers a luxurious primary suite, private guest suite, and dedicated office all on the main level. The expansive living room serves as the heart of the home, showcasing extensive custom trim work, an electric fireplace, and bespoke built-in cabinetry with LED underlighting. Walls of glass create a seamless connection to the outdoor living spaces while filling the home with natural light. The chef's kitchen is a true showpiece, designed to satisfy even the most discerning culinary enthusiast, featuring stunning Calacatta quartz countertops, custom cabinetry, a paneled built-in refrigerator, and a complete suite of Thermador appliances. Adjacent to the kitchen, the formal dining room creates an elegant setting for entertaining, featuring a custom dry bar complete with a wine refrigerator. Privately tucked away, the primary suite serves as a true retreat, featuring sliding glass doors leading directly to the backyard oasis, creating a seamless indoor-outdoor connection. The spa-inspired primary bath features marble mosaic tile, floating mirrors above dual vanities, a freestanding soaking tub, an oversized walk-in shower, and a generous walk-in closet. The upper level continues the home's thoughtful design with a spacious loft, accompanied by three generously sized bedrooms. Outdoor living is equally impressive, a covered lanai creates the perfect setting for year-round entertaining and is fully equipped with a summer kitchen. The beautifully designed backyard retreat showcases a sparkling pool and spa surrounded by lush green space, offering the ideal balance of recreation, relaxation, and privacy. Perfectly positioned in the heart of Winter Park, residents enjoy tree-lined streets while remaining just a golf-cart ride from the boutiques, award-winning restaurants, and cafés, of Park Avenue. The home is also conveniently located near Winter Park High School, Advent Health Winter Park, and the beloved Cady Way Park, where tennis courts, soccer fields, baseball fields, walking trails create one of Central Florida's most desirable active lifestyles. Don't miss out on this amazing new home!
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
644 N KNOWLES AVE #3, WINTER PARK, FL 32789
$475,00033 Days on yellowkey MLS ID: O6420484
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 767 Built: 1974 Tax: $4,218 (2025)Community: Knowles Manor North CondoCondo
Taxes:$4,218
Elementary School: Lakemont Elem
Remarks: LOCATION! LOCATION! LOCATION! Welcome to Knowles Manor...a charming 11 unit condo perched on quiet brick street in the heart of Olde Winter Park...just steps from the Winter Park 9 golf course, Casa Feliz, and the boutiques, restaurants, and vibrant lifestyle of Park Avenue, this location is hard to beat. This delightful first-floor residence is the perfect place to call home or an ideal pied-a'-terre for seasonal living. Inside you'll find easy maintenance tile flooring throughout, a full kitchen and bath, abundant closet space, and an adorable screened rear porch-perfect for relaxing with your morning coffee or unwinding at the end of the day. Additional highlights include a quaint community patio, one assigned parking space steps from your front door, a new HVAC system installed in 2021, and a new roof 2025. Whether you are looking for a full time residence, a weekend retreat, or a low maintenance Winter Park getaway, this charming condo is ready to welcome you home. Welcome Home!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
346 S RANGER BLVD, WINTER PARK, FL 32792
$475,000319 Days on yellowkey MLS ID: S5134662
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1592 Built: 1965 Tax: $5,339 (2024)Community: Winter Park PinesSingle Family
Taxes:$5,339
Elementary School: Aloma Elem
Tax Year: 2024
Remarks: PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has private access to the screened patio (Florida Room) and spacious backyard. The gated fence opens extra wide for boat, RV or your trailer entry. This entry is very convenient to back any trailer size. For outdoor activities, you just step out of the house and go on a Cady Way Trail for biking, skating, and walking activities. For tennis lovers there are very well kept tennis courts where sport enthusiasts practice their skills in pickleball. Right next to the tennis courts is a playground that offers cozy shaded areas with slopes, swings, and climbing walls. Publix, Costco, Walmart and the post office are all located nearby. For evening promenade the downtown Winter Park, located just a few miles away, offers unique restaurants, cozy coffee shops and bars. To see this amazing 3 bedroom home for sale in Winter Park, call today and schedule a showing! NOTE: Roof - July 2023. HVAC - 2015. No HOA, NO CDD.
Listing is courtesy of: IMPERIAL REALTY OF FLORIDA INC (407-346-4746)
Listing Agent: Tanya Vyushkina (407-346-4746)
729 MONMOUTH WAY, WINTER PARK, FL 32792
$799,00027 Days on yellowkey MLS ID: O6422168
0 Days Off yellowkey (back on 7/7/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2332 Built: 1970 Tax: $8,433 (2025)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$8,433
Remarks: Under contract-accepting backup offers. Completely reimagined with an extensive top-to-bottom renovation, this stunning four-bedroom, three-bathroom pool home offers over 2,300 square feet of beautifully curated living space in one of Winter Park's most desirable locations. Every detail was thoughtfully selected to blend timeless design with modern functionality, creating a truly move-in-ready home. Inside, large wood-look plank tile flooring installed throughout in 2024 creates a seamless flow, complemented by recessed lighting, plantation shutters, all-new designer lighting and ceiling fans, and energy-efficient windows replaced in 2024. A cozy wood-burning fireplace provides character to the beautiful living space while French doors installed in 2024 provide effortless access to the outdoor living space. Additional upgrades completed in 2024 include blown-in insulation and a gas tankless water heater. The showstopping kitchen was completely remodeled in 2024 and is designed to impress. Custom hardwood cabinetry accented with elegant gold hardware is paired with luxurious quartz countertops and a dramatic full-height quartz backsplash. A large center island with seating for four, a black farmhouse sink, pot filler, and abundant prep space make this kitchen equally suited for everyday living and entertaining. Split from the secondary bedrooms for added privacy, the spacious primary suite is a peaceful retreat featuring French doors leading directly to the pool, a dedicated makeup vanity, walk-in closet, and a beautifully renovated ensuite bathroom with a double vanity and an oversized tiled shower enclosed by frameless glass. All three bathrooms were tastefully remodeled in 2024 with timeless, high-end finishes. The oversized laundry room is as functional as it is attractive, offering built-in cabinetry for exceptional storage along with an included washer and dryer. Step outside to your own private backyard oasis situated on a beautifully landscaped .26-acre lot. The screened in-ground pool was resurfaced with mini pebble finishes in 2025, while a custom flagstone outdoor shower with a decorative rock bed creates a true resort-inspired atmosphere. Additional exterior improvements completed in 2024 include new exterior doors, gutters, French drains, and an updated two-car garage featuring epoxy flooring along with new torsion springs and rollers. Ideally located just minutes from UCF, Rollins College, Full Sail University, AdventHealth Winter Park, the Crosby Wellness Center, Winter Park Pines Golf Club, and the Cady Way Trail, residents also enjoy access to Cady Way Park with its community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Zoned for highly rated Aloma Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines a remarkable renovation with an unbeatable Winter Park lifestyle. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2024 PLUMBING - 2024 TANKLESS WATER HEATER - 2024
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Amy Turner (407-803-3885)
7500 WAUNATTA CT, WINTER PARK, FL 32792
$299,90027 Days on yellowkey MLS ID: TB8525179
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1998 Built: 1979 Tax: $6,383 (2025)Community: Lake Waunatta VillageSingle Family
Taxes:$6,383
Elementary School: None
High School: None
Middle School: None
Remarks: Multiple OFFERS.. highest and best due by 10pm Sunday July 5th, Seller to review offers on Monday. Seller is a corporation and has never occupied the home. Seller does not disclose. It is Buyer and Buyers brokers responsibility to verify all information. Seller chooses Mainstay National Title. 5 day inspection period max. Closing date on or before 45 days from effective date. All appliances stay in home but not warranted by seller. SOLD AS-IS. See offer instructions. AC 10/2020. WH and Roof ages unknown.
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Ryan Sack (813-351-9598)
4768 TANGERINE AVE #4768, WINTER PARK, FL 32792
$174,900156 Days on yellowkey MLS ID: S5144503
REDUCED by $4,100 (2.3%) on 07/07/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1973Monthly Fee: $280 Tax: $1,479 (2024)Community: Wrenwood CondoCondo
Taxes:$1,479
Remarks: Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless appliances. Community was freshly painted and roads repaved in 2025. Prime location near top dining, shopping, and parks. Move-in ready perfection!
Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)
Listing Agent: Christopher Franqui (347-703-7008)
333 CORNWALL RD, WINTER PARK, FL 32792
$579,00069 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.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Melissa Johnson (407-681-4393)
1250 S DENNING DR #109, WINTER PARK, FL 32789
$190,00024 Days on yellowkey MLS ID: R4911491
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 658 Built: 1967Monthly Fee: $350 Tax: $1,669 (2025)Community: Mead GardenSpa: NoCondo
Taxes:$1,669
Elementary School: Killarney Elem
Remarks: Welcome to this beautifully updated one-bedroom, one-bath condo in the heart of Winter Park. Thoughtfully maintained and move-in ready, this inviting home offers a bright, clean interior with tasteful finishes and a functional layout designed for comfortable, low-maintenance living. A spacious screened porch overlooks a serene courtyard, creating the perfect spot to enjoy your morning coffee or unwind at the end of the day. Perfectly situated, this home is nestled between two beautiful parks—Mead Botanical Garden, just steps away, and Seven Oaks Park—offering easy access to nature, walking paths, and green space. You're also just minutes from Rollins College, the boutiques and restaurants of Park Avenue, AdventHealth Winter Park, and the vibrant Mills 50 District. Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Orlando Urban Trail, Dinky Line Trail, and Baldwin Park, all just a short bike ride away. With convenient access to Orlando Avenue (US-17/92), I-4, and both the Winter Park and AdventHealth SunRail stations, commuting throughout Central Florida is effortless. Located in the desirable Mead Garden Condominiums community with a sparkling pool and beautifully maintained grounds, this charming condo offers an exceptional blend of comfort, convenience, and the best of the Winter Park lifestyle.
Listing is courtesy of: FAIRBANKS REALTY (407-758-1323)
Listing Agent: Randy Wilson (407-758-1323)
2157 LAKE DR, WINTER PARK, FL 32789
$689,00061 Days on yellowkey MLS ID: O6412258
3 Days Off yellowkey (back on 7/6/2026)
REDUCED by $70,000 (9.2%) on 05/31/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2124 Built: 1962 Tax: $1,605 (2025)Community: Killarney PointSingle Family
Taxes:$1,605
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake Killarney views, and a peaceful setting on a quiet private lakefront street. From the moment you enter, pride of ownership shines through, with custom built-ins throughout creating stylish and functional living spaces. The heart of the home is the updated kitchen and dining area, featuring high-end bamboo floors, stainless steel appliances, real wood custom cabinetry, and a large island overlooking a versatile flex space perfect for a formal living room, den, or office. The spacious great room is warm and inviting with a wood-burning fireplace and a dramatic wall of four French doors that fill the space with natural light. The elegant primary suite offers a walk-in closet and a spacious bath with dual vanities, a soaking tub, and separate shower. Step outside to a covered patio and expansive backyard with plenty of room to entertain, garden, or unwind. Just minutes from Park Avenue, premier shopping, dining, and Winter Park’s beloved parks and amenities, this is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods on .33 acres. Brand new roof and newer AC for total peace of mind. Schedule a private tour today.
Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)
Listing Agent: Jacob Johnson (407-353-0106)
751 WARRENTON RD, WINTER PARK, FL 32792
$319,90037 Days on yellowkey MLS ID: TB8522073
0 Days Off yellowkey (back on 7/6/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1196 Built: 1989Monthly Fee: $86 Tax: $2,795 (2025)Community: Winter Park Pines Patio HomesSpa: NoHalf Duplex
Taxes:$2,795
Remarks: Beautiful 3 bedroom 2 bath duplex in Winter Park in the Winter Park school district on a quiet dead end street near the Winter Park Pines Golf Course. Your new home is freshly painted inside and out, has updated kitchen and bathrooms, stainless steel appliances, new A/C system, new roof, and a new hot water heater. There is no need to worry about your yard, your bushes, or your fence, they are all covered under an inexpensive HOA, what a great deal! This updated home is move in ready and the neighbors are a pleasure! Come see your new home today!
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
2022 EASTBROOK BLVD, WINTER PARK, FL 32792
$353,00031 Days on yellowkey MLS ID: S5152746
1 Days Off yellowkey (back on 7/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1420 Built: 1966 Tax: $3,122 (2025)Community: Eastbrook Sub Unit 07Single Family
Taxes:$3,122
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully maintained 3-bedroom, 2-bathroom residence in the desirable Winter Park area! From the moment you arrive, you'll appreciate the long driveway, inviting curb appeal, and numerous recent upgrades that provide both style and peace of mind. Step inside to find updated bathrooms, newer appliances, and a functional layout designed for comfortable everyday living. Major improvements include a new roof and gutters (2023) and a newer water heater, making this home truly move-in ready. One of the standout features is the spacious, fully fenced backyard that backs up to preservation land, offering the privacy and tranquility of having no rear neighbors. Enjoy Florida living year-round from the large screened-in patio, perfect for entertaining, relaxing, or enjoying your morning coffee. Gardening enthusiasts will love the three raised garden beds, ready for planting your favorite flowers, herbs, or vegetables. Conveniently located near major highways, shopping, grocery stores, restaurants, and everyday conveniences, this home also offers easy access to the University of Central Florida (UCF), Valencia College, parks, and a variety of local attractions and family-friendly activities. Whether you're a first-time homebuyer, growing family, or simply looking for a home that combines comfort, privacy, and an unbeatable location, this Winter Park gem is one you won't want to miss. Schedule your private showing today!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Adriana Pena (407-494-7945)
1521 CAVENDISH RD, WINTER PARK, FL 32789
$470,00049 Days on yellowkey MLS ID: O6415985
5 Days Off yellowkey (back on 7/6/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1036 Built: 1946 Tax: $2,793 (2025)Community: Orwin Manor WestminsterSingle Family
Taxes:$2,793
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Located in the heart of Orwin Manor, one of Winter Park’s most beloved historic neighborhoods, 1521 Cavendish Road is a beautifully renovated 2-bedroom, 1-bath home offering 1,042 square feet of thoughtfully updated living space. Positioned between Winter Park, College Park, and Downtown Orlando, residents enjoy convenient access to AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, Park Avenue, Ivanhoe Village, and some of the area's most celebrated dining, shopping, and cultural destinations. Surrounded by mature landscaping, manicured hedges, colorful garden beds, and stately palms, the home's curb appeal reflects the character and pride of ownership found throughout the neighborhood. French front doors open to a spacious foyer that leads into a bright family and dining room combination, where new pine laminate flooring, crown molding, plantation shutters, and updated lighting blend historic character with modern comfort. The renovated kitchen features shaker cabinetry, Silestone countertops, stainless steel appliances, abundant storage, and natural light. Both bedrooms have been thoughtfully updated with new flooring, LED recessed lighting, ceiling fans, and plantation shutters, while the recently renovated bathroom pairs basketweave tile flooring, subway tile, quartz countertops, and classic finishes that honor the home's original style. Outside, the large backyard has been transformed into a private retreat featuring a composite deck, new fencing, mature palms, raised garden beds, steel-edged landscaping, and a paver walkway. Thoughtfully updated while preserving its architectural charm, this home offers a rare opportunity to enjoy historic character in a neighborhood that continues to benefit from the growth, investment, and enduring appeal of Winter Park and Downtown Orlando. Schedule your private tour today.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: John Goggin (321-332-3000)
1260 ALABAMA DR, WINTER PARK, FL 32789
$6,900,000149 Days on yellowkey MLS ID: O6387200
Bed: 6 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6396 Built: 1991 Tax: $59,749 (2025)Community: J Kronenberger SubSpa: YesSingle Family
Taxes:$59,749
Remarks: Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue. From the moment you arrive, the circular driveway, porte-cochère, and motor court signal that something extraordinary awaits. Solid brick construction and lush, manicured landscaping frame a grand entrance that sets the tone for every detail within. Step through the dramatic grand foyer into a home defined by elevated ceilings, rich hardwood floors, and exquisite crown moldings throughout. The formal living and dining rooms offer elegant spaces for entertaining, while a beautifully appointed wine room with stunning glass doors adds an unmistakable touch of sophistication. A chef's kitchen that truly inspires — outfitted with professional WOLF, Sub-Zero, and Miele appliances, dual islands with breathtaking countertops, a prep sink, built-in nugget ice machine, and a butler's hallway with floor-to-ceiling storage — flows effortlessly into the warm and inviting family room (complete with fireplace) and informal dining area. Bright, sun-drenched interiors and French doors open to a spectacular covered outdoor kitchen and a beautifully landscaped turf backyard, where a stunning saltwater pool and spa invite you to unwind in style. The first-floor primary suite is a sanctuary unto itself — featuring a private office, den, or sitting room anchored by a stunning double-sided fireplace, and a spa-caliber en suite with double vanities, jetted soaking tub, walk-in shower, and an oversized custom-built walk-in closet. A true retreat from the world. Upstairs, four generously sized bedrooms offer comfort and privacy for family and guests alike. One bedroom enjoys its own private en suite and a delightful secret bonus room — a magical hideaway perfect for children. Two bedrooms share a beautifully appointed Jack-and-Jill bath, each with its own private vanity area, and the fourth bedroom is spacious and well-served by the hall bath. The pièce de résistance of the upper level is a state-of-the-art home theater, complete with projector and screen, ceiling surround sound speakers, and a built-in dry bar with wine fridge — the ultimate in at-home entertainment. A detached guest casita with a full bath and wet bar provides ideal accommodations for visitors, while a detached three-car garage offers ample space for vehicles and storage. Two laundry rooms — one per floor — add everyday convenience, and custom storage solutions are found throughout. The whole-house Lutron lighting system and full-house generator ensure comfort, security, and seamless living at every turn. And then there is the water. The private boathouse along the Venetian Canal, with 95 feet of serene waterfront, offers a lifestyle that simply cannot be replicated — direct access to Winter Park's legendary chain of lakes, all from your own backyard. Located just a short stroll to the boutiques and dining of Park Avenue, the beauty of Kraft Azalea Gardens, and the Winter Park Racquet Club, this estate offers not just a home — but a way of life that the most discerning buyers have only dreamed of.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
252 SCOTTSDALE SQ #252, WINTER PARK, FL 32792
$85,00028 Days on yellowkey MLS ID: O6421977
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1085 Built: 1974 Tax: $1,637 (2025)Community: Winter Park Woods CondoCondo
Taxes:$1,637
Remarks: Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Lisa Wright (321-231-3141)
5184 LAZY OAKS DR, WINTER PARK, FL 32792
$280,00026 Days on yellowkey MLS ID: O6422366
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1984 Tax: $2,780 (2025)Community: Lazy Oaks CondoCondo
Taxes:$2,780
Remarks: Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you inside, leading down the hallway to the second bedroom at the front of the home, where a large window overlooks the front green space. The kitchen opens to a bright, inviting space with skylights that bring natural light into the combined living and dining area. A fireplace adds warmth to the room, while sliding glass doors lead to a private screened enclosure overlooking additional green space at the rear of the property. Ideally positioned within the home, the kitchen features all-new appliances and an oversized pantry with spice shelving for easy organization. The primary bedroom offers an inviting entrance with closet space upon entry. Sliding glass doors fill the room with soft natural light, creating a calm and peaceful atmosphere. The primary bath includes a double vanity and additional deep closet space. From the bedroom, step out to the screened enclosure and enjoy quiet moments in the Florida breeze. Lazy Oaks Condominium is a charming, peaceful community in Winter Park. Conveniently located near shopping, restaurants, schools, and universities, it offers an inviting place to relax and call home.
Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)
Listing Agent: Joyce Gary (407-782-3276)
120 BROADVIEW AVE, WINTER PARK, FL 32789
$1,450,00069 Days on yellowkey MLS ID: O6409860
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1747 Built: 1947 Tax: $2,693 (2025)Community: Killarney EstatesSingle Family
Taxes:$2,693
Remarks: Rare lakefront opportunity on the beautiful pristine Lake Killarney in the heart of Winter Park! Build your dream home on this coveted corner lot graced by original brick streets. Lake Killarney is a crystal-clear, spring-fed private lake — motorized boats welcome, yet no public boat ramp ensures a peaceful, exclusive experience. Enjoy sweeping 1-mile sunset views from one of only three homes on a quiet dead-end street. Walk to Hillstone, Trader Joe's, and 20+ world-class restaurants. An additional 40 X 65 ft from rear lot line is available to purchase to extend the footprint of your dream home. This extended lot size will create approx 10,000 sf lot. This is Florida lakefront living at its finest — don't miss it!
Listing is courtesy of: PROMAX PROPERTY SOLUTIONS (407-647-3377)
Listing Agent: David Murray (407-647-3377)
1695 LEE RD #B210, WINTER PARK, FL 32789
$95,000189 Days on yellowkey MLS ID: O6375872
REDUCED by $3,000 (3.1%) on 07/03/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 638 Built: 1966 Tax: $1,493 (2024)Community: Waterfall CoveSpa: NoCondo
Taxes:$1,493
Remarks: This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.
Listing is courtesy of: GM SUNSHINE REALTY LLC (407-376-1261)
Listing Agent: Giuseppina Moriconi (407-376-1261)
1751 GOODRICH AVE, WINTER PARK, FL 32789
$1,380,000182 Days on yellowkey MLS ID: O6377936
REDUCED by $45,000 (3.2%) on 07/03/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2170 Built: 2016 Tax: $9,263 (2024)Community: Sylvan HeightsSingle Family
Taxes:$9,263
Remarks: Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes continue through the home with a level 5 finish on all walls, spray foam insulation, solid-wood doors, designer shades on every window, and custom closet systems. The showstopping chef-inspired kitchen was designed to entertain with an expansive island, seating 6, and premium finishes- including custom cabinetry, quartz countertops, soft close cabinets and drawers, a concealed Bosh dishwasher, a 48" Thermidor 6-burner gas range, and a Viking Refrigerator. The kitchen seamlessly flows into the living room and dinning space, and also offers easy access for indoor/outdoor entertaining with the telescoping sliding glass door. Outside, you will find the extended patio with plenty of room for hosting friends and family under the bistro-lighting while cooking at the summer kitchen (grill, fridge, range hood). Back inside, you will find a laundry room, half bathroom, and downstairs bedroom with an ensuite offering flexibility to the first floor. Upstairs, you are greeted with a small loft space, 2 bedrooms with a Jack-and-Jill bathroom, and an exquisite primary suite. The primary suite is a true retreat with a large balcony, his and her walk-in closets, and a spacious primary ensuite, featuring a beautiful soaking tub, designer tile, quartz countertops, and great natural light. All upstairs bedrooms are also equipped with motorized black-out shades. This residence is modern, refined, and impeccably curated, offering elevated indoor-outdoor living just minutes from Park Avenue, AdventHealth Winter Park, Rollins College, museums, dining, shopping, and all that Winter Park has to offer! Reach out to schedule your private tour today.
Listing Agent: Stephanie Baldner (407-419-0629)
1565 FOREST AVE, WINTER PARK, FL 32789
$1,495,000107 Days on yellowkey MLS ID: O6398694
0 Days Off yellowkey (back on 7/2/2026)
REDUCED by $155,000 (9.4%) on 06/15/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2163 Built: 1925 Tax: $2,803 (2025)Community: Ellno WilloSingle Family
Taxes:$2,803
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Under contract-accepting backup offers. Virtually Staged. Set apart from the ordinary, this historic Winter Park residence offers a rare opportunity to own a home rich in character and authenticity. Homes like this, with timeless architectural detail and enduring charm, rarely come to market, especially in such a premier location just steps from the shores of Lake Virginia. Surrounded by multi million dollar estates, this 4 bedroom, 2 bath home blends classic warmth with everyday livability. Original wood floors, a wood burning fireplace, and thoughtfully designed living spaces reflect a level of craftsmanship and character that simply cannot be replicated. The spacious dining room is perfect for hosting memorable family gatherings, while the updated kitchen with wood cabinetry offers both function and charm. Upstairs, a versatile loft space provides flexibility for a media room, office, or play area, complete with peekaboo views of Lake Virginia that create a subtle connection to the surrounding landscape. Adding to the home’s appeal is a detached 20 x 20 studio flooded with natural light and offering endless possibilities, ideal for an artist’s retreat, home office, gym, or guest space.This is more than a home, it is an opportunity to own a piece of Winter Park’s character and history. Set among some of Winter Park’s most distinguished homes, this property delivers an unbeatable lifestyle, walkable to all that Park Avenue has to offer, surrounded by luxury, and full of potential to enjoy, enhance, or reimagine.
Listing is courtesy of: NORDQUIST & COMPANY INC (407-694-0996)
Listing Agent: Elizabeth Nordquist (407-694-0996)
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