Location: Winter Park
Do Not Show Listings
3370 CEDAR SPRINGS PL #156, WINTER PARK, FL 32792
$185,000353 Days on yellowkey MLS ID: O6326460
REDUCED by $4,000 (2.1%) on 05/11/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1984Monthly Fee: $420 Tax: $2,549 (2024)Community: Hidden Oaks Condo Ph 09Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,549
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own private bathroom. Step outside to a fenced-in patio that overlooks a serene water canal and conservation area—perfect for relaxing or entertaining. Additional features include an outdoor storage room and extra storage space under the stairs. The Hidden Oaks community offers residents access to a beautiful pool and playground. Whether you're a first-time homebuyer, an investor, or simply looking for a cozy place to call home, this property presents a standout opportunity close to major highways, universities, and popular dining spots in Central Florida.
Listing is courtesy of: SPRINGHILL PROPERTIES LLC (646-236-0299)
Listing Agent: Wendy Lin (646-236-0299)
316 BECKETT CT, WINTER PARK, FL 32792
$450,00034 Days on yellowkey MLS ID: O6411108
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1966 Tax: $2,232 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,232
Tax Year: 2025
Remarks: Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for your vision to come to life. Whether you’re an investor, builder, or buyer looking to create your dream home, this property offers the ultimate clean slate for a full renovation or custom redesign. Situated in highly desirable Winter Park, this property places you in the heart of one of Orlando’s premier communities, known for its tree-lined streets, charm, upscale shopping, dining, and cultural attractions. Enjoy easy access to Downtown Winter Park Historic District and iconic Park Avenue, home to boutique shopping, cafés, restaurants, and vibrant community events, along with the beauty of Central Park and the cultural appeal of The Charles Hosmer Morse Museum of American Art. Winter Park is also home to the prestigious Rollins College, adding to the area’s timeless character and desirability. Bring your contractor, your imagination, and your vision—properties with this kind of potential in Winter Park are rare. Endless possibilities await!
Listing is courtesy of: ITS REALTY (321-437-7363)
Listing Agent: Patrick Westervelt, Llc (407-533-1000)
1092 EASTBROOK BLVD, WINTER PARK, FL 32792
$399,00045 Days on yellowkey MLS ID: O6407251
REDUCED by $11,000 (2.7%) on 05/27/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1122 Built: 1959 Tax: $4,373 (2025)Community: Eastbrook SubSingle Family
Taxes:$4,373
Elementary School: Lakemont Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.
Listing is courtesy of: JC FLORIDA REALTY LLC (407-257-8265)
Listing Agent: Eva Firios (321-662-1501)
440 CAMBRIDGE BLVD, WINTER PARK, FL 32789
$380,00054 Days on yellowkey MLS ID: O6403694
1 Days Off yellowkey (back on 5/27/2026)
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 988 Built: 1950 Tax: $4,386 (2025)Community: Glencoe SubSingle Family
Taxes:$4,386
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. **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.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
621 HUNTINGTON AVE, WINTER PARK, FL 32789
$1,795,00091 Days on yellowkey MLS ID: O6394464
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2399 Built: 2008 Tax: $12,854 (2025)Community: Winter Park RevSpa: NoSingle Family
Taxes:$12,854
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!
Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)
Listing Agent: Noelle Leblanc (407-491-2744)
2500 LEE RD #237, WINTER PARK, FL 32789
$169,000175 Days on yellowkey MLS ID: V4946519
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 645 Built: 1969 Tax: $2,227 (2024)Community: Lakeside Manor Apts CondoCondo
Taxes:$2,227
Remarks: BRING ALL OFFERS! Welcome to lakeside living! This cozy one-bedroom, one-bathroom condo offers a blend of amenities and convenience. This perfectly located condominium has low HOA FEES and has no assessment fees! Enjoy your days fishing, boating, or hanging out by the pool overlooking gorgeous Lake Killarney, a 240 acre spring-fed lake! Cherish living on the shores of Lake Killarney, complete with coveted dock access and a refreshing pool. Located in the heart of Winter Park, one of the most sought-after zip codes in the Orlando metro area. Residents in the desirable Lakeside Manor community enjoy access to the boat slips, the clubhouse, the lakefront pool and the beautifully maintained landscaped courtyard. Bring your ideas and make this your own. HOA fees includes ground keeping, exterior and roof maintenance. Water is also included with a low monthly HOA fee of $240 a month. HVAC 2021 , Roof 2016, Conveniently located near I-4 for quick access to Orlando. Situated near Winter Park Village, College park and Baldwin Park. Appreciate the nearby hospitals, shopping, dining, museums, parks, botanical gardens and entertainment of Winter Park. Savor your lakeside retreat with low fees and low maintenance. All information deemed reliable but not guaranteed and should be independently verified. If qualified with preferred lender, a $1500 credit will be offered.
Listing is courtesy of: LPT REALTY LLC (DB) (877-366-2213)
Listing Agent: Lydia Cassaro (386-801-5365)
1307 FORMOSA AVE, WINTER PARK, FL 32789
$373,80070 Days on yellowkey MLS ID: O6400711
REDUCED by $100 (0.0%) on 05/26/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1150 Built: 1946 Tax: $6,007 (2025)Community: GolfviewSingle Family
Taxes:$6,007
Remarks: Under contract-accepting backup offers. Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living areas, ceramic tile in the kitchen and dining spaces, and strong natural light from multiple window exposures. The kitchen has been updated with white cabinetry, granite countertops, and a mix of stainless steel and black appliances. The bathroom features updated finishes including a modern vanity and shower. Additional features include a covered front porch, one car attached garage with laundry area, central air conditioning with updated ductwork, and a fenced backyard with deck space suitable for outdoor use. The property is connected to public water and sewer and offers practical living with no HOA. Located near Dubsdread Golf Course and within close proximity to AdventHealth, College Park, and Downtown Orlando. Easy access to I-4 and surrounding roadways supports convenient travel to employment, dining, and retail centers. This property is suitable for a primary residence or investment opportunity in a well located Winter Park area.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Tyler Gibson Llc (877-366-2213)
WINTER PARK, FL 32792
$430,000110 Days on yellowkey MLS ID: S5145631
REDUCED by $10,000 (2.3%) on 04/15/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1296 Built: 1958 Tax: $4,968 (2025)Community: Winter Park EstatesSingle Family
Taxes:$4,968
Remarks: Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, new AC System and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for comfortable living and entertaining. The property is being sold in its current condition; exterior improvements will not be completed, giving the future owner the opportunity to finish and customize the exterior to their preference. Conveniently located near shopping, dining, schools, and major roadways.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Arlenys Oviedo (786-803-4342)
2412 CHANTILLY AVE, WINTER PARK, FL 32789
$2,394,500139 Days on yellowkey MLS ID: O6381552
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $500 (0.0%) on 04/20/2026
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4506 Built: 2026 Tax: $4,779 (2025)Community: Winter Park VillageSingle Family
Taxes:$4,779
Elementary School: Dommerich Elem
Remarks: Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Tab Bish Llc (855-450-0442)
560 OLOLU DR, WINTER PARK, FL 32789
$925,000273 Days on yellowkey MLS ID: O6344540
REDUCED by $24,000 (2.5%) on 05/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1086 Built: 1953 Tax: $8,617 (2024)Community: Killarney CircleSingle Family
Taxes:$8,617
Remarks: Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Tiffany Yates (321-684-2399)
650 DIXIE PKWY, WINTER PARK, FL 32789
$4,250,00043 Days on yellowkey MLS ID: O6408708
5 Days Off yellowkey (back on 5/26/2026)
Bed: 6 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 6007 Built: 2018 Tax: $41,255 (2025)Community: Winflor Court Pt RepSpa: YesSingle Family
Taxes:$41,255
Remarks: Under contract-accepting backup offers. Introducing one of Winter Park's most extraordinary offerings — a meticulously designed transitional masterpiece by the acclaimed Winter Park Custom Homes, set on a rare 0.34-acre corner lot in one of the city's most coveted neighborhoods. From the moment you arrive at the circular front drive and step onto the marble-tiled covered front porch, it's clear this home is in a class of its own. Inside, soaring beamed ceilings and wide-plank engineered wood floors set an elevated tone throughout. The grand living room features a gas fireplace and dramatic accordion glass doors that dissolve the boundary between indoors and out, opening to the resort-style backyard with ease. The chef's kitchen is a true work of art: anchored by a massive island with wraparound seating, Thermador gas range and oven, built-in refrigerator and microwave, marble countertops, and a generous walk-in pantry — all complemented by stunning herringbone hardwood floors that make this space feel straight out of the pages of a design magazine. A butler's hallway and charming brick-floored cozy reading room add warmth and character to the everyday. Also on the main level, a full en-suite office — easily serving as a 6th bedroom — offers flexible living for guests or multi-generational needs, while a separate powder room is thoughtfully reserved for guest use. The primary suite is a sanctuary unto itself: a private vestibule entry leads to a spacious bedroom retreat with accordion-style doors that open directly to stepping stones leading into your personal spa. The spa-inspired primary bath showcases marble countertops and inlay floors, separate sink vanities, a freestanding soaking tub, a walk-in shower, and a custom-built walk-in closet that rivals any boutique. Upstairs, four generously sized en-suite bedrooms — each with walk-in closets — surround a spectacular bonus room complete with a wet bar, perfect for entertaining or movie nights. The third floor is a true Winter Park rarity — an expansive additional living level with a dedicated gym area and playroom ideal for home theater, creative pursuits, or whatever your lifestyle demands. Built-in speakers complete the experience. Step outside to your own private resort. A heated pool and spa with a sun shelf, fire bowl, and serene stepping stones are framed by lush artificial turf and elegant marble-inlaid pavers. The covered back patio with tongue-and-groove ceiling and fireplace creates an al fresco living room, while the outdoor grill with prep sink makes entertaining effortless. Natural gas throughout, a full-house generator, sauna, and an epoxy-floored two-car side garage round out this exceptional property — all seamlessly controlled through a whole-home Control4 automation system that puts lighting, climate, audio, security, and more at your fingertips. Zoned for A-rated Winter Park schools and just minutes from Park Maitland School (K–6), Park Avenue's world-class dining and boutiques, and all that Central Florida has to offer. Homes of this caliber, at this scale, in this location simply do not come available often. This is not just a home — it's a lifestyle.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
1780 BRYAN AVE, WINTER PARK, FL 32789
$849,000202 Days on yellowkey MLS ID: O6365369
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1617 Built: 1952 Tax: $7,345 (2024)Community: Lakeview TerraceSingle Family
Taxes:$7,345
Remarks: Build your dream home in one of Winter Park’s most desirable locations. This 66.6’ x 127’ homesite at 1780 Bryan Avenue offers a rare opportunity to secure the last remaining lot of three consecutive new construction parcels. Surrounded by newly built luxury residences, the property provides a clean slate for custom design while maintaining strong future value. The lot’s generous dimensions allow for a spacious floor plan, outdoor living areas, and a private backyard retreat. Situated on a quiet, tree-lined street, yet just minutes from Park Avenue, top-rated schools, dining, and shopping, the location strikes the perfect balance between convenience and neighborhood charm. Opportunities like this are increasingly rare in Winter Park—don’t miss your chance to be part of a growing enclave of new construction homes in a highly sought-after area.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Nick Mckee (407-913-0171)
1600 S PENNSYLVANIA AVE, WINTER PARK, FL 32789
$1,200,00050 Days on yellowkey MLS ID: NS1088189
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2158 Built: 1958 Tax: $5,218 (2025)Community: Banks Colonial EstatesSpa: YesSingle Family
Taxes:$5,218
Remarks: Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and space with a layout designed for everyday living and entertaining. The home features a inviting living area along with a unique sunken sunroom just off the two-car garage; perfect for a relaxing sitting room, home office, or play space. The well-appointed kitchen and dining areas flow easily into the main living spaces, creating a warm and functional environment for family and guests. Step outside to your private backyard retreat where you’ll find a sparkling pool and hot tub surrounded by a huge yard, offering plenty of room for outdoor gatherings, gardening, or simply enjoying Florida living. With its generous lot size, thoughtful layout, and prime Winter Park location close to shopping, dining, and top-rated schools, this home is a wonderful opportunity for anyone looking to enjoy the best of Central Florida living.
Listing is courtesy of: EXIT REAL ESTATE PROPERTY SOL (386-763-3008)
Listing Agent: Jami Giles (386-478-8284)
4858 TANGERINE AVE #4858, WINTER PARK, FL 32792
$209,900113 Days on yellowkey MLS ID: O6388649
0 Days Off yellowkey (back on 5/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973Monthly Fee: $392 Tax: $1,254 (2024)Community: Wrenwood CondoCondo
Taxes:$1,254
Remarks: Under contract-accepting backup offers. Charming Updated Home in Prime Winter Park Location Welcome to this beautifully updated home located in the highly desirable area of Winter Park. Combining comfort, style, and convenience, this property offers a thoughtfully designed open floor plan that creates a seamless flow between the main living spaces, making it ideal for both everyday living and entertaining. The home features two well-sized bedrooms and two full bathrooms, providing comfort and privacy for residents and guests alike. The spacious living room and dining room are filled with natural light, creating a warm and inviting atmosphere perfect for gatherings, relaxing evenings, or hosting family and friends. The kitchen is both elegant and functional, showcasing solid wood cabinets, beautiful stone countertops, and a full set of included appliances. With its stylish finishes and practical layout, this space is perfect for preparing meals while staying connected to the rest of the home. Several valuable updates have been made to the property, adding both appeal and peace of mind for future owners. The home features a NEW roof, brand-NEW appliances, NEW AC and NEW electrical panel , all enhancing the overall quality and efficiency of the property while reducing potential maintenance concerns. Ideally located near a main road, this home offers easy access to shopping, dining, and daily conveniences while still maintaining a peaceful residential feel. The property is also situated close to well-regarded schools, making it an excellent option for families or anyone looking to enjoy the benefits of living in one of Winter Park’s most sought-after communities. This is a fantastic opportunity to own an updated home in a prime location. Schedule your private showing today and discover everything this Winter Park property has to provide.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Angelica Diaz Bajo (407-223-5969)
311 E MORSE BLVD #7-11, WINTER PARK, FL 32789
$299,000307 Days on yellowkey MLS ID: O6337061
REDUCED by $10,900 (3.5%) on 05/24/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 570 Built: 1960 Tax: $668 (2024)Community: Phillips Circle RepCondo
Taxes:$668
Remarks: Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Mary Colton (407-222-7388)
1540 FLORENTINO LN, WINTER PARK, FL 32792
$335,00038 Days on yellowkey MLS ID: O6408841
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2004Monthly Fee: $175 Tax: $5,340 (2025)Community: Vistas At Lake HowellTownhouse
Taxes:$5,340
Elementary School: Sterling Park Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the bedrooms. You will find yourself within walking distance of restaurants, grocery stores, and other retail outlets. It's central location puts within minutes of 436 and 417. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ashley Fisak (407-848-7975)
2232 BANCHORY ROAD, WINTER PARK, FL 32792
$1,115,00057 Days on yellowkey MLS ID: O6404702
REDUCED by $45,000 (3.9%) on 05/21/2026
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2597 Built: 1966 Tax: $11,186 (2025)Community: Brookshire Heights 4Th AddSingle Family
Taxes:$11,186
Remarks: Step into the Winter Park lifestyle with a fully turnkey home designed to make daily living feel effortless. Set on an oversized corner lot, this fully updated home blends clean design with thoughtful upgrades. Inside, the home is built to bring people together. The open-concept layout flows seamlessly from living to dining to kitchen, anchored by a striking 9-foot Carrera Thassos quartz island. A full KitchenAid black stainless steel appliance suite, generous storage, and refined finishes make this a space that works as well on a busy weekday as it does when hosting a full house. Out back, everything is ready to enjoy. A private, resort-style setting features a saltwater pool with fire bowls, custom lighting, and a dedicated outdoor dining area, all framed by professionally designed landscaping and low-maintenance artificial turf. Beyond the aesthetics, this home delivers real, everyday value. A reverse osmosis system, fully updated electrical and plumbing, a 5-ton air conditioning system, and a metal roof provide peace of mind. An 18.4-kilowatt solar system keeps utility costs remarkably low, with many months producing surplus energy credits. Located in sought-after school zones and just minutes from Cady Way Park, with easy access to Orlando, this is a home where everything has already been considered. No projects, no waiting, just move in and start living. Buyer to assume $75,000 solar panel loan, offset by minimal to near-zero electric costs and ongoing energy credits during high-production months. Utility bills available on request.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Kirstie Hines (321-440-7716)
1617 CHILEAN LN, WINTER PARK, FL 32792
$367,500166 Days on yellowkey MLS ID: O6373026
1 Days Off yellowkey (back on 5/15/2026)
REDUCED by $2,400 (0.6%) on 04/30/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1359 Built: 1960 Tax: $3,432 (2024)Community: Eastbrook Sub Unit 05Single Family
Taxes:$3,432
Elementary School: Eastbrook Elementary
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Back on the market and better than ever! New water heater and minor repairs addressed and ready for the new owner! Come see this newly renovated home in the Eastbrook neighborhood of Winter Park. Offering 3 bedrooms and 2 full baths it’s the perfect sanctuary for families and entertainers alike. You will enjoy the bright, airy feel of the open floor plan accentuated by the vaulted ceilings that flood the space with natural light. The stylish interior includes luxury vinyl plank flooring throughout, complemented by elegant tile in the bathrooms and laundry room. Relax in not one, but two generous living areas, perfect for family gatherings, entertaining or cozy nights in. Cook like a pro in your eat-in kitchen featuring brand new ENERGY STAR stainless steel appliances, ample cabinetry, and convenient carport access for effortless unloading. The generous backyard provides a private oasis for outdoor activities, barbecues, and gardening enthusiasts. Plus, the expansive driveway and two-car carport ensure plenty of parking for your guests. Recent upgrades include ceiling fans, blinds, fresh paint, stainless steel appliances, a newer roof (2017) and a well-maintained air conditioner (only 4 years old) ensuring peace of mind for years to come. Located in Seminole County, known for great schools and in a community with NO HOA fees, giving you the freedom to enjoy your space. Plus, you're just moments away from shopping, dining, and parks!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Brenda Feliciani (407-405-0931)
1725 CAROLLEE LN, WINTER PARK, FL 32789
$1,005,00064 Days on yellowkey MLS ID: O6402656
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $10,000 (1.0%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2335 Built: 1960 Tax: $8,445 (2025)Community: Green TerraceSingle Family
Taxes:$8,445
Elementary School: Brookshire Elem
Middle School: Glenridge Middle
Remarks: Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias, gardenias, and more. Just minutes from Park Avenue’s beloved restaurants, cafés, and boutiques, as well as the scenic Winter Park Chain of Lakes, this home offers both character and convenience. With easy access to I-4, SR-417, Orlando International Airport, and top-rated schools, it is a wonderful opportunity to enjoy classic Winter Park charm in a beautifully cared-for home.
Listing Agent: Kyle Grafton (203-246-8512)
2973 SANBINA ST, WINTER PARK, FL 32789
$377,88046 Days on yellowkey MLS ID: O6407521
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1965 Tax: $5,253 (2025)Community: Howell HeightsSingle Family
Taxes:$5,253
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)
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