Location: Winter Park
Do Not Show Listings
7300 DANIEL WEBSTER DR #M7, WINTER PARK, FL 32792
$159,000132 Days on yellowkey MLS ID: O6388668
REDUCED by $6,000 (3.6%) on 06/01/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1108 Built: 1974Monthly Fee: $471 Tax: $2,050 (2025)Community: ColoniesSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,050
Elementary School: Cheney Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor features durable and stylish vinyl flooring for added comfort. The fully renovated bathrooms boast contemporary designs and quality craftsmanship, and a brand-new AC system ensures year-round efficiency and peace of mind. Natural light pours into every corner of the home, enhancing the open layout and highlighting the elegant upgrades. Ideally located just minutes from shopping, dining, and top-rated schools, this condo offers both luxury living and everyday convenience. Don’t miss the opportunity to own this move-in-ready gem in a prime location!
Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)
Listing Agent: Rosa Rodriguez (407-832-1185)
3027 AARON BURR AVE #L1, WINTER PARK, FL 32792
$159,000132 Days on yellowkey MLS ID: O6390662
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1090 Built: 1974Monthly Fee: $471 Tax: $2,050 (2025)Community: ColoniesCondo
Remarks: Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathrooms, this home has been thoughtfully upgraded from top to bottom. The first floor showcases elegant marble-look tile flooring, creating a sleek and durable living space ideal for both relaxing and entertaining. Upstairs, you’ll find stylish and low-maintenance vinyl flooring throughout, adding warmth and continuity to the private living quarters. The fully renovated bathrooms boast contemporary finishes and fixtures, delivering a fresh, spa-like feel. A brand-new AC system ensures year-round comfort and energy efficiency. With its modern upgrades, functional layout, and move-in-ready condition, this condo is a perfect choice for buyers seeking both style and convenience.
7522 ALOMA PINES CT, WINTER PARK, FL 32792
$375,00065 Days on yellowkey MLS ID: S5150544
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1872 Built: 2017Monthly Fee: $407 Tax: $4,304 (2025)Community: Aloma TrailsTownhouse
Taxes:$4,304
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout the spacious living and dining areas, kitchen, and half bath. The modern kitchen is designed for both style and convenience, featuring granite countertops, abundant cabinetry, a large center island, and a walk-in pantry, along with a full appliance package. Sliding glass doors provide abundant natural light and a peaceful backyard view. Upstairs, you’ll find all bedrooms, including a spacious primary suite with plush carpeting, a large walk-in closet, and an en-suite bathroom featuring dual vanities and a glass-enclosed shower. The second floor also includes a full guest bathroom, a convenient laundry closet with washer and dryer, multiple linen closets. Additional highlights include a one-car garage, extended driveway parking, and access to community amenities. Conveniently located near Park Avenue, University of Central Florida, Full Sail University, and Rollins College, with easy access to shopping, dining, and entertainment.
Listing is courtesy of: RIVA REALTY GROUP LLC (407-845-1003)
Listing Agent: Vildan Nigro (352-988-3824)
7393 GRAND AVE, WINTER PARK, FL 32792
$325,000114 Days on yellowkey MLS ID: S5147029
INCREASED by $125,000 (62.5%) on 06/01/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1518 Built: 1983 Tax: $4,367 (2024)Community: Oakcrest-516Single Family
Taxes:$4,367
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Short Sale. Short Sale – Subject to Lender Approval. Exceptional investment opportunity in the desirable Winter Park area. This property offers strong potential for value-add through renovation or repositioning. Located in an established community with no HOA, the home sits on a generously sized lot, providing flexibility for improvements and long-term upside. The current layout presents a solid starting point for updates, making it suitable for rental income, resale, or portfolio expansion. Conveniently positioned near shopping, dining, parks, and major roadways, with access to highly regarded schools and surrounding amenities. Winter Park continues to experience steady demand, supporting long-term investment potential. Property is being sold as-is. Buyer to verify all measurements, condition, and intended use. Don’t miss this opportunity to secure a property with upside in a sought-after Central Florida location. Highest and Best due April 17th
Listing is courtesy of: DREAM HOME REALTY GROUP AND ASSOCIATES LLC (407-504-7282)
Listing Agent: Latisha Smith (407-504-7282)
200 SAINT ANDREWS BLVD #704, WINTER PARK, FL 32792
$164,99961 Days on yellowkey MLS ID: O6411608
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 793 Built: 1970 Tax: $2,396 (2025)Community: Four Seasons CondoCondo
Taxes:$2,396
Remarks: Excellent opportunity in the heart of Central Florida! Welcome to this charming 1-bedroom, 1-full-bath condominium located in the desirable Four Seasons Condominiums of Winter Park. Step inside to a spacious living area that flows seamlessly into the dining and kitchen spaces, creating a comfortable and functional layout perfect for everyday living or entertaining. The primary bedroom features a large walk-in closet, offering comfort and convenience. Relax and enjoy the view from the oversized private balcony just off the living room. Ideally situated just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, shopping, and dining, this location truly offers convenience at every turn. Enjoy being only minutes from the renowned Park Avenue, local museums, and everything Winter Park has to offer. Four Seasons Condominiums is a beautifully maintained 20-acre community within the Winter Park city limits and located in a highly sought-after school district. Residents enjoy an array of amenities including three swimming pools, tennis courts, shuffleboard courts, laundry facilities, and a clubhouse with a library. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo is a must-see!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
1092 EASTBROOK BLVD, WINTER PARK, FL 32792
$399,00074 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
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)
621 HUNTINGTON AVE, WINTER PARK, FL 32789
$1,795,000120 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)
WINTER PARK, FL 32792
$430,000139 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 Agent: Arlenys Oviedo (786-803-4342)
560 OLOLU DR, WINTER PARK, FL 32789
$925,000302 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)
1725 CAROLLEE LN, WINTER PARK, FL 32789
$1,005,00093 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
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 is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kyle Grafton (203-246-8512)
2512 EASTBROOK BLVD, WINTER PARK, FL 32792
$390,00069 Days on yellowkey MLS ID: O6409544
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1607 Built: 1967 Tax: $4,171 (2025)Community: Eastbrook Sub Unit 8Single Family
Taxes:$4,171
Remarks: Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in highly desirable Seminole County! From the moment you arrive, you'll appreciate the inviting front porch, the perfect place to relax, enjoy conversations with friends, and greet neighbors passing by. Inside, the home features recently painted interiors and new laminate flooring in the bedrooms, creating a fresh and move-in-ready feel. Pride of ownership shines throughout, as this home has been lovingly cared for over the years. Step outside and enjoy the spacious, landscaped backyard complete with a private irrigation well, screened-in porch ideal for morning coffee or evening unwinding, and a charming brick fire pit perfect for cooler Florida nights. There's even an outdoor shower, a unique and convenient touch after gardening or enjoying time outside on warm summer days.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Joseph Firmin (954-296-8861)
266 W LYMAN AVE, WINTER PARK, FL 32789
$1,375,00081 Days on yellowkey MLS ID: O6406526
2 Days Off yellowkey (back on 5/15/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2000 Built: 2014Monthly Fee: $568 Tax: $11,410 (2024)Community: Lyman Ave Villas 1Spa: NoTownhouse
Taxes:$11,410
Remarks: Under contract-accepting backup offers. ONE BLOCK FROM PARK AVENUE! Welcome to this beautifully renovated townhouse in the heart of Winter Park, offering the perfect blend of luxury and convenience. Whether you're looking for a full-time residence or a lock-and-leave property, this home delivers on every level. Designed with entertaining in mind, the open-concept layout creates a seamless flow from the kitchen into the main living areas. The kitchen features high-end appliances, including a Wolf refrigerator and GE Monogram suite, along with dedicated wine and beverage refrigeration—perfect for hosting or everyday use. A new A/C unit has also been installed, providing added peace of mind. That same attention to entertaining continues outdoors, where a screened-in kitchen, hot tub, and professionally installed turf create a private, low-maintenance space ideal for hosting or relaxing. Inside, the home offers a very spacious primary suite complete with a walk-in closet. A full bathroom is conveniently located downstairs adjacent to the study, which can also function as a third bedroom, adding flexibility to the layout. The two car garage has been upgraded with a durable epoxy-coated floor for a clean, finished look. Located just minutes from Winter Park Village and only a short drive to major roadways including Interstate 4 and State Road 436, this home offers unmatched access to shopping, dining, and downtown. Enjoy the charm of tree-lined streets and historic surroundings, all just steps from the shops and restaurants of Park Avenue. This is a rare opportunity to own a turnkey property in one of Winter Park’s most desirable locations.
Listing is courtesy of: MAROON REALTY GROUP LLC (407-774-7083)
Listing Agent: Larry Lanpher (407-383-8759)
1903 N PARK AVE, WINTER PARK, FL 32789
$1,695,000189 Days on yellowkey MLS ID: O6375766
REDUCED by $100,000 (5.6%) on 05/14/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2807 Built: 2020 Tax: $17,232 (2025)Community: Twin AcresSingle Family
Taxes:$17,232
Remarks: Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home features floor-to-ceiling glass, a wraparound terrace, and a bold two-story façade. The quartz river rock and concrete drive leads to dual frosted glass garage doors, pre-wired for an EV charger. Inside, a dramatic floating staircase is framed by a 17’ window, anchoring the open-concept living space with views of the private backyard. The modern kitchen includes light gray touch-open cabinetry, soft-close drawers, black stainless appliances, and a Calacatta quartz waterfall island. The outdoor space is designed for entertaining, with a covered lanai, expansive marble terrace, and a mini-pebble pool with sun shelf and water features. Lush podocarpus hedging and a masonry wall provide privacy. The first floor offers a dedicated office and full pool bath. Upstairs features four bedrooms with Italian frameless doors and three European-inspired bathrooms. The primary suite includes a custom walk-in closet and private access to the wraparound terrace overlooking the pool. Surrounded by beautiful tree-lined streets ideal for strolling and golf-cart rides to nearby shops, restaurants, and friends’ homes, this property offers the best of the Winter Park lifestyle. The home is also zoned for top-rated Winter Park schools. A rare modern home in one of Winter Park’s most desirable locations. Call today for your private showing.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
432 W SWOOPE AVE, WINTER PARK, FL 32789
$695,000189 Days on yellowkey MLS ID: O6375719
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2317 Built: 2014Monthly Fee: $463 Tax: $9,138 (2025)Community: Swoope ParkTownhouse
Taxes:$9,138
Remarks: A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Thomas Bonner (407-401-3748)
408 HOLT AVE, WINTER PARK, FL 32789
$745,00082 Days on yellowkey MLS ID: O6405857
Bed: 2 Bath: 0.0 Liv Area Sq Ft: 1440 Built: 1942 Tax: $5,765 (2025)Community: Trotters RepSpa: NoApartment
Taxes:$5,765
Remarks: Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.
Listing is courtesy of: THE REAL ESTATE PRINCIPLE, INC (407-739-7209)
Listing Agent: Brian Opre (407-739-7209)
2500 LEE RD #202, WINTER PARK, FL 32789
$224,999538 Days on yellowkey MLS ID: O6277579
REDUCED by $10,000 (4.3%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $432 Tax: $2,327 (2025)Community: Lakeside Manor Condominium Association, Inc.Condo
Taxes:$2,327
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Cable & Internet, Lake Access & Dock, Pool & Clubhouse, and Designated Parking.
Listing is courtesy of: THE ANDERSON GROUP & CO PL (407-960-5657)
Listing Agent: Alison Maltby (407-325-1483)
150 DANA WAY, WINTER PARK, FL 32789
$3,799,000124 Days on yellowkey MLS ID: O6394012
0 Days Off yellowkey (back on 5/1/2026)
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4451 Built: 2026 Tax: $14,010 (2025)Community: CharmontSpa: YesSingle Family
Taxes:$14,010
Remarks: JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKET Proudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s most sought-after neighborhoods. Positioned just steps from Lake Chelton and Lake Sue, and located within a highly desirable Winter Park school district, the setting delivers an exceptional lifestyle in one of Central Florida’s most dynamic and tightly held areas. While new construction inventory exists in today’s market, this home stands apart offering a fresh, cutting-edge architectural vision brought to life through exceptional planning, material selection, and execution. Prominently sited on an elevated homesite with a striking front elevation, the home offers 4,500 square feet of living space, including nearly 3,000 square feet on the ground level alone... a rare and highly functional configuration. The layout is both expansive and intentional, featuring multiple large living spaces, a private ground-floor primary suite, and a well-appointed guest suite/study/flex space. Upstairs, each bedroom is thoughtfully designed with either an en-suite bath or direct access to a full bath, delivering both comfort and privacy throughout. The defining feature of this home...and one rarely seen in the market... is the massive Renlita Floataway door system, which opens an entire wall of the home to seamlessly connect the interior Florida room with the resort-style outdoor living environment. This creates a true four-season entertaining space, transforming the way the home lives and offering a level of indoor-outdoor integration that is both dramatic and highly functional. The outdoor setting is designed as a private resort, complete with a pool, spa, fire and water features, pergola, and summer kitchen... all curated to complement the home’s architectural vision. Inside, the level of finish and design is exceptional. From breathtaking Venetian plaster walls to a dramatic two-story foyer, the home is defined by a refined and highly curated selection of materials, fixtures, and hardware. Every element has been intentionally sourced and executed, resulting in a level of craftsmanship and aesthetic cohesion that is rarely achieved and immediately recognized by discerning buyers. A well-appointed kitchen with walk-in butler’s pantry and thoughtfully designed secondary spaces further enhance both function and livability. Integrated Control4 home automation, audio, and security systems complete the offering. Located just minutes from Downtown Orlando, Winter Park, Park Avenue, Winter Park Village, AdventHealth, and Orlando Health, this home delivers a rare combination of location, design, and execution at the highest level. This is not simply new construction, it is a distinct, design-driven custom residence offering a level of detail, presence, and livability that is truly rare in the current Winter Park market.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Robert Kurzreiter Pa (407-476-4156)
726/720 N PENNSYLVANIA AVE, WINTER PARK, FL 32789
$1,185,99991 Days on yellowkey MLS ID: O6402984
Bed: 6 Bath: 0.0 Liv Area Sq Ft: 2282 Built: 2015 Tax: $5,170 (2025)Community: Morseland SubApartment
Taxes:$5,170
Remarks: Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one unit and offset your mortgage, or lease both units to capitalize on long-term rental demand in a location where inventory remains extremely limited. Each unit is designed for durability and appeal, featuring open-concept layouts, stone countertops, stainless steel appliances, custom cabinetry, and wood and tile flooring throughout, finishes that attract quality tenants while keeping maintenance straightforward. Private, fenced patios extend the living space outdoors, while in-unit laundry and ample parking add everyday convenience that renters actively prioritize. The location is the true driver, just steps from the Winter Park Golf Course and a short walk to Park Avenue’s dining, shopping, and lifestyle. This level of walkability continues to support strong tenant demand and long-term appreciation, particularly in the rapidly growing West End of Winter Park. As an added benefit, the property includes a membership to the Winter Park Country Club, further enhancing its appeal for both owners and tenants. For buyers looking to secure a property that offers immediate usability, consistent rental demand, and long-term upside in one of Central Florida’s most sought-after markets, this is a rare opportunity to check all three boxes in a single acquisition.
Listing Agent: Brandon Geers (941-928-5152)
632 COUNTRY CLUB DR, WINTER PARK, FL 32789
$1,050,000641 Days on yellowkey MLS ID: O6250417
0 Days Off yellowkey (back on 9/29/2025)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2342 Built: 1952 Tax: $4,638 (2023)Community: Lords SubSpa: NoSingle Family
Taxes:$4,638
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Kristin Duncan (407-274-5911)
1695 LEE RD #C202, WINTER PARK, FL 32789
$205,000512 Days on yellowkey MLS ID: O6285607
REDUCED by $5,000 (2.4%) on 04/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1149 Built: 1966 Tax: $2,126 (2024)Community: Waterfall Cove At Winter ParkCondo
Taxes:$2,126
Remarks: This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.
Listing is courtesy of: PRIMESTATE REALTY, INC. (407-850-9494)
Listing Agent: Hoover Yap (407-342-9395)
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