Location: Winter Park
Do Not Show Listings
4858 TANGERINE AVE #4858, WINTER PARK, FL 32792
$209,90098 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,254
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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
$299,000292 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)
2500 LEE RD #219, WINTER PARK, FL 32789
$164,000318 Days on yellowkey MLS ID: O6332524
3 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 851 Built: 1969Monthly Fee: $360 Tax: $2,392 (2024)Community: Lakeside Manor Apts CondoCondo
Taxes:$2,392
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as well as a private boat launch, a brand-new dock with covered over-water seating, a lakeside pool, and a clubhouse. The beautifully manicured green spaces and quiet courtyard areas create a peaceful, community-oriented atmosphere.Inside, this move-in ready unit has been freshly painted throughout and features new carpeting. The kitchen has been tastefully refreshed and offers plenty of cabinet space. An assigned parking space is located just steps from the unit, and there's an on-site laundry facility plus a private storage unit for added convenience.Tucked away yet close to it all, you’re just minutes from the shops and restaurants of Winter Park, with easy access to I-4 and other major roadways. Residents love living here—units don’t come available often, so don’t miss your chance to call this lakeside gem home!
Listing is courtesy of: SUNDIAL REAL ESTATE LLC (407-601-2200)
Listing Agent: Nicole Van Treese (407-462-9050)
2923 ANTIQUE OAKS CIR #34, WINTER PARK, FL 32792
$190,00025 Days on yellowkey MLS ID: S5150301
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1984Monthly Fee: $441 Tax: $725 (2025)Community: Parkview VillageCondo
Taxes:$725
Tax Year: 2025
Remarks: TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax and enjoy the Florida weather. The kitchen comes complete with stainless steel appliances, ample cabinet and counter space, and a convenient pass-through opening overlooking the main living area for easy entertaining. Both bedrooms are generously sized with similar layouts, while the two full bathrooms provide everyday comfort and convenience. The interior laundry space adds functionality to the home. Located in Parkview Village Condominium, residents can enjoy community amenities including a clubhouse, community pool, gazebo, and more. This well-maintained community is surrounded by mature trees and landscaping and offers a prime location just minutes from Downtown Winter Park, Full Sail University, UCF, shopping, dining, entertainment, and major roadways including 417 and 436. Whether you’re looking for a primary residence, seasonal getaway, or investment opportunity, this centrally located condo offers comfort, convenience, and low-maintenance living.
Listing is courtesy of: EXP REALTY LLC (407-846-0940)
Listing Agent: Steve Pugh (407-846-0940)
7301 CEDAR CREEK CT #66, WINTER PARK, FL 32792
$184,95067 Days on yellowkey MLS ID: O6397477
REDUCED by $2,550 (1.4%) on 05/20/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1983Monthly Fee: $10 Tax: $2,731 (2025)Community: Hidden Oaks Condo Ph 04Condo
Taxes:$2,731
Remarks: Welcome home to this beautiful starter home or perfect student housing in Winter Park! Two story townhouse style condo with 2 bedrooms each with private full ensuite bathroom and an extra half bath on the main floor. Renovated with stone counters and all luxury plank flooring- no carpet! New appliances and a nice open kitchen with breakfast bar- very unusual in this development. Washer and dryer in unit. Private fenced back patio with outdoor storage and small front garden for your green thumb. Only 15 min to UCF, 5 min to Full Sail and near all major shopping and dining including COSTCO, Target, Publix and more. Winter Park schools.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
1500 GAY RD #17D, WINTER PARK, FL 32789
$259,90028 Days on yellowkey MLS ID: O6408516
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1026 Built: 1972 Tax: $3,244 (2025)Community: Chateaux Du LacSpa: NoCondo
Taxes:$3,244
Remarks: Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in 2023, Range 2019, Refrigerator in 2020, A/C in 2020, Double-Pane Windows and Sliding Door in 2016, Updated Electric Panel, Replaced Ductwork and added Attic Insulation. Master Bath has Double-Sink Vanity. Guest Bath has newer Vanity and Retiled Shower with replaced Shower Pan. Unit recently Replumbed. Plantation Shutters, recently Repainted and Carpeted. Short Walk to Shopping, Restaurants, Theaters, and minutes to Park Avenue with it's Village Style Shopping, Central Park with Bandstand, Spring and Fall Art Festivals, Farmer's Market and Downtown Train Station. Drive into the Community, catch a view of the Lake, watcha Sunset on the Deck and you will know "you're Home"!
Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)
Listing Agent: Janice Erickson (407-621-6856)
144 LEWFIELD CIR #144, WINTER PARK, FL 32792
$137,00095 Days on yellowkey MLS ID: O6390043
0 Days Off yellowkey (back on 5/18/2026)
REDUCED by $7,000 (4.9%) on 04/21/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Monthly Fee: $351 Tax: $720 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$720
Remarks: Under contract-accepting backup offers. LOCATION! LOCATION! LOCATION! Beautiful 2nd floor corner condo in desirable Winter Park, featuring 1 bed/1 bath, open concept living/dining area and balcony. 2018 ROOF. Move-in ready and conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando. Residents enjoy resort-style amenities including two pools, tennis court, a fitness center, and clubhouse available for rental for gathering or events. The unit includes a fully equipped kitchen, stackable washer and dryer in the bedroom, and access to free community laundry. HOA covers water, trash removal, internet, pest control, exterior maintenance, and grounds care. Close to shopping, dining, and major highways for easy access across the area.
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Sandra Da Silva (407-840-8500)
200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792
$225,00074 Days on yellowkey MLS ID: O6395720
3 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1266 Built: 1970Monthly Fee: $451 Tax: $2,131 (2025)Community: Four Seasons CondoCondo
Taxes:$2,131
Elementary School: Brookshire Elem
High School: Winter Park High
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood cabinetry, granite countertops, black appliances, and a dishwasher replaced in 2023, perfect for everyday cooking and entertaining. Just off the kitchen, enjoy a dedicated dining area, ideal for hosting dinners or creating a flexible space for a home office or additional seating. The inviting living room provides plenty of space to relax and gather, with sliding glass doors that lead to your private, fully fenced, tree-shaded patio complete with a storage shed - an ideal spot to enjoy your morning coffee or unwind in the evenings. The patio also offers convenient access to your covered, deeded carport space, #49. Both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The home includes a full bathroom and a convenient half bath, both thoughtfully updated with new toilets and upgraded vanities, including a quartz countertop and stylish shiplap accent in the guest bath. Additional interior highlights include custom closet features, a laundry closet with a new stackable washer and dryer(included), ceiling fans and blinds throughout, fresh interior paint (2024), and an HVAC system updated in 2023, providing peace of mind and modern convenience. Residents of Four Seasons enjoy access to a variety of amenities including 3 swimming pools, a clubhouse with fitness center, tennis and shuffleboard courts, all within a quaint, established neighborhood with tree-lined walkways. Ideally located just minutes from Ward Park, Winter Park Pines Golf Club, YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy easy access to shopping and dining along Aloma Avenue including Publix, Sprouts, and Aldi, as well as being less than 10 minutes from Park Avenue’s renowned restaurants and boutiques. Conveniently located near SR 436 with quick access to 417 and 408, and approximately 25 minutes to Orlando International Airport. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss your opportunity to own in one of Winter Park’s most desirable communities—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Amy Turner (407-803-3885)
2500 LEE RD #232, WINTER PARK, FL 32789
$164,90040 Days on yellowkey MLS ID: O6404916
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 645 Built: 1969Monthly Fee: $292 Tax: $2,216 (2025)Community: Lakeside Manor Apts CondoCondo
Taxes:$2,216
Remarks: LAKEFRONT living just steps from the shore of 239-acre, spring-fed Lake Killarney! Welcome to Lakeside Manor and this charming second-floor end-unit condo offering partial lake views, private lake access, and an ideal blend of comfort and convenience. This 1-bedroom, 1-bath unit features a bright and inviting layout with luxury vinyl plank flooring throughout the main living areas, complemented by granite countertops and a stylish backsplash in the kitchen. Pella energy-efficient windows fill the space with natural light while helping maintain efficiency. Additional highlights include a new HVAC system (11/2025) and an A/C closet providing extra storage. Residents enjoy a variety of amenities designed to enhance the lakefront lifestyle, including a pool and clubhouse overlooking the water, private boat ramp, boat slips (first-come, currently $35/month), guest parking, community laundry facility, and an outdoor grill and picnic area. A beautifully maintained central courtyard offers a peaceful, park-like setting right outside your door, with a laundry room conveniently located nearby. Low HOA fees add to the value, making this property even more attractive. Ideally located with quick access to I-4 and 17-92, and just minutes from Winter Park Village, Park Avenue dining and shopping, Rollins College, UCF, Valencia College Downtown Campus, and Downtown Orlando, this condo offers both tranquility and accessibility. Enjoy lakefront living in one of Winter Park’s most convenient locations—an excellent opportunity for a primary residence, second home, or investment.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Wendy Rodriguez (407-234-9696)
205 LEWFIELD CIR #205, WINTER PARK, FL 32792
$220,000154 Days on yellowkey MLS ID: S5141588
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973 Tax: $796 (2024)Community: Stratford A Winter Park CondoCondo
Taxes:$796
Remarks: MOTIVATED SELLER! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a BBQ with family and friends at the community clubhouse or enjoy shopping at the many neighborhood retail and grocery outlets nearby. The quaint restaurants, coffee houses, golf courses, and farmers markets of Winter Park and Baldwin Park are within biking distance. There is always something to see and do at this prime location. Recent upgrades include: new electric panel (2024), new washer/dryer in unit (2024), new dishwasher (2023), refrigerator (2020).
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eimi Moreno Carrera (321-945-6195)
2500 LEE RD #208, WINTER PARK, FL 32789
$175,000430 Days on yellowkey MLS ID: O6297570
REDUCED by $5,000 (2.8%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $432 Tax: $1,519 (2025)Community: Lakeside Manor Apts CondoCondo
Taxes:$1,519
Remarks: This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Debbie Jones (407-619-1850)
1500 GAY RD #5, WINTER PARK, FL 32789
$170,000130 Days on yellowkey MLS ID: S5143213
0 Days Off yellowkey (back on 5/13/2026)
REDUCED by $15,000 (8.1%) on 04/29/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 732 Built: 1972 Tax: $2,098 (2024)Community: Chateaux Du LacCondo
Taxes:$2,098
Remarks: Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features laminate flooring throughout, creating a modern and cohesive living space. The unit is ideally located close to shopping, dining, and everyday conveniences, making daily living easy and enjoyable. With lake access just steps away, you can take in the serene waterfront setting while still being minutes from everything Winter Park has to offer. Lawn care is included, ensuring a well-maintained and picturesque community year-round. Don’t miss this opportunity to enjoy lakefront living with resort-style amenities in one of Central Florida’s most desirable areas.
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792
$109,900233 Days on yellowkey MLS ID: O6355536
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 785 Built: 1974Monthly Fee: $2,097 Tax: $1,271 (2024)Community: Winter Park Woods CondoCondo
Taxes:$1,271
Remarks: This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Omar Rodriguez (321-442-2001)
1745 INDIANA AVE #J, WINTER PARK, FL 32789
$524,00042 Days on yellowkey MLS ID: O6402920
1 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 2008Monthly Fee: $464 Tax: $6,444 (2025)Community: La Casas De IndianaCondo
Taxes:$6,444
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Well-maintained townhome in Winter Park, ideally located near Park Avenue’s shops, restaurants, and everyday conveniences. The home features a bright, open floor plan with new luxury vinyl plank flooring throughout the main level. The kitchen has been updated with white cabinetry and newer appliances, offering a functional layout that flows seamlessly into the living and dining areas—well-suited for both daily living and entertaining. Upstairs, the bedrooms provide comfortable space with a practical and efficient layout. The primary bedroom includes an ensuite bathroom and a walk-in closet with built-in storage. The HOA covers roof, exterior maintenance, and landscaping, offering a low-maintenance ownership experience. Enjoy a fenced and enclosed back patio, creating a private outdoor setting ideal for entertaining, dining, or relaxing. In addition, the rear alley access offers a tucked-away, low-traffic environment with added flexibility and privacy. Additional features include a two-car garage and a central location with convenient access to major roadways, shopping, and dining.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Tala Nijmeh (901-417-3534)
2500 LEE RD #202, WINTER PARK, FL 32789
$224,999494 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
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)
1809 HAMMERLIN AVE, WINTER PARK, FL 32789
$549,000152 Days on yellowkey MLS ID: O6373616
REDUCED by $36,000 (6.2%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1818 Built: 2006 Tax: $5,826 (2024)Community: Terazzo Del Sol Condo Assn IncCondo
Taxes:$5,826
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Highly coveted Winter Park! 40+ Pictures! This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is effortless in the expansive kitchen featuring granite countertops, premium wood cabinetry, stainless steel appliances, and a generously sized pantry. A half bathroom and utility closet complete the ground floor, where ceilings soar to a height of 9'3". Ascend to the upper level to discover the luxurious master bedroom suite, boasting French doors leading to a balcony, a spacious walk-in closet, and a lavish ensuite bath featuring dual sinks, a glass-enclosed shower, and a relaxing garden tub. Two additional bedrooms await upstairs, both sharing access to a covered porch perfect for savoring your morning coffee. The second full bathroom and laundry closet round out the upstairs layout, with one of the bedrooms boasting its own walk-in closet. New 2026 Updates to include New Roof Feb 2026, Carpet, New main DBL pane windows, complete interior paint, light fixtures/fans. You will appreciate the convenience of an attached 2-car garage designed for SUVs, two covered entries, adorned with mature trees. Solid build quality utilizing concrete block construction on both floors. Located just a short stroll from the vibrant East End Market and various shopping, this residence also offers easy access to upscale Park Avenue, Rollins College, Baldwin Park, Florida Hospital, and the serene beauty of Leu Gardens. Zoned for Audubon and Winter Park HS, this home truly has it all!
Listing is courtesy of: NICOLE-HUDSON REALTY CORP (407-491-5488)
Listing Agent: Edward Rice, Jr (407-353-0331)
100 S INTERLACHEN AVE #101, WINTER PARK, FL 32789
$1,299,000116 Days on yellowkey MLS ID: O6382597
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1734 Built: 1971 Tax: $9,362 (2025)Community: Cloisters CondoCondo
Taxes:$9,362
Remarks: On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an award-winning luxury homebuilder, the residence features updated flooring, kitchen, baths, lighting and laundry. Wood flooring flows through the foyer, dining and living areas, while ceramic tile is installed in the bedrooms, and decorative tile in the baths. The kitchen is appointed with high-end appliances and custom solid wood cabinetry, designed for daily living and entertaining. The primary suite offers abundant natural light, a built-in closet and an en-suite bath with dual sinks, walk-in shower and a window providing natural illumination. A hall bath includes a tub-shower combination and additional storage. A sunroom off the third bedroom provides flexible space for a private office, den or reading room. The residence includes one assigned covered carport space and a dedicated climate-controlled storage unit on site. Two blocks from Park Avenue, residents enjoy convenient access to dining, shopping and cultural amenities in a lakefront community setting. The property presents an opportunity for full-time living, luxury downsizing or a lock-and-leave lifestyle in the heart of Winter Park.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Drew Henner (407-406-0662)
7484 CANFORD CT #8, WINTER PARK, FL 32792
$250,00049 Days on yellowkey MLS ID: O6402492
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1578 Built: 1974 Tax: $2,121 (2025)Community: Whisperwood CondoCondo
Taxes:$2,121
Elementary School: Cheney Elem
Remarks: This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer stainless steel appliances, and a closet pantry. There is a separate dining room that opens onto a very private brick paver patio with a new privacy fence. This unique condo features a flexible layout, an inside utility, and includes the washer & dryer. Modern-design porcelain tile flooring. The home has a large screen porch, which is considered by many in Florida, to be extra living space. There is also a front courtyard that is perfect for a raised bed garden or ???. Highly desired Winter Park schools. A 2-car carport with an ample lockable storage closet. New roof in 2020 and an updated electric system. The complex has a private community pool
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Greg Harrison (407-276-6141)
259 E CANTON AVE #259, WINTER PARK, FL 32789
$619,00097 Days on yellowkey MLS ID: O6389246
1 Days Off yellowkey (back on 4/25/2026)
REDUCED by $10,000 (1.6%) on 04/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1040 Built: 1971 Tax: $3,603 (2025)Community: Village Winterset IncCondo
Taxes:$3,603
Remarks: Under contract-accepting backup offers. Experience elevated living in this rare fifth-floor corner residence, perfectly positioned just one block from the iconic Park Avenue in the heart of Winter Park. With sweeping views of the downtown skyline and abundant natural light from multiple exposures, this residence offers an exceptional blend of comfort, elegance, and location. The thoughtfully updated kitchen features custom shaker cabinetry, granite countertops, and stainless-steel appliances, seamlessly connecting to the spacious living and dining areas. A charming sunroom provides the perfect setting for morning coffee, reading, or enjoying the city views. The generously sized primary suite offers a peaceful retreat, complete with an updated bath and a large walk-in closet with custom built-ins. The second bedroom has been thoughtfully opened to create a stylish office or den, ideal for working from home or relaxing with guests. Refined interior details include crown molding, bamboo flooring, and abundant natural light throughout, creating a warm and sophisticated atmosphere. Residents enjoy the security and convenience of a well-maintained mid-rise building featuring secure key entry, guest call box access, and a welcoming lobby. Perfectly suited for a lock-and-leave lifestyle, this residence is just steps from Park Avenue’s boutiques, acclaimed restaurants, museums, cafés, and the Winter Park Golf Course. Additional features include: • Private storage unit • Covered carport parking space • Guest parking and community pool. An exceptional opportunity to enjoy refined living in one of Central Florida’s most desirable locations. Please note: NO RENTALS, NO PETS.
291 LEWFIELD CIR #291, WINTER PARK, FL 32792
$144,000119 Days on yellowkey MLS ID: O6382547
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 678 Built: 1973Monthly Fee: $350 Tax: $1,942 (2025)Community: Stratford Winter ParkCondo
Taxes:$1,942
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water heater, freshly painted interior, new screened porch, and new toilet — giving you move-in-ready comfort and peace of mind. The kitchen comes fully equipped with range, dishwasher, refrigerator, and microwave. A stackable washer and dryer are conveniently located in the bedroom, and an additional community laundry room with two washers and dryers is available free of charge. Stratford residents enjoy an amenity-rich lifestyle including: • Two sparkling pools • Tennis courts • 24/7 fitness center • Clubhouse available for private gatherings • Pet station *Planned social events for residents. The HOA adds tremendous value by covering water, trash removal, internet, pest control, exterior maintenance, grounds care, and common areas — simplifying ownership and monthly budgeting. Located in a prime Winter Park area with easy access to 408, Semoran Blvd., 417, I-4, and State Road 50. Just minutes from shopping, dining, grocery stores, and within 20 minutes of UCF, Full Sail University, Rollins College, and Park Avenue. With its thoughtful updates, first-floor convenience, and exceptional community amenities, this condo offers more than just a home — it delivers an above-average lifestyle in one of Central Florida’s most desirable locations.
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Barbara Coy (407-497-1777)
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