Location: Winter Park , 32792
Do Not Show Listings
1944 NATALEN RD, WINTER PARK, FL 32792
$519,00029 Days on yellowkey MLS ID: O6405802
0 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1380 Built: 1957 Tax: $7,067 (2025)Community: Kenilworth Shores Sec 07Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,067
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Located in the highly desirable Winter Park area, 1944 Natalen Rd offers the perfect balance of tranquility, convenience, and lifestyle. This property enjoys deeded access to serene Lake Berry while being just minutes from top-rated schools, the vibrant dining and boutique shopping of both Baldwin Park and downtown Winter Park, and everyday conveniences including nearby grocery stores and the renowned Winter Park Farmers’ Market. Residents will appreciate exceptional healthcare access with both AdventHealth Winter Park and the Orlando VA Medical Center at Lake Baldwin close by. Centrally located with easy access to UCF, Orlando International Airport, and Central Florida’s world-famous theme parks and attractions, this home provides an ideal combination of peaceful living and connectivity to everything Orlando has to offer.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Trevor Thomas (407-337-8738)
1511 GLADIOLAS DR, WINTER PARK, FL 32792
$470,00022 Days on yellowkey MLS ID: O6412441
1 Days Off yellowkey (back on 6/11/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1594 Built: 1979 Tax: $2,543 (2025)Community: Garden Lake Estates Unit 1Single Family
Taxes:$2,543
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated 4 bedroom, 2 bathroom pool home in the heart of Winter Park, where modern upgrades, comfortable living spaces, and exceptional outdoor amenities come together to create the perfect place to call home. Thoughtfully renovated and move in ready, this home offers the ideal blend of style, functionality, and Florida living. The heart of the home is the stunning kitchen, completely remodeled in 2024 with approximately $60,000 in improvements. Featuring white shaker cabinetry, quartz countertops, stainless steel appliances, a spacious center island, and abundant storage, this space was designed for both everyday living and entertaining. Luxury vinyl plank (LVP) flooring installed in 2024 flows throughout the home, complementing the open layout, vaulted ceilings, and abundant natural light. The spacious primary suite provides a relaxing retreat, while three additional bedrooms offer flexibility for family, guests, a home office, or hobbies. Recent improvements continue throughout the home, including a beautifully renovated guest bathroom completed in 2025, a custom closet system added in 2024, and a roof replaced in 2021, giving buyers added confidence and peace of mind. Step outside and discover your own private backyard oasis. The screened lanai overlooks a sparkling pool, expansive patio area, fire pit, and outdoor kitchen, creating the perfect setting for weekend gatherings, summer cookouts, or relaxing evenings at home. The irrigation system operates from a private well, helping maintain the lush landscaping while keeping water costs down. Located in an established Winter Park neighborhood known for its excellent schools and convenient access to shopping, dining, parks, and major roadways, this home offers easy access to everything Central Florida has to offer. With extensive updates, a desirable floor plan, and incredible indoor and outdoor living spaces, 1511 Gladiolas Drive presents a rare opportunity to own a truly move in ready home in one of Winter Park's most desirable locations. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Richard Aybar (407-601-8109)
2465 BANCHORY RD, WINTER PARK, FL 32792
$1,295,00053 Days on yellowkey MLS ID: O6403997
3 Days Off yellowkey (back on 6/11/2026)
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3971 Built: 2007 Tax: $8,540 (2025)Community: Brookshire Heights 1St AddSpa: NoSingle Family
Taxes:$8,540
Remarks: Under contract-accepting backup offers. Built for long-term ownership rather than short-term resale, this custom-built Brookshire Heights residence offers a rare combination of thoughtful design, exceptional construction quality, and nearly 4,000 square feet of living space in one of Winter Park's most beloved neighborhoods. Unlike many homes that have been renovated or recently built for resale, 2465 Banchory Road was designed from the ground up with intention, combining timeless architecture, functional luxury, and quality craftsmanship throughout. Set on one of the most beautiful streets in Winter Park, where evening walks feel like something out of a storybook and the Cady Way Trail is just steps from your front door, this home offers the lifestyle buyers dream about and the quality they rarely find. A grand mahogany front door welcomes you inside, where soaring ceilings, oversized interior and exterior doors, and spacious living areas create a sense of elegance and comfort from the moment you enter. The thoughtfully designed floor plan offers nearly 4,000 square feet of living space, including four bedrooms, four full en-suite bathrooms, and a dedicated pool bath. One of the home's most unique features is its dual primary suites, with one located on the first floor and another upstairs. This flexible layout is ideal for multigenerational living, long-term guests, private retreats, or evolving lifestyle needs. Two additional bedrooms each feature their own private en-suite bathroom, while a generous upstairs flex space offers endless possibilities as a media room, playroom, home office, gym, or potential fifth bedroom. The kitchen was designed for both everyday living and entertaining, featuring premium cabinetry, a gas cooktop, double ovens, a built-in coffee system, and a built-in steamer. Every detail was selected to combine beauty, functionality, and convenience. Step outside to a resort-style backyard where the pool becomes the centerpiece of outdoor living. The dark pebble finish, sun shelf with bubblers, color lighting, natural gas heater, automated controls, and expansive outdoor entertaining space create an experience that feels more like a private resort than a backyard. Beyond what you can see, the home's construction quality truly sets it apart. Dual 19-SEER HVAC systems with independent WiFi controls, natural gas service, insulated floor systems between levels, a whole-home instant hot water system, insulated low-E windows, and a hurricane-rated insulated garage door reflect the level of planning and investment rarely found in today's market. These are the kinds of features that enhance comfort, efficiency, and long-term value for years to come. Perfectly positioned for the Winter Park lifestyle, you'll enjoy easy access to Cady Way Park, tennis and pickleball courts, playgrounds, Park Avenue's boutiques and dining, Rollins College, Full Sail University, UCF, AdventHealth Winter Park, and Orlando International Airport. Zoned for top-rated Winter Park schools. This is more than a beautiful home. It is a true custom residence built with intention, designed for living well, and positioned in one of Winter Park's most desirable neighborhoods.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Melissa Johnson (407-681-4393)
2384 SUN VALLEY CIR, WINTER PARK, FL 32792
$269,900120 Days on yellowkey MLS ID: O6386755
REDUCED by $5,000 (1.8%) on 04/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1311 Built: 1983 Tax: $688 (2024)Community: Cedarwood Village 1Condo
Taxes:$688
Elementary School: English Estates Elementary
Tax Year: 2024
Remarks: Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit condo located within the quaint community of Cedarwood Village with a desirable Winter Park address! This light and bright home features vaulted ceilings in the living room, creating an open and airy feel. The kitchen offers an eat-in space, stainless steel appliances, a convenient pass through to the living room, and a laundry closet with washer and dryer included. Enjoy seamless indoor-outdoor living with sliding glass doors leading to a private rear screened-in lanai, plus an additional front patio just off the kitchen. Recent upgrades include new luxury vinyl flooring, a new roof (2023), new A/C ducts and insulation (2023), and full re-plumbing (2021), providing peace of mind for years to come. Two reserved parking spaces are located directly in front of the condo for added convenience. Community amenities include a pool, tennis court, and clubhouse. Ideally located near shopping and dining, Rollins College, Full Sail University, UCF, and major thoroughfares for easy commuting. This move-in ready condo offers comfort, convenience, and value in an unbeatable location!
Listing is courtesy of: URBANISTA BROKERS (407-619-7272)
Listing Agent: Anna Lohr (321-277-4797)
1914 BONANZA CT, WINTER PARK, FL 32792
$429,99946 Days on yellowkey MLS ID: O6408461
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1727 Built: 1968 Tax: $4,497 (2025)Community: Eastbrook Sub Unit 13Single Family
Taxes:$4,497
Elementary School: Eastbrook Elementary
Remarks: Welcome to your winter Park retreat! Step into this beautifully renovated 3 bedroom, 2 bathroom home where modern meets timeless comfort. Designed with an open floor plan, the living space flows seamlessly, making it perfect for both entertaining and everyday living. The brand new kitchen shines with contemporary finishes, while the new flooring throughout the home adds warmth and style. Both bathrooms have been thoughtfully renovated, offering a clean and modern feel. The Florida room, wrapped in huge windows. floods the home with natural light, creating a bright and inviting space you'll love year round. Step outside to enjoy a covered patio, ideal for morning coffee or relaxing evenings with friends and family. With its prime location, this home is a blend of convenience, charm, and modern living ready for you to make it your own. Call and schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Judy Julien, Pa (407-234-4051)
7327 FOREST HILL CT #223, WINTER PARK, FL 32792
$180,00057 Days on yellowkey MLS ID: O6403841
REDUCED by $5,000 (2.7%) on 06/11/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1984Monthly Fee: $450 Tax: $2,597 (2025)Community: Hidden Oaks Condo Ph 12Condo
Taxes:$2,597
Elementary School: None
High School: None
Middle School: None
Remarks: Looking for the perfect starter home or great little rental. This townhhouse-style condo with 2 master suites. With granite countertop on kitchen. Open floor plan, inside laundry closet off the dinette. Tile flooring downstairs and carpet up, additional exterior storage room and fenced in patio. garbage. Hidden Oaks community features community pool & fenced playground area. Zoned for Winter Park Schools. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes to Orlando International Airport, 10 minutes to shopping and dining, 15 minutes to Valencia College, 25 minutes to UCF, 30 minutes to Disney World. Easy access to FL-408 & FL-417.
Listing is courtesy of: M L VAZ REALTY INC (407-380-9397)
Listing Agent: Leda Vaz (407-509-7947)
2923 ANTIQUE OAKS CIR #37, WINTER PARK, FL 32792
$178,900566 Days on yellowkey MLS ID: A4632112
3 Days Off yellowkey (back on 6/10/2026)
REDUCED by $3,500 (1.9%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1984Monthly Fee: $442 Tax: $2,648 (2023)Community: Parkview VillageCondo
Taxes:$2,648
Elementary School: Aloma Elem
Tax Year: 2023
Remarks: Attention Students & Parents! Updated First-Floor Corner Condo directly across the street from the Full Sail campus! Why rent when you can buy! 2 Bed | 2 Bath | 1,105 Sq. Ft., an updated first-floor northwest corner condo. -Brand-New Kitchen Appliances: Convection oven, refrigerator, dishwasher, and microwave -Interior Laundry Room with new LG stackable washer & dryer -New Air Conditioning System -Updated Kitchen Cabinets -Updated Plumbing & Electrical -New Ceiling Fans Throughout -Fresh Interior Paint -New Carpet in Bedrooms Community Features: Private screened patio Community pool and hot tub Beautifully maintained grounds Pet-friendly and fenced dog park Winter Park School District, zoned for A-rated schools, approximately 1 mile away.
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
2401 SUN VALLEY CIR #2401, WINTER PARK, FL 32792
$265,00097 Days on yellowkey MLS ID: S5146437
0 Days Off yellowkey (back on 6/10/2026)
REDUCED by $20,000 (7.0%) on 04/21/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1495 Built: 1984 Tax: $3,702 (2024)Community: Cedarwood Village 1Condo
Taxes:$3,702
Remarks: Under contract-accepting backup offers. Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and unwind on the private back porch—an ideal outdoor sitting space. The kitchen features a pantry and cozy breakfast nook. The spacious primary suite includes a walk-in closet, updated bathroom, and direct access to the back patio. The second bedroom also offers new flooring and its own walk-in closet, making it perfect for guests or additional living space. With its inviting design and unbeatable location, this condo is a must-see—schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (407-846-0940)
Listing Agent: Jamie Bollinger (407-908-1890)
3440 ALLSTON LN, WINTER PARK, FL 32792
$405,00065 Days on yellowkey MLS ID: O6401731
REDUCED by $15,000 (3.6%) on 05/26/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1533 Built: 1993Monthly Fee: $65 Tax: $1,364 (2024)Community: Villas Of Casselberry Ph 4Single Family
Taxes:$1,364
Remarks: Exceptional Single-Family Home in Winter Park, FL This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC system (2023), new water heater (2026), providing peace of mind for years to come. Enjoy Florida living at its finest on the private screened patio - perfect for relaxing or entertaining. Ideally situated 25 minutes from Downtown Orlando, 30 min from OIA, and 40 min from world-class attractions, this home is also just 6 minutes from Full Sail University, 12 minutes from the prominent Rollins College, and 19 minutes from UCF - making it an ideal choice for families and investors alike. A true must-see - schedule your showing today.
Listing is courtesy of: EXIT GLOBAL REALTY (407-725-7180)
Listing Agent: Hugo Hernandez (407-716-5594)
1354 TIERRA CIR, WINTER PARK, FL 32792
$425,000533 Days on yellowkey MLS ID: O6271121
0 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1827 Built: 1969Monthly Fee: $2 Tax: $3,812 (2023)Community: Casa AlomaSingle Family
Taxes:$3,812
Remarks: Located in the highly sought-after Casa Aloma community, this charming 1960s home offers the perfect blend of comfort, style, and convenience. Situated within a one-mile radius of all that Winter Park has to offer, this well-maintained home truly stands out in terms of location, location, location! The open floor plan is ideal for entertaining, with a spacious living room providing ample space for the whole family. The kitchen is a chef's dream, featuring stainless steel appliances, a gas stove, and a kitchen island that serves as a perfect spot for casual meals or as a serving area for family gatherings. A formal sitting room or secondary living area is conveniently located just off the kitchen, with sliding doors leading to the screened patio. The screened-in patio is perfect for unwinding after a long day, offering a relaxing space to enjoy Florida's rainy evenings. Don't forget to check out the built-in gas grill—great for outdoor cooking! The formal dining room provides an elegant space for holiday dinners or dinner parties throughout the year, with sliders leading to the patio for easy access to outdoor dining. The abundance of windows and sliders throughout the home ensures a bright, airy feel, while also showcasing the large backyard. The master bedroom is a standout feature, offering generous space and excellent closet storage. The recently updated master bath includes new flooring and a modern shower. In addition to the master suite, there are three more spacious bedrooms and a fully updated hall bath. Additional features and upgrades include Gas water heater roughly (2018) Fencing (2016) Windows and sliders (2016) Roof (2011). The backyard has a huge avocado tree as well for you lovers of avocado! This home is just minutes from shopping, top-rated schools, parks, and entertainment, including the iconic Park Avenue and Maitland shopping areas. Winter Park offers everything you need, and this home is the perfect place to enjoy it all. Don’t miss out—this move-in-ready gem is waiting for you! Schedule your showing today and make this beautiful home yours!
Listing is courtesy of: REAL ESTATE FIRM OF ORLANDO (407-581-5550)
Listing Agent: Carl Mataushek (321-229-8084)
505 CORNWALL RD, WINTER PARK, FL 32792
$675,00041 Days on yellowkey MLS ID: O6408759
1 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1813 Built: 1965 Tax: $7,194 (2025)Community: Winter Park PinesSingle Family
Taxes:$7,194
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated four-bedroom, two-bathroom pool home offering 1,813 square feet of thoughtfully designed living space in one of Winter Park’s most desirable locations. Perfectly positioned on a spacious lot backing up to the scenic Cady Way Trail, this residence seamlessly blends modern updates, timeless charm, and exceptional outdoor living. Inside, the versatile floor plan includes a dedicated den, office, or playroom, ideal for today’s flexible lifestyle needs. Engineered hardwood flooring flows throughout the home and is complemented by recessed lighting, crown molding, plantation shutters, ceiling fans, and elegant French doors that add warmth and character to every space. A spacious laundry/utility room offers additional storage and convenience, complete with a washer and dryer replaced in 2024. The beautifully remodeled kitchen, updated in 2020, serves as the heart of the home and showcases white shaker-style cabinetry, sleek black granite countertops, matte grey stainless steel appliances, a striking herringbone tile backsplash, and a charming exposed wood beam feature that adds architectural interest. A breakfast bar with seating for three creates the perfect gathering space for casual dining and entertaining, while the spacious dining room easily accommodates sit-down meals and larger gatherings. The private primary suite offers a relaxing retreat featuring a shiplap accent wall, ceiling fan, and an updated ensuite bathroom remodeled in 2020 with a single vanity and beautifully tiled shower with a glass partition. The secondary bedrooms are generously sized and share an updated hall bathroom featuring a tiled tub and shower combination along with a contemporary single vanity. Step outside into your own backyard oasis where a screened, heated, salt-generated pool installed in 2022 creates the ultimate setting for year-round enjoyment. The fully fenced backyard, updated in 2022, offers privacy and plenty of room for pets, play, and entertaining while overlooking the picturesque Cady Way Trail. A private gate provides direct access to the trail, allowing for convenient access to Brookshire Elementary and nearby community amenities. Additional exterior highlights include a spacious two-car carport, whole-house generator hookup, and two included storage sheds providing excellent functionality and additional storage space. This exceptional location places you just minutes from some of Central Florida’s most sought-after amenities including the Winter Park Pines Golf Course, the Cady Way Trail, and the popular Cady Way recreational amenities featuring a community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Conveniently located near University of Central Florida, Rollins College, and Full Sail University, this home also offers quick access to AdventHealth Winter Park and the Crosby Wellness Center, both less than five minutes away, while Orlando International Airport is approximately 25 minutes from home. Zoned for top-rated Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this property offers an incredible opportunity to enjoy the very best of Winter Park living. ROOF - 2014 HVAC - 2023 ELECTRICAL - 2021(new panel)
Listing Agent: Amy Turner (407-803-3885)
1082 WILDMEADOW RUN, WINTER PARK, FL 32792
$650,00040 Days on yellowkey MLS ID: O6408825
0 Days Off yellowkey (back on 6/8/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1770 Built: 2021Monthly Fee: $170 Tax: $5,154 (2025)Community: Meadows At Hawks CrestSingle Family
Taxes:$5,154
Remarks: Tucked within the sought-after gated community of Hawk’s Crest, this beautifully appointed residence blends timeless design with effortless everyday living. Showcasing a light and airy open concept floor plan, the home features elegant flooring, crown molding, designer lighting, plantation shutters and custom window treatments, and expansive living spaces filled with natural light. The chef’s kitchen serves as the heart of the home with oversized white-quartz countertops, 42-inch cabinetry, stainless steel appliances, a spacious walk-in pantry, and a large center island ideal for gathering and entertaining. The private owner’s retreat offers peaceful backyard views, a spacious custom-designed walk-in closet and a spa-inspired bath complete with dual vanities, quartz countertops and a glass enclosed shower. The home also features a versatile flex space offering endless possibilities such as a home office, private study, additional bedroom or inviting lounge area. Designed to embrace Florida living, the screened-in covered lanai creates the ideal setting to relax and unwind while overlooking the freshly landscaped backyard and tranquil greenery beyond. Additional enhancements include epoxy garage flooring, custom garage shelving and gutters, adding functionality and convenience. Residents of Hawk’s Crest enjoy access to an impressive collection of resort-style amenities including a clubhouse, fitness center, resort pool, splash pad, playgrounds, dog park, food trucks, a virtual guard-gate and private access to Lake Howell. Ideally near Park Maitland Preschool, Kelly’s Ice Cream, Foxtail Coffee and major roadways, this exceptional home offers a balance of luxury, comfort and convenience.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Harif Hazera Llc (407-953-9098)
1926 NATALEN RD, WINTER PARK, FL 32792
$638,900116 Days on yellowkey MLS ID: O6388308
3 Days Off yellowkey (back on 6/8/2026)
REDUCED by $1,000 (0.2%) on 05/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1469 Built: 1957 Tax: $7,308 (2024)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,308
Remarks: Under contract-accepting backup offers. ***MUST SEE WINTER PARK POOL HOME*** Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen with all the amenities... new stainless-steel GE appliances, elegant quartz countertops, sturdy oversized soft-close shaker cabinets and two large built-in wall pantries. The open living area includes a cozy formal dining room with additional countertop seating, and a picturesque sliding glass door opens to an extra-large 40 x 12 outdoor covered porch that provides additional casual outdoor living space. The spacious primary bedroom has a vaulted ceiling and his/her closets, with private access to the backyard covered porch, and features a fully renovated en-suite bath. The secondary bathroom has been tastefully upgraded, as well. Freshly painted inside and out, this immaculate home has new waterproof LVP flooring throughout, new light fixtures and ceiling fans, and stylish window shade coverings on every window. With an indoor laundry room and a two-car carport, this worry-free home features a new AC unit installed in 2025, a new electrical panel and updated plumbing, and a roof that was replaced in 2018. Setting this home apart is your private outdoor private backyard oasis, showcasing a gorgeous 32 ft long/10 ft deep in- ground pool plus a unique outdoor kitchen . . . perfect for family gatherings or hosting a Bar-b-que pool party . . . and with a generously sized 10’ x 18’ shed with full electric providing additional storage solutions or living options, this fully fenced-in backyard is truly a tranquil outdoor haven. Zoned for excellent Winter Park schools, this home is located four blocks from Winter Park High and less than a mile from Brookshire Elementary and Glenridge Middle. It comes with deeded access to the boat ramp and fishing dock at Lake Berry. Blue Jacket Park and Cady Way Park are just down the street, showcasing great bike trails for walking and jogging. The well-known shopping and restaurants of downtown Park Avenue and Baldwin Park are just minutes away. Rollins College, UCF, Full Sail University, and Winter Pines Golf Course are all close by. And Advent Health/Winter Park Hospital is less than a mile down the street. This is a quiet, family-friendly community known for its tranquility and peaceful living. Don’t miss this opportunity to make this wonderful home your very own. Schedule your showing today.
Listing is courtesy of: JAMIESON PROPERTIES, INC. (407-876-2730)
Listing Agent: Joseph Cosgrove (407-470-0892)
418 GILBERT RD, WINTER PARK, FL 32792
$710,00096 Days on yellowkey MLS ID: O6385950
REDUCED by $9,000 (1.3%) on 06/02/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 1964 Tax: $9,094 (2025)Community: Winter Park Pines Ut 5Single Family
Taxes:$9,094
Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
2808 BRIGHT BIRD LN, WINTER PARK, FL 32792
$399,00031 Days on yellowkey MLS ID: O6410294
0 Days Off yellowkey (back on 6/7/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Monthly Fee: $375 Tax: $6,126 (2025)Community: Grayson SquareTownhouse
Taxes:$6,126
Remarks: Under contract-accepting backup offers. Impeccable 2-story townhome, newly built in 2024 and located in Grayson Square, a Gated Luxury Townhouse Community in enchanting Winter Park, with modern, sophisticated architecture and landscaping. The interior features the high-end Lux Fresh package, complemented by owner upgrades including light dimmers, ceiling fans, and a custom kitchen island. The chef’s kitchen is equipped with new stainless-steel appliances and expansive white stone countertops. Alabaster cabinetry with ceramic tile plus smooth stone counters adds a touch of elegance throughout. Shaw LVP floors on the main level and 2nd level bathrooms. Owner's suite with an oversized walk-in closet and a dual-sink ensuite. Spacious second and third bedrooms. 9' ceilings throughout. The first floor features a stunning open-concept living area with vinyl wood-plank flooring. Laundry closet on 2nd level. Kohler raised commodes on the 2nd level. Private patio area surrounded by lush greenery. Attached garage with 2 extra off-street parking spaces. The home includes a Ring doorbell and a rear security camera. Eeros internet modem and Extender for boosted device connectivity. includes a resort-style pool oasis with a cabana, with a view of the community lake. Competitive HOA fees cover roof replacement, Spectrum internet and TV, and general property upkeep. Situated in a manicured community with a sparkling pool, this home is close to fine dining, shopping, and entertainment, with easy access to downtown Orlando and local theme parks. It is highly rated for its proximity to quality Seminole County public schools and its convenience to daily necessities like Publix and Starbucks, as well as the shopping and dining of Park Avenue.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Sean Flatley (609-208-8204)
4772 TANGERINE AVE #4772, WINTER PARK, FL 32792
$199,00053 Days on yellowkey MLS ID: O6405042
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 1973 Tax: $2,825 (2025)Community: Wrenwood CondoCondo
Taxes:$2,825
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Great opportunity to own this RENOvated and Move-IN ready 2 bedroom 2 bathroom one-story condo in sought after Winter Park location. This Condo has Special Streamlined Approval for Conventional Financing and is eligible for a discounted interest rate!! Whether you’re looking to establish roots, downsize to something simpler or an investment property, this size unit, floor plan and location fits the bill. Enjoy the recently updated kitchen and two bathrooms along with tile flooring. AND all major mechanical updates already taken care of with a New Roof, Updated Electrical, Newer A/C, Replaced Water Heater and so much more... plus the community amenities include a pool, sidewalks, pet stations, and a short distance to restaurants, grocery stores, shopping and biking distance to Full Sail.
Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)
Listing Agent: Lori Hutchinson (321-377-7026)
3312 HEARTWOOD AVE, WINTER PARK, FL 32792
$465,000255 Days on yellowkey MLS ID: O6352582
2 Days Off yellowkey (back on 6/8/2026)
REDUCED by $19,000 (3.9%) on 04/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2878 Built: 1983 Tax: $2,183 (2025)Community: Bel-Aire PinesSpa: NoSingle Family
Taxes:$2,183
Remarks: One or more photo(s) has been virtually staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.
Listing is courtesy of: MID-STATE PROPERTIES PSL LLC (561-843-9537)
Listing Agent: Stacy Morano (561-843-9537)
1052 MANCHESTER CIR, WINTER PARK, FL 32792
$460,000157 Days on yellowkey MLS ID: O6376260
REDUCED by $10,000 (2.1%) on 05/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1703 Built: 1983 Tax: $5,216 (2025)Community: Howell Estates 1St AddSingle Family
Taxes:$5,216
Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!
Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)
Listing Agent: Yuleisy Marquez (407-937-8450)
4768 TANGERINE AVE #4768, WINTER PARK, FL 32792
$179,000126 Days on yellowkey MLS ID: S5144503
REDUCED by $6,000 (3.2%) on 05/20/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1973Monthly Fee: $280 Tax: $1,479 (2024)Community: Wrenwood CondoCondo
Taxes:$1,479
Remarks: Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless appliances. Community was freshly painted and roads repaved in 2025. Prime location near top dining, shopping, and parks. Move-in ready perfection!
Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)
Listing Agent: Christopher Franqui (347-703-7008)
193 LEWFIELD CIR, WINTER PARK, FL 32792
$248,90035 Days on yellowkey MLS ID: O6409075
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1300 Built: 1973Monthly Fee: $533 Tax: $2,286 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$2,286
Remarks: Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of comfortable living space in the Stratford A Winter Park Condo community. This 2-bed townhouse in Winter Park features an open floorplan with a large living and dining area, updated wood-look flooring throughout the main living spaces and bedrooms, recessed lighting, ceiling fans, and sliding glass doors that bring in natural light. The kitchen offers ample cabinet storage, stainless steel appliances, tile flooring, and a functional pass-through breakfast bar that opens to the main living area, creating a seamless layout for everyday living and entertaining. Upstairs, the oversized primary suite includes a walk-in closet, private en-suite bathroom, and generous floor space, while the secondary bedroom also features wood-look flooring, natural light, and easy access to the second full bathroom. Additional highlights include inside laundry, updated lighting fixtures, open parking, and plenty of storage throughout. Residents enjoy access to community amenities including a pool, fitness center, tennis courts, sidewalks, and maintained grounds, with HOA dues covering water, exterior maintenance, recreational facilities, and grounds maintenance. Conveniently located near Howell Branch Rd and SR 436, this Winter Park townhome provides quick access to shopping, dining, Downtown Winter Park, Maitland, Full Sail University, UCF, and Downtown Orlando. Located near highly rated Seminole County schools, parks, restaurants, and everyday conveniences, this property offers low maintenance living in a well-connected Central Florida location.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Efrain Reyes (407-575-4226)
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