Location: Winter Park , 32792
Do Not Show Listings
3949 COOL WATER CT, WINTER PARK, FL 32792
$399,9007 Days on yellowkey MLS ID: O6415880
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 1994Monthly Fee: $28 Tax: $2,894 (2025)Community: Oxford CoveSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,894
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Located on a quiet cul-de-sac in Winter Park, this home has the kind of layout and lot that are hard to find at this price point. Vaulted ceilings open up the main living area, and built-in display niches along the wall give the space character you won't find in newer construction. The kitchen has a breakfast bar peninsula and connects to a sunny dining space with a pendant light overhead. The primary suite is generously sized with two windows, a ceiling fan, walk-in closet, and a private bath with a double vanity and soaking tub. A second full bath features detailed tile work and a vanity with granite-look countertops. Additional bedrooms have ceiling fans and solid closet space. Out back is a large covered patio that opens to a fenced yard shaded by mature oak trees, the kind of backyard that actually works for people who want to spend time outside in Florida. There's room to run, entertain, or just let the week decompress. All of this in Winter Park, minutes from Park Avenue dining and shopping, Rollins College, Winter Park Village, and with quick access to I-4 and downtown Orlando.
Listing is courtesy of: ACME REAL ESTATE FLORIDA LLC (407-601-4958)
Listing Agent: Regan Jackson (407-421-1420)
7327 FOREST HILL CT #223, WINTER PARK, FL 32792
$180,00044 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
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
$178,900553 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
High School: Winter Park High
Tax Year: 2023
Middle School: Glenridge Middle
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
$265,00084 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
Tax Year: 2024
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)
2220 FAIRGLENN WAY, WINTER PARK, FL 32792
$629,90061 Days on yellowkey MLS ID: O6399993
REDUCED by $20,000 (3.1%) on 06/08/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2636 Built: 1986Monthly Fee: $53 Tax: $3,357 (2025)Community: Quail RunSingle Family
Taxes:$3,357
Elementary School: Red Bug Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: WOW - Price Reduction!!! Experience the perfect blend of classic elegance and modern comfort in this spacious pool home. From the moment you step inside, the open spindle staircase sets a sophisticated tone that carries throughout the residence. In the Heart of the home is an upscale Kitchen equipped with solid wood cabinetry, sleek granite countertops, and a convenient breakfast bar for your morning breakfast or casual dining. Move freely from inside to outside through 3 sets of sliding glass doors in the kitchen, dining room and great room. Just walk out anytime to the massive brick paver patio and enjoy one of the two covered patio areas. The outside is Entertainment ready as the expansive brick pavers wrap around the pool, creating a seamless environment perfect for hosting summer parties or quiet evening dips. On the cool days you can retreat to the family room to enjoy the warmth of the wood-burning fireplace. The primary Suite is a true getaway featuring direct pool access via private sliders, a generous walk-in closet, and a spa-like bath. Indulge in the soaking tub or the walk-in shower with double shower heads. Includes double vanities and ample storage for a clutter-free environment. The upper level will allow family and guests to feel right at home with three spacious bedrooms and a dedicated full bathroom upstairs. You can also rest easy knowing that the Roof was installed in 2018, the Hot Water Heater was installed in 2018, and the HVAC system was installed in 2019. An oversized 2-car garage offers room for a workbench and "toys" plus an inside laundry room and convenient half-bath are located close by. This prime location is ideally situated near A/B-rated schools, UCF, and Oviedo Hospital. Enjoy easy access to the 417 and Aloma Ave with plenty of shopping, Winter Park’s nightlife and the Tuscawilla Country Club just minutes from your front door. If this sounds like YOUR Dream home, please come see it today!
Listing is courtesy of: ELLIS GROUP REALTY, LLC (407-960-4545)
Listing Agent: Jay Lacourt (386-313-5008)
2715 PRINCE JOHN RD, WINTER PARK, FL 32792
$519,9009 Days on yellowkey MLS ID: O6415084
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1565 Built: 1963 Tax: $7,101 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$7,101
Elementary School: Brookshire Elem
Remarks: GREAT HOME & GREAT VALUE — add your TLC and DIY and you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All dimensions must be independently verified by the buyer.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
3440 ALLSTON LN, WINTER PARK, FL 32792
$405,00052 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
Elementary School: Eastbrook Elementary
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)
1871 CASSELWOOD ST, WINTER PARK, FL 32792
$419,90046 Days on yellowkey MLS ID: O6404306
0 Days Off yellowkey (back on 5/26/2026)
REDUCED by $5,000 (1.2%) on 05/12/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 1988Monthly Fee: $39 Tax: $1,223 (2024)Community: Villas Of Casselberry Ph 2Townhouse
Taxes:$1,223
Remarks: Under contract-accepting backup offers. BRAND NEW ROOF 2026. Beautifully updated and move-in ready home in Winter Park featuring a BRAND NEW 2026 A/C system and Brand new 2026 water heater to be installed before closing. This 4-bedroom, 2.5-bath home with a 2-car garage offers waterproof luxury vinyl flooring, recessed lighting, updated fixtures, fireplace, screened patio, and a bright, functional layout filled with natural light. The upgraded kitchen and bathrooms are a must-see. The fully renovated kitchen features custom green cabinetry, quartz countertops, farmhouse sink, gold hardware, pantry, and new stainless steel appliances. The oversized primary suite includes a spa-style bathroom with soaking tub, double vanity, rainfall shower, and dual closets. Located in a community with a community pool and low HOA of only $39 x month. Conveniently located near Downtown Winter Park, Park Avenue, Rollins College, AdventHealth Winter Park, major highways, shopping, dining, and entertainment. Easy access to Downtown Orlando, Baldwin Park, Full Sail University, and Orlando International Airport makes this location ideal for both convenience and lifestyle.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
2454 BROOKSHIRE AVE, WINTER PARK, FL 32792
$1,399,000111 Days on yellowkey MLS ID: O6384924
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2509 Built: 2023 Tax: $11,586 (2024)Community: Brookshire Heights 1St AddSingle Family
Taxes:$11,586
Remarks: One or more photo(s) has been virtually staged. Welcome to this aesthetic custom luxury home in an unbeatable Winter Park location.From the moment you arrive, the custom landscaping and automated lighting make a statement, day or night.At the center of the home, the chef's kitchen is both a showpiece and a performance space. A commanding 48-inch Z-Line gas range with 8 Italian-made brass burners anchors the room, complemented by Café luxury appliances, a stainless steel refrigerator, quartz countertops, and custom cabinetry. The walk-in pantry with floating shelves and under-shelf lighting adds both beauty and function. An indoor wine bar with built-in cabinetry and wine refrigerator enhances the entertaining experience, while an upstairs beverage station keeps every level equally equipped.The primary suite is a full spa experience. The glass enclosed shower features a rain head, body jets, and handheld fixtures. A soaking tub, dual vanities with quartz counters, and a generously proportioned walk-in closet complete the retreat. Imported aged brass designer light fixtures are included in the sale. Philips Hue smart lighting synchronizes every indoor and outdoor light in one app, and a smart security camera system with fingerprint keypad entry completes the tech package. The outdoor living experience rivals the interior. A covered lanai with a fully equipped summer kitchen, including a built-in grill, dedicated refrigerator, and generous prep space, flows into a landscaped courtyard designed with an Italian villa, Mediterranean feel. As evening falls, intentional landscape lighting transforms the grounds into an intimate setting perfect for al fresco dinners, fireside gatherings, or projecting the big game under the stars. Walk to pickleball courts, athletic fields, and a premier wellness facility. Park Avenue's celebrated boutiques and dining are just minutes away. New construction of this caliber is increasingly rare in Winter Park. Schedule your private showing today. The furniture and décor, curated by a professional design team, are negotiable, making it possible to move in with the full look already in place.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Norma Gonsalves (407-451-9533)
1354 TIERRA CIR, WINTER PARK, FL 32792
$425,000520 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
Elementary School: English Estates Elementary
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)
2054 EASTBROOK BLVD, WINTER PARK, FL 32792
$500,00015 Days on yellowkey MLS ID: V4949389
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2031 Built: 1966 Tax: $5,054 (2025)Community: Eastbrook Sub Unit 8Single Family
Taxes:$5,054
Remarks: Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Melissa Stalzer (386-405-3457)
505 CORNWALL RD, WINTER PARK, FL 32792
$675,00028 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 is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Amy Turner (407-803-3885)
7471 CANFORD CT #19, WINTER PARK, FL 32792
$199,000251 Days on yellowkey MLS ID: G5103114
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1393 Built: 1974 Tax: $2,750 (2024)Community: Whisperwood CondoCondo
Taxes:$2,750
Elementary School: Cheney Elem
Remarks: This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were professionally serviced, including roller replacement, track repairs, and installation of new locks to ensure smooth, secure operation. Deluxe vinyl fencing was installed throughout the community by the HOA replacing the older wooden fencing. The fencing was replaced with the vinyl after the listing photos were taken, please view the video to see the replacement vinyl fencing. Enjoy convenient features including an in-unit washer and dryer combo, storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens to a large screened-in balcony. Ideally located just 15 minutes or less to UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes to Orlando International Airport. Whether you’re a first-time home buyer, student, investor, or looking to make your move into Winter Park, this home offers affordability, convenience, and plenty of potential!
Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)
Listing Agent: Karen Salter (352-227-0451)
1082 WILDMEADOW RUN, WINTER PARK, FL 32792
$650,00027 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
$638,900103 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
$710,00083 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)
1923 LINDEN RD, WINTER PARK, FL 32792
$450,00079 Days on yellowkey MLS ID: O6393643
REDUCED by $25,000 (5.3%) on 05/19/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2117 Built: 1955 Tax: $340 (2024)Community: Tanglewood Sec 4Single Family
Taxes:$340
Remarks: ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Milton James (407-572-4458)
2808 BRIGHT BIRD LN, WINTER PARK, FL 32792
$399,00018 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
$199,00040 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
$465,000242 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)
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