Location: Winter Park
Keyword(s): Tuskawilla Middle
Keyword(s) Middle School: Tuskawilla Middle
Do Not Show Listings
1232 VALLEY CREEK RUN, WINTER PARK, FL 32792
$535,00011 Days on yellowkey MLS ID: O6417190
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2071 Built: 1994Monthly Fee: $22 Tax: $2,283 (2025)Community: Lost CreekSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,283
Elementary School: Red Bug Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Welcome to this beautifully maintained pool home in the highly desirable Cross Creek community, where comfort, functionality, and location come together perfectly. This spacious residence features three generously sized bedrooms and a thoughtfully designed floor plan offering both formal and casual living spaces, including a living room, formal dining room, and a large family room that flows seamlessly into the kitchen beneath soaring vaulted ceilings. The private primary suite serves as a true retreat, dual vanities, a relaxing garden tub, and a separate glass-enclosed shower. The secondary bedrooms are well-proportioned and share a convenient Jack-and-Jill bathroom. Step outside and enjoy Florida living year-round from the covered patio overlooking the screened pool enclosure, creating the perfect space for entertaining or unwinding in privacy. Ideally located in Winter Park's Cross Creek community, residents enjoy easy access to top-rated Seminole County schools, abundant shopping and dining options, major commuter routes, and popular recreational destinations including Red Bug Lake Park with its sports fields, playgrounds, walking trails, tennis courts, and family-friendly activities. This is an exceptional opportunity to enjoy the lifestyle and convenience that make Cross Creek one of the area's most sought-after communities.
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: James Clark (407-575-7011)
2222 MARSH SEDGE LN, WINTER PARK, FL 32792
$739,000327 Days on yellowkey MLS ID: O6333145
4 Days Off yellowkey (back on 6/29/2026)
REDUCED by $25,900 (3.4%) on 06/13/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2192 Built: 2019Monthly Fee: $243 Tax: $7,847 (2024)Community: Preserve At Hawks CrestSingle Family
Taxes:$7,847
Elementary School: Eastbrook Elementary
Tax Year: 2024
Remarks: Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage Homes in the gated community of Hawk's Crest in Winter Park, includes numerous upgrades. This is the Pomelo model, equipped with an upgraded kitchen package that includes built-in double ovens and a stainless steel range hood. Beautiful quartz countertops feature an oversized kitchen island with excellent space for family gatherings. Other features include a walk-in pantry and fantastic lighting. The luxurious kitchen integrates with the dining and living areas. The dining area is enhanced by a screened-in deck overlooking a pond. The backyard features a new, large, extended patio for entertaining. The master bedroom has an ensuite bathroom with a double vanity, a small closet, and a large walk-in closet that can be customized for a future owner. The home also comes with new gutters. Other amenities in the Hawk's Crest community include a resort-style pool with a clubhouse, a splash pad, a fitness center, barbecue grills, playgrounds, a dog park, and a community fishing pier with views and access to beautiful Lake Howell. Nearby, you'll find shops, restaurants, and specialty physicians such as Kelly's Ice Cream, Foxtail Coffee, Sobol, Winter Park Pediatric Dentistry, and the Park Maitland Preschool Campus, along with excellent schools in the area. Enjoy a short drive to Downtown Winter Park, with its extensive dining and shopping options. Hawk's Crest is also very close to Rollins College and UCF. Schedule your private tour today!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Carmen Molina (321-331-5679)
5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792
$275,00076 Days on yellowkey MLS ID: O6398856
REDUCED by $5,000 (1.8%) on 06/29/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1008 Built: 1984 Tax: $668 (2024)Community: Lazy Oaks CondoCondo
Taxes:$668
Remarks: Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA. This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an attached garage. The home is ideally located near top-rated schools, shopping, dining, and provides convenient access to major highways. Inside, you’ll find a neutral color palette complemented by ceramic tile and wood laminate flooring throughout. The efficient kitchen boasts gleaming white countertops, rich wood cabinetry, and a large pantry for ample storage. The expansive great room offers flexible space for both dining and living areas, complete with a cozy wood-burning fireplace—perfect for relaxing or entertaining. Sliding glass doors open to a large, screened private lanai, ideal for morning coffee or evening unwinding. The spacious primary suite features an en suite bath with dual sinks, a large vanity, walk-in shower, and a generous closet. A split-bedroom layout provides added privacy, with a secondary bedroom and additional full bath. Additional highlight: HVAC replaced in 2021. Don’t miss this opportunity to make your home in one of Winter Park’s most charming and convenient communities!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Mindy Machock (407-461-1866)
1320 GLADIOLAS DR, WINTER PARK, FL 32792
$475,00031 Days on yellowkey MLS ID: O6412139
REDUCED by $5,000 (1.0%) on 06/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1624 Built: 1983 Tax: $1,380 (2025)Community: Garden Lake Estates Unit 3Single Family
Taxes:$1,380
Remarks: Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has ceramic tile throughout and bamboo flooring in the master bedroom. More updates include Trane A/C system, newer water heater, roof in 2021, and electrical panel in 2017. Also included are a garage door opener that has battery backup for power outages, ring door sensors on all main windows and doors, motion activated lights at night on all 4 sides of home, a water softener, and an I-Flo system on the A/C. All that, and a desirable neighborhood with highly rated schools! You don't want to miss this one! Make your appointment today!!!
Listing is courtesy of: OPTIMA REAL ESTATE (407-366-4500)
Listing Agent: Deborah Morgan (407-314-8610)
1840 ASTER DR, WINTER PARK, FL 32792
$439,90028 Days on yellowkey MLS ID: O6412364
REDUCED by $10,000 (2.2%) on 06/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1667 Built: 1978 Tax: $864 (2025)Community: Garden Lake Estates Unit 1Spa: NoSingle Family
Taxes:$864
Remarks: Step into this well maintained 3 bedroom 2 bath home located in a highly sought after Winter Park, Garden Lake Estates. Nestled in Seminole County, A rated school zone! The home also sits on a large lot with plenty of room for outdoor living, No rear neighbors for added privacy, gardening or future expansion. This property offers endless potential. Featuring a newer roof, this home offers added value and peace of mind for its next owner. Conveniently located near shopping, schools, dining, parks and major roadways, you'll enjoy both comfort and convenience.One or more photo(s) have been virtually staged.
Listing is courtesy of: KONA REALTY SERVICES LLC (407-960-6844)
Listing Agent: Brendon Spalding (407-929-1724)
8433 COMMANDER CV, WINTER PARK, FL 32792
$455,00016 Days on yellowkey MLS ID: O6416635
REDUCED by $10,000 (2.2%) on 06/28/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1903 Built: 1986Monthly Fee: $76 Tax: $3,556 (2025)Community: Trinity BaySpa: NoSingle Family
Taxes:$3,556
Remarks: Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!
Listing is courtesy of: CEPEDA REAL ESTATE LLC (407-900-1792)
Listing Agent: Brandi Cepeda (407-900-1565)
2521 GALLIANO CIR, WINTER PARK, FL 32792
$360,0005 Days on yellowkey MLS ID: O6419329
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1682 Built: 2003Monthly Fee: $175 Tax: $4,532 (2025)Community: Vistas At Lake HowellTownhouse
Taxes:$4,532
Elementary School: Sterling Park Elementary
Remarks: Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Daniel Lennon (954-483-9760)
3463 ARNEL DR, WINTER PARK, FL 32792
$419,900104 Days on yellowkey MLS ID: O6390301
REDUCED by $5,000 (1.2%) on 06/25/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1967 Tax: $4,648 (2024)Community: Eastbrook Sub Unit 11Single Family
Taxes:$4,648
Remarks: One or more photo(s) has been virtually staged. DO NOT MISS THIS OPPORTUNITY! PRICE IMPROVEMENT + Pool Home + Paid-Off Solar Panels + No HOA in Winter Park! Welcome to this move-in-ready 3-bedroom, 2-bathroom home with approximately 1,770 square feet of living space, a 2-car garage, and a private pool, all located in the established Eastbrook community. Roof replaced in 2018, fully paid-off solar panels installed in 2020, water heater 2019, and beautifully updated interior spaces. The paid-off solar panels are a tremendous advantage, helping reduce monthly electric costs from day one. The heart of the home is the renovated kitchen featuring modern cabinetry, quartz countertops, stainless steel appliances, an oversized island with induction cooking surface, and abundant space for cooking, gathering, and entertaining. The open-concept layout flows seamlessly into the living and dining areas, creating a bright and inviting atmosphere. One of the home's standout features is the impressive Florida Room with soaring wood ceilings, exposed beams, a built-in serving area, and direct access to the pool. This unique space is perfect for entertaining, hosting gatherings, enjoying morning coffee, watching the big game, or relaxing while overlooking the backyard and pool area. The primary suite features a unique split-layout design that creates a flexible area ideal for a reading nook, vanity space, nursery setup, fitness corner, or additional storage. The primary bathroom also provides direct access to the pool area, offering convenience for guests and easy indoor-outdoor living. Step outside and enjoy your private backyard retreat featuring a sparkling pool, spacious deck areas, and plenty of room to enjoy Florida living year-round. Conveniently located near Park Avenue, Rollins College, Full Sail University, UCF, shopping, dining, and major highways. Zoned for highly desirable Seminole County schools. Finding a Winter Park pool home with paid-off solar panels, no HOA, updated finishes, a unique Florida Room, pool bath access, and a 2-car garage at this price point is becoming increasingly difficult. Schedule your private showing today before this opportunity is gone.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
3135 HEARTLEAF PL, WINTER PARK, FL 32792
$649,00038 Days on yellowkey MLS ID: O6410276
5 Days Off yellowkey (back on 6/28/2026)
REDUCED by $10,900 (1.7%) on 06/17/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2749 Built: 1994Monthly Fee: $20 Tax: $2,825 (2025)Community: Lost CreekSpa: NoSingle Family
Taxes:$2,825
Remarks: Under contract-accepting backup offers. Tucked away along the tree-lined streets of the desirable Lost Creek community, this beautifully updated two-story residence is truly move-in ready. Major updates include a new roof in 2022 and a new water heater in 2026, offering peace of mind for years to come. Ideally situated in sought-after Winter Park, this exceptional home also includes exclusive creek-to-lake access leading to the sparkling waters of Lake Howell—perfect for enjoying Florida’s outdoor lifestyle while remaining close to premier amenities and entertainment. Step inside to soaring ceilings and an abundance of natural light that fill the spacious great room, creating an open and airy atmosphere. The gourmet kitchen flows seamlessly into a sunny breakfast nook and overlooks the inviting family room, complete with a cozy wood-burning fireplace—ideal for both everyday living and entertaining. The primary suite serves as a peaceful retreat with relaxing views of the sparkling pool. The ensuite bathroom features an oversized vanity with framed mirror, a garden soaking tub, and a beautifully tiled walk-in shower. Upstairs, an expansive open loft offers versatile living space perfect for a media room, home gym, office, or guest lounge. Two additional generously sized bedrooms and a full bathroom complete the second floor. Step outside to your own private backyard oasis featuring a screened-in pool and ample green space beyond—perfect for holiday cookouts, family gatherings, or simply relaxing outdoors. Conveniently located near premier dining, shopping, medical centers, and recreation, this home is just minutes from Oviedo on the Park, Park Avenue, and Waterford Lakes Town Center. Major employers including Siemens, Lockheed Martin, and UCF are all within easy reach, along with quick access to SR-417 for effortless trips to Orlando’s attractions, beaches, and beyond. Zoned for highly rated Seminole County schools: Red Bug Elementary, Tuscawilla Middle, and Lake Howell High School.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Shirley Jones (407-719-9180)
1610 GLADIOLAS DR, WINTER PARK, FL 32792
$430,0002 Days on yellowkey MLS ID: O6420292
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1808 Built: 1979 Tax: $1,442 (2025)Community: Garden Lake Estates Unit 1Single Family
Taxes:$1,442
Remarks: Welcome to this beautiful pool home in the heart of Winter Park, offering the freedom of NO HOA and situated on an oversized lot with a spacious enclosed lanai—perfect for year-round Florida living. This thoughtfully designed split floor plan provides added privacy, with the primary suite tucked away from the secondary bedrooms. The recently updated kitchen serves as the heart of the home & major updates include a 2023 HVAC system, 2019 water heater, and a newer roof, providing peace of mind for years to come. With plenty of outdoor space and endless potential to customize and add value, this home is a rare opportunity in one of Central Florida's most sought-after locations.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Jasmin Cabral (305-699-8099)
2503 TAHOE CIR #2503, WINTER PARK, FL 32792
$250,00088 Days on yellowkey MLS ID: O6395130
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1981 Tax: $506 (2025)Community: Cedarwood Village 1Condo
Taxes:$506
Elementary School: English Estates Elementary
Remarks: This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. The home showcases engineered hardwood floors, skylights and wonderful natural light. The kitchen provides ample cabinet space, granite counters, built-in wine rack and beautiful custom tile work. The kitchen overlooks the dining and living room combo. The living room has 2 skylights and flows right into the delightful Florida room. The Florida room boasts wonderful built-in shelving and a glass door giving access to the backyard. The primary bedroom showcases wonderful built-in cabinets, 2 closets and an ensuite bathroom with a granite counter vanity. The primary bedroom also looks into the Florida room but can be shut off for privacy with a sliding door. The second bedroom is at the front of the home and has access to the guest bathroom with a granite counter vanity. Two assigned parking spaces are directly in front of the home. To top it all off, this home is in close proximity to several restaurants and shops and is an easy drive to downtown Winter Park.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Beth Logullo (772-633-0670)
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$250,00070 Days on yellowkey MLS ID: O6400674
REDUCED by $9,000 (3.5%) on 06/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1985Monthly Fee: $499 Tax: $2,560 (2024)Community: Cedarwood Village 1Condo
Taxes:$2,560
Remarks: Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance living, with lawn care included in the HOA, along with amenities such as rebuilt tennis courts, a recently remodeled pool, a clubhouse, dog-walking areas, and newly paved roads. Conveniently located in a highly rated school district and close to shopping, dining, and entertainment, the property is also just minutes from Full Sail University, Valencia College, and UCF. Inside, the condo is beautifully updated and shows the care of meticulous owners. The modern kitchen features granite countertops, matching cabinetry, and an eat-in area with sliding doors leading to the private patio, while the bathrooms and dining room wet bar are finished with the same stylish cabinets and granite. The split floor plan includes tile flooring throughout the main living areas and wood floors in the bedrooms. The large living and dining spaces feature vaulted ceilings with skylights for abundant natural light, along with a cozy wood-burning fireplace. French doors from the living room open to the enclosed lanai, while the primary suite also has direct lanai access, ample closet space, and a private bath with both a tub and shower. Additional features include an interior laundry closet adjacent to the kitchen, updated plumbing, a roof replaced in 2018, and new ductwork installed in 2023. AC 2008. Seller providing a $4,500 Buyer credit at closing toward a new AC. Two assigned parking spaces are located directly in front of the unit.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Jeff Stewart (407-247-9762)
4353 STEED TER, WINTER PARK, FL 32792
$614,9904 Days on yellowkey MLS ID: TB8517548
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2275 Built: 1989Monthly Fee: $29 Tax: $7,031 (2024)Community: Kings CoveSingle Family
Taxes:$7,031
Remarks: MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the moment you arrive, you'll appreciate the spacious layout and impressive updates throughout. The heart of the home features a beautifully appointed kitchen with quartz countertops, ample cabinetry, and a seamless flow into the family room, making it perfect for everyday living and entertaining. Vaulted ceilings and a cozy wood-burning fireplace create a warm and inviting atmosphere. Step outside to your own private outdoor oasis. The screened-in pool area is designed for year-round enjoyment and features a spacious patio, covered lanai, and a fully equipped outdoor kitchen complete with refrigerator, sink, and cabinetry—ideal for hosting family and friends. The primary suite offers a relaxing retreat with dual sinks and plenty of space to unwind. Additional highlights include a fenced backyard, new windows (2021), new roof (2019), and a new AC system (2024), providing peace of mind for years to come. Conveniently located with easy access to SR 417, shopping, dining, and everyday conveniences, this exceptional home combines comfort, style, and location. Don't miss this opportunity—schedule your private showing today!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Barbara Robinson (706-540-4593)
1287 VERDANT GLADE PL, WINTER PARK, FL 32792
$825,00066 Days on yellowkey MLS ID: O6400331
REDUCED by $22,000 (2.6%) on 06/19/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3020 Built: 2020Monthly Fee: $413 Tax: $6,133 (2025)Community: Meadows At Hawks CrestSingle Family
Taxes:$6,133
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both comfortable living and easy entertaining. Inside, the home feels bright, expansive, and well connected, with generous living areas that flow naturally from one space to the next. The open design creates an inviting setting for everyday routines, gatherings, and holiday hosting, while the separate office adds flexibility for working from home, studying, or creating a quiet retreat. With two primary bedroom suites, a large game room, and an additional loft, there is plenty of space to accommodate guests, a growing household, or changing lifestyle needs. The home also features thoughtful upgrades that elevate both style and function. A gourmet kitchen serves as the heart of the home, complete with quartz countertops, 42-inch cabinetry, and the kind of workspace and storage today’s buyers appreciate. Eight-foot interior doors add to the sense of scale throughout, while details such as a pocket door in the bathroom enhance convenience and flow. Large sliding glass doors open wide to create a seamless connection between the indoor living spaces and the outdoor entertaining area. Step outside to an oversized screened and covered patio that extends the living space and creates a relaxing place to enjoy morning coffee, outdoor dining, or quiet evenings at home. Beyond the patio, the private yard offers even more appeal, with no rear neighbors behind the home for added privacy and a more open feel. The rear eastern exposure welcomes beautiful morning sun, making the backyard setting especially enjoyable at the start of the day. Located in Winter Park, the home benefits from a highly desirable area known for its established residential feel, convenient access to shopping and dining, and close proximity to parks, schools, and major roadways. The neighborhood adds to the home’s appeal by offering a blend of comfort, accessibility, and the everyday convenience that makes Winter Park such a sought-after place to live. With its flexible two-story layout, dual primary suites, game room, loft, gourmet kitchen, oversized patio, and private backyard setting, 1287 Verdant Glade Place delivers the space, upgrades, and lifestyle features buyers are looking for.
Listing Agent: Thomas Nickley, Jr (407-629-4420)
2676 BARBADOS DR, WINTER PARK, FL 32792
$340,00031 Days on yellowkey MLS ID: O6411958
2 Days Off yellowkey (back on 6/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1743 Built: 1978Monthly Fee: $98 Tax: $4,131 (2025)Community: Windward Square Sec 2Townhouse
Taxes:$4,131
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located in the heart of Winter Park. Offering 1,743 square feet of thoughtfully designed living space, this home combines comfort, style, and an unbeatable location just minutes from shopping, dining, parks, and top-rated schools. The desirable corner-unit placement provides added privacy, extra natural light, and a spacious feel throughout. Inside, you’ll find luxury vinyl plank flooring flowing seamlessly throughout the home and a stunning vaulted ceiling that creates an airy, open atmosphere in the living room. The beautifully updated kitchen is truly the centerpiece of the home, featuring gorgeous wood countertops, ample cabinet space, and an open-concept layout perfect for entertaining family and friends. Step outside to the rear screened-in patio and enjoy peaceful pond views in your own private outdoor retreat. Whether you’re sipping your morning coffee or unwinding after a long day, this tranquil space offers the perfect setting to relax and enjoy Florida living year-round. This exceptional Winter Park townhome is a rare opportunity you won’t want to miss.
Listing Agent: Joseph Sipp (407-820-7016)
3641 OAK VISTA LN, WINTER PARK, FL 32792
$475,00021 Days on yellowkey MLS ID: O6412855
0 Days Off yellowkey (back on 6/26/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1645 Built: 1981 Tax: $1,562 (2025)Community: Garden Lake Estates Unit 2Spa: NoSingle Family
Taxes:$1,562
Remarks: Under contract-accepting backup offers. Welcome to Winter Park. VIEW VIRTUAL TOUR! The Original Owner has meticulously cared for this home and the pride of ownership shines through. The real showstopper is your private outdoor oasis! Enjoy Florida’s endless sunshine in the expansive, screened-in back porch and pool area—perfect for year-round gatherings, pool parties, and quiet weekends at home. Have your morning coffee or afternoon cocktails sitting out back on the porch enjoying the birds. This large, fenced 120 x 80-foot yard provides plenty of room for little ones and pets to play, gardening, or simply unwinding. for comfortable Florida living! Perfectly situated in a desirable, close-in location and zoned for award-winning Seminole County schools, this remodeled, one-story home offers the ideal setting for all family households. Step inside and discover an inviting split floor plan featuring 3 spacious bedrooms and 2 modern bathrooms. The formal living and dining rooms create an elegant atmosphere for entertaining, while the stunning remodeled kitchen is light and bright, complete with contemporary finishes and new appliances. Relax in the cozy family room, where a charming brick wood-burning fireplace adds warmth and ambiance on cool evenings. You do have formal areas that have a multitude of options for space where YOU Need it. Once you get to the kitchen you will be amazed with the sleek white brand new cabinets with trendy quart counters and a gorgeous back splash. WOW! You can enjoy yourself while you are at the sink and watch whatever is going on in the backyard. No expense spared with banks of drawers too. Additional highlights include a 2-car garage, newer windows for energy efficiency, and NO HOA—giving you the freedom to truly make this home your own. Bring your camper, toys because you have loads of room in the backyard to work on multiple projects. Roof and A/C are 2021 adding to peace of mind with your insurance 4 point inspection. Garage is even 24x21. With ample parking, an amazing outdoor space, and proximity to top-rated schools, shopping, dining, and major highways, 3641 Oak Vista Lane delivers the ultimate Florida lifestyle for your family inside the home and outside. You deserve your own Backyard paradise. Don’t miss the opportunity to make this move-in ready Winter Park gem your forever home. Seminole County schools complete the package. Schedule your private tour today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Laurie Cain (407-484-9944)
3009 NICHOLSON DR, WINTER PARK, FL 32792
$449,9004 Days on yellowkey MLS ID: O6419862
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1645 Built: 1980 Tax: $1,274 (2025)Community: Wrenwood Unit 3 3Rd AddSingle Family
Taxes:$1,274
Remarks: Welcome home to this beautifully remodeled **4-bedroom, 2-bath** residence in sought after Winter Park! BRAND NEW ROOF IN 2024! Thoughtfully renovated from top to bottom, this move-in-ready home offers the perfect combination of modern style, quality craftsmanship, and peace of mind with virtually every major system already updated. Step inside to discover beautiful new luxury vinyl flooring throughout, a stunning kitchen featuring brand-new cabinetry, elegant quartz countertops, and updated finishes designed for both everyday living and entertaining. Both bathrooms have been completely remodeled with stylish tile, new vanities, fixtures, and toilets, creating a fresh, contemporary feel throughout the home. The spacious primary suite has been completely reimagined and now features a beautifully remodeled bathroom along with a custom built-in closet organization system. New double patio doors provide abundant natural light while creating a seamless transition to the screened patio—perfect for enjoying Florida's beautiful weather. Beyond the cosmetic updates, this home offers the kind of improvements buyers truly appreciate, including a **new HVAC system with all-new ductwork, complete house replumb, new water heater, new electrical panel, new switches and outlets throughout, fresh interior and exterior paint, and a newly rescreened patio with a new screen door.** These significant upgrades provide years of worry-free ownership. Located within the highly sought-after Seminole County Public School District, this home is zoned for Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School. You'll also enjoy an incredibly convenient location just minutes from shopping, restaurants, parks, entertainment, major roadways, and everything Winter Park and the surrounding area have to offer. With its extensive renovations, desirable **4-bedroom** floor plan, exceptional location, and true move-in-ready condition, this is a rare opportunity you won't want to miss. Schedule your private showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Benjamin Simanton (407-790-2277)
1871 CASSELWOOD ST, WINTER PARK, FL 32792
$419,90058 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.
7577 DOCKSIDE ST, WINTER PARK, FL 32792
$360,00027 Days on yellowkey MLS ID: O6412514
REDUCED by $10,000 (2.7%) on 06/25/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1245 Built: 1977 Tax: $3,722 (2025)Community: Woodcrest Unit 6Single Family
Taxes:$3,722
Remarks: Virtually Staged. FABULOUS 3 bedroom 2 bath RENOVATED home with a 1 car garage located in a PRIME LOCATION!! Perfect for the first time homebuyer, investor or someone looking to downsize. The large family room benefits from natural lighting provided by the NEW WINDOWS installed(2024) throughout the ENTIRE house. The open kitchen overlooks the covered porch and large, FULLY FENCED backyard. The primary bedroom has LPV flooring with an UPDATED bathroom. NEWER carpets in the other two bedrooms. Second bath has a new toilet with a bidet, a tile bath/shower combo, and an updated vanity. NEW lighting, outlet and switch plate covers throughout. A NEW roof ridge vent was added for extra ventilation! NEW LANDSCAPING in the front. NEW DRAINFIELD (2026), water heater (2023), roof(2021). It is in Seminole County school district, 15 minutes to UCF, 5 minutes to shopping, and 10 minutes to the highway. HURRY, you don't want to miss this opportunity!!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Heather Pryor (321-303-5393)
5340 N LAKE BURKETT LN, WINTER PARK, FL 32792
$489,90024 Days on yellowkey MLS ID: O6413717
REDUCED by $5,100 (1.0%) on 06/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1746 Built: 1994Monthly Fee: $76 Tax: $1,591 (2025)Community: Trinity Bay Ph 2Spa: NoSingle Family
Taxes:$1,591
Remarks: Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha. Reserved primarily for neighborhood residents and their guests, this unique amenity provides an incredible opportunity to enjoy biking, boating, waterskiing, and lakeside recreation just moments from home. This meticulously maintained residence stands out with fresh exterior paint, updated landscaping, and inviting curb appeal. Inside, soaring vaulted ceilings and abundant natural light create an open, airy atmosphere, enhanced by fresh interior paint throughout. The thoughtfully designed split-bedroom floor plan makes excellent use of every square foot, offering comfortable living with no wasted space. An indoor laundry room, spacious 2-car garage, and desirable semi cul-de-sac location add to the home's appeal. Beyond the lake, residents enjoy a community pool, playground, boat launch, and dock along with being located directly across the street from the Cross-Seminole Bike Trail, creating a true lifestyle community. Conveniently located with easy access to SR 417, shopping, dining, and everyday essentials, this home offers the perfect blend of recreation, convenience, and value. Experience the rare opportunity to enjoy private lake-access living in one of the area's most desirable neighborhoods.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Tanya Mcdonnell (407-625-2719)
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