Location: Winter Park
Keyword(s): Tuskawilla Middle
Keyword(s) Middle School: Tuskawilla Middle
Do Not Show Listings
1418 LONE FEATHER TRL, WINTER PARK, FL 32792
$750,00030 Days on yellowkey MLS ID: O6417341
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2197 Built: 2022Monthly Fee: $244 Tax: $6,224 (2025)Community: Landings At Hawks CrestSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,224
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Harif Hazera Llc (407-953-9098)
2914 REEF KNOT PL, WINTER PARK, FL 32792
$1,725,00028 Days on yellowkey MLS ID: O6418185
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4173 Built: 2019Monthly Fee: $186 Tax: $17,688 (2025)Community: Lake Florence PreserveSpa: NoSingle Family
Taxes:$17,688
Remarks: Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
1189 LAZY HOLLOW PL, WINTER PARK, FL 32792
$445,00013 Days on yellowkey MLS ID: O6422142
REDUCED by $5,000 (1.1%) on 07/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1525 Built: 1984 Tax: $2,369 (2025)Community: SpringviewSingle Family
Taxes:$2,369
Elementary School: Red Bug Elementary
Remarks: Welcome to your own private backyard oasis in the heart of Winter Park! This beautifully maintained two-story home offers 4 bedrooms, 2 bathrooms, and the perfect blend of comfort, style, and outdoor living. With no HOA, a fully fenced backyard, and a sparkling pool, this home delivers the Florida lifestyle buyers have been searching for. From the moment you arrive, you'll appreciate the pride of ownership throughout. The home features a 2022 metal roof, 2021 gutters, 2020 insulation, a 2019 A/C, and a new garage door and opener installed in 2023, giving buyers peace of mind for years to come. Inside, the home has been refreshed with fresh interior paint, updated door hardware throughout, updated kitchen hardware, and tasteful finishes that create a bright and welcoming atmosphere. Just beyond the living spaces, the screened patio provides the perfect transition to your backyard oasis. The backyard is truly the highlight of the home, featuring a pool resurfaced in 2024, a replaced pool pump motor, an expansive patio, a pergola, and a built-in sound system that conveys with the home, creating the perfect setting for relaxing or entertaining family and friends. The generous, fully fenced backyard offers plenty of space for pets, play, gardening, and enjoying the outdoors. Move-in ready and loaded with valuable updates, this exceptional Winter Park pool home offers comfort, functionality, and an unbeatable outdoor lifestyle. Conveniently located near shopping, dining, parks, and major roadways, this is one you won't want to miss!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Simi Lakhani (407-408-7393)
8433 COMMANDER CV, WINTER PARK, FL 32792
$440,00033 Days on yellowkey MLS ID: O6416635
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)
2383 SUN VALLEY CIR #2383, WINTER PARK, FL 32792
$245,00087 Days on yellowkey MLS ID: O6400674
REDUCED by $5,000 (2.0%) on 07/11/2026
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
Elementary School: English Estates Elementary
Tax Year: 2024
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 $5,000 Buyer credit at closing toward a new AC and Water Heater. 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)
3463 ARNEL DR, WINTER PARK, FL 32792
$409,900121 Days on yellowkey MLS ID: O6390301
REDUCED by $5,000 (1.2%) on 07/15/2026
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. Pool Home *No HOA *Paid-Off Solar Panels **Roof (2018) Welcome to this well-maintained 3-bedroom, 2-bathroom home offering approximately 1,770 square feet, a 2-car garage, private pool, Roof (2018), Water Heater (2019), and fully paid-off solar panels for added energy savings. The renovated kitchen features quartz countertops, stainless steel appliances, modern cabinetry, an oversized island with an induction cooktop, and an open layout that flows into the main living areas. The spacious Florida Room is one of the home's highlights, featuring soaring wood ceilings, exposed beams, a built-in serving area, and direct access to the pool. It's a great space to relax, entertain, enjoy your morning coffee, or watch the big game. The primary suite offers a flexible bonus area that can be used as a reading nook, home office, vanity, workout space, or additional storage. The primary bathroom also has direct access to the pool. Step outside and enjoy a backyard that's hard to find in many pool homes. In addition to the private pool, you'll still have green space to enjoy, plus a barbecue connection already in place for outdoor cooking. Whether you're hosting friends, grilling on the weekend, or simply unwinding by the pool after work, this backyard is ready to enjoy. Conveniently located just minutes from Park Avenue, Rollins College, Full Sail University, UCF, shopping, dining, and major highways. Zoned for highly rated Seminole County schools.
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
$649,00055 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)
1401 ASTER CT, WINTER PARK, FL 32792
$429,9002 Days on yellowkey MLS ID: O6425103
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1653 Built: 1983 Tax: $3,895 (2025)Community: Garden Lake Estates Unit 3Spa: NoSingle Family
Taxes:$3,895
Remarks: Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large Florida room. Shed. Existing irrigation well (but pump not working--no warranty on well). Double gate to back yard for parking RV/toys (back left). Roof 2018; water heater 2018; HVAC 2017; CPVC plumbing.
Listing is courtesy of: SPARROW REALTY & RENTALS (407-963-8326)
Listing Agent: Brian Dodd (407-963-8326)
4353 STEED TER, WINTER PARK, FL 32792
$614,99021 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)
2503 TAHOE CIR #2503, WINTER PARK, FL 32792
$250,000105 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
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)
1564 LAWNDALE CIR, WINTER PARK, FL 32792
$450,00023 Days on yellowkey MLS ID: O6418817
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1980 Built: 1985Monthly Fee: $46 Tax: $3,124 (2025)Community: Country LaneSingle Family
Taxes:$3,124
Remarks: Discover the potential of this spacious 4-bedroom, 2.5-bath home located at 1564 Lawndale Cir in desirable Winter Park. Featuring a comfortable floor plan with generous living space, this home offers flexibility for everyday living, entertaining, working from home, or hosting guests. The bedroom layout provides privacy and functionality, while the location offers convenient access to shopping, dining, parks, schools, major roadways, and nearby Orlando destinations. With its size, layout, and prime Winter Park location, this property is a great opportunity for buyers looking to personalize a home and create lasting value. Don’t miss your chance to schedule a private showing.
Listing is courtesy of: SET HOMES REALTY LLC (407-690-3314)
Listing Agent: Yahya Chhotani Llc (732-955-1302)
1605 PURITAN AVE, WINTER PARK, FL 32792
$399,00029 Days on yellowkey MLS ID: O6417098
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1285 Built: 1963 Tax: $3,605 (2025)Community: Eastbrook Sub Unit 06 2Nd RepSingle Family
Taxes:$3,605
Remarks: SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Angelica Tomlinson Llc (407-222-8676)
1840 ASTER DR, WINTER PARK, FL 32792
$419,90045 Days on yellowkey MLS ID: O6412364
0 Days Off yellowkey (back on 7/14/2026)
REDUCED by $10,090 (2.3%) on 07/09/2026
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: Under contract-accepting backup offers. 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)
5340 N LAKE BURKETT LN, WINTER PARK, FL 32792
$469,90041 Days on yellowkey MLS ID: O6413717
REDUCED by $5,100 (1.1%) on 07/14/2026
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)
1914 BONANZA CT, WINTER PARK, FL 32792
$429,99962 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
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 Agent: Judy Julien, Pa (407-234-4051)
4469 OLD BEAR RUN, WINTER PARK, FL 32792
$1,799,999157 Days on yellowkey MLS ID: O6375415
REDUCED by $50,001 (2.7%) on 05/22/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4288 Built: 1978 Tax: $10,710 (2024)Community: Pervis Survey For R ESpa: NoSingle Family
Taxes:$10,710
Remarks: Under contract-accepting backup offers. Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully Lake is spring-fed and open to water vehicles, making it ideal for boating, water skiing, wakeboarding, tubing, fishing, and year-round enjoyment. The lakefront experience is exceptional, featuring a fully equipped dock with power, covered boat lift, and sun deck, perfectly positioned for enjoying stunning sunsets. Outdoor living is a highlight of the property. The expansive lanai and pool area overlook the lake and are ideal for entertaining, complete with a renovated summer kitchen featuring a grill, sink, mini refrigerator, and granite countertops. The oversized backyard provides ample space for gatherings, recreation, and pets. Inside, the home opens to a dramatic great room with vaulted ceilings, a striking stacked-stone feature wall with custom built-ins, and large sliding glass doors that fully retract to create seamless indoor-outdoor living. The space was reimagined during extensive renovations to maximize natural light and lake views. The chef’s kitchen, redesigned by award-winning designer Sandra Agurto of CCI, features all-wood cabinetry, quartz countertops, contemporary backsplash, oversized island with beverage and wine refrigerators, induction cooktop, convection ovens, and a separate full refrigerator and freezer, with abundant custom storage throughout. The primary suite is privately located in its own wing and offers serene lake views, high ceilings, and a spa-style en-suite bath renovated in 2022 with soaking tub, walk-in shower, expansive custom vanity, upgraded lighting, and private water closet with bidet. A large walk-in closet with custom built-ins completes the suite. All bedrooms feature their own bathrooms and walk-in closets, providing exceptional privacy and flexibility, with three full en-suite bedrooms ideal for guests or multigenerational living. Additional flexible spaces include a gym or bonus room suitable for formal living, dining, or a game room. Recent upgrades include a new roof (2018), new hot water heater (2024), fully fenced yard, Russound sound system, updated security system, new pool deck pavers, and a rebuilt dock with Trex decking and updated boat lift components. The home is part of a lake association with no mandatory dues, providing community updates and seasonal events such as the holiday boat parade. Conveniently located near SR-417, UCF, downtown Winter Park, and Trinity Prep, this is a rare opportunity to own a true spring-fed lakefront home on one of Winter Park’s most coveted lakes.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Keigan Lewis (305-393-8683)
1320 GLADIOLAS DR, WINTER PARK, FL 32792
$475,00048 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)
2087 LAURELWOOD WAY, WINTER PARK, FL 32792
$625,00035 Days on yellowkey MLS ID: O6415387
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1920 Built: 2019Monthly Fee: $244 Tax: $4,970 (2025)Community: Hawks CrestSingle Family
Taxes:$4,970
Remarks: Nestled within the gated community of Hawks Crest, this thoughtfully designed single-story residence offers an exceptional blend of comfort, style and convenience in the heart of Winter Park. Spanning 1,920 square feet, this home features an open-concept floor plan that seamlessly connects the living, dining and kitchen areas, creating an inviting setting for both everyday living and entertaining. The kitchen serves as the centerpiece of the home, appointed with granite countertops, stainless steel appliances and a spacious center island with seating. The private owner's suite offers a walk-in closet and a well-appointed bath, while three additional bedrooms provide flexibility for guests, a home office or evolving lifestyle needs. A covered lanai overlooks the tranquil pond, creating the perfect backdrop for outdoor relaxation and year-round Florida living. Residents of Hawks Crest enjoy access to an impressive collection of amenities, including a clubhouse, fitness center, resort-style pool, splash pad, dog park, playgrounds, virtual guard gate and private access to Lake Howell for kayaking and paddleboarding. Ideally located just minutes from highways, Park Avenue, downtown Maitland, top-rated schools, Foxtail Coffee and Kelly's Ice Cream, this residence offers the opportunity to enjoy one of Winter Park's most sought-after gated communities.
2651 CAYMAN WAY, WINTER PARK, FL 32792
$255,000177 Days on yellowkey MLS ID: O6375086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1978Monthly Fee: $99 Tax: $3,553 (2024)Community: Windward Square Sec 2Townhouse
Taxes:$3,553
Remarks: Virtually Staged. ALL PLAY and NO WORK! Imagine coming home to a space where weekends are made for relaxing, entertaining, and enjoying the best of Florida living. This single-story, two-bedroom, two-bath townhome offers an effortless lifestyle in a location that puts everything within reach. Vaulted ceilings create an open, airy feel in the spacious living and dining area, while sliding glass doors lead to a private, fenced backyard with a large concrete patio?perfect for morning coffee, weekend barbecues, or unwinding after a long day. With no rear neighbors and views of the community green space, you?ll enjoy added privacy and tranquility. The kitchen is designed for everyday ease, featuring ample cabinetry, a breakfast bar, and all appliances included, making move-in simple. Retreat to the oversized primary suite with a walk-in closet and direct patio access, creating a true indoor-outdoor flow. The second bedroom offers flexibility for guests, a home office, or creative space. Step outside your front door and enjoy resort-style amenities, including three swimming pools, tennis courts, a clubhouse, and a playground—all with low HOA fees. With parking for three vehicles, convenience is built right in. Located close to shopping, dining, major roadways, and just minutes from Winter Park’s Park Avenue, this home delivers both comfort and connection. Owner-occupant only community—ideal for those looking to put down roots and enjoy a true neighborhood feel. Live more. Maintain less. Welcome home.
Listing Agent: Kyle Clark (407-921-3287)
1956 JAPONICA RD, WINTER PARK, FL 32792
$549,00015 Days on yellowkey MLS ID: O6421731
0 Days Off yellowkey (back on 7/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1923 Built: 1972Monthly Fee: $2 Tax: $4,849 (2025)Community: Winter WoodsSingle Family
Taxes:$4,849
Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bath move-in ready home living on a spacious quarter-acre lot in one of Winter Park’s established neighborhoods. From the moment you arrive, you’ll appreciate the home’s inviting curb appeal with refreshed landscaping, and gutters. Inside, the open, light-filled layout features luxury vinyl plank flooring and tile throughout, creating a cohesive and modern feel that’s both beautiful and easy to maintain.The heart of the home is the thoughtfully renovated kitchen, complete with quartz countertops, soft-close cabinetry, Whirlpool and KitchenAid stainless steel appliances - including an induction stove top and double ovens. Major home features have recently been updated giving buyers confidence and peace of mind. The roof was replaced in 2020, the HVAC system in 2023, the water heater in 2019, and windows plus the sliding glass door were replaced in 2025 to improve energy efficiency and comfort. Step outside to your own private backyard retreat. The fully fenced yard offers exceptional space for pets, play, gardening, or even a future pool. An oversized extended paver patio creates the perfect setting for outdoor dining, entertaining friends, or simply relaxing on a Florida evening.
Listing is courtesy of: PROPLOGIK REALTY INC (407-658-8566)
Listing Agent: Marcos Marchena (407-658-8566)
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