Location: Winter Park
Keyword(s): Lake Howell High
Keyword(s) High School: Lake Howell High
Do Not Show Listings
256 LEWFIELD CIR #256, WINTER PARK, FL 32792
$184,900164 Days on yellowkey MLS ID: O6367842
1 Days Off yellowkey (back on 6/19/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973Monthly Fee: $465 Tax: $1,916 (2025)Community: Stratford A Winter Park CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,916
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: Tuskawilla Middle
Remarks: This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to a covered and screened rear porch with a pool view. The primary suite features a walk-in closet and a private bath with a floor-to-ceiling tiled walk-in shower. The HOA completed roofing and plumbing improvements in 2019, and all exterior and grounds maintenance is handled by the on-site HOA. The Stratford community offers two pools, a community and fitness center, and tennis courts. Just minutes from popular Downtown Winter Park with its dining and shopping, with easy highway access via the 417 and I-4, and surrounded by nearby lakes and parks, this is one opportunity you don’t want to miss. Call today to schedule your private tour!
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Renee Kumar Llc (407-756-4422)
3463 ARNEL DR, WINTER PARK, FL 32792
$429,90099 Days on yellowkey MLS ID: O6390301
REDUCED by $20,000 (4.4%) on 06/01/2026
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
Elementary School: Eastbrook Elementary
Tax Year: 2024
Remarks: Virtually Staged. NEW PRICE! 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. Major updates have already been completed, including a roof replaced in 2018, fully paid-off solar panels installed in 2020, water heater replaced in 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)
1468 AUBURN GREEN LOOP, WINTER PARK, FL 32792
$475,00065 Days on yellowkey MLS ID: O6399199
0 Days Off yellowkey (back on 5/17/2026)
REDUCED by $5,000 (1.0%) on 05/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 1984Monthly Fee: $49 Tax: $6,243 (2024)Community: Country LaneSingle Family
Taxes:$6,243
Remarks: Under contract-accepting backup offers. Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, wood burning fireplace, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living areas, hallways and one bedroom have engineered hardwood flooring, wet areas have tile flooring and there is carpet in the primary bedroom and bedroom 3. There is also a small nook that would be perfect for a craft area, office or library and it opens to the side courtyard which is fully fenced and a good size storage shed for your convenience. The Kitchen has all standard appliances including refrigerator, range, dishwasher and disposal. There is also a cozy eat in breakfast nook. The Primary Bedroom is located in the back of the home and has a nice walk-in closet with en-suite bath. There are sliding glass doors that open to the huge screened-in patio with optimal views of the lake! You will love to wake up to the gorgeous view! There are two additional Bedrooms and Full Hall Bathroom. Each bedroom has direct access to the screened in porch. This home has a finished two car garage with opener and washer/dryer hookups. Enjoy coffee in your hammock while watching the ski boats inside the screened patio that runs the full rear length of the home, providing the amazing view to the lake and is perfect for entertaining or enjoying an evening cocktail. Close to most major roadways, this home will not last long!
Listing is courtesy of: COLDWELL BANKER VANGUARD EDGE (800-948-0938)
Listing Agent: Jodie Ma (407-221-0775)
2054 EASTBROOK BLVD, WINTER PARK, FL 32792
$500,00022 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)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000231 Days on yellowkey MLS ID: O6357934
0 Days Off yellowkey (back on 5/14/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1719 Built: 1977Monthly Fee: $95Community: Windward Square Sec 1Townhouse
Taxes:$0
Remarks: Under contract-accepting backup offers. Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family room. Enclosed Florida room with high impact windows is great extra living space marking this home just over 1700sf. Master bedroom is a good size with walk in closet. Secondary rooms are spacious and full 2nd bath. You have a wonderful front fenced courtyard and a nice sized fenced back yard. End unit and 2 assigned car parking spaces. Community features low HOA and community pool, gated back entrance for easy access to Semoran, tennis courts and club house. Zoned for great Seminole County schools and minutes to shopping/dining, Altamonte Springs Mall, Downtown Winter Park, Full Sail University and to UCF. This is a great one level townhome with very reasonable HOA.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: George Freelove (407-408-5167)
1605 PURITAN AVE, WINTER PARK, FL 32792
$399,0007 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: 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)
2008 HOUNDSLAKE DR, WINTER PARK, FL 32792
$515,0009 Days on yellowkey MLS ID: O6414369
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2250 Built: 1980 Tax: $5,253 (2025)Community: Cedar RidgeSingle Family
Taxes:$5,253
Remarks: Virtually Staged. Spacious and full of potential, this 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community includes an attached flex room. Perfect for a nursery, mother in law suite, office, or man cave! In the heart of Winter Park, designed for both everyday living and entertaining, this home gives your family room to spread out and enjoy. Inside, you'll find ceramic tile throughout most of the home, with warm wood laminate flooring in three of the bedrooms for added comfort and style. The kitchen has been updated and has ample kitchen and pantry cabinetry. The bathrooms have been updated, creating the perfect space full of modern touches. Major system updates provide peace of mind, including replumbing, a new electrical panel, and a newer roof. The side-entry 2-car garage adds curb appeal and functionality, while the oversized fenced backyard is a true highlight, shaded by two enormous oak trees that create a beautiful setting for relaxing, entertaining, or family gatherings. Conveniently located near shopping, dining, parks, and top-rated schools, this Cedar Ridge gem combines space, updates, and a fantastic location. Don’t miss your rare chance to own this spacious home with timeless charm and endless possibilities in a Winter Park neighborhood WITH NO HOA.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Nicholas Feinsod (407-607-7485)
1448 LAKE FLORENCE WAY, WINTER PARK, FL 32792
$1,149,90028 Days on yellowkey MLS ID: O6411164
REDUCED by $49,100 (4.1%) on 06/17/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3652 Built: 2018Monthly Fee: $186 Tax: $7,277 (2025)Community: Lake Florence PreserveSpa: NoSingle Family
Taxes:$7,277
Remarks: Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showcases over $200,000 in builder and custom upgrades with luxury finishes and thoughtful design throughout. Residents enjoy access to a private community dock, perfect for launching a canoe or paddleboard or simply relaxing while enjoying sunset views over the water. This stunning Michelson floorplan offers the perfect blend of elegance, comfort, and functionality with spacious living areas designed for both everyday living and entertaining. Upon entry, you’re welcomed by a private office, formal dining room with custom accent features, recessed lighting throughout, beautiful wood-look tile flooring, and designer details at every turn. The open-concept family room features built-in speakers that continue throughout the main living spaces, upstairs, and outdoor lanai area, creating a seamless entertainment experience throughout the home. The gourmet kitchen is beautifully appointed with quartz countertops, 42” cabinetry, stainless steel appliances, gas cooktop, oversized island, modern backsplash, butler’s pantry with wine fridge, and an incredible walk-in pantry with custom built-in shelving. Massive 12-foot triple sliding glass doors open to the resort-style backyard featuring a beautiful open pool, custom fire pit, pergola seating area, pre-wire for a gas grill, and a backyard perfect for relaxing or entertaining. The first floor also includes a guest suite with a full bath and direct pool access, a mudroom, a coat closet, a convenient half bath, and an oversized three-car tandem garage with overhead storage. Upstairs, a beautiful wood tread staircase leads to an expansive loft and bonus room area along with spacious secondary bedrooms, all featuring walk-in closets. A Jack-and-Jill bathroom with dual sinks, additional full bath, oversized linen closets, and a large laundry room with sink and extensive cabinetry provide exceptional functionality and storage. The luxurious owner’s retreat is a true sanctuary featuring tray ceilings, built-in speakers, a stunning accent wall, coffee bar area, spa-inspired bath with an oversized walk-in shower, abundant storage, and an enormous walk-in closet with multiple sections. Additional highlights include a brand-new A/C unit and countless high-end finishes throughout. Ideally located near top-rated schools, shopping, dining, and major roadways, this meticulously maintained home offers elevated Florida living in one of the area’s most desirable gated communities.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Abby Nelson (407-571-1445)
3374 HAMLET LOOP, WINTER PARK, FL 32792
$365,00055 Days on yellowkey MLS ID: O6403488
REDUCED by $5,000 (1.4%) on 06/16/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1397 Built: 1994Monthly Fee: $63 Tax: $5,326 (2024)Community: Villas Of Casselberry Ph 3Single Family
Taxes:$5,326
Remarks: Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining room flow into the kitchen, where you’ll find lots cabinet storage, eat in space, and a view out to the backyard. The primary suite is conveniently located on the main floor, featuring generous windows that bring in natural light, a walk-in closet, and an updated en suite bath. A half bath downstairs adds convenience for guests. Upstairs, two spacious bedrooms share a full bath, offering comfortable separation from the main living areas. The Villas of Casselberry community has a pool for you to enjoy. The location places you just minutes from Park Ave’s shops, dining, events and great parks. With easy access to major roads and a central location close to Rollins, UCF, Full Sail and downtown Orlando, this home offers both comfort and connectivity. If you’ve been looking for space, privacy, and a well located Winter Park address, this one is worth seeing in person. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Barrett Spray (407-927-3650)
1032 MANCHESTER CIR, WINTER PARK, FL 32792
$464,900126 Days on yellowkey MLS ID: O6383113
0 Days Off yellowkey (back on 6/16/2026)
REDUCED by $5,100 (1.1%) on 06/11/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1787 Built: 1976 Tax: $1,535 (2025)Community: Howell Estates RepSpa: NoSingle Family
Taxes:$1,535
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath pool home nestled in one of the desirable neighborhoods of Winter Park within Seminole County. Offering the perfect blend of comfort, space, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining. Step inside to discover a spacious, light-filled floor plan featuring generous living areas, well-sized bedrooms, and a thoughtfully designed layout ideal for families or guests. Out back, you’ll find your own private oasis. The freshly resurfaced sparkling pool and expansive backyard provide the perfect setting for weekend barbecues, gatherings with friends, or simply relaxing under the Florida sunshine. With plenty of room to entertain, play, or unwind, this outdoor space truly sets the home apart. The property also features a metered irrigation system, helping maintain the lush landscaping efficiently and economically. Conveniently located near top-rated schools, shopping, dining, and major roadways, this exceptional property combines comfort, convenience, and the charm that makes Winter Park such a wonderful place to call home. Recent updates include: Pool resurfaced – April 2026 Roof replaced – 2022 New electrical panel – 2025
Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)
Listing Agent: Nancy Morales (321-747-7448)
8433 COMMANDER CV, WINTER PARK, FL 32792
$465,00011 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)
1320 GLADIOLAS DR, WINTER PARK, FL 32792
$475,00026 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
Elementary School: Red Bug Elementary
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)
3641 OAK VISTA LN, WINTER PARK, FL 32792
$475,00016 Days on yellowkey MLS ID: O6412855
0 Days Off yellowkey (back on 6/15/2026)
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)
2222 MARSH SEDGE LN, WINTER PARK, FL 32792
$739,000322 Days on yellowkey MLS ID: O6333145
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
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 Agent: Carmen Molina (321-331-5679)
7577 DOCKSIDE ST, WINTER PARK, FL 32792
$370,00022 Days on yellowkey MLS ID: O6412514
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 Agent: Heather Pryor (321-303-5393)
1090 WILDMEADOW RUN, WINTER PARK, FL 32792
$835,00089 Days on yellowkey MLS ID: O6394208
REDUCED by $10,000 (1.2%) on 06/02/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2021Monthly Fee: $243 Tax: $6,258 (2024)Community: Hawks CrestSingle Family
Taxes:$6,258
Remarks: Virtually Staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity. Ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This off-grid solar system comes with a WHOLE HOUSE BATTERY BACKUP, keeping your lights on when the power goes out. This home already comes wired for electric vehicles with room to expand. Excess power generated is sold back to the power company through the NET METERING program, resulting in credits back to the owners at the end of the year. The solar system also has two power monitoring systems for tracking your energy usage & production, conveniently controlled by your phone and computer. Hawks Crest is your home to community, where residents enjoy gated access into a landscaped resort atmosphere, featuring water fountains throughout, with an abundance of amenities. The clubhouse features a resort pool & kiddie pool, a fitness center, with sidewalks & playgrounds, along with the community’s private dock access to Lake Howell with a canoe/kayak launch. Now imagine, relaxing and enjoying park and pond views from your expansive lanai, soaking in the serene sunsets & manicured landscaping, all from the comfort of your spacious, 4-bedroom 3.5 bath home, conveniently located just a short distance from the resort clubhouse. Owners can relax and unwind while management handles all landscaping around your home, truly providing you a maintenance-free living lifestyle. Additional upgrades with this home include, commercial grade luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, and two HVAC units, all designed for comfort, convenience, and a very clean home, where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings with awe-inspiring views of the illuminated pond fountain, creating a serene view & relaxing atmosphere you’ll enjoy, even from the kitchen sink. Your chandelier can be lowered 20-feet to the floor for easy maintenance & cleaning, using a winch lift system in the attic.(Rated up to 200 lbs). And even watch the rockets launch at The Cape from the front yard. Uniquely designed, this home was built to withstand extreme weather, featuring a concrete/granite tile roofing system, steel reinforcement, concrete-filled block walls & slab, all anchoring to the foundation, uniquely tying everything together. Meticulously maintained by the owners, this home comes with a complete set of blueprints, along with many photos & videos taken of the home during the building process. Owners even have documents for all equipment & appliances. And the premium solar system comes with a transferable warranty that will keep the lights on when the power is out. This home features a split floor-plan, with a primary bedroom on both the first and second floors. Spanning 2,589 sq.ft., this home offers an additional 540 sq.ft. of screened-in lanai, providing a private outdoor oasis where you’ll find owners enjoying the tranquility of Florida sunsets. Schedule a showing for your buyers today! And…***Remember to see the list of the owners’ upgrades***.
Listing is courtesy of: BHHS FLORIDA REALTY (352-729-7325)
Listing Agent: Rod Chevalier (352-729-1818)
4469 OLD BEAR RUN, WINTER PARK, FL 32792
$1,799,999135 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: 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 Agent: Keigan Lewis (305-393-8683)
7771 COUNTRY PL #7, WINTER PARK, FL 32792
$219,900204 Days on yellowkey MLS ID: O6364384
3 Days Off yellowkey (back on 6/12/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1230 Built: 1987Monthly Fee: $340 Tax: $2,950 (2024)Community: Goldenrod Villas CondoCondo
Taxes:$2,950
Remarks: Under contract-accepting backup offers. Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate Flooring Flows Throughout, and the Split Floor Plan Offers Ideal Privacy. Down One Hallway, You Will Find Two Well-Sized Bedrooms and a Shared Full Bathroom with a Shower/Tub Combo. Off The Family Room, The Master Suite Is Generously Sized and Includes Two Separate Sinks. A Large Walk-In Closet Provides Excellent Storage, and the Sliding Glass Door Leads to Your Own Private Fenced-In Yard, Perfect for Plants, Gardening, or Extra Seating When Entertaining. Just A Short Walk from Your Reserved Parking Spaces, You'll Find the Clean and Refreshing Community Pool, Making Relaxation Effortless. Don’t Miss This Opportunity—Call Today to Schedule Your Showing! Lease Must Be Honored Until 11/30/26 with a Rental Rate of $1,850.00 Monthly
Listing is courtesy of: OUTLET REALTY (407-353-5518)
Listing Agent: Ivan Tobon (407-353-5518)
3159 GREENWOOD ST, WINTER PARK, FL 32792
$290,00035 Days on yellowkey MLS ID: G5112192
1 Days Off yellowkey (back on 5/25/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1241 Built: 1984Monthly Fee: $57 Tax: $1,085 (2024)Community: Villas Of Casselberry Ph 2Townhouse
Taxes:$1,085
Remarks: Location truly matters—and this Winter Park gem delivers. This beautifully maintained 2-bedroom, 2-bath townhouse offers charm, functionality, and a rare bonus: a spacious screened-in lanai and private yard. Tucked within a well-established neighborhood, the home provides a peaceful residential setting while keeping you just minutes from everything Winter Park has to offer. Inside, you’ll find a stunning kitchen with stainless steel appliances, upgraded flooring, and modern countertops—making this home completely move-in ready. Whether you're searching for a primary residence or a smart investment, this property offers the perfect blend of comfort, flexibility, and convenience. Ideally located near Downtown Winter Park, Park Avenue, Rollins College, AdventHealth Winter Park, major highways, shopping, dining, and entertainment. You’ll also enjoy easy access to Downtown Orlando, Baldwin Park, Full Sail University, and Orlando International Airport. Opportunities like this are rare—schedule your private showing today.
Listing is courtesy of: GLOBAL PROPERTIES SALES/MGMT (352-383-4175)
Listing Agent: Joe Pietzyk (407-222-8064)
1535 LAWNDALE CIR, WINTER PARK, FL 32792
$450,00013 Days on yellowkey MLS ID: C7527235
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 1986Monthly Fee: $50 Tax: $5,433 (2025)Community: Country LaneSpa: NoSingle Family
Taxes:$5,433
Remarks: Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP (305-662-1502)
Listing Agent: Raul Pino (305-662-1502)
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