Location: Winter Park
Keyword(s): Tuskawilla Middle
Keyword(s) Middle School: Tuskawilla Middle
Do Not Show Listings
1905 BONANZA CT, WINTER PARK, FL 32789
$490,000Listed 04/16/2026 12:08AM MLS ID: O6398772
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1774 Built: 1968 Tax: $5,015 (2024)Community: Eastbrook Sub Unit 13Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,015
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: This beautifully updated 4-bedroom, 2-bath bungalow with a 2-car garage sits on a quiet cul-de-sac and underwent a major renovation in 2023. Nearly every big-ticket item has been replaced, including the roof, A/C, water heater, and double-pane windows-giving you peace of mind for years to come. The home also features a fully updated kitchen with new cabinets, countertops, and a complete appliance package—refrigerator, dishwasher, range, range hood, and microwave—along with new carpeting, ceiling fans, and a new front door. Inside, the spacious family room includes custom built-ins, offering an abundance of storage. Both bathrooms have been tastefully remodeled. The primary bath features a beautiful walk-in shower and dual sinks, while the guest bath offers dual sinks, a jetted tub, a linen closet, and convenient access to the pool area. Step outside to an oversized, fully fenced backyard where you’ll find a sparkling screened-in pool and a large covered patio with an extended overhang—perfect for relaxing or entertaining year-round. And best of all…No HOA! Conveniently located minutes from Downtown Winter Park, key highways, shopping and within an hours drive of all the major theme parks and Orlando International Airport. Welcome Home!
Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)
Listing Agent: Lynn Roeder (407-758-8565)
1515 WINTER GREEN BLVD, WINTER PARK, FL 32792
$315,00042 Days on yellowkey MLS ID: O6384755
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1652 Built: 1984Monthly Fee: $188 Tax: $3,993 (2024)Community: Winter GreenTownhouse
Taxes:$3,993
Elementary School: English Estates Elementary
Remarks: Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the spacious layout is complemented by low-maintenance tile flooring throughout and a cozy wood-burning fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with granite countertops, stainless steel appliances, and a newer refrigerator, while the generously sized bedrooms provide comfortable retreats. The primary suite features two closets and an ensuite bath with dual sinks. Major system updates provide exceptional peace of mind, including a brand-new roof and HVAC system installed in January 2026, along with fresh exterior paint, newer gutters (approximately three years old), and a newer fence. The washer and dryer convey, making this home truly move-in ready. The community offers an exceptionally low HOA fee of under $200 per month, adding to the home’s overall value. Ideally located with easy access to Winter Park, Maitland, Full Sail University, UCF, Rollins College, and Valencia College, as well as nearby shopping, dining, and major roadways. With its spacious design, private outdoor space, and proven rental history, this property presents an outstanding opportunity as either a primary residence or investment. Reach out to schedule your private showing now!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jill Healey (407-797-1420)
5473 BRACKEN CT, WINTER PARK, FL 32792
$295,000111 Days on yellowkey MLS ID: O6368415
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1178 Built: 1986Monthly Fee: $101 Tax: $2,205 (2024)Community: Fernbrook TrailsTownhouse
Taxes:$2,205
Remarks: One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open and architectural focal point. The functional layout includes a large bedroom and full bath on the main level—ideal for guests, a home office, or multi-generational living. Upstairs, two additional bedrooms share a Jack-and-Jill style bath, offering privacy and efficiency. The kitchen opens to the dining and living areas, making the space well-suited for everyday living and entertaining. Sliding doors lead to a screened-in patio and a private, white PVC-fenced yard—low maintenance and perfect for relaxing or pets. Additional features include wood-look flooring in main living areas, neutral finishes, and abundant natural light. Conveniently located near Winter Park shopping, dining, parks, and major roadways. A strong option for buyers seeking space, location, and low-maintenance townhome living.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
1340 BLUE STEM LN, WINTER PARK, FL 32792
$724,900107 Days on yellowkey MLS ID: O6365415
REDUCED by $5,000 (0.7%) on 04/11/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2587 Built: 2022Monthly Fee: $235 Tax: $6,594 (2025)Community: Landings At Hawks CrestSingle Family
Taxes:$6,594
Tax Year: 2025
Remarks: Located within the gated community of Hawk’s Crest, one of Winter Park’s most desirable neighborhoods, this beautifully maintained two-story home is set on an oversized lot with tranquil pond views and a layout designed to live effortlessly. Light-filled, open, and thoughtfully upgraded, the home offers a balance of comfort, style, and everyday functionality. A pavered driveway and walkway create an inviting arrival, leading into a bright interior with soaring ceilings and abundant natural light. The main living space flows seamlessly, anchored by a chef’s kitchen featuring quartz countertops, stainless steel appliances, solid wood cabinetry, and a generous island with breakfast bar—perfect for casual meals, entertaining, or gathering at the end of the day. The kitchen opens naturally to the dining and family rooms, creating a connected space that feels both open and welcoming. Sliding doors lead to a covered lanai overlooking the pond, extending the living space outdoors and providing a peaceful backdrop for morning coffee or evening relaxation. Inside, upgraded luxury vinyl flooring and custom roller shades add warmth and a polished finish throughout the main living areas. The first-floor primary suite offers a private retreat with serene water views, a spacious walk-in closet, and a spa-inspired bath with dual vanities and a walk-in shower. A dedicated office on the main level adds flexibility and can easily function as a fifth bedroom if needed. Upstairs, a generous loft provides additional living space—ideal for a media room, play area, or secondary lounge—while three well-sized bedrooms offer comfort and versatility for guests, hobbies, or working from home. Energy-efficient features, ample storage, and thoughtful design make the home as practical as it is inviting. Residents of Hawk’s Crest enjoy resort-style amenities including a community pool, fitness center, clubhouse, playgrounds, and scenic walking paths, along with HOA-included lawn care for low-maintenance living. Ideally situated near shopping, dining, outdoor recreation, and major roadways, this home offers both convenience and a sense of retreat within Winter Park. Come experience the lifestyle and setting that make this home truly special—schedule your private showing today.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Beth Hobart (407-227-8192)
5143 LAZY OAKS DR #5143, WINTER PARK, FL 32792
$285,0001 Day on yellowkey MLS ID: O6398856
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)
1036 MANCHESTER CIR, WINTER PARK, FL 32792
$400,00014 Days on yellowkey MLS ID: O6395138
3 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1574 Built: 1974 Tax: $4,126 (2024)Community: Howell Estates RepSingle Family
Taxes:$4,126
Remarks: Under contract-accepting backup offers. Welcome to this well-maintained three-bedroom, two-bathroom home offering 1,574 square feet of thoughtfully designed living space in the established and highly desirable Howell Estates neighborhood of Winter Park. From the moment you enter, an abundance of natural light, ceiling fans throughout, and a functional layout create an open and inviting atmosphere. The flexible floor plan includes a dedicated family room/den in addition to a formal dining area, providing versatile space for entertaining, working from home, or everyday living. Blinds throughout, generous closet space, and sliding glass doors leading to the backyard add both comfort and practicality. The kitchen blends classic style with everyday convenience, featuring blond-toned wood cabinetry, a closet pantry, and newer stainless steel appliances including a refrigerator, dishwasher, and microwave(2024). The layout connects seamlessly to the surrounding living spaces, making it ideal for both daily use and hosting. The primary suite serves as a private retreat, complete with a ceiling fan and an ensuite bathroom featuring a single vanity, a tiled walk-in shower with glass sliding doors, and a newly updated toilet. The two additional bedrooms are well-sized and versatile, perfect for family, guests, or a home office, and share a hall bathroom with a single vanity, tiled tub/shower combination, and a new toilet. Outdoor living is enhanced by a spacious and open 0.24-acre fully fenced lot, offering plenty of room for relaxation, entertaining, or future additions. The exterior has been freshly painted and features brand-new landscaping completed in 2026, creating excellent curb appeal. A two-car garage with a new garage door provides additional convenience and storage. Significant updates offer peace of mind, including a roof installed in 2020, electrical updates completed in 2020, HVAC system installed in 2017, and a water heater replaced in 2023. Ideally located, this home is just 7 minutes from Red Bug Lake Park, close to top-rated schools, and within close proximity to restaurants, grocery stores, and retail shopping—offering the perfect blend of comfort, convenience, and location. Roof – 2020 | HVAC – 2017 | Electrical – 2020 | Water Heater – 2023
Listing Agent: Amy Turner (407-803-3885)
3110 HEARTLEAF PL, WINTER PARK, FL 32792
$629,0006 Days on yellowkey MLS ID: O6397396
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2704 Built: 1998Monthly Fee: $21 Tax: $7,231 (2025)Community: Lost CreekSpa: YesSingle Family
Taxes:$7,231
Elementary School: Red Bug Elementary
Remarks: Nestled in the upscale Lost Creek community, this maintained 4-bedroom, 3-bathroom screened pool home offers the perfect blend of comfort and natural beauty with over an acre of land that extends all the way to Howell Creek. Upon entering, you are greeted by high ceilings and an open-concept great room layout. The formal living room flows seamlessly into the dining room, creating an ideal setting for entertaining. Beyond, a spacious family room opens to views of the pool, while the adjacent gourmet kitchen and breakfast area complete the heart of the home. The kitchen features New quartz countertops and stainless steel appliances. The main level is home to a spacious primary bedroom, offering serene views of both the pool and surrounding forest. Sliding doors provide direct access to the pool deck, while inside you'll find a generous walk-in closet, a double-sink vanity, a relaxing garden bathtub, and a separate shower. Additional guest bedroom and a full guest bathroom complete the main floor. Upstairs, a charming loft with a built-in desk provides the perfect work-from-home or study retreat, accompanied by two additional bedrooms and a shared bathroom. Outside, the screened pool backing up to a natural wooded area with no rear neighbors is your private oasis — perfect for year-round Florida living. Winter Park is close to numerous shops and eateries along with easy access to major expressways. You get all this in a great school district. Sod intalled(2026), Quartz Countertops(2026), Pool pump(2026), Range & Dishwasher(2026), Roof(2022)
Listing is courtesy of: FUSILIER MANAGEMENT GROUP (407-476-0476)
Listing Agent: Hajime Shimabukuro (407-435-1910)
2400 DOMINICA RUN, WINTER PARK, FL 32792
$225,00020 Days on yellowkey MLS ID: O6394406
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 854 Built: 1979Monthly Fee: $99 Tax: $433 (2025)Community: Windward Square Sec 3Townhouse
Taxes:$433
Remarks: CHARMING 2/1 MOVE IN READY TOWNHOME in highly sought-after Windward Square community of Winter Park! NEWER Roof 2025! Spacious floor plan with soaring ceilings! Inviting entertainment space with dining/living combo off kitchen. Ample natural light fills this home with double glass sliders and multiple skylights all in living area! Relaxing views of back park like green space! Convenient location near major highways, the Orlando International Airport, shopping, dining, universities and only 30 min to attractions! Property has 2 parking spaces directly in front for easy access! Community boast various amenities include a pool, tennis courts, clubhouse, and playground! DON"t MISS out on this RARE OPPORTUNITY! A VALUE FOR THIS MARKET INDEED! TRULY A MUST SEE!
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Laura Toppin (407-489-0415)
7529 VILLAGE GREEN DR, WINTER PARK, FL 32792
$325,0007 Days on yellowkey MLS ID: O6396985
1 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1575 Built: 1972 Tax: $1,320 (2024)Community: Village GreenSingle Family
Taxes:$1,320
Remarks: Under contract-accepting backup offers. ***Multiple Offers Received. Please submit your highest and best offer by Monday, April 13th at 12 noon.***Buyer incentives you don't want to miss! This home qualifies for a 1% lender credit with our preferred lender. Location meets affordability with this rare opportunity in Winter Park with no HOA! With some TLC, this 3 bedroom, 2 bath home offers endless potential to make it your own. Major updates provide peace of mind, including a metal roof (2014), water heater (2024), and updated electrical panel (2012). Situated on a spacious .28 acre lot, the property features a fully fenced backyard- perfect for pets, play, or future outdoor living enhancements. Inside, you'll find a functional layout with a split-bedroom floor plan, a generous living room, and a separate family room for added flexibility. The kitchen offers ample cabinet space and room for casual dining. A 2 car garage and extended driveway provide plenty of parking. Ideally located near top rated Seminole County schools, with convenient access to UCF, SR 417, shopping, dining, and area attractions. Dont miss this incredible opportunity to own in a prime location with room to grow! Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Kim Goldin (407-712-4792)
1280 GLADIOLAS DR, WINTER PARK, FL 32792
$489,000105 Days on yellowkey MLS ID: O6370371
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1624 Built: 1983 Tax: $5,162 (2024)Community: Garden Lake Estates Unit 3Spa: NoSingle Family
Taxes:$5,162
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a New Roof 2021, screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting layout is perfect for everyday living and entertaining, and the screened pool area creates a private Florida retreat for relaxing weekends, family gatherings, or evening swims—without the bugs. Conveniently close to Winter Park’s shopping, dining, parks, and local favorites, this home offers the best of Central Florida living in a prime location. More photos coming soon—don’t miss your chance to see this one!
Listing is courtesy of: FLORIDA PRESTIGIOUS HOMES INC (754-246-2070)
Listing Agent: Ian Trumbach (754-246-2070)
1052 MANCHESTER CIR, WINTER PARK, FL 32792
$470,00082 Days on yellowkey MLS ID: O6376260
REDUCED by $5,000 (1.1%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1703 Built: 1983 Tax: $5,216 (2025)Community: Howell Estates 1St AddSingle Family
Taxes:$5,216
Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!
Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)
Listing Agent: Yuleisy Marquez (407-937-8450)
1367 TIERRA CIR, WINTER PARK, FL 32792
$424,90086 Days on yellowkey MLS ID: O6375221
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2083 Built: 1969 Tax: $4,948 (2024)Community: Casa AlomaSingle Family
Taxes:$4,948
Remarks: Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers unique architectural appeal paired with thoughtful modern enhancements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers excellent curb appeal and outdoor functionality. Inside, the home has seen numerous recent updates, including new quartz kitchen countertops (2025), updated bathrooms, and updated walls and flooring throughout. The bonus room provides flexibility for use as an additional bedroom, home office, or secondary living area. Major system improvements include PEX plumbing, a newly installed 17 SEER AC system, a new water heater, electrical updates completed in 2008, and a metal roof installed in 2013 over 1x12 tongue-and-groove decking, offering exceptional strength and longevity. The home is protected by an active termite bond, with Sentricon installed in 2025. The backyard is highlighted by a 15’ x 30’ in-ground pool, a new vinyl fence (2023), and a five-zone in-ground sprinkler system with a programmable timer. The property is located in Flood Zone X (no flood insurance required) and has no HOA. Enjoy an excellent location known for top-rated schools, just minutes from AdventHealth, Full Sail University, FL-436, and an abundance of shopping and dining options. Do not miss the opportunity to purchase a well-maintained home with proven rental income and long-term investment potential.
Listing is courtesy of: SOUTHERN LAND & HOMES (850-973-2200)
Listing Agent: Benjamin Jones (850-673-7888)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000162 Days on yellowkey MLS ID: O6357934
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1719 Built: 1977Monthly Fee: $95Community: Windward Square Sec 1Townhouse
Taxes:$0
Remarks: 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 Agent: George Freelove (407-408-5167)
7485 ALOMA PINES CT, WINTER PARK, FL 32792
$390,0006 Days on yellowkey MLS ID: O6398259
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1787 Built: 2017Monthly Fee: $407 Tax: $4,585 (2025)Community: Aloma TrailsSpa: NoTownhouse
Taxes:$4,585
Remarks: Experience the perfect blend of luxury and convenience in the highly sought-after GATED community of Aloma Trails. This meticulously maintained 3-bedroom, 2.5-bathroom townhome, built in 2017, offers 1,787 sq. ft. of living space designed for comfort and modern style. Step inside to find an inviting open-concept first floor featuring beautiful ceramic tile flooring and high ceilings. The gourmet chef’s kitchen is a true standout, boasting upgraded granite countertops, a stylish tiled backsplash, 42” solid wood cabinetry, and a large island with plenty of breakfast bar seating. The full suite of stainless steel appliances makes this kitchen as functional as it is beautiful. The second level features plush carpeting throughout the bedrooms for ultimate comfort. The oversized Master Suite is a private sanctuary, complete with a massive walk-in closet and a spa-like en suite bathroom featuring a glass-enclosed shower, dual-sink vanity, and expansive cabinetry. Two additional well-appointed bedrooms share a second full bath, while the dedicated interior laundry closet adds a layer of daily convenience. Uniquely positioned with a spacious 2-car garage and a private paved driveway, this home easily accommodates multiple vehicles. The community of Aloma Trails provides a true "lock-and-leave" lifestyle with hassle-free lawn care and pristine common areas included in the HOA. Active lifestyles will thrive with the Cady Way Trail and Cross Seminole Trail just steps from your front door. For fitness buffs, Crunch Fitness is located directly across from the community entrance. Retail: 3 minutes to Walmart, Costco, and Publix. Education: Zoned for top-rated Seminole County Schools and minutes from UCF and Full Sail University. Entertainment: Short drive to the world-class dining and shopping of Park Avenue in Winter Park. Commute: Easy access to SR 417 puts you at the airport in 20 minutes or the beach in just 40! Don't miss your chance to own a piece of Winter Park luxury in a premier gated enclave.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Gunel Aydamirli (407-907-7704)
3711 VINSETTA CT, WINTER PARK, FL 32792
$1,350,00083 Days on yellowkey MLS ID: O6376139
5 Days Off yellowkey (back on 4/13/2026)
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4214 Built: 2015Monthly Fee: $178 Tax: $7,488 (2025)Community: Lakeside EstatesSingle Family
Taxes:$7,488
Remarks: Under contract-accepting backup offers. Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater pool, framed in by a podocarpus hedge for privacy, creating a backdrop for entertaining. An additional green space behind hedge for plenty of room to grow. This home has all functions you need with a formal dining and living spaces alongside a spacious family room that is open to kitchen and overlooks backyard. The island takes center stage with a waterfall edge feature and bar seating, custom 42-inch cabinetry, stainless appliances, a cozy eat-in kitchen nook with loads of workspace and closet pantry for ease of storage. A fantastic first-floor guest suite or flex space makes working from home easy. Go upstairs to where all the fun happens. A super large bonus room has additional home theatre rooms accessed through stylish barn doors and it is all snuggled in, everyone will want to stay. Primary suite enjoys a large walk-in closet and a spa bath retreat with soaking tub, walk-in shower and dual vanities. Other features of the home include wood floors throughout, custom window treatments, custom pool with paver decking and a summer kitchen with an abundance of privacy, professionally landscaped, three-car tandem garage with brick drive, long-lasting barrel tile roof, designer light fixtures and more. Lakeside Estates offers exclusive access to a community pier, playground and a boat dock for non-motor kayaks, fishing, canoes, paddleboards and more. In the highly rated Seminole County School district as well as minutes from Trinity Prep, Geneva School, Christian Circle and more. Enjoy world-class restaurants, shopping and beautiful parks and trails, close to major roadways, UCF, Valencia and downtown Orlando. A pristine location, coupled with a unique Winter Park community, is a rare find. Homes do not come along in this neighborhood often, making it a special opportunity for the discerning buyer.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
2020 COCOS CT, WINTER PARK, FL 32792
$459,99034 Days on yellowkey MLS ID: O6389901
REDUCED by $4,910 (1.1%) on 04/06/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1715 Built: 1966 Tax: $1,410 (2024)Community: Eastbrook Sub Unit 8Spa: NoSingle Family
Taxes:$1,410
Remarks: One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright open-concept layout with abundant natural light and a seamless flow between the living, dining, and kitchen areas—ideal for both everyday living and entertaining. The updated kitchen features modern cabinetry, stainless steel appliances, and generous counter space. Both bathrooms have been tastefully renovated, and the spacious bedrooms provide comfort and flexibility. Step outside to a private backyard with a sparkling pool and plenty of outdoor space perfect for relaxing or hosting gatherings. Additional highlights include a 1-car garage, roof replaced in 2016, updated electrical, and a newer water heater (2021). Located within the top-rated Seminole County school district and just minutes from Park Avenue, Rollins College, shopping, dining, museums, and Winter Park Hospital. A fantastic opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Julimar Barreiro Pastrana (407-590-8604)
7796 FERNBROOK WAY, WINTER PARK, FL 32792
$290,00027 Days on yellowkey MLS ID: O6392180
REDUCED by $10,000 (3.3%) on 04/13/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1332 Built: 1985Monthly Fee: $110 Tax: $3,296 (2024)Community: Fernbrook Trails Ph 3Townhouse
Taxes:$3,296
Remarks: Excellent price in Winter Park! On a quiet cul-de-sac in Seminole County just off Howell Branch Road, this inviting townhouse offers comfort and convenience in a desirable location. Inside, you’ll find a bright, spacious living room with large windows, a cozy dining nook adjacent to the kitchen with extensive cabinets, and a flexible first-floor third bedroom used as an office/gym that can easily convert to a bedroom again. Upstairs features generously sized bedrooms and a hall bath. The home has been recently painted inside and offers new laminate flooring upstairs, with tile and LVP throughout the main floor. Outside, enjoy a covered front porch, fenced backyard, storage shed and an extended driveway. The roof and air conditioner were replaced in 2018. With low monthly HOA dues of $110 that include lawn maintenance, this home offers easy, low-maintenance living. Along beautiful tree-lined streets with mature oak canopies, this neighborhood offers a peaceful, shaded setting that enhances everyday living. Conveniently just five miles from Park Avenue shopping and dining and three miles from Red Bug Lake Park, with quick access to SR 417, this home provides a balance of nearby amenities and quiet, established surroundings.
Listing Agent: Carrie Bantel (321-217-8750)
256 LEWFIELD CIR #256, WINTER PARK, FL 32792
$184,90095 Days on yellowkey MLS ID: O6367842
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 927 Built: 1973Monthly Fee: $465 Tax: $1,916 (2025)Community: Stratford A Winter Park CondoCondo
Taxes:$1,916
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)
1174 WILDMEADOW RUN, WINTER PARK, FL 32792
$669,90016 Days on yellowkey MLS ID: O6394974
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1770 Built: 2021Monthly Fee: $150 Tax: $6,672 (2025)Community: Hawks CrestSingle Family
Taxes:$6,672
Remarks: Welcome to 1174 Wildmeadow Run in Winter Park’s gated Hawk’s Crest community. Located on a quiet, non-thru street, this SINGLE-STORY residence offers modern construction, refined finishes, and a comfortable, well-designed layout in the heart of Winter Park. Built in 2021, the home was thoughtfully planned for everyday living and easy entertaining. The open-concept design feels light and welcoming, featuring WOOD-LOOK TILE FLOORING, crown molding, recessed lighting, CUSTOM PLANTATION SHUTTERS, and ENERGY-EFFICIENT DOUBLE-PANE WINDOWS throughout the main living areas. At the center of the home, the kitchen is both functional and inviting, offering quartz countertops, stainless steel appliances, white cabinetry with crown molding, a custom backsplash, a PREP ISLAND, and a SECOND LARGE ISLAND WITH SEATING that naturally draws people together in the living and dining spaces. Just off the main living area, a FRENCH-DOOR FLEX ROOM provides a quiet, flexible space that works beautifully as a formal dining room, home office, or additional living area. The primary suite is positioned for privacy and offers a relaxing retreat with a TRAY CEILING, generous walk-in closet, and a well-appointed en-suite bath featuring a dual-sink quartz vanity, upgraded cabinetry, and a GLASS-ENCLOSED WALK-IN SHOWER. Two additional bedrooms are well positioned in this split plan and share a FULL BATHROOM WITH A TUB AND SHOWER COMBINATION and a QUARTZ VANITY, while a SEPARATE HALF BATH WITH PEDESTAL SINK is conveniently located for guest use. A TRIPLE SLIDING GLASS DOOR opens from the main living area to a COVERED REAR LANAI overlooking a FULLY FENCED BACKYARD with room to accommodate a FUTURE POOL, creating an easy indoor-outdoor connection that’s ideal for morning coffee, relaxed evenings, or casual gatherings. Additional features include a two-car garage with built-in storage, BRICK PAVER DRIVEWAY, TERRACOTTA TILE ROOF, GUTTERS, smart-home and security pre-wiring, and an HVAC SYSTEM WITH AN UPGRADED IONIZATION FEATURE DESIGNED TO HELP PURIFY THE AIR. Hawk’s Crest is a gated community known for its RESORT-STYLE AMENITIES, including a lakeside pool, fitness center, clubhouse, splash pad, playgrounds, walking trails, BBQ areas, and SCENIC COMMUNITY DOCKS AND BOARDWALKS. Lawn care and landscaping are included. Ideally located near Winter Park dining, shopping, and everyday conveniences. AVAILABLE FOR PRIVATE SHOWINGS.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Kara Lushear (321-663-5550)
3463 ARNEL DR, WINTER PARK, FL 32792
$459,90030 Days on yellowkey MLS ID: O6390301
REDUCED by $20,000 (4.2%) on 04/12/2026
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: PRICE IMPROVEMENT!! Your pool home in Winter Park just became an even better opportunity. This home offers 3 bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, with a 2-car garage and extended driveway for extra parking — all located in the established Eastbrook community with NO HOA. Major updates already done for you: roof 2018, solar panels 2020 (fully paid off), water heater 2019, and AC replaced in July 2013. A home warranty through First American Home Warranty is included, giving added peace of mind on major systems. Inside, you’ll find a bright and functional layout with comfortable living and dining spaces that flow naturally. The kitchen has been updated with granite countertops and modern cabinetry, and both bathrooms feature clean, updated finishes. The bonus room gives you flexibility — perfect for a home office, gym, playroom, or even a 4th bedroom setup. Step outside to your fully fenced backyard with a private pool — ideal for relaxing, entertaining, and enjoying Florida living year-round, with a great balance of pool deck and green space. Location is key — just minutes to Park Avenue, Rollins College, Full Sail University, and University of Central Florida, plus easy access to major highways and top-rated Seminole County schools. With the new price, this is a strong opportunity in Winter Park — especially for buyers looking for space, a pool, and no HOA.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
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