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8061 Pleasant Pine Circle, Winter Park
$750,000
5 Beds ⋅ 4 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code
Welcome to this great 5 bedroom, 3 and a half bathroom almost 3500 square foot Winter Park home! The home not only has these spaces but also is in excellent condition with; new interior paint, new carpet, 2 heating and cooling systems replaced in 2024! The open concept center island kitchen has upgraded counters, 42" cabinets and a double convection oven! Downstairs there is a formal living and dining room, an open concept kitchen, nice warm low maintenance ceramic tile, a convenient downstairs bedroom that would also be a great office/craft/game/guest room!! Upstairs are the other private bedrooms and a huge bonus theater/media/entertainment space.. The oversized primary bedroom is upstairs for complete privacy and has a well appointed bathroom as well as two walk in closets!! Come home and relax in your fenced back yard that has a peaceful forest behind it, set up a hammock and.... This fine gated community is located so close to so much, The University of Central Florida, Winter Park, Downtown Orlando, Trinity Preparatory Academy, The Masters Academy, The Geneva School, the Space Coast, Cocoa Beach and more!!

8061 Pleasant Pine Circle, Winter Park

3409 Ferndell Drive, Winter Park
$415,900
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bathroom home in Winter Park’s established Eastbrook community, with no HOA! New front entrance door and windows, recessed lighting in the spacious living room, and new stainless steel kitchen appliances bring fresh appeal to the home. Two sliding glass doors draw natural light into the living area and connect it to the covered, screened porch. A separate dining room sits alongside the kitchen, where ample cabinetry, bar seating, and a colorful subway tile backsplash create an inviting space for everyday meals and entertaining. Enjoy outdoor living with a covered, screened porch overlooking the fenced backyard, an above-ground pool for sunny Florida days, and room to relax, garden, or entertain. Two backyard storage sheds provide additional space for tools, outdoor equipment, and recreational gear. A standout feature is a separate room within the garage area, complete with a barn door, a dedicated A/C unit, and electrical outlets, an inviting space for a home office, hobby room, or creative projects. Major updates include a roof replaced (2023) and air conditioning (2021) and a water heater replaced (2021). Conveniently located near Advent Hospital, Full Sail University, Rollins College, downtown Winter Park, and shopping and dining, this home combines thoughtful updates with versatile spaces inside and out. Schedule your private showing today!

3409 Ferndell Drive, Winter Park

2356 Shadowland Loop, Winter Park
$460,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Stylish 3-bedroom, 2.5-bath end-unit townhome in the gated Enclave at Hawks Crest community in Winter Park! This bright, open-concept home features newer luxury vinyl plank (LVP) flooring, abundant natural light, a spacious kitchen with a large center island and stainless steel appliances, and an inviting living and dining area. Enjoy the convenience of an upstairs laundry room, a 2-car garage, and a double-sized covered porch perfect for relaxing or entertaining. Community amenities include a swimming pool and playground. Conveniently located near Winter Park shopping, restaurants, and entertainment, with easy access to SR 417, UCF, Full Sail University, and major Central Florida destinations. Don't miss this opportunity to enjoy comfortable, low-maintenance living in a desirable gated community!

2356 Shadowland Loop, Winter Park

216 Lewfield Cir Unit 216, Winter Park
$230,000
3 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condominium SubDv. ⋅ 32792 Zip Code
Rare Find - 3 BR/2 BA - 2nd Floor CONDO at The Stratford a Winter Park Condominium! Spacious Living Room accesses 2nd Floor Balcony with a gorgeous view of one (1) of the sparkling community pools. Balcony features additional outside storage room. Dining/Breakfast Nook adjacent to Living Room & Kitchen. Kitchen features refrigerator, electric range, dishwasher, microwave, garbage disposal, pantry, and laundry closet with stackable washer/dryer. Nice sized bedrooms, see attached floor plan. Primary Suite features walk in closet, walk in shower and tile flooring. Guest Bath features tub & shower and tile flooring. Unit conveniently located at back of community by both community pools and tennis courts. Lovely shady, treed community with sidewalks, Clubhouse, two (2) Pools, BBQ areas, and Tennis Court. HOA Fees Cover: trash removal, water, internet only, amenities maintenance, landscaping, and roof. Community Docs and 2026 Budget available for review. Conveniently located to shopping, parks, restaurants, and major transportation routes. Property sold "AS IS", it won't last long!

216 Lewfield Cir Unit 216, Winter Park

2174 Shadyhill Terrace, Winter Park
$529,900
4 Beds ⋅ 2 Baths ⋅ Autumn Glen Ph 3 SubDv. ⋅ 32792 Zip Code
Tucked near the quiet end of Shadyhill Terrace, a few doors down from the lake, this four-bedroom pool home sits in Autumn Glen, one of Winter Park’s most sought-after neighborhoods, where homes rarely come up for sale. Picture opening your electric bill in the middle of a Florida summer and seeing a bill of ~$75 or less. That’s the average here, thanks to the 12.5 kW Enphase solar system that cost $65,000 and is fully paid off: no lease, no loan, nothing to assume. The rest of the house was upgraded with the same long view. The ROOF and AC are both under five years old, the argon-filled, double-pane hurricane-resistant windows throughout the main house that were recently installed keep the house quieter and cooler year-round. The home may also qualify for wind mitigation discounts on homeowners insurance. The Tall double doors open to four bedrooms and two baths, finished with modern lighting, ceiling fans and a custom built-in bookshelf. The updated kitchen, with granite counters and stainless steel appliances, looks straight into the family room, so whoever’s cooking stays part of the conversation. Out back, slide open the Florida room’s removable windows, let the breeze in, and look out over the screened salt water pool, running on a new energy-efficient Hayward pump. A two-car garage keeps the cars and pool gear out of the weather. The home sits near the end of a quiet dead-end street that finishes at the lake, in Autumn Glen, where sidewalks lead to the community park, playground and tennis courts. It’s zoned for Red Bug Elementary, Tuskawilla Middle and Lake Howell High, with Red Bug Lake Park and the Cross Seminole Trail close by, the 417 and 436 minutes away, and Park Avenue, UCF and Full Sail all an easy drive.

2174 Shadyhill Terrace, Winter Park

1931 Aster Drive, Winter Park
$575,000
3 Beds ⋅ 3 Baths ⋅ Garden Lake Estates Unit 2 SubDv. ⋅ 32792 Zip Code
MOVE-IN READY, BEAUTIFULLY UPDATED, AND DESIGNED FOR FLORIDA LIVING! Welcome to 1931 Aster Drive, where modern upgrades, inviting living spaces, and your own private screened pool come together on an expansive .30-acre corner lot in Winter Park! This beautifully maintained 3-bedroom, 2-bath home offers 2,031 square feet of light-filled living space, PLUS a versatile bonus room ideal for a home office, second living area, or flex space to fit your lifestyle. Soaring vaulted ceilings, fresh interior paint, and NEW luxury vinyl plank flooring create a bright, open, and welcoming atmosphere throughout. At the heart of the home, the beautifully updated kitchen impresses with crisp white shaker cabinetry, elegant quartz countertops, a stylish tile backsplash, stainless steel appliances, built-in microwave, custom wine rack, and an oversized island with seating for four—perfect for everyday living and entertaining. The desirable split-bedroom floor plan provides privacy, while the completely renovated primary bathroom offers a spa-inspired retreat featuring a dual-sink quartz vanity, updated fixtures, tile flooring, and a stunning seamless glass-enclosed shower. Step into the enclosed lanai, an inviting extension of your living space, before heading outside to your private screened pool and spacious backyard—ideal for weekend gatherings, relaxing afternoons, and year-round Florida enjoyment. MAJOR UPDATES ALREADY COMPLETED! Enjoy peace of mind with a NEW ROOF (2025), NEW HVAC (2026), NEW POOL SCREENS, NEW POOL PUMP, NEW FENCE, NEW IRRIGATION SYSTEM, and FRESH LANDSCAPING! See the home features sheet for the complete list of improvements. Tucked into a peaceful Winter Park neighborhood, this exceptional property offers convenient access to Red Bug Road, SR 417, shopping, dining, and everyday essentials. Trinity Preparatory School is approximately 10 minutes away, A rated public schools and Central Florida’s world-famous attractions and beautiful East Coast beaches within easy reach. BEAUTIFULLY UPDATED, INCREDIBLY INVITING, AND READY FOR ITS NEXT OWNER! Don’t miss your opportunity to experience the space, style, and poolside lifestyle of 1931 Aster Drive. Schedule your private showing today!

1931 Aster Drive, Winter Park

2228 King Charles Court, Winter Park
$575,000
4 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
Virtually Staged. PRICED TO SELL, UNDER APPRAISED VALUE!! Come check out this GORGEOUS, SOLID 4/5 BR, 3 BA, 2,500+ sqft home in Winter Park with everything you need. This exceptional concrete block home was built to last, and major systems are current, updated, and documented. This home is MOVE-IN READY! Step inside and you’ll FEEL the difference. Fresh, neutral paint throughout and new vinyl flooring in both living areas create a light, welcoming backdrop. The kitchen, remodeled in 2023, shines with gleaming quartz counters, backsplash, shaker cabinets, and a breakfast bar. Upstairs, the HUGE master bedroom features a fireplace and balcony overlooking a large backyard—your personal private retreat! The bottom level offers GREAT flexibility—configure it as an IN-LAW SUITE with its own private bath and patio with French doors, or as a second living room and Florida room. Out back is where you’ll actually WANT to spend time with family and friends! Enjoy a naturally shaded deck every morning and evening. The oversized garage has a FAST EV charger. The property also comes with a large storage building with electricity AND a smaller shed. Major systems and structural upgrades include: HURRICANE-RATED double-pane windows and exterior doors opening to 4 feet! (2024), full home replumb (PEX-A), roof (5 years), electrical brought to current code (2025), water heater (2025), attic insulation with SOLAR FAN and sealed opening, and a high-efficiency Lennox AC (5-ton, 16 SEER) maintained yearly. Energy monitoring system included. Located in Seminole County’s top-rated school district, it is 15 minutes from Full Sail, 20 minutes from Rollins, and 30 minutes to UCF. This is the home that checks off all the boxes! MOTIVATED SELLER!!

2228 King Charles Court, Winter Park

2067 Poinciana Road, Winter Park
$560,000
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 04 SubDv. ⋅ 32792 Zip Code
No need to look further! This move-in-ready 4-bedroom, 2-bathroom home in Winter Woods is ready for you! Enjoy a fenced yard, no rear neighbors, lush greenery, and private country club views. Inside, you are greeted by a modern Scandinavian-inspired kitchen and split-bedroom floor plan. The primary suite offers a bonus room, walk-in closet, and private bath, while three additional bedrooms and a second full bath complete the home. All appliances are included, plus a generator that connects through the electrical panel—an ideal Florida feature during power outages. The owner is open to negotiating other select furnishings throughout the home. Conveniently located near Semoran Boulevard/SR 436, with easy access to Winter Park amenities. Schedule your showing of 2067 Poinciana Road today!

2067 Poinciana Road, Winter Park

2020 Leanne Court, Winter Park
$479,900
4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 14 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome home to 2020 Leanne Ct, a spacious pool residence offering versatile living and classic Florida charm in Winter Park! According to updated Seminole County tax and public records, this property features 4 bedrooms, 3 full bathrooms, and 2,088 square feet of functional interior living space set on an expansive 0.31-acre lot (13,504 sq ft). Inside, bright common areas feature formal living and dining spaces alongside a open central kitchen with breakfast bar overlooking a cozy family room. The desirable split-bedroom floor plan includes four well-proportioned bedrooms and three full baths, ideal for family accommodations, a primary suite, or dedicated home workspace options. Outside, enjoy a private backyard setting complete with a sparkling swimming pool and garden space—perfect for outdoor entertaining. Conveniently located near top-rated local schools, parks, shopping, and major routes

2020 Leanne Court, Winter Park

302 Lewfield Circle Unit 302, Winter Park
$140,000
1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
ENJOY THE WINTER PARK LIFESTYLE from this charming one-bedroom, one-bath condo offering low maintenance living in a convenient Central Florida location. Step inside to a bright and comfortable floor plan with a private second floor balcony that extends the living space outdoors, perfect for sipping coffee, reading a book, or enjoying the Florida weather. The community offers a refreshing pool and clubhouse, providing additional spaces to relax and enjoy. Located just minutes from the shops and restaurants of Park Avenue, Rollins College, local parks, and everyday conveniences, you’ll have easy access to everything that makes Winter Park such a desirable place to call home. A great opportunity for a full-time residence, seasonal getaway, or anyone looking to enjoy a simplified lifestyle in Winter Park! Listing photos have been virtually staged for visualization and illustrative purposes only. The property is currently vacant and move-in ready.

302 Lewfield Circle Unit 302, Winter Park

2052 Wood Thrush Lane, Winter Park
$900,000
4 Beds ⋅ 3 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to Waters Edge at Hawks Crest, one of Winter Park’s premier gated communities! This beautifully appointed 4-bedroom, 3-bath home offers nearly 3,000 square feet of thoughtfully designed living space, exceptional curb appeal, and an outdoor entertaining area that truly sets it apart. Step inside to a welcoming foyer flanked by a formal dining area and a versatile formal living room with double doors—perfect for a home office, den, or flex space. At the heart of the home is an impressive gourmet kitchen featuring quartz countertops, a large center island with stainless undermount sink, wall oven/microwave combination, cooktop with stainless steel range hood, metallic hexagon tile backsplash, modern pendant lighting, and a technology-equipped refrigerator. The kitchen flows seamlessly into the casual dining and family room, creating an open-concept gathering space filled with natural light from oversized triple sliding glass doors. An electric shade provides added privacy and makes movie nights a breeze. The spacious primary suite offers a striking stacked-stone entry and a separate flex area ideal for a sitting room, office, nursery, or workout space, with direct access to the lanai. The ensuite bath features dual quartz vanities, a soaking tub, large tiled shower, private water closet, and an impressive custom-designed walk-in closet with abundant storage. The split-bedroom floor plan provides three additional bedrooms, two full baths—including a convenient pool bath—and a dedicated laundry room. The garage offers additional storage racks, while solar-powered Tesla panels and two Powerwalls add another notable feature to the home. The showstopper is the expansive screened lanai, designed for year-round Florida living and entertaining. Multiple conversation and dining areas, an outdoor kitchen, TV area, oversized premium spa with additional jets, and app-controlled lighting create the perfect setting for everything from intimate evenings to large gatherings. A 6-foot privacy fence completes this private backyard retreat. Residents of Hawks Crest enjoy an impressive collection of community amenities, including a clubhouse with indoor and outdoor entertaining spaces and grills, resort-style pool, splash pad, playgrounds, fitness center, putting green, outdoor games, dog park, neighborhood parks, and access to a community dock on Lake Howell.

2052 Wood Thrush Lane, Winter Park

7348 Grand Avenue, Winter Park
$285,000
3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code
Welcome! This three-bedroom, two-bathroom home in Winter Park presents a genuine opportunity for buyers ready to reimagine this one-story residence. The open floor plan creates a flexible living space, and the thoughtful layout gives you a solid foundation to work with. Inside, the cathedral ceiling in the main living area draws the eye upward and enhances the sense of openness throughout the home. The covered rear lanai extends your entertaining and living space outdoors, perfect for relaxation or gatherings. The location delivers great convenience, with proximity to Publix-anchored shopping and Walmart for everyday needs, Red Bug Lake for outdoor recreation activities, grade schools, and the Winter Park Village for shopping and dining. Schools are nearby, making this neighborhood accessible for residents. The central location means you're less than 30 minutes from Orlando International Airport, Universal, Downtown Orlando, and UCF, offering both lifestyle flexibility and strong rental demand drivers for those considering income-producing use. Convenient access to major roadways makes commuting and daily needs straightforward. Schedule your private showing today and bring your vision for what this home can become.

7348 Grand Avenue, Winter Park

5303 Pine Lily Circle, Winter Park
$659,000
3 Beds ⋅ 2 Baths ⋅ Sanctuary At Aloma SubDv. ⋅ 32792 Zip Code
POOL HOME IN WINTER PARK! Beautifully maintained 2015-built one-story in the quiet, gated community of Sanctuary at Aloma, offering 2,265 sq ft with 3 spacious bedrooms, a dedicated den/flex/home office, and a separate formal dining room, all on one level with no stairs. The open-concept great room flows into a light-filled kitchen featuring a large center island, stone countertops, a sleek backsplash, and abundant cabinetry, perfect for entertaining. The private primary suite is a true retreat with a separate soaking tub and shower plus plenty of storage. Secondary bedrooms are well sized with great closet space. Step outside to your screen-enclosed in-ground pool, added in 2020, with a covered sitting area and a fully fenced, beautifully landscaped backyard, privacy rarely found at this price point. Additional features include tile and laminate flooring, an owned security system, an attached 2-car garage, public water and sewer, and excellent curb appeal with stucco exterior and carriage-style garage door. Low quarterly HOA and NO CDD. Minutes from SR-417 at Aloma Ave, placing UCF, Research Park, Oviedo, and downtown Orlando within an easy commute. Close to Winter Park Village, historic Park Avenue, Full Sail, Rollins College, and Orlando International Airport. All information deemed reliable but not guaranteed; buyer and buyer's agent to verify all measurements and features. Schedule your private showing today!

5303 Pine Lily Circle, Winter Park

4260 Bear Gully Road, Winter Park
$599,000
4 Beds ⋅ 4 Baths ⋅ Bear Gully Forest SubDv. ⋅ 32792 Zip Code
RENOVATED 4 BED / 3.5 BATH TWO-STORY | GOURMET KITCHEN | LUXURY VINYL FLOORING | ROOF 2018 | FENCED BACKYARD | CLOSE TO ALOMA AVE & SR 417 Welcome to 4260 Bear Gully Road, a beautifully updated, move-in-ready home for anyone who wants a truly nice place to live. The heart of the home is the gourmet kitchen, fully remodeled just two years ago with upscale cabinetry and modern appliances, perfect for everyday meals and entertaining. Luxury vinyl flooring gives the home a clean, modern look that is easy to maintain. With four bedrooms and four full bathrooms across two stories, everyone has room and privacy, whether for family, guests or a home office. Enjoy the screened lanai and the fenced backyard, ready for pets, play and weekend get-togethers. Added peace of mind: roof replaced in 2018, concrete block and stucco construction, and Flood Zone X. Location is a major plus. You're near the Publix-anchored shopping, dining and services along Aloma Avenue, AdventHealth Winter Park, and the Cross Seminole Trail, with easy access to SR 417 (Central Florida GreeneWay). Winter Park Village and the boutiques and restaurants of Park Avenue are a short drive away. Served by Seminole County Public Schools: Eastbrook Elementary, Tuskawilla Middle and Lake Howell High (buyer to verify). Schedule your showing today!

4260 Bear Gully Road, Winter Park

5080 Seminole Avenue, Winter Park
$299,900
3 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code
FULLY FURNISHED and ready for its next owner! This 3-bedroom, 2-bath Winter Park home offers an excellent combination of recent improvements, location, and flexibility. Major updates include a NEW ROOF (2021), FULL HOUSE REPIPE (2025), and NEW FLOORING (2025), giving buyers peace of mind on several important big-ticket items. Situated on an OVERSIZED 0.24-ACRE LOT with NO HOA, the property offers a spacious yard with plenty of room to enjoy the outdoors. Inside, the home features a comfortable and functional layout with an eat-in kitchen, indoor laundry, and inviting living spaces. Even better, the home is being sold FULLY FURNISHED, making it an easy option for a primary residence, second home, or investment property. The location is hard to beat, with convenient access to Full Sail University, Rollins College, UCF, Park Avenue, Baldwin Park, shopping, dining, and major roadways connecting you throughout Central Florida. With NO HOA and short-term rental potential, this property provides flexibility that can be difficult to find in Winter Park. Whether you're looking for a place to call home or an investment opportunity, 5080 Seminole Ave is ready for its next chapter!

5080 Seminole Avenue, Winter Park

1386 Clematis Lane, Winter Park
$427,000
4 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 06 SubDv. ⋅ 32792 Zip Code
LOCATION! LOCATION! Winter Park property located in Seminole County. Proximity to Rollins, Full Sail, UCF, and Valencia colleges. Great income producer, with "Flex Space" as a two income rental or live on one side and rent the other. Main area has 3 bedrooms and 2 full baths, flex space has a private entrance, 1 bedroom and full bath, kitchenette, and it's own laundry area. Two driveways and parking pad for your use. Great side and separate rear yard, with lard storage shed, Home was recnently updated, with fresh paint, granite countertops, shaker cabinets, updated bathrooms, new windows, new mini-splits in flex space and tankless water heater. Fully fenced in backyard and mature trees. Plumbing has already been updated to PEX, cast iron wasteline has been updated to PVC. New flooring in main house, new baseboards installed, and freshly painted. MOVE IN READY!

1386 Clematis Lane, Winter Park

7560 Aloma Pines Court, Winter Park
$355,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Welcome to 7560 Aloma Pines Ct, a move-in-ready 3-bedroom, 2.5-bathroom townhome offering 1,866 square feet of comfortable living space in a gated Winter Park community. Built in 2016, this thoughtfully designed home offers a practical layout with plenty of space to spread out, including a primary suite conveniently located on the second floor. The kitchen features stone countertops and opens naturally to the main living areas, creating an easy flow for everyday living and entertaining. Tile and carpet flooring run throughout the home, while the attached one-car garage adds everyday convenience and storage. Step outside and enjoy the ease of low-maintenance townhome living without giving up the comfort of having your own private residence. The gated community provides an added sense of privacy, while the home's location puts you close to the shopping, dining, schools, and everyday conveniences that make the Winter Park area so desirable. Whether you're looking for your first home, a place to simplify your lifestyle, or an investment property in a convenient Central Florida location, 7560 Aloma Pines Ct offers a comfortable combination of space, functionality, and location. Move in, settle in, and enjoy everything Winter Park and the surrounding area have to offer.

7560 Aloma Pines Court, Winter Park

2301 Conifer Avenue, Winter Park
$405,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code
VIRTUALLY STAGED! EXCEPTIONAL POOL HOME IN EASTBROOK! Welcome to Conifer Avenue, where pride of ownership, and an unbeatable Winter Park-area location come together beautifully. This impressive pool home offers an outstanding opportunity to own a well-maintained residence in the highly sought-after Eastbrook community. This FOUR BEDROOM 2 Bath home offers almost 2200 square feet! Split bedroom plan PLUS 21 x 12 office/bonus room; formal living, dining & family rooms;2024 NEW HVAC-POOL PUMP 2025-ROOF 2019-zoned for excellent Seminole County Schools! Oversized 20 x 22 two car garage with additional storage space. Extras include: updated windows; all appliances including washer & dryer; quaint front porch. Call for your private showing! Step outside and discover your own private retreat! Multiple sets of sliding glass doors open to the large screened-in lanai, sparkling swimming pool, and expansive pool deck, creating an exceptional indoor-outdoor living and entertaining space. The nearly quarter-acre lot is fully fenced, offering plenty of room for pets, play, gardening, and outdoor enjoyment. The oversized two-car garage provides generous parking and an abundance of storage options. This is truly an entertainer's dream home—whether you're hosting friends around the pool, enjoying a quiet evening outdoors, or simply relaxing in your own private backyard oasis. And then there's the LOCATION! LOCATION! LOCATION! Convenient access to I-4 and SR 417 makes traveling throughout Central Florida a breeze, with easy access toward Orlando's attractions, Disney, the beaches, shopping, dining, and entertainment. Enjoy being close to the charm of Historic Downtown Winter Park and Park Avenue, including its fabulous restaurants, boutique shopping, cultural attractions, and popular weekly Farmers Market. SunRail is also conveniently nearby, providing another great transportation option throughout Central Florida.

2301 Conifer Avenue, Winter Park

2302 Barbados Drive, Winter Park
$275,000
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment and major roadways. This spacious end-unit home offers 2 bedrooms, 2 full bathrooms with 1,544 square feet of living space. The home adds fabulous sun room with French doors to a private rear space. Originally designed as a 3-bedroom home, the third bedroom has been converted into a versatile flex room—ideal for a home office, den, hobby room or additional living space. The primary suite features a spacious walk-in closet with custom built-ins. Recent updates include a new roof in 2023, new flooring, fresh interior paint and more. As an end unit, the home provides additional privacy and a more open feel than interior units. The enclosed sunroom offers additional space for relaxing, entertaining or enjoying your morning coffee. Windward Square residents enjoy community amenities including a swimming pool and tennis courts. The convenient location provides easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this move-in-ready home offers space, flexibility and an excellent Winter Park location.

2302 Barbados Drive, Winter Park

2622 Lake Howell Lane, Winter Park
$3,750,000
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, water sports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property features a full 50 amp RV hookup with water and sewer hookups. The property is Agriculture zoned and allows horses. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating—the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home—it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

2622 Lake Howell Lane, Winter Park

1257 Wading Waters Circle, Winter Park
$1,550,000
6 Beds ⋅ 5 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most coveted premium lots, featuring a larger lot line, wooded HOA land behind the property, and serene views toward Lake Howell. The thoughtfully designed floor plan offers two primary suites, one on each level, plus a dedicated office, a theater room, a loft, and a three-car tandem garage with built-in shelving and a workbench. Designer finishes include Restoration Hardware and Pottery Barn chandeliers, plantation shutters, crown molding, motorized blinds, app-controlled LED trim lighting, and custom built-ins throughout the home. The resort-style backyard features a saltwater, solar-heated pool, expansive pool deck, motorized Sunpro awnings, landscape lighting, and lanai market lights—perfect for entertaining or relaxing in complete privacy. Additional upgrades include a custom entertainment center with an electric fireplace, a Sony theater system and projector in the media room, a water softener, gutters, and extensive custom storage solutions by Inspired Closets throughout the home. The hot tub, Paradise Grill, and custom workout equipment are also available for negotiation, offering the opportunity to make this already exceptional home truly turnkey for your lifestyle. Hawks Crest residents enjoy an impressive collection of community amenities, including a resort-style pool, splash pad, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. With highly regarded private schools nearby—including Park Maitland School, The Geneva School, Trinity Preparatory School, and The Master’s Academy—along with the exceptional shopping and dining of Park Avenue, this coveted Winter Park location truly offers the best of convenience, lifestyle, and luxury. Every box has been checked. From the premium homesite to the designer finishes, custom upgrades, resort-style pool, and thoughtful details throughout, this is a home where everything has already been done—just move in and enjoy.

1257 Wading Waters Circle, Winter Park

2349 Shadowland Loop, Winter Park
$425,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to the Enclave at Hawks Crest, where this modern 3-bedroom, 2.5-bath townhome gives you 1,755 square feet of space without a long list of things to maintain. A paver driveway, two-car garage, and clean exterior make a great first impression, and inside, high ceilings and plenty of natural light keep the main level feeling open and bright. The kitchen sits right in the middle of it all with a large island, stainless steel appliances, and a walk-in pantry, opening naturally to the dining and living areas. Out back, sliding doors lead to a covered, screened patio overlooking greenspace, giving you a little breathing room without a backyard to take care of. Upstairs, the primary suite is spacious with a tray ceiling, large walk-in closet, and ensuite bath with dual sinks and a tiled shower. Two additional bedrooms sit at the opposite end of the hall, along with a second full bath and, thankfully, the laundry room is upstairs too. This home has been meticulously maintained by its original owner since 2021. The HOA handles the exterior and landscaping, and the gated community includes a resort-style pool, playground, and dog park. Zoned for A-rated Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High, and you're just minutes from Park Avenue, with Kelly's Ice Cream and Foxtail Coffee a short walk from your front door. Low maintenance, high convenience, and Winter Park right outside your door. Call today for your private showing!

2349 Shadowland Loop, Winter Park

3020 Nicholson Drive, Winter Park
$495,000
4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code
UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

3020 Nicholson Drive, Winter Park

2211 King Richards Court, Winter Park
$529,000
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated 4-bedroom, 2-bath pool home located in the highly desirable Winter Woods community of Winter Park. From the moment you step inside, you’ll appreciate the bright, open-concept floor plan, abundant natural light, and plantation shutters that complement the home’s expansive windows. The spacious living area flows seamlessly into the beautifully appointed kitchen, featuring a large center island with breakfast bar seating, stainless steel appliances, ample cabinetry, and a distinctive herringbone tile backsplash. Just off the kitchen, the dining area provides an inviting space for both everyday meals and entertaining. The private primary suite offers an ensuite bath and sliding glass doors that open directly to the pool deck, creating an effortless connection between indoor and outdoor living. A desirable split-bedroom floor plan places the three additional bedrooms and full guest bath on the opposite side of the home, offering added privacy. The laundry room provides convenient direct access to the two-car garage. Step outside to an expansive screened-in patio spanning the rear of the home and overlooking the private pool. Surrounded by tropical landscaping, this backyard retreat offers the perfect setting for entertaining, relaxing poolside, or enjoying Florida living year-round. The home has been thoughtfully maintained and updated, with improvements including a saltwater pool system (2019), asphalt shingle roof (2020), new sewer line from the home to the street and whole-home repipe (2021), kitchen and bathroom renovations (2021), new pool equipment (2023), and a new A/C system (2023). Ideally situated in Winter Park, this home offers convenient access to Downtown Winter Park, Downtown Orlando, shopping, dining, medical facilities, and major roadways. With its combination of thoughtful updates, flexible living spaces, private pool, and sought-after location, this Winter Woods home offers an exceptional opportunity to enjoy the best of Central Florida living. Schedule your private showing today.

2211 King Richards Court, Winter Park

5108 Lazy Oaks Drive Unit 5108, Winter Park
$255,000
2 Beds ⋅ 2 Baths ⋅ Lazy Oaks Condo SubDv. ⋅ 32792 Zip Code
Welcome to 5108 Lazy Oaks Drive, a 2-bedroom, 2-bathroom condo in a desirable Winter Park location. This light-filled home has approximately 1,008 square feet of comfortable living space with a functional floor plan, abundant windows, skylight and sliding glass doors that bring in plenty of natural light. The spacious living room features a beautiful brick fireplace and sliding glass door access to the screened-in back patio. The patio can also be accessed directly from the primary bedroom, creating a wonderful private outdoor space to enjoy your morning coffee, relax, or entertain. The primary suite features an en-suite bathroom with a walk-in shower, spacious two-sink vanity, and plenty of closet space. The guest bedroom is conveniently located just two steps from the second full bathroom, providing an ideal setup for family, guests, or a home office. The well-maintained original kitchen includes an electric range and oven, refrigerator, dishwasher, and two-basin stainless steel sink. Well-maintained tile flooring runs throughout the home, offering durability and easy maintenance. The spacious one-car garage has more than just parking, with a washer and dryer and plenty of additional storage space. The HOA fee is $277 per month and includes lawn maintenance and responsibility for the entire exterior of the condo, including the roof, providing added convenience and peace of mind for the homeowner. With its fresh interior, abundant natural light, brick fireplace, screened-in patio, private primary suite, attached garage, and low-maintenance lifestyle, 5108 Lazy Oaks Drive is a wonderful opportunity to own a comfortable home in Winter Park.

5108 Lazy Oaks Drive Unit 5108, Winter Park

2181 Linden Road, Winter Park
$419,990
5 Beds ⋅ 3 Baths ⋅ Ridge High 1st Add SubDv. ⋅ 32792 Zip Code
Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this home offers a versatile layout, contemporary finishes, and a private separate-entry suite that adds valuable space for guests, a home office, or additional living arrangements. With no HOA, the property offers added flexibility rarely found in this sought-after area. The location is a standout. Enjoy easy access to Winter Park’s renowned Park Avenue, with its boutiques, restaurants, cafés, galleries, and local events, while nearby Winter Park Village adds even more shopping, dining, entertainment, and everyday conveniences. Outdoor enthusiasts will appreciate close access to the Cross Seminole Trail, Lake Baldwin Park, the Winter Park Chain of Lakes, scenic parks, and recreational opportunities. Downtown Orlando, major employment centers, Advent Health Winter Park, Rollins College, Full Sail University, SR-436, SR-426, and I-4 are also conveniently accessible. Winter Park continues to invest in its future, with ongoing improvements to Park Avenue, expanded infrastructure and streetscape enhancements, and a citywide Parks & Recreation Master Plan focused on improving parks, trails, open spaces, recreation, and community facilities for years to come. This is more than a renovated home it is an opportunity to enjoy the lifestyle, connectivity, character, and continued growth that make Winter Park one of Central Florida’s most desirable places to call home.

2181 Linden Road, Winter Park

285 Lewfield Circle Unit 285, Winter Park
$147,000
1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. LOCATION, CONVENIENCE, AND EASY LIVING IN WINTER PARK! This move-in-ready first-floor, 1-bedroom, 1-bath condo features an open living and dining area, wood flooring throughout the main living areas, tile flooring in the primary bedroom, a private screened-in balcony, a fully equipped kitchen, and a stackable washer and dryer. Conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando, with easy access to shopping, dining, and major highways. Community amenities include two pools, a tennis court, fitness center, and clubhouse. HOA includes water, trash, internet, pest control, exterior maintenance, and grounds care. A great opportunity to enjoy a low-maintenance lifestyle in a highly convenient Winter Park location.

285 Lewfield Circle Unit 285, Winter Park

2857 Clever Lane, Winter Park
$399,995
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Talk about VALUE! Almost brand new and move in ready CORNER townhome in Winter Park! This beautiful 3 bedroom 2.5 bathroom home with just under 1,800 sq. ft. offers a large 2 car garage, light and bright living spaces, clean and modern designer features, and comes equipped with a full kitchen appliance package and washer/dryer. The first floor offers expansive living spaces with enough room for a dining area and family room. All of which flow seamlessly into the open kitchen. With white cabinets and Quartz counter tops, the kitchen is a show stopper! The entire first level is adorned with tile and offers a half bathroom and access to the covered back porch. Just up the stairs, you will find all of your bedrooms and full bathrooms. The primary bedroom and en suite bathroom are ample in size and also offer a large walk in closet. Both secondary bedrooms are down the hall and share a large full bathroom. The small gated community of townhomes offers a community pool and serene pond. HOA includes cable! Make sure to put this on your must see list!

2857 Clever Lane, Winter Park

1287 Verdant Glade Place, Winter Park
$745,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park

1842 Puritan Avenue, Winter Park
$419,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code
Virtually Staged. Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your storage convenience. This beautiful done home was renovated in ,2024 with lot of upgrades and it is situated in desirable winter Park , which is close proximity to shopping, downtown ,highways , airport , universities( U.C.F) etc. No H.O.A fees ,the open concept layout gives this home a sense of comfort , convenience , spaciousness and a pleasant and relaxing ambiance. The home is move in ready and the front yard is ready for your customized landscape.Be the lucky one to own this home.Roof was redone in February/2020.

1842 Puritan Avenue, Winter Park

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