Refine Search
Sort by
$519,000
3 Beds 2 Baths Kenilworth Shores Sec 07 SubDv. 32792 Zip Code
Virtually Staged. Located in the highly desirable Winter Park area, 1944 Natalen Rd offers the perfect balance of tranquility, convenience, and lifestyle. This property enjoys deeded access to serene Lake Berry while being just minutes from top-rated schools, the vibrant dining and boutique shopping of both Baldwin Park and downtown Winter Park, and everyday conveniences including nearby grocery stores and the renowned Winter Park Farmers’ Market. Residents will appreciate exceptional healthcare access with both AdventHealth Winter Park and the Orlando VA Medical Center at Lake Baldwin close by. Centrally located with easy access to UCF, Orlando International Airport, and Central Florida’s world-famous theme parks and attractions, this home provides an ideal combination of peaceful living and connectivity to everything Orlando has to offer.

1944 Natalen Road, Winter Park

$399,000
3 Beds 3 Baths Grayson Square SubDv. 32792 Zip Code
Impeccable 2-story townhome, newly built in 2024 and located in Grayson Square, a Gated Luxury Townhouse Community in enchanting Winter Park, with modern, sophisticated architecture and landscaping. The interior features the high-end Lux Fresh package, complemented by owner upgrades including light dimmers, ceiling fans, and a custom kitchen island. The chef’s kitchen is equipped with new stainless-steel appliances and expansive white stone countertops. Alabaster cabinetry with ceramic tile plus smooth stone counters adds a touch of elegance throughout. Shaw LVP floors on the main level and 2nd level bathrooms. Owner's suite with an oversized walk-in closet and a dual-sink ensuite. Spacious second and third bedrooms. 9' ceilings throughout. The first floor features a stunning open-concept living area with vinyl wood-plank flooring. Laundry closet on 2nd level. Kohler raised commodes on the 2nd level. Private patio area surrounded by lush greenery. Attached garage with 2 extra off-street parking spaces. The home includes a Ring doorbell and a rear security camera. Eeros internet modem and Extender for boosted device connectivity. includes a resort-style pool oasis with a cabana, with a view of the community lake. Competitive HOA fees cover roof replacement, Spectrum internet and TV, and general property upkeep. Situated in a manicured community with a sparkling pool, this home is close to fine dining, shopping, and entertainment, with easy access to downtown Orlando and local theme parks. It is highly rated for its proximity to quality Seminole County public schools and its convenience to daily necessities like Publix and Starbucks, as well as the shopping and dining of Park Avenue.

2808 Bright Bird Lane, Winter Park

$340,000
3 Beds 2 Baths Windward Square Sec 2 SubDv. 32792 Zip Code
Under contract-accepting backup offers. Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located in the heart of Winter Park. Offering 1,743 square feet of thoughtfully designed living space, this home combines comfort, style, and an unbeatable location just minutes from shopping, dining, parks, and top-rated schools. The desirable corner-unit placement provides added privacy, extra natural light, and a spacious feel throughout. Inside, you’ll find luxury vinyl plank flooring flowing seamlessly throughout the home and a stunning vaulted ceiling that creates an airy, open atmosphere in the living room. The beautifully updated kitchen is truly the centerpiece of the home, featuring gorgeous wood countertops, ample cabinet space, and an open-concept layout perfect for entertaining family and friends. Step outside to the rear screened-in patio and enjoy peaceful pond views in your own private outdoor retreat. Whether you’re sipping your morning coffee or unwinding after a long day, this tranquil space offers the perfect setting to relax and enjoy Florida living year-round. This exceptional Winter Park townhome is a rare opportunity you won’t want to miss.

2676 Barbados Drive, Winter Park

$299,000
3 Beds 2 Baths Windward Square Sec 1 SubDv. 32792 Zip Code
Welcome Home in the heart of Winter Park! Fantastic single-level townhouse fully remodeled with 3 bedrooms and 2 bathrooms, featuring beautiful cathedral ceilings upon entry and modern upgrades throughout. This move-in ready property offers a brand-new 2026 roof, freshly painted interior and exterior, a beautifully renovated kitchen, and fully updated bathrooms with elegant quartz countertops. Featuring a newer A/C system and new water heater, this home provides extra peace of mind for the new owners. Situated on a spacious corner lot, this home is perfect for families seeking comfort, style, and convenience. Enjoy your own private fenced backyard, ideal for relaxing, entertaining, or pets. The community offers a low HOA with fantastic amenities including a swimming pool, tennis courts, and playground. Conveniently located just 8 miles from UCF with quick access to shopping, dining, entertainment, and major highways. A perfect blend of location, lifestyle, and value!

2529 Windward Way, Winter Park

$390,000
3 Beds 2 Baths Laurel Springs SubDv. 32792 Zip Code
*MULTIPLE OFFERS! FINAL AND BEST OFFERS BY 10 PM 06/01/26* Welcome home to this beautifully maintained 3-bedroom, 2-bath *POOL* home in desirable Winter Park! Offering 1,678 square feet of single-story living, this home features an open floor plan with a spacious kitchen/family room combination. The open kitchen features 36” oak cabinetry, upgraded SS appliances, a garden window, and a kitchen island overlooking the dinette and family room. You’ll find laminate and tile flooring throughout the home, updated bedroom light fixtures (2026), and a converted 2-car garage offering flexible bonus space if you desire. Owners can escape to their primary suite with a walk-in closet, en-suite bathroom, and private French doors leading out to the HEATED SALTWATER POOL. Step outside to your own private backyard featuring an oversized covered patio with screened-in pool and a built-in spa, plenty of yard space to enjoy, a backyard shed for additional storage, a swing set, and a playhouse perfect for outdoor fun. With NO HOA, you’ll have the freedom to truly make this space your own! Major updates provide peace of mind, including a NEW water heater (2026), electrical panel replacement (2023), salinator replacement (2023), pool heater replacement (2024), roof (2019), and AC (2025). Conveniently located near shopping, dining, parks, and top-rated Seminole County schools, this move-in-ready home is the perfect blend of comfort, functionality, and Florida living!

7517 Laurel Springs Drive, Winter Park

$375,000
3 Beds 3 Baths Aloma Trails SubDv. 32792 Zip Code
Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout the spacious living and dining areas, kitchen, and half bath. The modern kitchen is designed for both style and convenience, featuring granite countertops, abundant cabinetry, a large center island, and a walk-in pantry, along with a full appliance package. Sliding glass doors provide abundant natural light and a peaceful backyard view. Upstairs, you’ll find all bedrooms, including a spacious primary suite with plush carpeting, a large walk-in closet, and an en-suite bathroom featuring dual vanities and a glass-enclosed shower. The second floor also includes a full guest bathroom, a convenient laundry closet with washer and dryer, multiple linen closets. Additional highlights include a one-car garage, extended driveway parking, and access to community amenities. Conveniently located near Park Avenue, University of Central Florida, Full Sail University, and Rollins College, with easy access to shopping, dining, and entertainment.

7522 Aloma Pines Court, Winter Park

$390,000
3 Beds 2 Baths Laurel Springs SubDv. 32792 Zip Code
Must see! This adorable three-bedroom, two-bath home is in a great location close to shopping, restaurants and freeways. A 2023 roof and no HOA! The home features gorgeous travertine flooring and a huge laundry room with extra storage. This exceptionally cared for home has character, charm and warmth. The fenced backyard and patio offer peaceful privacy. It's great outdoor space for entertaining or relaxing. The kitchen is bright and sunny with granite countertops and updated cabinets, along with a pass-through window to the patio. The bedrooms are spacious and one bedroom offers beautiful closet built-ins for maximum and stylish storage. You'll find updated baths and ample closet space (coat closet in the foyer, pantry, linen closet in the hallway). Sliding glass doors off the family room and dining room lead to the large patio for a wonderful outdoor living space. The home has lots of natural light, you can enjoy the character of the front bay window in the living room as well as the faux fireplaces. This home is a must-see with personality and has been impeccably maintained. Pride in ownership. Schedule your showing today.

7505 Laurel Springs Drive, Winter Park

$786,000
3 Beds 2 Baths Winter Park Pines SubDv. 32792 Zip Code
Welcome to this beautifully fully renovated pool home nestled in the highly desirable Winter Park area, where comfort, convenience, and lifestyle come together perfectly. Situated on a quiet, tree-lined street, this exceptional property offers spacious living areas, abundant natural light, and a warm, inviting atmosphere ideal for both relaxing and entertaining. Recent exterior upgrades include fresh exterior paint, new sod, a new front door, and new windows, adding to the home’s curb appeal and energy efficiency. The updated kitchen features granite countertops, a new deep sink, and ample cabinetry, making it both stylish and functional for everyday living and entertaining. Major improvements also include a NEW A/C unit and water heater replaced in 2021, providing peace of mind for years to come. Step outside to your private backyard oasis featuring a resurfaced pool (2016), perfect for enjoying Florida living year-round. The oversized .26-acre lot offers plenty of space for outdoor gatherings, pets, gardening, or simply relaxing in your own private retreat all with NO HOA restrictions! Enjoy the charm and convenience of living near some of Central Florida’s most sought-after destinations. Residents appreciate the close proximity to Cady Way Trail, Ward Park, and nearby recreational centers offering sports courts, fitness facilities, playgrounds, walking trails, and outdoor activities for all ages. Golf enthusiasts will also enjoy easy access to Winter Park Pines Golf Club and surrounding green spaces. Perfectly positioned just minutes from Park Avenue, Winter Park Village, Baldwin Park, and multiple shopping plazas, you’ll enjoy endless options for boutique shopping, dining, cafés, and entertainment. Convenient access to major roadways, Downtown Orlando, Rollins College, Full Sail University, and top-rated schools makes this location ideal for primary residents, professionals, and investors alike. Experience the best of Winter Park living with timeless charm, modern updates, excellent amenities, and unmatched convenience in one exceptional property.

2940 De Brocy Way, Winter Park

$425,000
3 Beds 3 Baths Grayson Square SubDv. 32792 Zip Code
Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathrooms, a powder room, single-car garage, a covered rear lanai, washer, dryer, refrigerator, and window blinds. The spacious first floor with over 9' ceilings is ideal for entertaining, featuring an open concept gathering room, cafe and kitchen equipped with a pantry, bright white cabinetry, white subway ceramic tile backsplash, Lyra quartz countertops, and durable ceramic tile flooring, and a powder room. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and ensuite bathroom with double sink, quartz-topped vanity, linen closet, a private water closet and walk-in glass framed shower. Offering privacy and space for everyone, two additional bedrooms, the secondary bathroom and laundry are also on the second floor. Professionally curated design selections for this popular Springdale II townhome include designer cabinets with crown molding, quartz countertops, oversized ceramic tile flooring covering the first floor living areas and bathrooms, a washer, dryer, refrigerator, and blinds, soft, stain-resistant Shaw carpet in the bedrooms and second floor living areas and so much more! Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off of Howell Branch Road! Grayson Square is a low-maintenance neighborhood with gated access, a pond, no rear neighbors, a resort-style community pool with cabana,1GM high-speed fiber optic internet, along with 75 streaming cable and music channels, ground maintenance - all with no CDD. Boasting an unbeatable location in coveted Winter Park, just one mile from 436, 434, and less than 3 miles from 417, your like-new home at Grayson Square offers all of your daily conveniences, such as Starbucks and Publix, just minutes away! Plus, you'll have access to quality Seminole County schools. When it's time for a change of pace, you'll love your proximity to the famous shopping and dining of Park Avenue. Make Grayson Square at Winter Park your new address today!

1995 Canny Cove, Winter Park

$399,000
3 Beds 2 Baths Eastbrook Sub SubDv. 32792 Zip Code
Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.

1092 Eastbrook Boulevard, Winter Park

$450,000
3 Beds 2 Baths Howell Branch Woods SubDv. 32792 Zip Code
MUST SEE! Fully Renovated Pool Home with Major Upgrades in Winter Park! Welcome to this beautifully remodeled Winter Park pool home offering modern finishes, major system upgrades, and true move-in-ready convenience. Every detail has been thoughtfully updated to combine style, comfort, and long-term peace of mind. This fully renovated interior and exterior home features a stunning brand-new kitchen with elegant quartz countertops, all-new stainless steel appliances, modern cabinetry, and a clean open layout perfect for entertaining and everyday living. Throughout the home, you’ll find durable porcelain tile flooring that creates a seamless contemporary look while being ideal for Florida living. The fully remodeled bathrooms showcase stylish modern finishes, upgraded fixtures, and a fresh luxury feel. The home also includes a brand-new roof and new double-pane energy-efficient windows designed to improve comfort, efficiency, and long-term value. Step outside into your private backyard oasis featuring a recently resurfaced swimming pool along with a brand-new pool pump and filter system, creating the perfect space for relaxing, entertaining, and enjoying Florida living year-round. Additional features include updated lighting and modern finishes throughout, a bright open floor plan, spacious living areas, and a large backyard ideal for gatherings and outdoor enjoyment. Conveniently located near Downtown Winter Park, Park Avenue, UCF, Full Sail University, shopping, dining, parks, and major highways, this completely move-in-ready home combines luxury upgrades with an excellent location.

7001 Jackman Boulevard, Winter Park

$379,000
3 Beds 2 Baths Garden Lake Estates Unit 3 SubDv. 32792 Zip Code
Virtually Staged. Welcome to this charming 3-bedroom, 2-bath home with a 2-car garage, perfectly situated on a quaint, low-traffic street. This thoughtfully designed split floor plan offers both privacy and functionality, while soaring vaulted ceilings create an open, spacious feel throughout. The updated kitchen serves as the heart of the home, offering modern touches and great flow for everyday living or entertaining. Enjoy peace of mind with a newer A/C, adding comfort and value for years to come. Step outside to a fully fenced backyard overlooking a tranquil pond—perfect for relaxing, entertaining, or enjoying Florida’s beautiful weather. Whether you’re a first-time buyer, downsizing, or looking for a smart investment property, this home offers the ideal combination of comfort, charm, and opportunity in Florida.

1433 Aster Court, Winter Park

$434,000
3 Beds 2 Baths Wrenwood Heights SubDv. 32792 Zip Code
Virtually Staged. Welcome to this beautifully renovated home tucked away on a quiet cul-de-sac in Winter Park. Thoughtfully redesigned with a modern open-concept layout, this home offers an expansive single-story layout with over 1,500 square feet of inviting living space designed for both everyday living and effortless entertaining. From the moment you enter, you’re greeted by a welcoming foyer with new flooring running throughout the home, complemented by fresh interior and exterior paint and updated lighting that creates a bright, contemporary feel. The spacious living room flows effortlessly into a new kitchen, featuring updated cabinetry, sleek countertops, and a large breakfast bar, creating an ideal space for gathering with family and friends. The private primary suite serves as a relaxing retreat, featuring generous proportions, abundant natural light, and a well-appointed en-suite bath. Two additional bedrooms are thoughtfully positioned, each offering spacious closets and flexibility for family, guests, or a home office setup. With two full bathrooms, comfort and convenience are built into every corner. A large enclosed patio extends the living space outdoors, creating the perfect spot for morning coffee and year-round entertaining while overlooking the backyard, ready to create your own outdoor retreat. A large detached workshop is perfect for additional storage or to convert into a dedicated workshop for your creative projects. Major upgrades include the replacement of aluminum wiring with copper, providing long-term reliability and added buyer confidence. Additional highlights include updated finishes throughout, recessed lighting, new flooring throughout, fresh neutral interiors, and ample storage. Located in an established neighborhood just minutes from shopping, dining, and major roadways, this move-in-ready home is a rare opportunity to own a fully updated property in Winter Park without the wait or hassle of renovations. Schedule your showing today, homes like this don’t last. Save Big: 1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details!

5117 Cypress Court, Winter Park

$420,000
3 Beds 3 Baths Enclave At Hawks Crest SubDv. 32792 Zip Code
Virtually Staged. As you arrive at the gated community of Enclave at Hawks Crest, you’ll note a feeling of privacy, relaxation, and understated luxury of an unbeatable Winter Park location! Pull up the pavered-driveway at 1611 Little Wren Lane and the striking architectural lines of your modern townhome create a lasting first impression. TOUR THE HOUSE WITH THE VIRTUAL TOUR and WALK THRU VIDEO LINKS. Inside the house, you’ll be welcomed in to a light-filled space, with high ceilings and tiled floors across the first level. This is a home designed not just to look beautiful, but to live effortlessly. At the center of it all is a kitchen that truly anchors the home, featuring stainless steel appliances, large center island, and a spacious closet pantry. Designed for both everyday living and entertaining, the kitchen flows seamlessly into the dining and living areas, creating a connected environment that feels natural, comfortable, and refined. Sliding glass doors open to a covered and screened rear patio that will become a refreshing outdoor haven where mornings begin peacefully and evenings unwind with ease, as you look down the greenspace just outside the rear of your home. Upstairs, the layout continues to impress with both comfort and flexibility. You’ll be blown away with the space the primary suite offers, along with a tray ceiling, large walk-in closet, and a well-appointed en suite bath with dual sink vanity and a spacious tiled shower. Two additional generously-sized bedrooms and an additional bathroom at the opposite end provide flexibility for guests, a home office, or your future needs. You’ll also find a laundry room in an upstairs hallway, making regular tasks convenient. Beyond the home itself, this community provides you a carefree lifestyle with the reasonable HOA caring for the exterior and landscaping, along with exceptional amenities that include a large resort-style pool perfect for relaxing moments or social gatherings, and a playground. The gated entry provides an added layer of privacy and security, creating a sense of exclusivity while still fostering a connected community atmosphere. Located just minutes from the great shopping and restaurants on the iconic Park Avenue in Winter Park, yet also conveniently walkable to favorites like Kelly’s Ice Cream and Foxtail Coffee just a one-block stroll away. Opportunities like this don’t come often… don’t miss your chance to call this Winter Park beauty your new home!

1611 Little Wren Lane, Winter Park

$588,000
3 Beds 2 Baths Winter Park Pines SubDv. 32792 Zip Code
**$30,000 Price Improvement!! Welcome to your beautifully updated slice of the Florida Dream here in Winter Park! Perfectly positioned on a desirable corner lot, this thoughtfully renovated home blends modern design, comfort, and functionality - minutes away from Advent Health, Park Avenue, and Schools! From the moment you step inside, you’ll notice the extensive tile flooring, upgraded lighting, and stylish finishes throughout. The heart of the home is the stunning RENOVATED KITCHEN featuring QUARTZ countertops, rich NAVY cabinetry, stainless steel appliances, and a gorgeous wine & coffee bar complete with a built-in WINE FRIDGE—perfect for entertaining or slow Florida mornings at home. Need space to work or unwind? The dedicated OFFICE with MODERN BARN DOORS creates the ideal work-from-home setup, while the additional BONUS ROOM offers endless flexibility as a playroom, reading retreat, media space, or hobby room. Down the hall, the spacious and serene Primary Suite invites you to unwind in the renovated, spa-inspired rain showerhead for a relaxing start or finish to your day. The 2nd bedroom has been dubbed the "Hotel Room" by guests because of its larger size and additional sitting area. This space is perfect for MULTIGENERATIONAL LIVING, whether they are coming home for the summer, guests visiting Central Florida on vacation, or extended family needing a space of their own! The 3rd bedroom is across the hall from the Primary and features laminate flooring, so you truly have 3 dedicated bedrooms PLUS an office! Practical upgrades set this home apart from others in the community, including CUSTOM BLINDS Throughout & 5 1/4 INCH BASEBOARDS in the main living areas, an indoor, heated & cooled LAUNDRY ROOM, Replaced A/C (Inside 2020, Outside 2019), NEW ROOF (2022), PVC REPIPE (2018), NEW SEWER, NEWLY FENCED BACKYARD (2022), WIFI Garage Opener (2020)a storage shed, and a NEW (2021) COVERED & SCREENED LANAI with waterproof and weatherproof interlocking flooring, designed for year-round indoor/outdoor living enjoyment. This move-in-ready abode delivers the perfect balance of style and everyday living! Whether you’re hosting friends, working remotely, or simply enjoying the Florida lifestyle, this remarkable gem is located blocks away from Cady Way Trail and Ward Park, and just minutes from the award-winning restaurants on Park Avenue, and in the Baldwin Park & Mills50 shopping districts! Don't sleep on this one, call and schedule your private showing today!

2756 Sheriff Way, Winter Park

$410,000
3 Beds 2 Baths Laurel Spgs SubDv. 32792 Zip Code
Located on a quiet cul-de-sac with NO HOA, this adorable Winter Park home sits on an oversized lot with an incredible backyard and endless room for entertaining, relaxing, or play. With a mid-century modern feel and charming curb appeal, this 3-bedroom, 2-bath home is full of character and functionality. As you enter through the foyer, you’re welcomed by an oversized living room to the left, complete with a cute flex space perfect for a home office, reading nook, or play area. The updated kitchen sits at the center of the home and features quartz countertops, bar seating, and views overlooking the dining room, creating a seamless flow for everyday living and entertaining. Laminate flooring runs throughout all main living areas and bedrooms for a clean and modern look. Down the hallway, you’ll find all three bedrooms and two bathrooms, including the spacious primary suite with a large closet and an updated ensuite bathroom featuring a brand-new vanity and stylish paneling details. The dining room and flex area both lead out to the screened-in patio, giving you the perfect indoor-outdoor setup. Step outside to the true showstopper — a massive backyard with endless possibilities, a fire pit area, and plenty of room for activities, gatherings, pets, or even future additions. (zoned R-1A) Additional highlights include an extra-long driveway with space for up to 6 cars plus a 2-car garage. A rare find in Winter Park!

7532 Azurebrook Court, Winter Park

$375,000
3 Beds 2 Baths Winter Park Estates Sec 2 SubDv. 32792 Zip Code
Welcome to 819 Densmore Drive, a beautifully refreshed concrete block ranch home in the heart of Winter Park Estates, one of Winter Park's most established neighborhoods with no HOA. This move-in ready home checks every box for buyers who want turn-key condition with an accessible price and a coveted Winter Park address. From the moment you pull up, the curb appeal speaks for itself. A crisp white exterior with fresh paint, an extra large driveway with RV, Boat, or trailer parking, and a lush green lawn, sit against the quiet, tree-lined street that makes this neighborhood so beloved. Step inside and you'll notice the brand-new Palmer Oak Rigid Core Luxury Vinyl Plank flooring running throughout the entire home, installed in 2026! It delivers the warmth of hardwood with the durability Florida living demands, and ties every room together beautifully. The interior was freshly painted top to bottom in 2026, giving every room a bright, clean feel that makes the home feel completely renewed. The layout is open and functional, with generous living areas, a dining room anchored by a chandelier that stays with the home, and bedrooms filled with natural light and ceiling fans throughout. The kitchen comes equipped with the refrigerator included, a functional breakfast bar, recessed lighting, and plenty of storage. Blinds, decorative framed bath mirrors, ceiling fans, and keypad entry all stay. Both bathrooms received new vanities and toilets in 2026, delivering a completely fresh, modern look. The big-ticket systems are solid. The roof was replaced in February 2022. The HVAC system is less than two years old. The plumbing was repiped to PEX in 2016, and the home connects to city sewer, public water, and public irrigation. No well, no septic, no solar obligations. Clean, uncomplicated ownership. The backyard is shaded by a mature tree with room to spread out, BBQ, add playgrounds, pools, or bounce houses, and the property sits high and dry away from flood zones. Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School, this home places you in one of Orange County's most sought-after school districts. Minutes to Park Avenue dining and boutique shopping, Advent Health Winter Park, Winter Park Pines Golf Course, the Cady Way Trail, and easy access to SR-436, Aloma Avenue, and the 408. Winter Park Estates is the kind of neighborhood where properties like this, genuinely updated and truly move-in ready in a community this well-established and well-located, don't sit long. Schedule your showing today.

819 Densmore Drive, Winter Park

$390,000
3 Beds 2 Baths Winter Woods Unit 01 SubDv. 32792 Zip Code
MULTIPLE OFFERS RECEIVED, PLEASE SUBMIT YOUR BEST OFFER BY 5PM EST ON MONDAY 5/11/2026. Welcome to this beautifully maintained three-bedroom, two-bathroom home offering nearly 1500 square feet of thoughtfully designed living space on an expansive pie-shaped lot. Featuring a desirable split floor plan, this move-in ready residence combines functional living spaces with tasteful updates throughout, all in a convenient location close to shopping, dining, major roadways, and some of Central Florida’s most sought-after destinations. Inside, fresh interior paint and updated wood-grain laminate and tile flooring create a warm and inviting atmosphere. Multiple living and gathering spaces include a comfortable sitting room, dedicated dining area, and a spacious layout ideal for both everyday living and entertaining. The laundry room offers exceptional storage space and a utility sink, with the washer and dryer included, for added convenience. The kitchen features honey-toned oak cabinetry, black appliances, a closet pantry, and ample workspace for meal preparation and hosting. Privately positioned away from the secondary bedrooms, the primary suite serves as a peaceful retreat with fresh paint, a walk-in closet, ceiling fan, and en-suite bathroom complete with a white single vanity and tiled shower. The updated hall bathroom, renovated in 2021, showcases a contemporary white vanity and tiled tub/shower combination. Step outside to enjoy the oversized fully fenced backyard offering endless opportunities for outdoor living, gardening, pets, or future enhancements. A screened lanai with brand-new screening installed in 2025 provides the perfect spot to relax year-round. Additional exterior improvements include an updated paver driveway and updated garage doors completed in 2024, enhancing both curb appeal and functionality. The two-car garage and mature landscaping complete the exterior package. Ideally located just minutes from everyday conveniences, this home is approximately 10 minutes from the dining, shopping, and charm of Park Avenue in Winter Park, 25 minutes from Orlando International Airport, and offers close proximity to UCF, Full Sail University, and Rollins College. Convenient access to major transportation routes, restaurants, retail stores, and entertainment makes this location as practical as it is desirable. ROOF - 2019 HVAC - 2021 PLUMBING - 2025 ELECTRICAL - 2025

2225 Winter Woods Boulevard, Winter Park

$350,000
3 Beds 2 Baths Eastbrook Sub Unit 03 SubDv. 32792 Zip Code
Welcome to 3627 Seagrape Drive, a move-in ready home for sale in Winter Park featuring NO HOA, an oversized lot, and energy-efficient upgrades in a prime Central Florida location. This 3-bedroom, 2-bath home offers an updated kitchen with granite countertops, stainless steel appliances, tile flooring throughout, crown molding, and indoor laundry for everyday convenience. Major improvements include a 2019 roof and solar panels, helping reduce energy costs. The large backyard provides rare space to expand, entertain, or create your own outdoor retreat. Ideally located just minutes from Costco Wholesale, Park Avenue, dining, shopping, and major highways, this property is perfect for buyers searching Winter Park FL homes for sale with land, updated features, no HOA, and strong long-term value or investment potential.

3627 Seagrape Drive, Winter Park

$514,900
3 Beds 2 Baths Casa Aloma SubDv. 32792 Zip Code
Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!

1438 Tierra Circle, Winter Park

$205,000
3 Beds 3 Baths Hidden Oaks Condo Ph 03 SubDv. 32792 Zip Code
Under contract-accepting backup offers. Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved parking spots included. The HOA covers the community pool, water, trash, grounds maintenance, and structural upkeep, making this a truly low-maintenance lifestyle. Pets welcome. Hidden Oaks lives up to its name with lush, mature landscaping throughout. Unbeatable location — minutes from Full Sail University, UCF, and Valencia College, with easy access to major Central Florida employers. Downtown Winter Park's dining, shopping, and Park Avenue charm are all within reach. Properties in this community move quickly — schedule your showing today.

3371 River View Way Unit 46, Winter Park

$450,000
3 Beds 2 Baths Lost Creek SubDv. 32792 Zip Code
MULTIPLE OFFERS RECEIVED, SUBMIT YOUR BST OFFER BY 5PM 5/18/2026. Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering 1,815 square feet of comfortable living in the established Lost Creek community of Winter Park. This light-filled residence features a thoughtfully designed split floor plan with vaulted ceilings, fresh interior paint (2026), and a blend of formal and casual living spaces. The formal living and dining rooms provide an elegant setting for entertaining, while the inviting family area is anchored by a cozy wood-burning fireplace and enhanced by ceiling fans and abundant natural light throughout. The well-appointed kitchen features warm blond-toned wood cabinetry, stainless steel appliances, and a cozy breakfast nook, perfect for both everyday living and casual dining. The kitchen flows easily into the main living areas, creating a functional and welcoming space for gathering with family and friends. A nearby laundry closet with included washer and dryer adds everyday convenience. The spacious primary suite serves as a private retreat, complete with a ceiling fan and an en-suite bathroom featuring a large double vanity, relaxing garden tub, and a separate shower with sliding doors. Split from the primary suite, the secondary bedrooms are well-sized and versatile, ideal for a growing family and guests, a home office, or additional living space, with easy access to the second full bathroom. Sliding glass doors lead to a screened lanai overlooking a spacious .21-acre lot shaded by mature oak trees and lush landscaping, an ideal setting to relax, unwind, or enjoy outdoor living year-round. Additional highlights include a two-car garage and major system updates including a roof (2018), HVAC (2019), and water heater (2021). Located just minutes from Red Bug Lake Park, top-rated schools, and a variety of shopping, dining, and everyday conveniences, this home offers the perfect balance of tranquility and accessibility. Don’t miss the opportunity to enjoy comfortable living in one of Winter Park’s most desirable and well-established neighborhoods.

1205 Valley Creek Run, Winter Park

$360,000
3 Beds 3 Baths Villas Of Casselberry Ph 3 SubDv. 32792 Zip Code
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!

3374 Hamlet Loop, Winter Park

$576,000
3 Beds 2 Baths Winter Park Pines Unit 17 SubDv. 32792 Zip Code
Welcome home to the Winter Park Pines where the trees line the streets and the mailman delivers to your door. This beautifully maintained 3-bedroom, 2-bathroom home offering 1,873 square feet of comfortable living in the highly desirable and serene Winter Park Pines community. This light-filled residence features a thoughtfully designed split floor plan with high ceilings, fresh interior paint (2026), skylights, and laminate and tile flooring throughout, creating a bright and inviting atmosphere from the moment you enter. The open living and dining areas are anchored by a charming wood-burning brick fireplace, while crown molding, ceiling fans, and French doors add both style and functionality throughout the home. The well-appointed kitchen includes white and gray cabinetry, stainless steel appliances, and a convenient pantry closet, perfect for both everyday living and entertaining. It flows seamlessly into the main living areas, making it easy to gather with family and friends. The spacious primary suite offers a private retreat, thoughtfully separated from the secondary bedrooms, and features a walk-in closet with custom built-ins, ceiling fan, and French doors leading to the expansive and shaded backyard. The renovated en-suite bathroom showcases double vanities and a beautifully tiled shower with frameless glass enclosure. The secondary bedrooms are well-sized and versatile, with easy access to the renovated hall bathroom featuring a granite double vanity, navy cabinetry, and direct access to the backyard, ideal for indoor-outdoor living. Step outside to enjoy a fully fenced, landscaped backyard situated on a generous .22-acre lot. The expansive patio with terracotta tile flooring provides the perfect space for outdoor dining, entertaining, or simply relaxing in a private setting. Additional highlights include a two-car garage and a Ring home security and surveillance system for added peace of mind. Located just minutes from top-rated Winter Park schools, the Cady Way Trail, Winter Park Pines Golf Course, Advent Health Winter Park campus, Crosby Wellness Center and a variety of shopping and dining options, this home offers both tranquility and convenience. Residents also enjoy access to nearby community amenities including a pool, playground, beach volley ball courts and tennis/pickleball courts. With close proximity to major roadways, downtown Winter Park, and Orlando International Airport, this property truly combines comfort, location, and lifestyle. Don’t miss the opportunity to make this exceptional home yours in one of Winter Park’s most sought-after neighborhoods. Roof 2020, HVAC 2022, Plumbing 2014, Water Heater 2021.

517 Roughbeard Road, Winter Park