Refine Search
Sort by
531 Worthington Drive, Winter Park
$1,100,000
3 Beds ⋅ 3 Baths ⋅ Kenilworth Shores SubDv. ⋅ 32789 Zip Code
Virtually Staged. OUTSTANDING OPPORTUNITY!! Delightful 2,626 sq ft home, perfectly positioned on a charming corner lot in the vibrant 32789 neighborhood! With its array of newly constructed homes nearby, this well-cared-for property stands as a fantastic blank canvas, just waiting for your creative touch. The updated kitchen boasts modern cabinets, chic countertops, and all the appliances you need, complete with a cozy breakfast nook to enjoy your morning coffee. Entertain in style in the formal dining room or gather around the fireplace in the living room. The original primary suite, alongside a guest bedroom and bathroom, features exquisite parquet floors and beautiful crown molding that add a touch of elegance. Imagine hosting friends in the spacious family room, adorned with beamed ceilings, or retreating to the incredible second-story master suite, where an impressive 18x12 bathroom, huge walk-in closet, and private 31x9 balcony await, all overlooking a charming, landscaped backyard. Step outside to enjoy the roomy L-shaped covered porch and take advantage of the two separate garages (24x23 & 22x14) plus gated side yard perfect for storage (NO HOA!)—completing this exceptional offering! This home is zoned for the highly regarded Brookshire Elementary, Glenridge Middle, and Winter Park High, plus the delightful shops and dining along Winter Park’s Park Avenue are just a short drive away. Don’t miss your opportunity to make this enchanting home yours! WELCOME HOME!

531 Worthington Drive, Winter Park

2885 Roxbury Road, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 2nd Add SubDv. ⋅ 32789 Zip Code
Original hardwood floors, an updated kitchen, and a versatile bonus room highlight this three-bedroom, two-bath home with 1,511 heated square feet at 2885 Roxbury Road, Winter Park, FL 32789. A fenced backyard, outdoor deck, and practical system improvements complement the home’s original character. The kitchen features quartz countertops, stainless steel appliances, an island, and pantry cabinetry. Hardwood flooring extends throughout the main living spaces and bedrooms, with tile in the kitchen, bathrooms, and bonus room. Use the bonus room for additional seating, hobbies, or a home office while maintaining all three bedrooms. Cedar-lined closets in the primary bedroom and an additional bedroom provide a distinctive detail. Improvements include a roof installed in 2019, air conditioning replaced in 2020, an electrical panel replaced in 2021, and double-pane windows in the bedrooms. Additional updates include exterior paint, replacement front, back, and kitchen doors, and front and rear gutters. The backyard deck extends the living space outdoors, with room for dining, relaxing, or container gardening. A fenced yard and an private storage shed provide additional functionality. A carport, irrigation system, and available fiber-optic internet round out the features. The septic system was pumped in 2026. This Winter Park home combines hardwood floors, an updated kitchen, flexible bonus space, and outdoor living in one inviting property.

2885 Roxbury Road, Winter Park

1934 Taylor Avenue, Winter Park
$499,000
4 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome to 1934 Taylor Avenue, a charming mid-century modern home offering 4 bedrooms and 1.5 bathrooms in Winter Park's established Eastgate neighborhood. Full of character and personality, this single-story home blends timeless design with comfortable everyday living. Hardwood floors throughout the main living areas add warmth and character, while the 1.5 bathrooms feature classic, colorful details that add a fun and distinctive charm. The kitchen makes its own statement with a pop of color on the cabinets and playful vinyl flooring. The open floor plan seamlessly connects the living and dining areas, creating an inviting space for relaxing and entertaining. The split-bedroom layout provides added privacy and flexibility for family members and guests. French doors lead to the backyard, creating a lovely connection between indoor and outdoor living. A welcoming front porch offers a cozy spot to enjoy your morning coffee. The private backyard provides plenty of space for outdoor activities and relaxation, with a spacious deck perfect for gatherings and an open patio offering additional room for outdoor seating. Conveniently located near Aloma Avenue, this home offers easy access to shopping, dining, parks, and everyday essentials. Nearby destinations include the Winter Park YMCA, Rollins College, and Downtown Winter Park's popular Park Avenue, known for its boutique shops, restaurants, and entertainment. With its mid-century modern character, colorful details, versatile outdoor spaces, and convenient location, 1934 Taylor Avenue offers a unique opportunity to enjoy Winter Park living.

1934 Taylor Avenue, Winter Park

1400 Pelican Bay Trail, Winter Park
$968,000
5 Beds ⋅ 4 Baths ⋅ Pelican Bay SubDv. ⋅ 32792 Zip Code
Awesome 5 bedroom 3.5 bathroom custom built home on gorgeous 1.2 acre WATERFRONT cul-de-sac lot in lovely Pelican Bay of Winter Park. A True Gem on the Lake on a private dead-end street! Step through the front door and into a welcoming foyer with beautiful wood floors and oversized living and family rooms featuring dual wood-burning fireplaces. 4 BRAND NEW CUSTOM BAY WINDOWS (NOV 2026) installed in living room. The gourmet kitchen features classic oak cabinetry and upgraded granite counters, as well as BRAND NEW STAINLESS STEEL SIDE BY SIDE REFRIGERATOR (NOV 2026). Kitchen bay windows overlook massive screened rear porch, screened pool oasis, and breathtaking backyard waterfront views of Lake Florence. Main bedroom is downstairs and features large ensuite bathroom with dual sinks, garden tub, and walk in shower. Additional 4 bedrooms and 2 full bathrooms as well as bonus room are located upstairs and enjoy wonderful lakefront views. BRAND NEW ROOF INSTALLED NOV 2021. This oversized lot contains a variety of wonderful fruit trees and edible plants located around the property including avocado, purple yam, lychee, chinese chives, jujube, apple cactus, persimmon, mango, and dragon eye. The lake frontage speaks for itself, but as you can imagine the sunsets are truly superb. The Winter Park location is one of the best, close to shopping, schools, major roads, international airport, and amazing restaurants. Bring your buyers so they can make this beautiful custom home their own.

1400 Pelican Bay Trail, Winter Park

3157 Shady Pine Avenue, Winter Park
$425,000
3 Beds ⋅ 2 Baths ⋅ Bel Aire Pines SubDv. ⋅ 32792 Zip Code
This home is move-in ready! One year old new roof installed which comes with a four (4) year warranty which covers all repairs. The interior was recently painted down to the baseboards and primary and guest bathrooms have been completely renovated. Orion Modern Flames Traditional Insert Fireplace Heater has been installed which can heat the living areas of the home in the winter! Brand new kitchen appliances include refrigerator, stove, microwave and dishwasher as well as new garbage disposal. There is a large two car garage with laundry area and driveway can accommodate additional cars. Home is completely fenced in for safety. All systems of this home have been WELL maintained. Too many updates to mention. Excellent location in Winter Park, close to schools and shopping. Take a look!

3157 Shady Pine Avenue, Winter Park

1507 Golfside Drive, Winter Park
$849,000
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Virtually Staged. Perfectly positioned on the 13th tee box and 16th fairway of the Winter Park Pines Golf Course, this home sits on an corner lot and offers a rare opportunity to create your dream home while enjoying breathtaking golf course views.  **The current floor plan features three bedrooms, as the original fourth bedroom has been converted into an expansive walk-in closet for the primary suite, Featuring over 2,000 square feet of single-story living space, this home has been extensively renovated throughout the interior, offering the charm of an established Winter Park neighborhood with the comfort and appeal of modern finishes. Step inside to discover new luxury vinyl flooring, beamed ceilings, modern fireplace. Brand new kitchen appliances with modern grey cabinetry, crown molding and white quartz counter tops.  Step outside to your own private backyard retreat, complete with a 30x11 covered patio and screen-enclosed swimming pool overlooking the lush fairways of WP18. Whether enjoying your morning coffee, entertaining guests, or simply relaxing poolside, this outdoor living space offers a peaceful setting that’s increasingly difficult to find in Winter Park. Additional highlights include a NEW ROOF (NOVEMBER 2024), New pool pump, resurfaced pool with new pavers surrounding,  a large indoor laundry room and no HOA. Located just a few doors from the Cady Way Trail on one of the neighborhood's most picturesque oak-canopied streets, the setting is truly exceptional. This is a rare opportunity to purchase a home set directly on one of Winter Park's premier golf courses, where major mechanical system upgrades and costly infrastructure improvements have already been completed, creating the perfect opportunity to transform the interior into your own custom vision. This is move in ready so schedule your showings today!

1507 Golfside Drive, Winter Park

2176 Crandon Avenue, Winter Park
$399,000
2 Beds ⋅ 1 Baths ⋅ Olympia Heights Annex SubDv. ⋅ 32789 Zip Code
Welcome to Dubstread Heights. This in-town community is perfect for the busy professional that needs access to downtown, college park or Winter Park. Located just 1 block from the back side of Dubstread Golf Course grab your golf cart for an afternoon round. This renovated home just received a New Roof, as well as paint in and out. Solid hard-wood flooring greets you upon entry. An open floor plan with vaulted ceilings offers a grand theme throughout the home. A spacious living space is joined by a breakfast bar and opens to the newly updated kitchen. New designer porcelain tile flooring, with newer cabinetry sets the stage for the Cafe and Subzero appliances. Stone countertops add to the designer feel. Just off of the kitchen is a flex space that could be a dining/office area. A stained-glass French door opens to a covered/screened rear porch and looks out onto the private fenced back-yard. Back inside, the two bedrooms are in a split fashion with new paint, ceiling fans, and a closet organizer in the primary bedroom. The bath has updated fixtures/lighting and features a stone travertine shower enclosure. The property is quite private as there are no homes across the street and is maintained by the City. This quaint home is ready to be enjoyed by its new owners.... please set you appointment soon...

2176 Crandon Avenue, Winter Park

1735 Meadowgold Lane, Winter Park
$480,000
3 Beds ⋅ 2 Baths ⋅ Autumn Glen Ph 1 SubDv. ⋅ 32792 Zip Code
Virtually Staged. More photos coming soon! YOUR FLORIDA DREAM LIFESTYLE STARTS HERE! Welcome to 1735 Meadowgold Lane in the desirable Autumn Glen community! This beautifully updated pool home combines modern style, comfortable living, and the outdoor lifestyle Florida is famous for. Step inside and discover soaring ceilings, skylights, beautiful flooring, and a stunning white marble wood-burning fireplace. The renovated kitchen is a showstopper, featuring crisp white and frosted-glass cabinetry, Blue Moon granite countertops, a contemporary glass backsplash, and stainless steel appliances. Need extra space? The spacious, climate-controlled bonus room offers endless possibilities for a home office, gym, media room, or additional living area. Enjoy beautifully updated bathrooms, including a primary suite with a double vanity and elegant marble-accented, glass-enclosed shower as well as a spacious walk in closet in the primary suite and an oversized walk in closet in the bonus room. Your private backyard oasis awaits! Relax in the screened-in pool, entertain on the spacious covered patio, or enjoy the privacy of your fully fenced backyard. BIG UPDATES. BEAUTIFUL LIVING. PEACE OF MIND. Major improvements include: - 2019 Roof and skylight - 2019 Pool resurfaced - 2022 New Windows - 2023 Whole-house repiping, Updated flooring, New HVAC - 2026 New pool pump This is Move-in ready home, located in the established Autumn Glen Community, featuring sidewalks, tennis/pickleball courts and a neighborhood playground. Plus, you're zoned for top rated Seminole County schools.

1735 Meadowgold Lane, Winter Park

1663 N Park Avenue, Winter Park
$2,750,000
4 Beds ⋅ 5 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
An exceptional expression of contemporary luxury on Winter Park’s historic Park Avenue! This newly constructed residence presents a luxurious design and elevated craftsmanship. From the sleek metal roof to the dramatic 11-foot custom statement entrance door, this 4 bedroom, 5 bath home makes an unforgettable first impression. At the heart of the home, the expansive designer kitchen makes a striking statement with sleek GOLA-profile cabinetry, an expansive 9 foot center island, and exquisite quartzite countertops and backsplash. Premium Wolf and Thermador appliances deliver exceptional culinary performance. Discreetly concealed behind a door adjacent to the main kitchen, a fully equipped secondary prep kitchen features a six burner gas range with double ovens, offering an exceptional level of functionality for everyday living and entertaining. The living area is equally impressive, featuring a pre-wired entertainment wall ready for a personalized audio-visual experience. The first-floor primary suite serves as a private sanctuary, highlighted by a luminous LED aura ceiling. The spa-inspired primary bathroom features floating contemporary cabinetry with integrated sensor lighting, Kohler Purist collection faucets and fixtures, and anti-fog LED mirrors. A luxurious freestanding soaking tub creates an elegant focal point, while the spacious, glass enclosed, walk-in shower showcases beautiful tilework and separate shower systems on both sides. Sensor-activated lighting throughout the bathrooms and closets add another layer of modern sophistication. The custom-designed primary closet rivals a luxury boutique, featuring a full-length mirrored door, valet rod, convertible vanity, central island with integrated electrical outlets, and built-in shoe bench. The second level features a dedicated bonus room offering the flexibility to create a private home theater, office, or a creative studio. A separate den area provides another versatile living retreat along with three generously appointed bedrooms, each with its own en-suite bathroom and custom walk-in closet. Additional appointments include modern switches and outlets, smart thermostats, Minka-Aire ceiling fans, CAT 6 cabling in every room, and smart-home pre-wiring. The garage is well-appointed, featuring wall-mounted garage door openers with battery backup, a Tesla charging station compatible with other electric vehicles, and a separate 50-amp outlet to accommodate additional EV charging equipment. The outdoor living experience is a defining feature of this extraordinary property. Designed by Complete Outdoors, a stunning, salt water swimming pool featuring two dramatic 24-inch water bowls, a custom pebble interior, natural stone coping, and integrated heating and cooling capabilities, is being installed. A complete summer kitchen creates an inviting setting for alfresco dining,. This creation offers a distinctive lifestyle opportunity in the heart of Winter Park. Enjoy a walkable lifestyle surrounded by upscale boutiques, restaurants, charming sidewalk cafés, and the lush beauty of Central Park. Experience the beautiful Winter chain of lakes and the Winter Park Golf course, a 9 hole gem in the heart of Winter Park. Explore the Saturday Farmers Market, discover local art museums, and experience the vibrant community events and timeless traditions that make downtown Winter Park such an exceptional place to call home.

1663 N Park Avenue, Winter Park

1824 Jessica Court, Winter Park
$1,149,000
4 Beds ⋅ 3 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Set within Waterbridge, a tight knit, tree lined enclave, this fully renovated four-bedroom residence on the cul-de-sac pairs quiet residential living with exceptional connection to the best of Winter Park. Park Avenue's galleries, boutiques, and weekend farmers market sit just minutes away, as do AdventHealth Winter Park and the employers and services that make this corridor one of the city's most connected. The restaurants, shops, and walkable village center of Baldwin Park are practically next door. The home is zoned for Glenridge Middle and Winter Park High, among the most respected schools in Orange County and a key reason buyers seek out the 32789 zip code. New pavers at the front entry and fresh exterior paint set a polished, welcoming tone from the first approach. Inside, new white oak flooring flows throughout, paired with fresh interior paint that gives every room a clean, light filled foundation. The kitchen anchors the main living space, fully renovated with quartz countertops, soft close shaker cabinetry, a marble backsplash, and an entirely new appliance suite. It is a space designed for both everyday rhythm and easy entertaining, opening naturally to the living areas around it. The private spaces carry the same thoughtful level of finish. The primary suite is set on the first floor, a private retreat anchored by a fully renovated bath with marble tile and white oak cabinetry. The remaining full bath and powder room have been completely renovated as well, finished in marble with shaker vanities. Three additional bedrooms offer flexible space for guests, a home office, or creative pursuits. Even the laundry room has been reimagined with quartz counters, shaker cabinetry, and a tile backsplash, a detail that reflects the care taken in every corner of the renovation. Outside, new pavers extend across the back patio, creating an inviting setting for morning coffee, dinners outdoors, and relaxed Florida evenings. Behind the finishes, the infrastructure offers equal peace of mind with a new roof installed in 2026 and a newer HVAC system from 2023. The lot to the left is for sale and available for purchase as well. With the best of Winter Park and Baldwin Park just outside the door, the residence stands as a rare, fully renewed offering in one of Winter Park's most coveted pockets.

1824 Jessica Court, Winter Park

5415 N Lake Burkett Lane, Winter Park
$435,000
3 Beds ⋅ 3 Baths ⋅ Trinity Bay Ph 2 SubDv. ⋅ 32792 Zip Code
Welcome to 5415 N Lake Burkett Lane, a beautiful home located in the desirable Trinity Bay community of Winter Park, with a neighborhood boat slip, dock, and lake access! Offering 3 bedrooms, 2.5 bathrooms, and 2,027 square feet of thoughtfully designed living space, this home makes a lasting first impression with its soaring vaulted ceilings and inviting atmosphere. The open, well-designed floorplan creates a natural flow throughout the main living areas, making it perfect for both everyday living and entertaining. The downstairs features spacious living and dining areas, a convenient half bathroom, a dedicated laundry room, and direct access to the attached two-car garage. Upstairs, you'll find all three bedrooms, offering a comfortable separation between the main living spaces and private retreats. The layout provides a wonderful balance of functionality and comfort, with plenty of room to accommodate a variety of lifestyles. Step outside to enjoy the screened-in rear patio, the perfect spot to enjoy your morning coffee or unwind in the evenings while taking in the outdoors. Beyond the patio, you'll find a generously sized backyard with endless possibilities! Whether you envision creating your dream outdoor entertaining space, adding a garden, designing a play area, or simply enjoying the extra room to relax, this backyard is a blank canvas waiting for your personal touch. With its spacious layout, soaring ceilings, and fantastic potential, this Trinity Bay home is an opportunity you won't want to miss!

5415 N Lake Burkett Lane, Winter Park

2315 Kestrel Perch Place, Winter Park
$739,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with water view—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with a solid wood staircase. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.

2315 Kestrel Perch Place, Winter Park

1398 Grove Terrace, Winter Park
$1,949,000
4 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Improved! Positioned on a charming brick-lined street in historic Winter Park adjacent to Windsong, this custom-built residence pairs solid architectural craftsmanship with extensive modern upgrades. Refinished Mahoghany double doors open to 12-foot ceilings, soft curved archways and a thoughtful layout finished with travertine on the main level and reclaimed maple and beech hardwoods upstairs and in the primary suite. The expansive, open family room centers around a gorgeous gas fireplace and flows seamlessly into a true chef’s kitchen featuring a new marble tile backsplash, Rejuvenation drum chandelier, granite countertops, prep island, custom lighted cabinetry, a six-burner gas range with pot filler, double ovens with warming drawer and a Thermador French-door refrigerator. An adjoining butler’s pantry with wine fridge and wet bar connects directly to the formal dining room, complemented by a newly constructed dedicated wine room and a quiet main-level office or library. The first-floor primary suite offers a private retreat with detailed tray ceilings, dual walk-in closets, a jetted soaking tub, twin vanities and direct French-door access to the outdoor living area. Upstairs, three spacious bedrooms and two full baths including a private en-suite accompany a classic Juliet balcony overlooking the pretty front yard. Designed for effortless Florida living, the covered summer kitchen is perfect for relaxing with friends and watching football, featuring a built-in grill, custom copper hood and beverage fridge, while the second covered lanai is perfectly situated for a hot tub. Both look out over a private saltwater pool framed by maintence-free turf, lighting and a newly planted podocarpus privacy hedge. Recent capital improvements include new dual HVAC units, a tankless water heater, whole-home surge protection, central vacuum, smart-home automation for pool, security and irrigation, six new exterior fixtures, complete interior and exterior repainting, epoxy-coated garage floors, extensive kitchen renovations, refinished front entry doors and fully refreshed landscaping. Enjoy no HOA dues, seasonal neighborhood block gatherings and quick access to Lake Mizell, premier schools (Brookshire, WPHS, Park Maitland, Lake Highland, Geneva) and a convenient pedestrian cut-through directly to Park Avenue dining and shopping.

1398 Grove Terrace, Winter Park

1350 Lyndale Boulevard, Winter Park
$1,499,000
4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32789 Zip Code
Photos coming soon. Experience timeless elegance and exceptional living in the heart of Winter Park! Nestled along a charming, quiet brick-lined street just moments from iconic Park Avenue, this beautifully designed custom residence offers the perfect combination of sophistication, comfort, and Florida indoor-outdoor living. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and 3,478 square feet of living space, this impressive home welcomes you with soaring 10-foot ceilings, rich Brazilian cherry hardwood floors, elegant architectural details, and an abundance of natural light. At the heart of the home, the gourmet kitchen is designed for both everyday living and effortless entertaining, featuring a spacious center island, natural wood cabinetry, premium cooking appliances, built-in refrigerator, and wine refrigerator. The kitchen flows seamlessly into the inviting family room, complete with a beautiful gas fireplace. The luxurious first-floor primary suite offers a peaceful retreat with generous walk-in closets, a spa-inspired bathroom, and French doors opening to the private screened pool and patio. Upstairs, additional bedrooms and a spacious bonus room provide flexibility for a home office, fitness studio, media room, or guest accommodations. Step outside to your own private oasis, where a sparkling pool, relaxing spa, mature landscaping, and inviting outdoor living spaces create an ideal setting for entertaining or unwinding year-round. Additional highlights include formal living and dining spaces, an attached two-car garage, abundant storage, and a desirable location with no HOA. Enjoy the best of the Winter Park lifestyle, with convenient access to Park Avenue's celebrated restaurants, boutique shopping, cafés, cultural attractions, parks, and nearby lakes. An exceptional opportunity to own a distinctive residence in one of Central Florida's most desirable communities. Schedule your private showing and discover everything this Winter Park home has!

1350 Lyndale Boulevard, Winter Park

1441 Grove Terrace, Winter Park
$5,950,000
5 Beds ⋅ 6 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park lot with 130 feet of water frontage, the home pairs timeless architecture, richly detailed interiors, and expansive outdoor living. Led by a husband-and-wife team originally from Europe, Vimaro Homes brings together her expertise in interior design and his in construction. Their hands-on approach brings a personal commitment to every selection and detail, prioritizing lasting quality, thoughtful design, and craftsmanship over the cost-driven formulas common in investment-built spec homes. A striking façade and tile roof establish an elegant arrival, complemented by a dual-entry driveway featuring a diamond-patterned composition of turf and concrete. An underground three-car garage preserves the architectural approach, while an elevator connects all three levels. Inside, a marble mosaic entry introduces intricate trim work and classic reeded crown molding, establishing the home’s enduring character. The spacious living room features a marble-wrapped fireplace, custom built-ins with LED up-lighting, and expansive sliding doors framing views of the pool and lake. The kitchen pairs marble countertops and custom inset cabinetry with Perrin & Rowe fixtures and Thermador appliances, including a paneled refrigerator. A substantial scullery with a prep kitchen and pantry supports entertaining, while the nearby dining room overlooks the water. The downstairs primary suite offers a private retreat with its own fireplace and an expansive, custom-fitted walk-in closet with a center island. The primary bath features Casablanca marble tile, dual vanities, Perrin & Rowe fixtures, and a spacious walk-in shower. Upstairs, four additional bedrooms each offer an ensuite bath and walk-in closet, alongside a bonus room, laundry room, and terrace. Throughout the home, natural stone, finely crafted cabinetry, and classic architectural details reflect the team’s European influences. Outdoors, a generous lanai with retractable screens and a full summer kitchen extends the living spaces toward Lake Sylvan. A three-tiered deck brings together a pool, spa, and sweeping water views, while expansive green space and a dock complete the waterfront setting. Set on a brick street moments from Park Avenue’s restaurants, boutiques, and cafés, this residence combines Winter Park’s distinctive character with an exceptional lakefront setting. Shaped by the personal vision and craftsmanship of Vimaro Homes, it offers a refined expression of waterfront living.

1441 Grove Terrace, Winter Park

2237 Woodcrest Drive, Winter Park
$1,425,000
4 Beds ⋅ 5 Baths ⋅ Kenilworth Estates SubDv. ⋅ 32792 Zip Code
Under Construction. Nestled on a quiet street on an oversized homesite in Winter Park, this stunning new construction home by David Weekley Homes blends timeless design with modern comfort. Featuring 4 spacious bedrooms and 4.5 beautifully appointed baths, the home offers an ideal layout for both everyday living and entertaining. A private study provides a perfect work-from-home retreat, while the dedicated media room invites movie nights and game-day gatherings. Upstairs, a versatile loft adds flexible living space for a playroom, lounge, or fitness area. Thoughtfully designed with high-quality finishes and abundant natural light, this home delivers exceptional craftsmanship in one of Central Florida’s most desirable neighborhoods—just minutes from top schools, parks, dining, and shopping.

2237 Woodcrest Drive, Winter Park

1534 Miller Avenue, Winter Park
$1,379,900
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Under Construction. NEW CONSTRUCTION! New photos coming soon! Photos of a similar model. Welcome to Winter Park Grove — Winter Park’s newest community by one of the area's finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and comfort. Step onto the inviting front porch and through the elegant 2 story entryway to discover a spacious, open floor plan filled with natural light. Just off the foyer, you’ll find a flexible fourth bedroom or private study with a full bath—ideal for a home office or serene guest suite. The heart of the home is the gourmet kitchen, featuring quartz countertops, an oversized island, custom cabinetry, and a premium Bosch appliance package including a 36" gas cooktop. The kitchen flows into the living and dining areas—perfect for entertaining or family gatherings. Enjoy Florida living at its finest on the covered lanai, overlooking your sparkling pool & lushly landscaped backyard—your own private retreat. The first-floor primary suite offers a spa-inspired bath with dual sink vanity, a freestanding soaking tub, and a spacious walk-in closet with custom shelving. Upstairs, a large bonus room with a closet offers versatility as a second living, game room and it can even be enclosed to create an additional bedroom. Two spacious bedrooms feature walk-in closets and share a beautifully appointed bath with dual sinks. An upstairs laundry room with a sink and plenty of natural light adds everyday convenience. Photos are of a similar model, finishes may vary. Located near top-rated schools, local parks, and all that Winter Park has to offer — this home truly has it all. Schedule your private showing today before this exceptional new build is gone!

1534 Miller Avenue, Winter Park

2011 Harmon Avenue, Winter Park
$849,900
4 Beds ⋅ 3 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Under Construction. Welcome to your NEW Home! This residence to-be-built is a rare single story home. This bright open floor-plan features a large great room open to the kitchen. Enjoy dining at the island and plenty of space to entertain, featuring stainless appliances, and an extra large walk-in pantry (6.8 x 7 ft) to meet all your storage needs. The Primary bedroom is located off of the main living with a spacious (10x 6.5 ft) walk in closet. The primary bath features double sinks and a separate shower and soaking tub as well as a private toilet room. All of the secondary bedrooms are generously sized with signifcant built-in closet space. The extra large laundry space gives ample additional storage. 2 Car garage. Summer Kitchen with a grill available to add-on. Don't wait, take this opportunity to make this pre-construction residence you perfect place to call home.

2011 Harmon Avenue, Winter Park

7361 Grand Avenue, Winter Park
$385,000
3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code
Move-In Ready & Priced to Sell! Nestled in a prime Winter Park location, this 3-bedroom, 2-bathroom completely renovated and upgraded single-story home delivers effortless living on an oversized lot. Designed with a sought-after split-bedroom layout, the light-filled interior showcases an upgraded kitchen with Stainless Steel appliances, new Quartz countertops and two completely refreshed bathrooms, one with a new tub. Fresh paint, new flooring, new doors, smooth ceilings, new window coverings, updated hardware, fixtures and fans leave nothing for a buyer to worry about. Major updates include a newer HVAC system and a roof replaced in 2015. Home was re-piped by Emerald Plumbing. The backyard awaits your imagination and offers a unique opportunity to design your own outdoor oasis, ideal for entertaining, building an outdoor kitchen or adding your dream pool. The long-time owner made a significant investment to upgrade this home and has pre-inspected it, offering buyers peace of mind with a full report ready for review. Enjoy convenient suburban living just minutes from Publix, Walmart, top-rated schools, Red Bug Lake Park and local dining. With easy highway access, you are under 30 minutes from UCF, Downtown Orlando, Universal Studios and the airport. Whether you are looking for a turnkey home or a high-demand investment property, this gem won’t last long.

7361 Grand Avenue, Winter Park

1441 Palm Avenue, Winter Park
$2,449,000
5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, and a location that puts so much of daily life within easy reach. Opportunities to find new construction in this established neighborhood are becoming harder to come by, making this home an especially exciting offering. The front façade makes a memorable first impression, with beautiful curb appeal that carries naturally into the interiors. In the spacious living room, a stone-wrapped fireplace anchors the space, complemented by a built-in entertainment center and display shelving with soft LED underlighting. The kitchen is a standout. Calacatta quartz countertops and an intricate mosaic backsplash set an elegant tone, while a full suite of Thermador appliances, including a paneled refrigerator, brings substance to the beautiful design. A spacious pantry keeps everything tucked away, and a wine bar with a dedicated wine refrigerator makes hosting feel effortless. The primary suite offers a lovely sense of retreat. This spacious bedroom is complemented by a beautifully finished bath with marble mosaic tile, a freestanding tub, and a generous walk-in shower with a rain showerhead. An oversized closet adds the kind of everyday luxury that is just as valuable as the finishes themselves. A rare first-floor guest bedroom gives visitors a comfortable place of their own or offers a space for a dedicated office. Upstairs, three additional bedrooms, each with a walk-in closet, surround a loft that offers room for a second living area, movie nights, or a quiet place to unwind. The outdoor living is equally impressive, with a spacious covered lanai and full summer kitchen overlooking the pool and spa, a beautiful setting for dinners or a quiet afternoon at home. Surrounding green space gives the backyard a sense of openness and room to enjoy the Florida sunshine. With Phelps Park and the YMCA moments away, and Park Avenue’s restaurants and boutiques just a golf cart ride from home, the location is every bit as appealing as the residence itself. Beautifully finished and thoughtfully arranged, this is a chance to enjoy the ease of a brand-new home in a neighborhood whose charm has long been established.

1441 Palm Avenue, Winter Park

1935 Azalea Avenue, Winter Park
$410,000
3 Beds ⋅ 2 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code
URBAN CONVENIENCE MEETS QUIET "OLD FLORIDA" CHARM! Rarely does a truly move-in-ready home hit the market in the heart of Seminole County Winter Park—especially one with no HOA, a massive private backyard, and an exceptional price point. Tucked away on a quiet, low-traffic dead-end street, this solid concrete-block ranch is the ultimate starter home or a turnkey addition to any high-performing investment portfolio. The exterior welcomes you with an extra-wide paver driveway, mature professional landscaping, and a charming paver front walkway and patio, while the fully fenced backyard offers an oversized outdoor living space complete with a patio for entertaining and a convenient storage shed. Step inside to discover a bright open-concept living, dining, and kitchen area enhanced by continuous luxury vinyl flooring flowing throughout. The chef’s kitchen is beautifully appointed with sleek granite countertops, solid wood cabinetry, stainless steel appliances, an eat-in island, and a practical closet-style pantry. Designed with a desirable split bedroom layout, the private primary suite boasts three closets and an ensuite bath with an updated vanity and custom tile shower, while two additional guest bedrooms and a fully updated guest bath sit on the opposite side of the home for optimal privacy. Additional conveniences include a spacious indoor laundry room and a front-lawn irrigation system, backed by peace-of-mind upgrades including a 2014 roof and a 2018 HVAC. Zoned for highly rated Seminole County schools and situated just moments from N Park Ave—while remaining centrally located 15 minutes from Downtown Orlando and 30 minutes from MCO Airport—opportunities at this price point and in this location do not last long. Schedule your private showing today!

1935 Azalea Avenue, Winter Park

1500 Harris Circle, Winter Park
$1,175,000
3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set among distinguished residences and substantial lakefront estates, the home occupies a corner lot along a charming brick street and offers three bedrooms, three full bathrooms and approximately 2,096 square feet of living space. Extensive improvements in recent years bring together exceptional finishes, thoughtful craftsmanship and substantial updates behind the walls. With interior design by New York City–based Paulette Pascarella, traditional architectural details find fresh expression through sophisticated materials and beautifully considered modern appointments. Expansive windows welcome natural light, while polished marble flooring in warm ivory tones extends throughout much of both levels. The kitchen features solid wood cabinetry, quartz countertops and a full-height backsplash, complemented by a Bertazzoni refrigerator, Bosch 800 Series gas range and Miele dishwasher. A separate study and sitting room has wood flooring and custom built-ins. With a full bathroom immediately adjacent, this versatile space presents potential for conversion into a fourth bedroom with an en-suite bath. Carefully selected details include Visual Comfort and Currey lighting, Buster + Punch and Baldwin hardware, and custom window treatments incorporating designer textiles and motorized shades from The Shade Store. Nine Marvin Ultimate windows with wood interiors, a VELUX skylight and a mahogany Craftsman front door further distinguish the renovation. A custom stair railing by Boris Petkoff Iron Works and millwork by Dunning Custom Carpentry add distinctive craftsmanship. All three bedrooms are upstairs, where the primary suite features soaring ceilings, treetop outlooks and an extensively fitted California Closets walk-in dressing room with custom cabinetry and soft-close dovetail drawers. Its beautifully appointed bathroom features Perrin + Rowe Georgian Era vanity and shower fixtures, reflecting the caliber of fittings selected throughout the home. Two additional bedrooms, one with an en-suite bathroom, provide flexibility for guests or a home office. Upstairs views of Lake Sylvan connect the interiors to their picturesque surroundings. Substantial improvements include whole-house repiping, electrical upgrades, a Rinnai tankless water heater and a whole-house water treatment system. The roof was replaced in August 2023. Outside, cottage gardens frame a welcoming entrance, while an intimate brick patio nestled within the garden and a quiet garden corner offer peaceful places for morning coffee or an afternoon outdoors. A private parking pad adds convenience. Beyond the garden, oak-shaded brick streets invite leisurely walks past beautiful homes and scenic views of Lakes Sylvan and Osceola. A small lakeside green space lies just down Harris Circle, with Crosby Wellness Center, AdventHealth and Park Avenue’s dining, boutiques and cultural attractions conveniently nearby. An inviting choice for a primary residence or Winter Park retreat.

1500 Harris Circle, Winter Park

2038 Ponderosa Avenue, Winter Park
$415,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the highly desirable Eastbrook neighborhood of Winter Park! Light, bright, and inviting, this home offers an abundance of natural light through its numerous windows, creating a warm and welcoming atmosphere throughout. The updated kitchen features crisp white cabinetry, beautiful quartz countertops, and stainless steel appliances. Luxury vinyl plank flooring extends throughout most of the home, offering both style and easy maintenance. Both bathrooms have been tastefully updated, adding to the home's fresh, modern appeal. Step outside to the screened and covered patio, the perfect spot for morning coffee, outdoor dining, or simply relaxing while overlooking the generously sized, fully fenced backyard. There's plenty of room to entertain, garden, or enjoy the Florida sunshine! Major improvements provide added peace of mind, including a new roof (2019), replumbing (2022), new HVAC system (2022), and new double-pane windows and sliding glass door (2023). Both the interior and exterior were freshly painted in 2023, completing the home's move-in-ready appeal. Ideally situated in the established Eastbrook community, this home offers the charm of Winter Park living with convenient access to shopping, dining, parks, and major roadways. With its thoughtful updates, inviting living spaces, and wonderful outdoor setting, this is a home you won't want to miss!

2038 Ponderosa Avenue, Winter Park

1825 Chilean Lane, Winter Park
$450,000
5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

1825 Chilean Lane, Winter Park

345 Beloit Avenue, Winter Park
$1,625,000
3 Beds ⋅ 3 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
Historic Winter Park charm with modern updates, close to N Park Avenue. Set on a picturesque, tree-lined street, this thoughtfully renovated home puts you minutes from Winter Park's restaurants, sidewalk cafés, boutique shops, art galleries, Central Park, and year-round festivals. You get the character of an established historic neighborhood with the comforts of modern living. Set back amid mature landscaping, the home greets you with a charming front porch and an elegant entry with marble floors, arched windows, and beautiful architectural details. Inside, spacious rooms feature rich hardwood floors, crown molding, wainscoting, and plantation shutters. The updated kitchen offers bright cabinetry, stone countertops, a generous island, stainless steel appliances, and a gas range, all opening to a living area with a classic fireplace and custom built-ins. An exceptionally spacious flex room lined with custom cabinetry and shelving works beautifully as a home office, library, or creative studio. The primary suite includes a beautifully remodeled bath with a freestanding soaking tub, oversized glass-enclosed shower, dual vanities, and a customized walk-in closet. Generously sized secondary bedrooms add flexibility for family, guests, or a second workspace. Outside, a private fenced backyard shaded by mature trees features a brick-paver patio made for outdoor dining or quiet relaxation. A rear-access garage adds convenience without disrupting the home's charming streetscape. Timeless character, extensive modern updates, and an exceptional location near the heart of Winter Park. Come enjoy the distinctive lifestyle that makes this community so desirable. Schedule your private showing today.

345 Beloit Avenue, Winter Park

1830 Gladiolas Drive, Winter Park
$375,000
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
Welcome to 1830 Gladiolas Drive, a beautiful 3 bedroom, 2 bathroom home in Winter Park’s Garden Lake Estates community. This move-in ready home features a 2023 AC, a 2022 water heater, a 2020 roof, and a brand new freshly painted interior. Inside, the spacious open living and kitchen area is the heart of the home. The thoughtful layout keeps everyone connected, whether you’re cooking, hosting friends, or settling in for a quiet evening. Natural flow between the spaces makes the home feel open and welcoming. The primary suite is a private retreat. It’s generously sized and has a large walk-in closet, so you have plenty of room for your wardrobe and a calm place to start and end your day. Outside, the expansive rear patio extends your living space into the Florida outdoors. It’s ready for morning coffee, weekend barbecues, or dinner under the stars. Beyond it, the big backyard gives you room to play, garden, or add the features you’ve been dreaming of. Functional, inviting, and close to everything in Winter Park, this home is ready for its next chapter with several major updates already completed. This home is a great opportunity for someone looking to add their own personal touch.

1830 Gladiolas Drive, Winter Park

1386 Clematis Lane, Winter Park
$417,000
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 recently 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 waste line has been updated to PVC. New flooring in main house, new baseboards installed, and freshly painted. MOVE IN READY!

1386 Clematis Lane, Winter Park

1021 Princess Gate Boulevard, Winter Park
$410,000
3 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to this 3-bedroom, 2-bath pool home in the established Howell Estates neighborhood of Winter Park! Situated on a spacious 0.31-acre lot, this single-story residence offers 1,318 square feet of living space with a split-bedroom layout and a combination of tile and luxury vinyl flooring. The living room features built-in cabinetry with a granite countertop, while the kitchen offers stone countertops, a tile backsplash, and a closet pantry. The primary suite includes dual closets and a private bathroom with a walk-in shower. Sliding glass doors from the dining area open to a covered lanai and screened-in pool, creating an inviting setting for outdoor relaxation and entertaining. The spacious, fenced backyard offers additional room to enjoy the outdoors. Other highlights include a brand-new water heater, a 2018 roof, a 2024 HVAC system, and no HOA fees. Conveniently located near Howell Branch Road and Semoran Boulevard, the property provides access to shopping, dining, parks, and everyday essentials throughout the Winter Park area. With its private pool, generous lot size, and convenient location, this home offers a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

1021 Princess Gate Boulevard, Winter Park

1940 Magnolia Avenue, Winter Park
$1,190,000
4 Beds ⋅ 4 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code
New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

1940 Magnolia Avenue, Winter Park

How much is your home worth?

Get instant property value now!