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$502,000
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines Merrie Oaks SubDv. ⋅ 32792 Zip Code
MULTIPLE OFFERS. Calling for highest and best by Tuesday, 1/27/2026 at 9AM. Welcome home to a beautiful 4-bedroom, 3-bath split-plan residence, tucked away on a quiet dead-end street in unincorporated Winter Park. Offering 1,835 square feet of thoughtfully designed living space, this home offers timeless comfort. Enjoy true peace of mind with major improvements already completed, including a whole home re-plumb (Nov 2025), updated electrical (2025), roof (2018), HVAC (2021), hurricane windows, newly painted interior and exterior, tile flooring throughout, crown molding, and a cozy wood-burning fireplace. The updated kitchen opens seamlessly to the family room, creating the perfect flow for everyday living and entertaining. A split floor plan provides privacy and functionality for family and guests alike. Step outside to your private, fully fenced backyard featuring a huge covered and screened patio; ideal for morning coffee, evening gatherings, or simply unwinding in peace. Also featured in the backyard is a generator, so you never need to worry about power. Zoned for Aloma Elementary, Glenridge Middle, and Winter Park High School. This property is located in desirable Winter Park Pines near shopping, dining, parks, and all that Winter Park has to offer. This exceptional property on Fitzhugh Road delivers comfort, quality, and location—an opportunity not to be missed. Schedule your private showing today!

326 Fitzhugh Road, Winter Park
$260,000
3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 2 SubDv. ⋅ 32792 Zip Code
Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter Park has in store. The interior features new appliances, making it move-in ready with modern convenience. A brand-new roof will be installed once the property is under contract, offering added value and peace of mind to the future owner. Whether you’re seeking a primary residence or an investment opportunity, this property delivers flexibility, comfort, and location. Enjoy nearby parks, shopping, dining, and easy access to major roads—convenience meets lifestyle in one of Central Florida’s most sought-after communities. Don’t miss this exceptional opportunity—schedule your private showing today.

1952 Spring Street, Winter Park
$310,000
3 Beds ⋅ 1 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome home to this darling, move-in-ready Winter Park gem! Perfectly suited as a starter home or investment opportunity, this beautifully remodeled 3-bedroom, 1-bath residence features laminate flooring throughout, a fully remodeled bathroom, and an updated kitchen with granite countertops and stainless steel appliances. Updated plumbing completed in 2014 and a 2017 AC system offer added peace of mind, and tasteful window treatments are already in place. Step outside to a large, fully fenced backyard complete with a fire pit and shed—perfect for entertaining, relaxing, or enjoying Florida evenings. Ideally located in a great area of Winter Park, close to shops, dining, and approximately 30 minutes to everything you want to enjoy in Orlando. One of the best-priced remodeled homes in the area—this charming property is a must-see! NO HOA! Tour this home at

1792 Chilean Lane, Winter Park
$182,900
2 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
Move-in ready! Exceptional value in the heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath ground-floor condominium, where comfort, convenience, and an unbeatable location come together. The thoughtfully designed floor plan features an open-concept living and dining area, a screened patio overlooking peaceful landscaped gardens, and recent upgrades and maintenance, including a new electrical panel (2024), washer & dryer (2024), dishwasher (2023), refrigerator (2020), and a complete A/C system service (2025). Enjoy resort-style amenities at Stratford at Winter Park, including two swimming pools, two lighted tennis courts, a fitness center, clubhouse, and car care facilities, all within a beautifully maintained community. Perfectly located just minutes from Park Avenue, Baldwin Park, Full Sail University, Rollins College, AdventHealth Winter Park, shopping, dining, cafés, golf courses, and major highways, this home offers the ideal balance of everyday convenience and the sought-after Winter Park lifestyle. Competitively priced and offering exceptional value in today's market, this move-in-ready home is an excellent choice for a primary residence, seasonal getaway, or long-term investment. Motivated seller. Schedule your showing today. Note: Some photos have been virtually staged for illustrative purposes.

205 Lewfield Circle Unit 205, Winter Park
$405,500
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Priced BELOW appraised value for a quick sale! Welcome to this stunning newer-construction townhome offering modern design, spacious living, and unbeatable value in one of Orlando’s most convenient locations. Featuring 3 bedrooms, 3 bathrooms, and nearly 2,000 sq ft of living space, this home boasts an open-concept layout, contemporary finishes, and abundant natural light throughout. The kitchen flows seamlessly into the main living area—perfect for entertaining—while the generously sized bedrooms provide comfort and flexibility for any lifestyle. Built in 2024, this home offers the peace of mind of newer construction with stylish, move-in-ready appeal.

2834 Bright Bird Lane, Winter Park
$325,000
3 Beds ⋅ 3 Baths ⋅ Coronado Twnhms SubDv. ⋅ 32792 Zip Code
UNIQUE OPPORTUNITY TO OWN AN AFFORDABLE TOWNHOME IN THE DESIRABLE WINTER PARK AREA! LOADED WITH LUXURY FEATURES AND DECORATED IN TRENDY EARTH TONES, THIS HOME OFFERS 42 INCH DESIGNER WOOD CABINETRY, GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES & FRESH PAINT. NEW LAMINATE FLOORING HAS JUST BEEN INSTALLED & THERE IS NO CARPET IN THIS HOME. ENJOY GENEROUS LIVING SPACES AND ABUNDANT NATURAL LIGHT & OUTDOOR LIVING WITH A COVERED PATIO & SEMI PRIVATE BACK YARD WITH NO REAR NEIGHBORS! THERE IS PLENTY OF PARKING WITH A DOUBLE WIDE PAVED DRIVEWAY. CONVENIENTLY LOCATED JUST MINUTES FROM DOWNTOWN WINTER PARK WITH MANY SHOPPING & DINING OPTIONS, DOWNTOWN ORLANDO, ORLANDO AIRPORT, SCHOOLS, PARKS & PUBLIC TRANSPORTATION. CURRENTLY ZONED FOR EXCELLENT WINTER PARK SCHOOLS. CROWN JEWEL CT IS A DEAD END STREET WITH NO THROUGH TRAFFIC.

3136 Crown Jewel Court, Winter Park
$379,990
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Stunning Newly Remodeled Move-In Ready Home! Property Highlights: • 3 Bedrooms | 2 Bathrooms – Both bathrooms fully modernized with contemporary fixtures, sleek tile work, and high-end finishes • Brand-New Flooring Throughout – Fresh, durable, and stylish flooring for a clean, modern look • Gourmet Kitchen with Quartz Countertops – Gorgeous new quartz surfaces, updated cabinetry, and stainless steel appliances • Newer Roof & Brand-New AC System – Key updates completed for efficiency, comfort, and worry-free living • Open-Concept Living – Bright, airy layout with excellent flow and plenty of natural light • Spacious Bedrooms – Three comfortable bedrooms with good closet space and natural light • Private Backyard – Low-maintenance outdoor area perfect for relaxing or entertaining • Ample Parking – Roomy driveway accommodates multiple vehicles • Prime Location – Close to great schools, parks, shopping, and convenient transit This beautifully remodeled home is 100% move-in ready with all the important upgrades already done! Enjoy fully modernized bathrooms, brand-new flooring throughout, stunning quartz countertops, a newer roof, and a brand-new AC system—everything you need for comfortable, contemporary living without lifting a finger. Priced to sell and ready for its new owner—schedule your private tour today! One or more pictures are virtually staged !

1378 Chilean Lane, Winter Park
$385,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood in winter park. The townhouse has perfect layout when you walk into the house, beautiful tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and shopping center.

2232 Shadowland Loop, Winter Park
$315,000
3 Beds ⋅ 4 Baths ⋅ Fernbrook Trails SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome home to this beautifully updated 3-bedroom, 3.5-bath townhome tucked away on a quiet cul-de-sac in a desirable Winter Park community. Designed with comfort and functionality in mind, each bedroom features its own private bathroom, including a convenient first-floor bedroom with a fully updated, handicap-accessible bath showcasing a spacious tiled shower. The light-filled interior offers an open-concept great room that seamlessly blends the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen is complemented by abundant natural light, while neutral paint and modern flooring flow throughout the home with no carpet anywhere. Upstairs, both bedrooms feature generous walk-in closets and private baths, offering excellent storage and privacy. An interior laundry closet adds everyday convenience. Step outside to a large backyard retreat complete with a hot tub—ideal for relaxing or hosting guests. Additional highlights include a private two-car driveway and a peaceful setting just minutes from Winter Park’s endless shopping, dining, and entertainment options. This move-in-ready townhome combines thoughtful updates, flexible living spaces, and an unbeatable location—don’t miss the opportunity to make it yours.

5475 Bracken Court, Winter Park
$439,900
3 Beds ⋅ 3 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Opportunities like this are rare. Perfectly suited for multi-generational living, mother-in-law suite potential, or rental income, this versatile POOL home sits on an oversized lot with no HOA in one of Central Florida’s most desirable locations — Winter Park. The flexible floor plan allows for comfortable separation of living spaces, making it ideal for extended family, guests, or income-producing arrangements, while still maintaining a natural sense of connection throughout the home. All major high-ticket items have already been taken care of, offering true peace of mind for years to come. Updates include a newer roof 2022, new AC system 2025, new water heater 2025, energy-efficient double-pane windows 2025, resurfaced pool with a new pool pump 2025, fresh interior and exterior paint 2025, and new quality flooring throughout. The updated kitchen features 42-inch shaker cabinetry with soft-close drawers, generous storage, and new appliances, creating a functional and inviting space for daily living and entertaining. Step outside to your private outdoor retreat—ideal for gatherings, relaxation, or future enhancements. The location truly elevates this property. Just minutes from Rollins College, Full Sail University, AdventHealth Winter Park Hospital, and the Cady Way / Gateway Trail. Everyday conveniences are nearby, including Sprouts Farmers Market, Publix, Costco, boutique shopping, cafés, and fine dining along Park Avenue and Baldwin Park. Quick access to major highways ensures easy connectivity throughout Central Florida. Zoned for highly regarded Winter Park schools and surrounded by consistent buyer demand, this home offers a compelling combination of versatility, extensive upgrades, and a prestigious address. Call for your private tour today!

2835 Bongart Road, Winter Park
$499,000
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code
Under contract-accepting backup offers. PRICE REDUCED!!! ROOF 4 yrs. old, newer A/C, In-ground Pool. Enclosed Patio — a beautifully maintained turnkey home nestled in the heart of Winter Park, one of Central Florida’s most sought-after communities. Surrounded by renowned golf courses, top-rated Seminole County schools, lush parks, and family-friendly neighborhoods, this exceptional residence offers the perfect blend of comfort, convenience, and the elevated Winter Park lifestyle buyers are searching for. This spacious 4-bedroom + office home is completely move-in ready and vacant — just bring your furniture and clothes and start living! From the moment you walk through the front door, you’ll love the bright open-concept layout filled with natural light, updated finishes, granite countertops, modern appliances, and an inviting wood-burning fireplace that creates the perfect family gathering space. Designed for entertaining and Florida living, the oversized Florida room/lanai overlooks a stunning private pool and beautifully landscaped fenced backyard, creating the ultimate indoor-outdoor experience. Whether hosting weekend BBQs, pool parties, holiday gatherings, or simply relaxing after work, this home was built for making memories. Additional highlights include: • 2,092 square feet of living space • 4 bedrooms plus dedicated office/bonus room • Large open kitchen with granite countertops and abundant cabinet space • Spacious primary suite with pool views • Huge covered Florida room perfect for entertaining • Private in-ground pool • Full irrigation system and landscaped yard • Wood-burning fireplace • NO HOA • Attached 2-car garage plus additional parking • Fully fenced backyard for privacy and pets • Move-in ready condition Located in the highly desirable Winter Woods/Lake Howell area, this home is centrally positioned near major highways including SR-417, I-4, Howell Branch Road, and SR-436, making commuting to Downtown Orlando, Winter Park Village, UCF, Orlando International Airport, beaches, shopping, dining, and all Central Florida attractions incredibly convenient. Winter Park is known for its charm, tree-lined streets, upscale dining, boutique shopping, beautiful golf communities, and strong sense of community. Families love the area for its excellent schools, nearby parks, recreational amenities, and safe neighborhood atmosphere. This is more than just a home — it’s a lifestyle opportunity in one of Florida’s premier communities.

2217 Sussex Road, Winter Park
$197,382
2 Beds ⋅ 2 Baths ⋅ Oaks Condo SubDv. ⋅ 32792 Zip Code
Winter Park gem! This tastefully updated 2-bedroom, 2-bath corner unit with a spacious patio offers a rare opportunity in a boutique community of only 11 residences, surrounded by million-dollar homes. The unit was repiped in October 2025 and features high-quality enhancements including plantation shutters, built-in closets, a hurricane-rated sliding glass door, smart recessed lighting throughout, a smart fan with light kit in the primary bedroom, and a Nest thermostat. The airy kitchen boasts granite counters with backsplash, soft-close cabinetry, and stainless steel appliances. An open floor plan connects the living and dining areas—ideal for entertaining. The owner’s suite includes a large walk-in closet, custom built-in storage, and a spa-like bathroom. Enjoy a large private balcony overlooking the community pool—perfect for morning coffee or hosting friends. Centrally located, this home is within walking distance to Glenridge Middle School and minutes from grocery stores, AdventHealth, Baldwin Park’s shops and scenic trails, and the dining and boutiques of Park Avenue. Just 15 minutes to Downtown Orlando and under 30 minutes to Orlando International Airport. Zoned for the highly regarded Winter Park school district. HOA fee includes water, pest control, and exterior insurance, and the community is pet-friendly. Excellent option for first-time buyers, downsizers, investors, or students attending Rollins or Full Sail. Call for your private tour today!

1913 Woodcrest Drive Unit B, Winter Park
$172,500
2 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
A Wonderful Opportunity Awaits!! Discover the ease of low-maintenance living in this well-maintained GROUND-FLOOR unit in the always-popular Four Seasons community. Currently leased for $1,800/month to an excellent tenant who would love to stay (month-to-month with 60-day notice), this condo offers built-in stability for investors or a smooth transition for future owner-occupants. Inside, enjoy luxury vinyl flooring throughout, an in-unit washer & dryer, an updated electrical panel, A/C replaced in 2016, and an updated primary bath. The primary bedroom features a spacious walk-in closet, adding great storage and functionality. Four Seasons residents enjoy a host of amenities, including an onsite manager, two pools, tennis court, shuffleboard, clubhouse, and an exercise room. The location is unbeatable—zoned for top-rated schools and walking distance to Brookshire Elementary, Ward Park & Playground, and the Center for Health & Wellbeing, with shopping and dining just minutes away. This is a fantastic opportunity to experience Winter Park living at an affordable price. Whether you’re a first-time buyer, downsizing, or seeking a low-maintenance second home, this property checks all the boxes. Call today for your private showing—this one won’t last!

200 Saint Andrews Boulevard Unit 1905, Winter Park
$420,000
3 Beds ⋅ 2 Baths ⋅ Bel Aire Pines SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated Winter Park home offering modern finishes, strong mechanical upgrades, and a spacious open layout. Major improvements include a brand-new roof installed in October 2025, new windows and sliding door (2024), and a new A/C system (2020), providing long-term comfort and efficiency. Inside you’ll find new porcelain tile flooring installed in 2022, neutral interior tones, and abundant natural light flowing through the main living areas. The kitchen was fully renovated in 2022 and features upgraded cabinetry, corian countertops, pantry storage, and stainless steel appliances. All bedrooms include walk-in closets, and the primary suite showcases an updated dual-sink vanity and a walk-in shower, while the guest bath offers granite countertops, a tub/shower combo, and direct access to the screened lanai. Stepping outside, the property sits on a generous corner lot with mature landscaping and multiple outdoor spaces perfect for entertaining. The backyard features new pavers added in 2024, a covered outdoor grill/kitchen station, a gazebo, fruit trees, garden beds, an enclosed lanai, and a storage shed. The home also offers a shaded carport, a two-car garage, an irrigation system spourced from a private well, and a beautifully maintained front exterior with stone façade and lush greenery. To complete the package, this residence enjoys a prime Winter Park location just minutes from Costco, Publix, Full Sail University, UCF, Rollins College, Baldwin Park, Downtown Orlando, 417, Orlando Executive Airport, shopping, dining, and numerous conveniences.

3236 Knottypine Avenue, Winter Park
$495,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32792 Zip Code
Exceptional land opportunity in the heart of Winter Park! This just-under-¼-acre homesite offers the perfect canvas to build your custom dream residence. Surrounded by multi-million-dollar homes, this prime location places you minutes from Baldwin Park, Winter Park Hospital, Cady Way Park, and the renowned shops and dining along Park Avenue. Enjoy close proximity to top-rated restaurants, boutique shopping, and everyday conveniences. A rare find in one of Central Florida’s most sought-after neighborhoods — the value is truly in the land.

625 S Lakemont Avenue, Winter Park
$160,000
2 Beds ⋅ 2 Baths ⋅ Lancelot/Winter Park SubDv. ⋅ 32792 Zip Code
PRICE IMPROVEMENT!! Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor condo, offering comfort, convenience, and peace of mind with major updates completed in 2023. This move-in-ready home features a brand-new TRANE A/C unit (2023), a new roof (2023), and new exterior paint (2023)—ensuring long-term efficiency and a fresh, modern look from the moment you arrive. Step inside to bright, inviting living spaces filled with abundant natural light. The main living areas feature durable tile flooring, while both bedrooms offer soft carpeting for a cozy retreat. The modern bathrooms add a stylish touch with updated finishes, clean lines, and a spa-like feel. The open layout makes entertaining easy, with seamless flow from the living room to the dining area and kitchen. Large windows throughout the home provide a warm, airy atmosphere that feels welcoming at any time of day. Enjoy the perks of a low HOA, which conveniently includes water and trash services, adding extra value and simplicity to your monthly expenses. The community offers a beautiful pool, perfect for relaxing on sunny Florida days. Located on the first floor, this unit offers easy access with no stairs—ideal for all ages and lifestyles. Whether you're looking for a primary residence, a seasonal home, or an investment opportunity, this condo checks every box. With major updates already done and a bright, modern interior, all that’s left is to move in and make it yours!

3651 N Goldenrod Road Unit E102, Winter Park
$1,088,000
4 Beds ⋅ 3 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code
66,500 PRICE IMPROVEMENT! Experience resort-style living every day in this stunning Meritage Homes masterpiece, perfectly situated on a premium waterfront lot with over 200k in upgrades, in the highly sought-after Water’s Edge section of Hawk’s Crest. This elegant home offers breathtaking pond and fountain views, especially enchanting at sunset, and an unparalleled combination of luxury, comfort, and energy efficiency. Step into your private outdoor oasis featuring a custom screened, saltwater, self-cleaning pool and spa with electric heat, LED color-changing lights, and an illuminated screen enclosure that creates an unforgettable nighttime ambiance. The expanded patio includes a custom outdoor kitchen complete with Quartz counters, stainless grill with hood, Green Egg, refrigerator, sink, backsplash, and ample cabinetry—perfect for entertaining family and friends. Enjoy beautifully manicured landscaping, French drains to the pond, and gutters for worry-free maintenance. Inside, sophistication meets comfort. The home features 10-foot ceilings, 8-foot doors, wood plank tile flooring throughout (no carpet), and plantation shutters in all main living areas, besides the Living room. Elegant crown molding, neutral Sherwin Williams paint, and upgraded lighting and fans add to the refined atmosphere. The chef’s kitchen is a showstopper with solid wood, soft-close shaker cabinets, Quartz countertops, a large island with breakfast bar, pendant and recessed lighting, stainless steel LG and KitchenAid appliances including a double oven, tile backsplash, a walk-in pantry, and a separate Butler’s pantry for additional storage and prep space. This desirable 3-way split floor plan offers privacy for everyone. One secondary bedroom enjoys its own private bath, while two others share a beautifully appointed pool bath featuring Granite counters, shaker cabinetry, and a tiled shower. The dedicated office with double French doors is ideal for working from home. The spacious primary suite is truly a retreat with its own views to the pool area, a luxurious en suite bath featuring double vanities, Granite counters, a garden tub, walk-in shower with glass panels, private water closet, and a custom walk-in closet system that will impress. Additional highlights include: • Laundry room with cabinetry and plumbing for a utility sink • 3-car garage with epoxy flooring and mounted television • All televisions convey, including the outdoor-rated SunbriteTV • Carrier HVAC systems for comfort and efficiency • Recently painted garage doors • Recently cleaned and sealed pavers front and back • Pet screen at bottom and a few side panels of pool Residents of Hawk’s Crest enjoy resort-style community amenities, including a community center with gym, resort pool with a splash pad, elegant clubhouse, multiple playgrounds, dog park (just three doors down!), cornhole area, hammocks, and grilling/picnic areas. Take a relaxing stroll on the private boardwalk to Lake Howell, where you can fish, kayak, paddleboard, or watch the sunset from the gazebo. This gated community with a virtual guard offers both privacy and peace of mind. Don’t miss your chance to own this one-of-a-kind home that perfectly blends elegance, functionality, and the best of Florida living. All you need to do is hire the movers!

1092 Wading Waters Circle, Winter Park
$505,000
4 Beds ⋅ 2 Baths ⋅ Tamarak SubDv. ⋅ 32792 Zip Code
Welcome to this charming 4 bedroom, 2 bath home located in the desirable Charter Oaks subdivision of Winter Park. The centrally located kitchen features stainless steel appliances, granite countertops, and a breakfast bar that seamlessly connects to the family room. Enjoy cozy evenings by the wood burning fireplace or host gatherings in the separate dining room and spacious living room. Step outside to your own private retreat with a fully fenced yard and a covered screened patio with pool, perfect for year round entertaining and relaxation. This home also includes fully owned solar panels offering energy efficiency and reduced utility costs. Nestled in a quiet tree lined neighborhood with no HOA, this home provides the perfect balance of peace and convenience. You will be just minutes from Park Avenue, boutique shopping, world class dining, and the scenic Winter Park Chain of Lakes. Families will appreciate access to top rated schools, nearby parks, and recreational opportunities. With easy access to major highways and a short drive to downtown Orlando, this location simply cannot be beat.

1691 Bomi Circle, Winter Park
$660,000
4 Beds ⋅ 3 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code
Beautifully updated Winter Park home showcasing fifteen years of thoughtful renovations and “forever-home” quality throughout. Sited on just over 1/4 acre of manicured grounds, the inviting single level layout wraps around a bright, vaulted great room with tongue-and-groove ceiling, exposed central beam, and a stunning 20-foot folding Origin door system that opens fully to the pool and patio for seamless indoor-outdoor living. The expansive and private primary suite features a newly remodeled bath with timeless finishes as well as a surprisingly large walk-in closet. Three additional bedrooms and one-and-a-half baths are located on the opposite wing of the home, all connecting to the great room via French doors that create both openness and privacy. Multiple living spaces spotlight cozy vignettes at every turn - from the wood burning fireplace in the family room to the bright view out to the pool from the dining room; even the laundry room is outfitted with a gorgeous molded counter top sink and designer lighting! Notable systems upgrades include a new Trane variable-speed HVAC (2024), roof (2018), windows (2021), driveway (2024), pool pump and filter (2025), and spray-foam insulation. Distinctive details—custom brickwork, wood-inlaid eaves, solid core doors with top shelf hardware, detailed window casings and smooth-finish walls—add character and craftsmanship. Set in a quiet neighborhood near Lake Waunatta with easy access to University Boulevard, this home offers exceptional quality, comfort, and turnkey functionality in desirable Winter Park. Don't miss your chance to see it before its gone.

4019 Quenita Drive, Winter Park
$109,500
1 Beds ⋅ 1 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.

311 Scottsdale Square Unit 311, Winter Park
$1,500,000
7 Beds ⋅ 4 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code
Waterfront dream home in the exclusive, gated community of Lakeside Estates on beautiful Garden Lake. This exquisite 7-bedroom plus office, 4-bath “Del Rio” model offers over 5,000 sq. ft. and has been COMPLETELY RENOVATED in 2025 with high-end finishes, designer lighting, and modern upgrades throughout. Situated in a gated, quiet cul-de-sac community, this property features the largest yard (.5 ACRE) in the neighborhood and direct lakefront access, perfect for adding a dock, pool, or basketball court. Accordion doors lead to an expansive brick paver patio with a covered lanai, yard with fruit trees and breathtaking sunsets over Garden Lake High ceilings, all interiors painted, new porcelain tile, custom lighting, 7-inch baseboards, dual HVAC units and a stunning new glass-and-wood staircase. The gourmet kitchen showcases a new technological refrigerator, new upper cabinetry, granite countertops, stainless steel appliances, butler’s pantry, and custom shelving. Entertain in style with two custom wet bars, fireplace, and a new home theater complete with 7 recliners, surround sound, projector, and subwoofers. Two luxurious primary suites-one on each level offer spa-like bathrooms, custom vanities, and lake views. Additional highlights include Nest thermostats, four high-end automatic bidet toilets, custom closets, and a new laundry room with ceiling-height cabinetry, sink, and mudroom built-ins. The three-car tandem garage provides extra storage and convenience in addition to the extra space brick paved driveway. Enjoy the private lakefront lifestyle with stunning sunsets, community pier, playground, and dock for kayaks and paddleboards. Conveniently located near Winter Park, Oviedo, UCF, and top-rated Seminole County schools. Trinity Prep, Geneva School, Circle Christian and more plus shopping very close by. This home combines modern luxury, comfort, and waterfront living in one unforgettable property. FURNISHED PRICES and more details available upon request.

1460 Via Sangro Place, Winter Park
$435,500
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this stunning Winter Park pool home, offering 3 bedrooms and 2 bathrooms across 1,668 square feet of thoughtfully designed living space. Upon entering, you are greeted by a spacious, open living area where the living and dining rooms flow seamlessly together, creating a perfect space for entertaining or relaxing with family. The kitchen features stainless steel appliances, abundant cabinetry, and generous counter space, complemented by a breakfast nook that opens to the family room. A sliding glass door leads from the family room to the enclosed Florida room, providing a bright, versatile space to enjoy year-round. The split bedroom floorplan ensures privacy, with the primary suite boasting an en suite bathroom complete with a walk-in shower. Step outside to a beautifully landscaped backyard with an in-ground pool and a pergola, ideal for outdoor gatherings or quiet afternoons. The enclosed Florida room with A/C overlooks the yard, making it perfect for indoor-outdoor living. Sitting on over a quarter acre, this home offers ample space for relaxation and recreation. Recent upgrades include fresh paint, new carpet, a brand-new hot water heater, and a new kitchen sink and faucet. Conveniently located near grocery stores, restaurants, and with easy access to highways, UCF, downtown Orlando, and all the city has to offer, this home combines comfort, style, and location in one exceptional package. Don’t miss the opportunity to make this Winter Park gem your new home. Mortgage savings may be available for buyers of this listing.

1630 Gladiolas Drive, Winter Park
$85,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
Entry for Sale Data Only

346 Scottsdale Square Unit 346, Winter Park
$295,000
3 Beds ⋅ 3 Baths ⋅ Winter Green SubDv. ⋅ 32792 Zip Code
Updated 3-Bedroom, 3-Bath Townhouse in Winter Green Community – Move-In Ready! Welcome to this beautifully updated 3-bedroom, 3-bath townhouse located in the desirable Winter Park community in Florida. This spacious and well-maintained home features modern upgrades throughout, including granite countertops, neutral interior colors, and an inviting open layout that's perfect for both everyday living and entertaining. Enjoy the convenience of a move-in ready home with access to fantastic community amenities, including a sparkling pool and clubhouse. Ideally situated near shopping, dining, and just minutes from UCF, this location offers both comfort and connectivity. Co-List Agent related to Seller

1509 Winter Green Boulevard, Winter Park
$458,000
4 Beds ⋅ 3 Baths ⋅ Bel-Aire Pines, Unit Two SubDv. ⋅ 32792 Zip Code
Virtually Staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.

3312 Heartwood Avenue, Winter Park
$365,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Welcome Home to Eastbrook in Winter Park! This beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of comfort, charm, and modern updates — all nestled on an OVERSIZED CORNER LOT in the desirable Eastbrook community with NO HOA and NO CDD. Step inside to find 1,530 sq ft of thoughtfully designed living space, freshly painted in 2025 to give every room a bright, inviting feel. The renovated primary bathroom shower (2025) adds a touch of luxury, while the repiped plumbing (2024) comes with a transferable 30-year warranty for peace of mind. Enjoy outdoor living at its best with a brand-new fence and paved driveway (2023). Major updates have already been taken care of, including a new HVAC (2021), new water heater (2023), and a 9-year-old roof, ensuring this home is move-in ready and worry-free. You’ll love the convenient location — just 10 minutes to Downtown Winter Park and 15 minutes to Baldwin Park, putting shopping, dining, and local charm right at your fingertips. Located in the heart of Winter Park, Eastbrook is known for its welcoming vibe, tree-lined streets, and proximity to top-rated schools, parks, and more. Whether you're a first-time buyer or simply ready for your next chapter, this home has everything you’ve been looking for — style, updates, and location all in one!

1083 Eastbrook Boulevard, Winter Park
$699,450
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
**Multiple offers received*** Please submit highest and best by 10/20/2025 at 4:00 pm This beautifully maintained golf course home offers effortless living in an established Winter Park neighborhood. As you drive along the charming tree-lined streets, the home greets you with impeccable landscaping and timeless curb appeal. Step inside the foyer and discover a bright, open floor plan that seamlessly connects the dining area, kitchen, and living room. Soft natural finishes create a breezy, relaxed feel, while the cozy fireplace anchors the living space, which is perfect for gathering with loved ones. The kitchen is both stylish and functional, featuring stainless steel appliances, stone countertops, a farmhouse sink, and refinished cabinetry. The stylish island provides casual dine-in seating, and the custom pantry and laundry room offer exceptional storage, plus a convenient folding counter and hanging space. Your private primary suite is tucked away to the left of the kitchen, offering serene views and sliding doors that open to the screened lanai overlooking lush, mature landscaping. The walk-in closet provides generous storage, and the updated ensuite bath includes a walk-in shower with both handheld and fixed showerheads. A split floor plan offers three additional bedrooms and an updated guest bath with a tub and glass enclosure perfect for guests. Relax on the screened lanai and enjoy peaceful golf course views and privacy. The brand-new roof provides peace of mind, and the widened paver driveway offers both style and convenience. The garage is equipped with a workbench and built-in shelving for all your storage needs, plus an additional shed and fenced side yard create more outdoor space to enjoy. Located within the Winter Park school district, this home offers the perfect blend of privacy and convenience — just 8 minutes from Lake Baldwin Park, 10 minutes to Corrine Drive’s shopping and dining, 12 minutes to Park Avenue, and 20 minutes to Downtown Orlando.

1346 Golfside Drive, Winter Park
$70,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
First floor, Move in ready unit! Tile floors throughout. Perfect for a first time buyer or an investor. Close to great schools, restaurants, major highways and more! Call or text to schedule a showing!

107 Scottsdale Square Unit 107, Winter Park
$660,000
4 Beds ⋅ 2 Baths ⋅ Williamsburg SubDv. ⋅ 32792 Zip Code
Welcome to this well-maintained Winter Park home, proudly cared for by its original owner. With a BRAND NEW ROOF and BRAND NEW AC system, this property combines peace of mind with long-term value. Set on a spacious quarter-acre lot with NO HOA, it offers flexibility, privacy, and convenience in one of Central Florida’s most desirable locations. This home features a durable roof with a 10-year transferable warranty, engineered to withstand winds of up to 130 mph for lasting protection and peace of mind. Step inside through the front entry into a light-filled formal living room, where large windows set a warm and welcoming tone. Just to the right, the formal dining room provides the perfect space for family gatherings or entertaining. Flowing naturally into the main family room, you’ll find a cozy fireplace that anchors the space and creates an inviting setting for everyday living. The kitchen is designed for function with all appliances included, ample counter space, and a thoughtful connection to the laundry room, which features generous storage and everyday convenience. Off the family room, the Florida room is bright and versatile—ideal for a home office, reading nook, or playroom. One of the standout features is the expansive 483 sq. ft. bonus room, offering endless possibilities as a game room, studio, or additional living space to suit your lifestyle. Outdoors, a screened-in porch overlooks the fenced backyard, providing a comfortable spot to relax, garden, or host gatherings. An included shed adds extra storage for tools and equipment. Each bedroom is well-sized, offering comfort and practicality, with bathrooms that have been cared for and maintained with attention to detail. The thoughtful layout balances privacy and community spaces, making it both functional and inviting. Location is key, and this home delivers. Just a few minutes’ walk takes you to the scenic Cady Way Trail, Winter Park Pines Golf Course, and Winter Park High School. Nearby parks, shopping, dining, and top-rated schools add to the convenience, while downtown Winter Park, Orlando attractions, and major highways are only a short drive away. Perfect for buyers seeking a primary residence, an Orlando relocation home, or a smart Central Florida real estate investment, this property is a rare find. With only one owner since construction and NEW major systems in place, this Winter Park gem is ready for its next chapter. Contact us today for a private tour or more details on this exceptional opportunity.

2421 Summerfield Road, Winter Park
$684,000
3 Beds ⋅ 4 Baths ⋅ Kawilla Crest SubDv. ⋅ 32792 Zip Code
BEAUTIFULLY RENOVATED CUSTOM HOME IN WINTER PARK. THIS STUNNING 3 BEDROOM 3.5 BATH CUSTOM HOME BLENDS STYLE, COMFORT, AND CONVENIENCE IN ONE OF WINTER PARK'S MOST DESIRABLE NEIGHBORHOODS. ENJOY A NEW ROOF, RECENTLY RENOVATED KITCHEN AND MAIN LIVING AREA, CATHEDRAL CEILINGS THAT FILL THE HOME WITH NATURAL LIGHT. THE OPEN FLOOR PLAN IS PERFECT FOR FAMILY LIVING AND ENTERTAINMENT, WITH SEAMLESS FLOW TO RECENTLY UPDATED POOL WITH OUTDOOR FULL POOL BATH. BEAUTIFULLY LANDSCAPED FULLY FENCED BACKYARD. WITH SPACIOUS BEDROOMS AND LUXURIOUS PRIMARY BEDROOM SUITE WITH SITTING ROOM AND POSSIBLE OFFICE, AND LARGE BATHROOM WITH WALK IN CLOSET. THIS HOME HAS PLENTY OF ROOM FOR EVERYONE TO UNWIND. LOCATED NEAR TOP WINTER PARK SCHOOLS, SHOPPING AND DINING. THIS HOME COMBINES MODERN UPDATES WITH TIMELESS APPEAL. PERFECT FOR FAMILIES LOOKING TO ENJOY THE BEST OF WINTER PARK LIVING.

1909 Cyril Court, Winter Park