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$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
$268,000
2 Beds ⋅ 2 Baths ⋅ Gallery At Winter Park Sec 01 SubDv. ⋅ 32792 Zip Code
PRICE REDUCED!!!!!!!!!IMMACULATE !!!!! Close to everything from this quiet 2nd floor 2/2 condo at THE GALLERY in Winter Park! Safe 3-minute walk to Publix, restaurants, movies and Crealde Art Center via gated back entrance to complex, Starbucks just outside the other way. Stainless steel and granite, dishwasher, built-in microwave. High ceilings in LR/DR and master. Walk-in closet in master. Screened balcony overlooks community pool and a beautiful pink crape myrtle, blooming soon. A/C replaced in 2019. Hall laundry closet includes W/D. Neutral colors are ready for you to make it your own. Short drive from Rollins, Park Avenue, Trader Joe's, Winter Park Hospital, YMCA and more.

609 Gallery Drive Unit B204, Winter Park
$315,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Patio Homes SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Don’t miss out on this beautifully maintained, 2 bed, 2 bath, single story townhome in the sought after Winter Park Pines with a LOW HOA! As you make your way towards the entrance you have 2 private, fenced-in courtyard areas for sitting out for a morning coffee, home gardening, or just getting out to enjoy the weather. As you enter the home you see nicely updated kitchen with granite countertops, stainless steel appliances, and white cabinets. The great room is exactly that, with large vaulted ceilings and plenty of natural light. The spacious Owner’s Suite is complete with a gorgeous, recently renovated bathroom and walk-in closet!

615 Warrenton Road, 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
$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
$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
$899,000
4 Beds ⋅ 3 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Discover elevated living in this stunning 4 bedroom, 2.5 bathroom pool home, perfectly situated overlooking a tranquil pond and Winter Park 18 hole golf course. Surrounded by a lush tropical backyard oasis, this residence blends modern sophistication with effortless comfort, creating a serene retreat that’s ideal for that perfect start to the morning with a cup of coffee or a relaxing wind down at sunset with a glass of wine. Inside, vaulted wood-trimmed ceilings and a wood-burning fireplace set a warm, inviting tone across 2,455 sq. ft. of thoughtfully designed space. The kitchen features contemporary cabinetry paired with quartz and butcher block wood countertops and a designer tile backsplash. Stainless steel appliances, including a beverage refrigerator, add a professional touch, while a built-in banquette provides seating for six—perfect for entertaining and everyday living. The primary suite offers wood floors, a walk-in closet, and a spa-like bath with dual floating vanity, soaking tub, and seamless glass shower. Enjoy outdoor living at its finest with pergola-covered sitting areas, outdoor shower, fire pit, and sparkling pool. Situated on a private tree-lined cul-de-sac, this home is located in a prime location just minutes from Cady Way Trail, Cady Way pool & courts, Winter Park Pines Golf Course, Crosby Center for Health and Wellbeing, Ward Park, Showalter Athletic Complex, Advent Health Winter Park Hospital and less than 10 minutes to Historic Park Avenue fine dining and shopping. Don’t miss your chance to own this rare Winter Park gem—schedule your showing today! ROOF - 2016 HVAC - 2023(2) PLUMBING - 2020 ELECTRICAL - 2021 WATER HEATER - 2020

1648 Cypress Point Lane, Winter Park
$501,000
3 Beds ⋅ 2 Baths ⋅ Lost Creek SubDv. ⋅ 32792 Zip Code
This is the Winter Park pool home you’ve been waiting to find in the small and upscale Lost Creek neighborhood. Beautiful custom low maintenance landscaping (no grass to mow) welcomes you as you walk up the front path to the covered porch. Soaring vaulted ceilings inside will impress as you enter this lovely 3 bed, 2 bath abode with pool and spa and over 1,900 sq ft of living space. Wood flooring is found in the formal dining and living rooms with views through the glass sliders out to the covered lanai and screen-enclosed pool and spa. Attractive neutral stone-look ceramic tile flows through the updated kitchen with all NEW stainless-steel appliances (Sept 2025), granite counter tops, and breakfast nook overlooking the pool. The family room is a causal place to spend time with its wood-burning fireplace with stacked stone surround and built-in bookshelves flanking each side. A split layout offers 2 guest bedrooms, full hall bath, and inside laundry room off the kitchen side of the home; while the spacious primary bedroom is separate, with a huge walk-in closet (10’ x 5’), double French doors leading to the lanai, separate en-suite with double vanities/sinks, private toilet room, and large walk-in shower. Imagine al fresco dining or lounging poolside under the covered lanai and screen-enclosed pool patio area, and there’s plenty of side yard space for a garden or dog run. Improvements to the home include all NEW kitchen appliances and hot water heater 2025; NEW garage door spring and mechanisms 2024; NEW barn door installed to primary bathroom 2020; NEW HVAC 2019; Roof 2015; plumbing CPVC. Zoned for fantastic Seminole County Schools. This is the house you’ve been waiting to find and call HOME.

1185 Valley Creek Run, Winter Park
$285,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
This is one of the largest floor plans in the community. Two bedrooms, two bathrooms, and a loft that you can use as a third bedroom, home office, or gym. Welcome to the established and well-maintained community of Cedarwood Village, located in highly desirable Winter Park! TREE-LINED STREETS lead you to this two-story, 2-bedroom, 2-bath BLOCK-CONSTRUCTED condominium offering 1,669 square feet of interior living space, this includes an enclosed lanai (under air), for extra living space. The open living and dining area features VAULTED CEILINGS, two skylights, creating a bright and inviting space. From here, enjoy serene views of the enclosed lanai and lush green space beyond. A WET BAR adds a perfect touch for entertaining. Upstairs the loft has a skylight, ceiling fan and is carpeted. The kitchen is thoughtfully designed with a space for a charming eat-in nook that overlooks your PRIVATE COURTYARD and is accessible through sliding glass doors—perfect for morning coffee or outdoor dining. For added convenience, the laundry closet with a WASHER AND DRYER is tucked right into the kitchen. The primary suite is a peaceful retreat, with a beautifully en-suite bathroom with a brand-new vanity with granite, featuring both a WALK-IN closet, and a shower enclosure and the lanai under air, is accessible through sliding glass doors. The spacious second bedroom also features a walk-in closet and attached access to the second bathroom, offering privacy while still serving guests comfortably. Additionally, this home is located across from green space, has two designated parking spaces, and a private mailbox. Re-roofed and new skylights were installed in 2020; entire complex was recently painted. Upgrades include newer AC and just painted in July 2026. A beautiful master bathroom cabinet and sink —providing comfort and style. With low HOA dues, residents enjoy access to a sparkling community pool, clubhouse, tennis and basketball courts, pickleball, a FENCED DOG RUN, and a pet walk with waste stations. Monthly fees also cover roof and exterior building maintenance, pest control, and landscaping. This ideal Winter Park location is just minutes to Park Avenue, UCF, Rollins College, Full Sail University, shopping, restaurants, entertainment, and medical facilities.

2336 Sun Valley Circle Unit BLDG 20, Winter Park
$320,000
3 Beds ⋅ 2 Baths ⋅ Bridgewater Ph 2 SubDv. ⋅ 32792 Zip Code
Welcome to your own tropical escape nestled in a quiet street in desirable Winter Park. This beautiful home features a private screened-in pool surrounded by lush landscaping, creating the perfect setting for relaxing weekends and entertaining friends. Inside, the bright and spacious living area is anchored by a cozy fireplace, adding warmth and charm to the heart of the home. The modern kitchen offers stainless steel appliances and plenty of counter space, while the comfortable bedrooms provide a peaceful retreat for rest and privacy. Step outside to your tranquil backyard oasis and enjoy swimming, lounging, or dining al fresco by the pool. Conveniently located near top-rated schools, shopping, dining, and major highways, this home perfectly blends comfort, style, and resort-style living.

5433 S Bracken Court, Winter Park
$260,000
3 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Spacious End-Unit Condo in Prime Winter Park Location – Quiet Dead-End Street! Welcome to this well-maintained 3-bedroom, 2-bath end-unit condo offering 1,311 sq ft of comfortable living space in the heart of Winter Park. Situated on a quiet dead-end street, this desirable end unit provides extra privacy, added natural light, and a peaceful setting within a beautifully kept community. Step inside to an inviting open floor plan featuring a cozy family room with a wood-burning fireplace, perfect for relaxing evenings or entertaining guests. The space flows into a bright dining area and a well-maintained kitchen, while a private screened-in back porch extends your living area outdoors. The spacious primary suite includes an en-suite bath, and the two additional bedrooms offer flexibility for guests, family, or a home office. Enjoy a variety of community amenities including a sparkling pool, dog run, and two tennis courts, all within a quiet, friendly neighborhood setting. Located just minutes from Downtown Orlando, MCO Airport, Full Sail University, and Rollins College, this condo offers convenience, comfort, and great value in one of Central Florida’s most sought-after areas. Don’t miss your chance to see this charming home—schedule your private tour today!

2489 Tahoe Circle, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Cedar Ridge Unit 1 SubDv. ⋅ 32792 Zip Code
Newly renovated 3 Bedroom 2 Bath in a well establish community of Cedar Ridge. Conveniently located in Winter Park Seminole County. Pool home. The office can easily turn into a 4th bedroom if needed. New tile floors throughout. Open, airy and bright. Updated kitchen with quartz countertop. New stainless steel appliances. New roof 2024, new water heater 2024, whole house plumbing re-piped 2025, electrical panels will be replace prior to closing, and most of the windows are newly replaced/repaired. Spacious Master Bedroom. Oversized 2 car garage attached. No Homeowners Association. Short drive to Park Avenue, Rollins College, UCF and 436.

1932 Houndslake Drive, Winter Park
$450,000
4 Beds ⋅ 3 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
4 Bedrooms | 2.5 Baths | New Roof | Winter Park’s Country Lane Welcome to this well-cared-for 4-bedroom, 2.5-bath home in the highly desirable Country Lane neighborhood of Winter Park! On the first floor, you’ll find a bright and inviting layout with a kitchen featuring stainless steel appliances, along with ample cabinet and counter space. There’s plenty of room to entertain, with a formal living and dining area on one side and a dinette and family room on the other. Major updates bring peace of mind, including a brand-new roof (2025) with solar panels for energy efficiency, plus fresh new sod that enhances the curb appeal. Upstairs, all four bedrooms are located together, creating a private retreat away from the main living areas. The highlight is the large primary suite, complete with a spacious walk-in closet, offering both comfort and convenience. Living here means more than just a home—you’ll enjoy the fantastic Country Lane community amenities. As a resident, you’ll have exclusive access to Lakeside Park on Lake Florence, featuring a fishing pier, kayak and paddle board launch, playground, and tennis courts. It’s the perfect setting for both relaxation and an active Florida lifestyle. Don’t miss this opportunity to own a move-in-ready home in one of Winter Park’s most loved neighborhoods!

1660 Tremont Lane, Winter Park
$340,000
3 Beds ⋅ 2 Baths ⋅ Garden Grove SubDv. ⋅ 32792 Zip Code
Welcome to Winter Park! Nestled in a cozy, established neighborhood with NO HOA, this charming 3-bedroom, 2-bath single-family ranch is ready for its next chapter. With a spacious fenced backyard, huge screened-in pool, and a covered patio, this home is perfect for relaxing or entertaining. Inside, you’ll find vaulted ceilings, ceiling fans, and plenty of natural light. The two-car garage provides storage and convenience, while the mature landscaping enhances the home’s curb appeal. This property is a true Winter Park gem and an excellent fixer-upper investment opportunity — ideal for buyers looking to add their own style, renovate, or create long-term rental income. Conveniently located just minutes from SR 417 and UCF. This home offers both comfort and a prime location. Come schedule a showing and find your next home to Bloom in!

5631 Garden Grove Circle, Winter Park
$180,000
1 Beds ⋅ 1 Baths ⋅ Winter Park Villas Condo Bldg 12 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated 1-bedroom, 1-bathroom end-unit condominium in the sought-after Winter Park Villas community. Blending style and functionality, this move-in ready home offers thoughtful updates and a spacious layout ideal for comfortable living. Step inside to discover an updated kitchen featuring newer Samsung stainless steel appliances, an eat-in breakfast bar, and a convenient pass-through to the dining area—all with views of your private patio - perfect for morning coffee or relaxing evenings. The open-concept living area boasts vaulted ceilings and a cozy wood-burning fireplace, creating a warm and inviting atmosphere. The generously sized primary bedroom includes a ceiling fan and a large walk-in closet. The remodeled bathroom showcases chic gray cabinetry, quartz countertops, brand-new lighting, and a private water closet with a shower area for added comfort. Additional highlights include luxury vinyl plank flooring throughout, a dedicated laundry area with full-sized washer and dryer, and ample storage near the entry, bathroom, and off the patio. A newer AC unit ensures year-round comfort. Enjoy access to fantastic community amenities including a pool, clubhouse, fitness center, basketball and tennis courts—ideal for both active lifestyles and relaxed weekends. Located just minutes from Full Sail University, UCF, shopping, dining, and Winter Park Pines Golf Course, this charming Winter Park condo is the perfect place to call home! HVAC - 2023

680 Grenadine Court Unit S, Winter Park
$360,000
3 Beds ⋅ 2 Baths ⋅ Autumn Glen SubDv. ⋅ 32792 Zip Code
Welcome to your new Winter Park home! Located in the highly sought-after community of Autumn Glen, this beautifully maintained property offers peace of mind and modern comfort with a new roof, newer A/C system, updated plumbing, and a remodeled kitchen featuring granite countertops, stainless steel appliances, and a spacious pantry. The L-shaped living and dining area boasts vaulted ceilings, perfect for both relaxing and entertaining. The primary suite includes a walk-in closet and sliding doors that lead to the covered and screened patio. Enjoy a split-bedroom layout with generously sized guest rooms, ceiling fans throughout, and a 2-car garage. The fenced yard provides privacy and room to enjoy the outdoors. The community is located just around the corner from Red Bug Elementary, Tuskawilla Middle and Lake Howell High School.. Other community features include tennis/pickleball courts, a playground, and a gazebo overlooking the community pond—perfect for bringing your fishing pole. If you're looking for the right house in the right location, this is the one.

1767 Meadowgold Lane, Winter Park
$545,000
3 Beds ⋅ 2 Baths ⋅ Golfside Sec 03 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully maintained original-owner home nestled along the Winter Pines Golf Course! This property boasts breathtaking golf course views, a newly extended rear patio, and timeless curb appeal with cedar siding that enhances its warm, inviting character. Inside, you'll find all-new flooring throughout, a custom kitchen with solid wood cabinets, and abundant natural light filling every room. The family room features a cozy fireplace, perfect for relaxing or entertaining. Enjoy a quiet cup of coffee in the morning while in the sitting area with views of the perfectly landscaped backyard and golf course. The AC is only 2 years old and the home was replumbed in June 2025. Don’t miss this rare opportunity to own a lovingly cared-for home in one of Winter Park’s most sought-after locations! For a 3-d tour of this home, click on Virtual Tour 2.

1123 Fairway Drive, Winter Park
$468,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Mid-Century Modern vibes in this spacious 3 bedroom, 2 bathroom home with an innovative courtyard design that offers scenic views of the expansive lot from almost every room. The house is nestled under a canopy of mature trees on one of the largest lots in Winter Park Pines. Kitchen and baths are original but recent updates include: ROOF 2019, HVAC 2017, REPLUMBED 2009, GARAGE DOOR REPLACED, LAMINATE FLOORING 2014, INTERIOR PAINT 2025, UPDATED VINYL WINDOWS AND SLIDING DOORS 2015(MOST). The L-shaped formal living and dining rooms feature terrazzo floors and the living room has a vaulted ceiling and sliding doors into the private courtyard. The kitchen features a pass-through window into the courtyard for all of your outdoor entertaining options as well as a nook space ideally suited for a booth, breakfast table or a special piece of furniture. The adjacent family room is anchored with a brick wood burning fireplace and hearth, and another set of sliding doors into the courtyard. The primary suite has a large walk-in closet, a spacious en-suite bath and sliding doors overlooking the enormous rear yard. The house and lot have endless potential and are ready for your personal touch. The oversized lot is perfect for a pool, swing set, pets or sporting activities. Ideally situated just minutes from the shops and restaurants of Park Avenue, Rollins College, UCF and Full Sail Universities, the Cady Way Trail, Winter Pines Golf Club, and a short drive to downtown Orlando and Orlando International Airport.

541 London Road, Winter Park
$530,000
3 Beds ⋅ 2 Baths ⋅ Glenmoor SubDv. ⋅ 32792 Zip Code
Welcome to 7682 Glenmoor Lane – Located in the established community of Glenmoor, zoned for Winter Park HS, Maitland Middle and Lakemont Elementary. This beautifully renovated Winter Park gem is situated on a generous 0.26-acre lot, this stunning single-family home blends timeless style with modern updates throughout. Step inside to discover custom tile flooring, solid wood cabinetry in both the kitchen and bathrooms, and custom tile work that adds elegance to every space. The thoughtfully designed kitchen features a sleek exhaust system, while the laundry room offers built-in cabinets and a desk—perfect for added functionality. The backyard is your private retreat, complete with a covered patio, expansive wood deck, and a gorgeous pool built in 2022, surrounded by a paver deck ideal for entertaining. A dedicated shed provides additional storage, and the spacious yard offers endless possibilities. Major upgrades include a new roof (2018), AC (2022), and water heater (2022), ensuring peace of mind for years to come

7682 Glenmoor Lane, Winter Park
$255,000
2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
**This property qualifies for a closing cost credit up to $3,900 through the Seller’s preferred lender.** Charming Winter Park Townhome with Vaulted Ceilings and Sun-Filled Spaces. Welcome to 2398 Dominica Way, a beautifully maintained 2-bedroom, 2-bathroom townhome nestled in the heart of Winter Park. From the moment you arrive, you'll be drawn in by the inviting front patio, complete with a pergola and clear roofing—perfect for soaking up the sunshine while staying protected from Florida’s afternoon showers. Step inside and you’re greeted by a warm and functional layout. The kitchen, located just off the entry, boasts rich, warm cabinetry, sleek black and stainless steel appliances, and a serving window that opens into the spacious dining and living room combo, doubling as a breakfast bar for casual meals or entertaining guests. Continue into the main living area, where soaring vaulted ceilings and a wall of glass sliders flood the space with natural light and provide a beautiful view into the Florida room. Off to the left, a private hallway leads to the home’s bedrooms. The guest bedroom overlooks the front patio and features a ceiling fan and easy access to the second full bathroom, which includes a tub/shower combo. Across the hall, the primary suite offers a peaceful retreat with a walk-in closet, an ensuite bathroom with a walk-in shower, and private access to the rear porch through sliding glass doors. The spacious Florida room at the back of the home offers flexible indoor-outdoor living, with direct access to a shared grassy area—perfect for pets, gardening, or simply enjoying the fresh air. Whether you're a first-time homebuyer, downsizing, or looking for a low-maintenance lifestyle in a prime location, this gem in Winter Park is ready to welcome you home.

2398 Dominica Run, Winter Park
$655,000
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Welcome to 1640 Cypress Point – a home like no other in Winter Park. This beautifully maintained 3-bedroom, 2-bathroom home offers 1,704 sq. ft. overlooking a serene spring-fed pond and the Winter Park Pines Golf Course. Nestled on a quiet street with a cul-de-sac, this property combines privacy, natural beauty, and convenience in one exceptional location. As you walk up to the front door, you’ll notice an inviting and private courtyard area. Step inside to a light-filled entryway and an open layout accented by wood laminate flooring, fresh interior and exterior paint (2025), high ceilings, and a wood-burning fireplace with coquina rock detail and a wood mantel. The kitchen was remodeled in 2012, and features natural wood cabinetry, jade green granite countertops with a chiseled edge, stainless steel appliances, and a cozy dinette area, which looks out to the side yard through the sliding doors. Off of the living area you can access the third bedroom with french doors that lead out to the pool area. This space could also be used as a den or office space. Down the hall, the primary suite boasts a large walk-in closet, and Italian inspired ensuite bathroom with imported Italian tile in the walk-in shower, a marble vanity, and open shelving for plenty of storage. You can also access the side yard from the primary bedroom which leads out to a mulched patio area to enjoy your morning or sunset water views. The additional bedrooms share a hall bath with a granite vanity and tub/shower combo. Enjoy Florida living in your private backyard oasis! The sparkling pool, resurfaced with new coping in 2016, features three waterfalls and a decorative stone wall, all set against lush landscaping and sweeping views of the pond and 18 hole golf course.This home is located in a prime location just minutes from Cady Way Trail, Cady Way pool & courts, Winter Park Pines Golf Course, Center for Health and Wellbeing, Crosby Fitness Center, Ward Park, Showalter Field, YMCA, Advent Health Winter Park Hospital and less than 10 minutes to Historic Park Avenue fine dining and shopping. Close to Rollins College, UCF, Full Sail, and only 30 minutes to OIA airport. Zoned for top-rated Brookshire Elementary, Glenridge Middle, and Winter Park High.Don’t miss your chance to own this rare Winter Park gem—schedule your showing today! Roof 2017, HVAC 2017, Re-plumbed 2015, Water Heater 2009, Garage Door 2023

1640 Cypress Point Lane, Winter Park
$335,000
2 Beds ⋅ 2 Baths ⋅ Hyde Park SubDv. ⋅ 32792 Zip Code
Welcome to Hyde Park, off Howell Branch Road in Seminole County. First time offered. Wonderful two-bedroom, two-bath split plan, with two-car garage and fireplace. The roof has been replaced as well as the air-conditioning unit. Over 1,400 heated square feet, with fabulous large porch (no rear neighbors). This is ready to decorate to your liking! Bring a paintbrush and replace flooring. Tons of potential with a lake, tennis court and basketball court. Easy lock and go. Vacant and ready.

3103 Ash Park Loop, Winter Park
$255,000
3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 1 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Freshly updated and ready for easy living, this concrete-block villa delivers three bedrooms, including a versatile flex room, plus two full baths across a smart 1,080-square-foot, single-story layout. The curb appeal pops thanks to 2023 exterior paint, a brand-new roof (2023), and a privacy fence (2023) that frames the fully fenced backyard. Step inside to an open living-dining core that flows to a screened back porch, perfect for morning coffee or evening grilling, while an attached storage shed keeps tools and toys neatly tucked away. Key systems inspire confidence: the electrical panel has been upgraded, a new water heater arrived in 2024, the HVAC dates to 2015, and the bathrooms feature recently installed raised toilets. Add in the community pool, low $39/month HOA, and Seminole County school zoning, and you’ve found a turn-key Winter Park address that keeps both maintenance and monthly costs pleasantly low.

3005 Casselwood Street, Winter Park
$625,000
4 Beds ⋅ 3 Baths ⋅ Bear Gully Bay SubDv. ⋅ 32792 Zip Code
EXPECT TO BE IMPRESSED! Tucked away in a quaint and quiet Winter Park neighborhood, this beautifully maintained two-story 4-bedroom, 2.5-bath pool home sits on a lushly landscaped conservation lot with a charming paver walkway and inviting curb appeal. From the moment you step inside, you’ll appreciate the thoughtful updates and timeless character that make this home truly special.The newly renovated kitchen is a showstopper—featuring granite countertops, modern cabinetry, stylish backsplash, and recessed lighting—perfectly positioned to overlook the serene screened-in patio and saltwater pool, complete with a solar heating system for year-round enjoyment. The formal living and dining rooms offer volume ceilings, while the stunning two-story family room is anchored by a cozy wood-burning fireplace and custom built-ins, creating an ideal space for both entertaining and everyday living. The first-floor primary suite offers a peaceful retreat with an updated en-suite bathroom featuring granite counters, a clawfoot soaking tub, separate shower, and a spacious walk-in closet with California closet systems. Upstairs, you’ll find three generously sized bedrooms, an updated full bath, and a loft area—ideal for a home office, playroom, or second living space. Additional highlights include newer asphalt shingle roof (2020), a new HVAC system installed in 2023, and a vinyl privacy fence (2015) enclosing the St. Augustine-grassed backyard. The garage is fully functional with two remotes, and the home features a 13 x 5 inside laundry room, security system, and attic space above the garage. Flooring includes ceramic tile in most downstairs spaces, wood laminate in the living room, hardwood in the upstairs office, and carpet in two upper bedrooms (potentially over hardwood). The saltwater pool is owner-maintained, the setting—backing to conservation—makes it a private oasis. The home is connected to municipal sewer, has a termite protection plan, and is free of known structural or inspection concerns. The HOA fee is only $450 per year, covering common area maintenance, street lighting, and a festive neighborhood holiday celebration. Between the exceptional layout, upgrades, peaceful setting, and unbeatable location, 3759 Kinsley Place offers the perfect blend of style, space, and tranquility. Zoned for “A” rated schools and minutes from Trinity Prep, 417, UCF, shopping, and restaurants. WELCOME HOME!

3759 Kinsley Place, Winter Park
$331,985
2 Beds ⋅ 2 Baths ⋅ Winter Park Pines Patio Homes SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. BACK ON THE MARKET AFTER EXTENSIVE RENOVATIONS!!! BRAND NEW KITCHEN, BATHS, BRAND NEW GORGEOUS LUXURY VINYL PLANK FLOORING THROUGHOUT! BRAND NEW ROOF AS WELL! Some Photos are Virtually Staged for decorating options. Welcome to this beautiful 2-Bedroom, 2-Bathroom patio home located in desirable Winter Park. This duplex offers a range of amenities that will surely enhance your living experience. This beauty has BRAND NEW Luxury Vinyl flooring that looks like hardwood that is seamless throughout the ENTIRE home. The Kitchen is all BRAND NEW with Shaker Cabinets, tile backsplash and Quartz Counters, as well as one year old stainless steel appliances. There is an eat-in area space with wonderful natural light from the window looking to the backyard, perfect for enjoying your morning coffee. There is also a pantry as well as a separate closet with washer/dryer hookups. With a split floor plan, you'll have added privacy, and the vaulted ceilings add an airy and spacious ambiance. There is a huge Great Room to ensure no wasted space. Sliding Glass doors open to an open patio and fenced backyard, providing a private space for outdoor activities or simply relaxing in the fresh air. With the sliding glass door open, this is true indoor/outdoor FL living! The Primary Bedroom has a large walk-in closet, and the ensuite Bathroom is completely BRAND NEW with a double Vanity, and a separate area with a Walk in Shower and toilet that can be closed off. On the other side of the home is Bedroom 2 and the BRAND NEW Full Hall Bathroom with a tub/shower combination, and is accessed from the common hallway. The interior is painted a beautiful neutral decorator paint color throughout, creating a blank canvas for you to personalize and make it your own. Some other features are ceiling fans in Great Room and the Primary Bedroom, updated fixtures, brand new baseboards, and all handles and door knobs are updated as well. The one-car garage offers convenience and additional storage space. ROOF is BRAND NEW MAY 2025. Situated in the Winter Park School District, this home is perfect for those seeking quality education. Additionally, you'll enjoy the convenience of being close to shopping and dining options, making errands and nights out a breeze. Conveniently situated just minutes from Advent Health Winter Park, Rollins College, Full Sail University, and UCF. This location is also right around the corner from multiple parks, Cady Way Pool and the Winter Park Pines Golf Course. Don't miss the opportunity to make this recently renovated duplex yours and experience the comfort and convenience this gorgeous Winter Park gem has! This newly renovated, move in ready home will not last long!

638 Warrenton Road, Winter Park
$240,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Seminole County and Winter Park! Centrally located on the border of Orange County, this well-established community of Cedarwood Village is conveniently located to beautiful Park Ave and all of the greater Orlando suburbs, locations and attractions. This well maintained single story cinderblock stucco has amble skylight natural light, open kitchen to family room, soaring vaulted ceilings and uniform beautiful wide panel water resistant vinyl flooring running throughout the entire residence. No carpet anywhere!! Nice dining area space to fit a large table, but also room in the kitchen for a small breakfast table by the window for morning coffee. The Primary bedroom suite has dual his and her closets and direct access to the screened private patio. The second bedroom has access to the front open and private patio. Other recent improvements are 5.25" high baseboards, range, water heater, door hardware and lighting. Roof was replaced in 2020. Additional locked storage in large closet on the patio. Community roads were recently repaved. This pet-friendly community is well maintained and offers a community pool, clubhouse and tennis courts. Winter Park Condo living at it's best with shopping, restaurants, UCF, Rollins College and Full Sail all minutes away.

2480 Tahoe Circle Unit 2480, Winter Park
$279,000
2 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Phase 2 SubDv. ⋅ 32792 Zip Code
Move-In Ready and AFFORDABLE one-story townhouse with FENCED YARD, 1-Car Garage and LOW HOA!!!!Situated on a corner lot with a screened patio and no rear neighbors, it offers just the right mix of privacy and convenience. Inside, you’ll find ceramic tile and luxury vinyl flooring throughout...so no carpet in sight! A spacious kitchen, living and dining spaces, large bedrooms and 2 tastefully UPDATED Full Bathrooms... all topped off with a BRAND NEW ROOF! The layout is functional, the maintenance is easy, and it's move-in ready. All appliances stay- even the Washer & Dryer! Excellent investment for rental, perfect starter home and ideal for anyone looking for a turn-key, low maintenance property located in an established Seminole County neighborhood of Winter Park with community pool and low HOA!! Don't sleep on this one... it's a great deal!

3153 Greenwood St Unit Winter Spr, Winter Park
$806,000
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Impeccably Redesigned Pool Home in Coveted Winter Park Neighborhood Welcome to 1261 Burning Tree Lane, a beautifully updated 4-bedroom, 2-bathroom pool home located in the highly sought-after Greenview at Winter Pines subdivision. Tucked beneath a canopy of mature oak trees and surrounded by manicured landscaping, this architect-owned residence combines timeless design with thoughtful upgrades in one of Central Florida’s most desirable communities. Inside, you'll find a smart split floor plan with the primary suite privately situated on one side and three spacious bedrooms plus a second living area on the other. The heart of the home—its kitchen—was masterfully redesigned in 2019 to feature granite countertops, double ovens, stainless steel appliances, luxury vinyl plank and travertine tile flooring, and elegant lighting throughout. Every detail has been meticulously maintained: a new roof, gutter system with guards, fresh interior and exterior paint, new ceiling fans, and recessed lighting bring peace of mind and modern appeal. Step outside to your private oasis complete with a sparkling pool, privacy fencing, and a fully equipped outdoor bar with grill, fridge, and mounted TV—perfect for entertaining or relaxing under the stars. This home is zoned for top-rated Winter Park schools and just minutes from Winter Pines Golf Course, local marinas, and charming downtown Winter Park. With no HOA, families enjoy the freedom to live, play, and grow. Move-in ready and priced under $1 million, this home offers incredible value in an unbeatable location. Don’t miss your chance to own a piece of Winter Park paradise. Schedule your private tour today!

1261 Burning Tree Lane, Winter Park
$86,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated 2-story condo located in the heart of Winter Park, just minutes from UCF, Full Sail University, major highways, shopping, and dining. Nestled on the second level, this inviting home offers a functional layout with 2 spacious bedrooms and a full bathroom upstairs, plus a convenient half bathroom on the main floor. Step inside to find stylish luxury vinyl plank flooring throughout, installed just two years ago, along with updated electrical including a new panel and outlets. Natural light floods the open living space through two sliding glass doors (2 years old), leading to a restructured balcony and an additional private balcony off the primary bedroom—both offering views of the community pool. Whether you're a first-time buyer, investor, or looking for a low-maintenance home in a highly desirable area, this condo is move-in ready and packed with thoughtful updates. Don’t miss this opportunity to own a piece of Winter Park charm!

208 Scottsdale Square Unit 208, Winter Park
$550,000
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Tucked away on a peaceful cul-de-sac, 1387 Sawgrass Court welcomes you home. This pristine, 1867 sq ft, single-story residence stands out with its distinctive and mature landscaping, perfectly nestled within a tree-lined, golf-front community. Located on a serene pond along the 15th hole of Winter Park Pines Golf Course (WP18), it offers a retreat with no rear neighbors- ideal for quiet enjoyment and privacy. Step inside to a spacious foyer that opens to formal living room leading to formal dining room. The updated kitchen features a cozy breakfast nook with views of the lush backyard. A dedicated indoor laundry room with storage closet provides convenient access to the oversized side-entry two-car garage. The welcoming family room boasts vaulted ceilings with skylight creating an inviting space for gatherings and relaxation. The primary suite includes a beautifully updated shower and his-and-her closets. Zoned for Brookshire Elementary, Glenridge Middle and Winter Park High School. Recent updates include: New windows 2023-24, New AC 2022, New driveway 2022, New fence 2022, roof 2015, New electrical panel 2022, updated porcelain tile. WELCOME HOME!

1387 Sawgrass Court, Winter Park