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$500,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 05 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this well-maintained home in the desirable Kenilworth Shores Neighborhood of Winter Park. The three-bedroom, two-bath home has just over 1,750 square feet and has lots of extra storage. Wonderful floorplan with large living room, dining room, and separate family room with wood-burning fireplace. Updates include BRAND-NEW Roof (4/2025), AC compressor (2024), replumbed (2003), refrigerator (2023), and electric panel. The new roof has a transferrable 5-year workmanship warranty and a manufacturer's limited lifetime product warranty. Zoned for Winter Park High, Glenridge Middle, and Brookshire Elementary. Just minutes to Cady Way Trail, Cady Way Pool and Courts, Winter Pines Golf Club, Showalter & Ward Park Fields, Baldwin Park, Park Avenue, Advent Health, YMCA, Rollins College, and Full Sail University. This is ready for your personal touches and new memories. Contact me to schedule your private showing today.

2138 Whitehall Drive, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code
Welcome to your dream home in the heart of Central Florida! This immaculate, move-in ready 3-bedroom, 2-bath pool home is a true gem, nestled in an established neighborhood known for its top-rated schools, friendly community, and unbeatable location. Step inside to find tastefully updated living spaces that blend comfort with modern style. As you enter the foyer, you will find the formal living room to your immediate left. Continue on to find a family/bonus room with built-in cabinetry. The kitchen boasts updated finishes, stainless steel appliances (fridge and dishwasher 2023), and plenty of counter space. The dining room is through the kitchen, and is currently being used as an office, with a great view of the outdoor space. The bedrooms are split, offering a separate owner's suite. The home also features a bright and airy Florida room, perfect for morning coffee or quiet evenings. Step outside to your private backyard oasis with a sparkling pool, perfect for cooling off on warm Florida days or hosting weekend BBQs. Mature landscaping adds both privacy and curb appeal, and there's plenty of space for pets or gardening. Just minutes from downtown Winter Park, with easy access to shopping, dining, and major highways, this home truly has it all. Roof is 4 years old. Brand new Carpet in bedrooms. Schedule your showing today.

3317 Dormer Court, Winter Park
$426,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 04 SubDv. ⋅ 32792 Zip Code
In the sought-after Winter Woods community of Winter Park, this 3-Bedroom and 2-Bathroom home with almost 1,700 SQFT of recently updated living space offers both functionality and convenience. Situated on an oversized lot overlooking a pond, this home is perfect for anyone seeking a turn-key opportunity with optimal privacy. Upon entering the home, a large and spacious living area is to the right, bright with plentiful natural light through the front windows. A hallway leads to the open family room and kitchen providing the ideal space for gathering with family and friends. The updated well-equipped kitchen features granite countertops, bar-top seating, wood cabinetry with ample storage, and newer appliances. The kitchen blends seamlessly to a dining area, also adjacent to the front living room. The master bedroom is located on the left of the home with an en-suite updated bathroom. The other two bedrooms are in the back of the home giving privacy for family or guests. The second bathroom is conveniently located in the hallway from the family room leading to the back bedrooms. All bedrooms are complemented with Luxury Vinyl Flooring. Sliding glass doors lead you to the covered back patio and yard overlooking a pond providing a quiet, peaceful, and serene place to relax and unwind. Just outside the kitchen is a large mudroom with Washer/Dryer and additional pantry or storage space. The mudroom leads to the large two-car garage with an additional work worm. A new roof was installed in 2023 as well as fresh interior and exterior paint. This home is ideally located just minutes from the renowned Park Ave and Rollins College as well as close to Full Sail University. Interlachen Country Club is just around the corner and the golf course runs just behind the pond. With easy access to major roadways leading to the 417 and Orlando International Airport, this home is ideal for active families, professionals, and anyone looking for the perfect Winter Park place to call their own.

2028 Sussex Road, Winter Park
$382,000
3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
Great location of this 1950's ranch home in need of love. The home sits on a nice sized corner lot in the Winter Park schools district. The vaulted ceilings with a almost floor to ceiling windows makes the home feel nice and open with tons of natural light. This charming home has 3 bedrooms, 2 bathrooms, laundry room and open floor plan living spaces.

1909 Edwin Boulevard, Winter Park
$475,000
3 Beds ⋅ 1 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
This adorable 3 bedroom, 1 bath mid-century modern bungalow is tucked into a highly coveted part of Winter Park. Thoughtfully updated with a newer kitchen and bathroom, plus recent upgrades including new windows, a newer A/C system, and a brand-new deck—this home is move-in ready and full of charm. Set on a spacious lot, the property offers exciting potential: expand the existing home, renovate further, or build your dream house from the ground up. Live comfortably now while you plan your future vision. Whether you’re a first-time homebuyer, investor, or someone ready to create a custom residence, this property is a rare find in a prime location. If you’ve been dreaming of a Winter Park address—this is your chance!

407 S Lakemont Avenue, Winter Park
$689,500
3 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Nestled on an idyllic tree-lined street, this charming 3-bedroom, 2-bathroom POOL HOME offers the Winter Park Lifestyle you've been dreaming of! Step inside to discover a beautifully appointed kitchen featuring granite countertops and NEW STAINLESS STEEL APPLIANCES. The light and bright formal dining room flows seamlessly into the spacious family room, complete with vaulted ceilings and a cozy wood-burning fireplace. Elegant plantation shutters throughout, adding a touch of sophistication and privacy. Escape to your private primary suite through elegant double doors, boasting a relaxing shower and bathtub, plus a convenient walk-in closet. Enjoy your privacy with the split floor plan. Both guest bedrooms share a bathroom and enjoy their own corner of the house. Outside, your own sparkling pool awaits for endless days of sun-soaked enjoyment, or lounging under the covered brick paver patio. This quarter acre lot allows for plenty of additional yard space around the pool. Upgrades Include: New AC and DUCTWORK (2023), NEW FENCE (2023), NEW PAINT (2023), NEW LANDSCAPING, IRRIGATION, and SOD (2023), NEW APPLIANCES (Dishwasher, Microwave, Refrigerator, Oven, Washer & Dryer) (2022), NEW DISPOSAL (2021), NEW POOL FENCE (2025), & NEW ELECTRICAL PANEL (2019). ZONED for High Rated Winter Park Schools: Brookshire, Elementary, Glenridge Middle School, and Winter Park High School. With quick access to the Cady Way Trail, and a short walk for Golfers to enjoy the Winter Pines Golf Club, this home has everything you’re looking for. ZONED for High Rated Winter Park Schools: Brookshire, Elementary, Glenridge Middle School, and Winter Park High School.

1129 Golfside Drive, Winter Park
$420,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
Seize this exceptional opportunity to acquire a remarkable property in the esteemed town of Winter Park. The roof is only 4yrs old, with rain gutters around the entire house! The kitchen is updated, featuring a stone countertop, breakfast bar, and ample natural lighting. The GE refrigerator, dishwasher, and stove top are 2yrs old. The professionally maintained oversized swimming pool adds to the property’s allure. This home has been lovingly cared for and cherished by the same owner since 1972! Additional features include a new vinyl fence, new garage door, updated outdoor electrical box, lawn irrigation, and a wheelchair ramp in the garage. The asking price is a fair reflection of the property’s current condition. Come and get your great deal, then make it your own inside and out.

1604 Nottingham Drive, Winter Park
$587,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
- NO HOA - Welcome to this exquisitely designed and fully remodeled block home! As you enter you step into a stunning open layout featuring a FULLY remodeled kitchen with quartz countertops, real oak soft-close cabinetry, and top-tier appliances—including a wine fridge and an induction cooktop with built-in air fryer/oven combo. On the east wing of the home you will have 3 spacious bedrooms and 2 FULLY UPGRADED bathrooms, and the primary ensuite will feature a sleek standalone glass rain shower and a spacious walk in closet with a get-ready station. Out back you will have a 24ft long screened in lanai with a spacious tree lined backyard perfect for family and friends activities. This growing community will also feature an 18-hole amateur golf course, a 2.6mi nature trail and fields for soccer, baseball, football and tennis just a short walk from the home. More importantly, for your peace of mind, all major structural and mechanical systems were replaced in 2025, we paired up these upgrades with a HOME WARRANTY that will be provided to you at closing.

236 N Ranger Boulevard, Winter Park
$450,000
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code
Discover your dream home in Winter Park! This stunning 3-bedroom, 2-bathroom gem sits on a spacious 1/3-acre lot, offering the perfect blend of comfort, style, and outdoor living. Step inside to an inviting open-concept layout, where natural light floods the living, dining, and kitchen areas, creating an ideal space for entertaining or cozy nights. The modern kitchen boasts sleek appliances and ample counter space, flowing seamlessly into the living area. Retreat to the generous primary suite with its own updated bathroom, while two additional bedrooms provide flexibility for guests, a home office, or growing families. Both bathrooms feature contemporary finishes for a touch of luxury. Outside, paradise awaits! Dive into your private pool, perfect for Florida’s sunny days, or relax on the expansive screened lanai, ideal for al fresco dining or morning coffee or a dip into the jetted hot tub. The fully fenced yard offers privacy and plenty of space for pets, play, or gardening. With a new roof, new HVAC system, and plumbing re-pipe in 2016 this home is as worry-free as it is beautiful. Nestled in vibrant Winter Park, you’re minutes from top-rated schools, charming boutiques, gourmet dining, and scenic parks.

5326 Lanyard Court, Winter Park
$586,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 1st Add SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the highly desirable Brookshire Heights neighborhood! Nestled on the charming, tree-lined Banchory Road with sidewalks on both sides, this home is just a short stroll from Brookshire Elementary, the Cady Way Pool, Pickleball Courts, and Trail. In 2018, this home underwent extensive renovations, including a new roof, HVAC system, water heater, and fully updated kitchen and bathrooms. As you arrive, the inviting front porch greets you—a perfect spot to enjoy your morning coffee or unwind with a glass of wine in the evening while watching the kids play. Inside, you'll find an open-concept floor plan designed for effortless entertaining. The kitchen is a chef's dream, featuring soft-close cabinetry, quartz countertops, a spacious breakfast bar, and stainless steel appliances. It seamlessly flows into the living and dining areas, ensuring a bright and welcoming atmosphere. Adjacent to these spaces, a spacious Florida room offers endless possibilities as a playroom, sunroom, or relaxation area. The primary bedroom is a true retreat with two closets, including a walk-in, and extra space ideal for an office or nursery. The en-suite bathroom boasts a large shower, soft-close cabinetry, and quartz countertops. The secondary bathroom is equally well-appointed with a tub/shower combination and matching finishes. Step outside to a generously sized, fully fenced backyard with ample space for kids and pets to play. The home also features an attached 2-car garage and an additional laundry room for added convenience. Other updates include newer windows, re-plumbing, and updated electrical systems. This home offers the perfect blend of modern updates and a prime location, close to top-rated schools, fantastic restaurants, shopping, Ward Park, and the vibrant Park Avenue. Don’t miss this incredible opportunity to make this house your home!

2441 Banchory Road, Winter Park
$390,000
3 Beds ⋅ 3 Baths ⋅ Merrie Oaks Village Ph 01 SubDv. ⋅ 32792 Zip Code
Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart of Winter Park designed by architect Nils Schweizer. a student of Frank Lloyd Wright. Offering an attached two-car garage and a premier location, this home blends sophistication with comfort in every detail. Step into a grand living room where soaring ceilings and expansive windows bathe the space in natural light. The formal dining room transitions effortlessly into a thoughtfully designed galley kitchen, showcasing a newly renovated island, high-end Bosch dishwasher, and a French door leading to a truly remarkable outdoor retreat. The covered courtyard, adorned with a trellised garden and overlooking manicured community green space, offers the perfect setting for elevated entertaining and tranquil evenings under the stars. Upstairs, discover a versatile loft ideal for a refined home office, along with a luxurious primary suite featuring a glass-enclosed porch — a serene escape for morning coffee or evening unwinding. Two additional guest bedrooms and a well-appointed guest bath complete the upper level. This discreet and desirable community offers unmatched access to shopping, dining, Advent Health Medical Campus, Full Sail University, Cady Way Park with bike trails & pickleball courts and a short drive to the renowned charm of Park Avenue. Roof 2012, HVAC 2016. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High. WELCOME HOME!

264 Balfour Drive, Winter Park
$380,000
3 Beds ⋅ 3 Baths ⋅ Autumn Glen Ph 3 SubDv. ⋅ 32792 Zip Code
N/A

3877 Waterview Loop, Winter Park
$498,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code
Step into a slice of mid-century magic, your private oasis awaits. On an oversized corner lot with no rear neighbors, this one-of-a-kind mid-century gem is more than just a home, it’s an experience. With classic architectural charm, lush landscaping and thoughtful updates, you’ll feel like you’ve stepped back in time without sacrificing modern-day comforts. Enjoy the tranquility of nature with lush, low maintenance landscaping featuring palms, oaks, gardenia, jasmine, plumeria and more. A raised garden bed offers a taste of the good life, growing pineapple, asparagus, Japanese sweet potatoes and melon, ideal for home chefs and garden lovers alike. The irrigation system, with seven zones (two in use), keeps everything thriving with ease. Whether you're entertaining or simply unwinding, the large 9.5-foot-deep pool, newly refinished with tile and pebble tec for a natural lagoon feel, is the ultimate showstopper. And when you're done with a dip? The outdoor shower adds a beachy, resort-like vibe to your daily routine. Inside, enjoy a newly remodeled kitchen that’s as functional as it is stylish, complete with an immense walk-in pantry and great indoor storage throughout. A dedicated indoor washer/dryer area adds everyday convenience, making laundry feel less like a chore. Recent upgrades include new windows and sliders, updated plumbing and air conditioner (approximately three years old), and a roof in excellent condition (approximately 10 years old). The home’s new back windows and sliders frame views of the serene backyard, making indoor-outdoor living seamless. Outside, you’ll love the fabulous airy covered carport, and the long, shaded driveway provides ample space for guests or multiple vehicles, enhancing function and curb appeal. Families will love the top-rated schools nearby, and commuters will appreciate being just 10 minutes to downtown Winter Park, UCF, and *moments from State Road 417 and major highways. Don’t miss your chance to own this rare, private retreat in an unbeatable location. With its timeless style, modern updates and natural beauty, this home is a one-of-a-kind gem.

808 Denton Road, Winter Park
$423,000
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Built in 2024, this move-in ready 3-bedroom, 2.5-bathroom townhome is located in the gated community of Grayson Square, just a little over 15 minutes from Park Avenue in downtown Winter Park. Designed with a sleek, neutral gray color scheme and modern finishes throughout, the home features an open-concept layout filled with natural light that enhances its bright and airy feel. The main level includes tile flooring throughout, a convenient half bath for guests, and a spacious living and dining area that flows seamlessly into the upgraded kitchen. You'll love the 42" cabinets, quartz countertops, stainless steel appliances, large breakfast bar, and closet-style pantry — perfect for both everyday living and entertaining. Upstairs, the primary suite offers a peaceful retreat with a walk-in closet, dual quartz vanity, and walk-in shower. The hallway loft then leads to two generously sized secondary bedrooms that provide excellent closet space and share a full bathroom just down the hall. A laundry closet with washer and dryer is also conveniently located upstairs. Additional highlights include a 1-car garage, a private covered back patio overlooking a quiet yard area, and plenty of guest parking throughout the community. HOA includes lawn care and internet, and residents enjoy amenities such as a resort-style swimming pool, community mailboxes, and a secure gated entrance. Ideally located with quick access to shopping, dining, and major attractions — approximately 30 minutes to Orlando International Airport, 35 minutes to Universal Orlando, and 40 minutes to Walt Disney World. Don’t miss your chance to own a bright, modern, low-maintenance home in one of Central Florida’s most convenient locations — schedule your showing today!

2812 Bright Bird Lane, Winter Park
$618,900
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 05 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the sought-after Kenilworth Shores neighborhood of Winter Park. Featuring an open-concept layout, the home is anchored by a modern kitchen with an island, stainless steel appliances, granite countertops, and stylishly renovated bathrooms. Enjoy cozy evenings by the fireplace or relax in the spacious, screened porch overlooking the low-maintenance backyard. Bedrooms are ample, with plenty of closet space. Thoughtful upgrades shine throughout the home. Including new ductwork, A/C system, updated wiring, a new water heater (2024), and replumb. The home also offers gas cooking, easy-to-maintain terrazzo floors, and mature landscaping and irrigation system. Additional updates include impact resistant windows, slider and a new front door w/ sidelights. All with no HOA. Perfectly located just minutes from Winter Park Hospital, Cady Way Trail, the Center for Health & Wellbeing, and top-rated Winter Park schools. You're also close to parks, dining, shopping, and a short drive to downtown Winter Park, Baldwin Park, and Orlando. The fully fenced backyard is generously sized—ideal for adding a pool or creating your dream outdoor oasis. Don't miss your opportunity to live in this amazing neighborhood, schedule your private showing now!

624 Dunraven Drive, Winter Park
$468,500
3 Beds ⋅ 2 Baths ⋅ Pelican Bay SubDv. ⋅ 32792 Zip Code
MULTIPLE OFFERS HAVE BEEN RECEIVED. PLEASE SUBMIT BEST AND FINAL BY 12:00PM TOMORROW, TUESDAY, JULY 22nd. Beautiful home is the sought-after community of Pelican Bay in Winter Park. Pelican Bay only has 48 homes in the community and has a small HOA of $500 a year. This 3- bedroom, 2-bathroom pool home is full of charm, warmth, and love, and ready to move-in. Located on a corner lot as you enter the community. Extra parking pad to the left of the garage. As you walk up the pathway to the front entrance, you see the cozy front seating area to enjoy your mornings or afternoons. As you enter the front door, you'll be in awe of the open space the living room and dining room provides with beautiful high ceilings and spectacular double sided wood burning fireplace that faces the living room and the Florida room. The home has beautiful well-padded high-end carpet everywhere except Kitchen, bathrooms, and Florida room. Split floor plan provides you the comfort and privacy desired. There are 2 bedrooms and a guest bathroom to the left. You can also access the guest bathroom from the second bedroom located at the end of the hallway. Both bedrooms have dual closet doors that cover one closet the length of the wall. The Florida room is quite a spectacular space with windows and a slider for a spectacular pool view. Enjoy your completely fenced backyard. The Florida room is equipped with tile floors, wood-burning fireplace, new windows and slider, bar area with sink, granite counter tops, tons of cabinets for storage, and a wine refrigerator. What a fantastic area to relax and unwind. There is a large kitchen with an island. There are also two sinks on either side of the kitchen. Both sinks have garbage disposals. Newer refrigerator. The kitchen has a dining area that overlooks the atrium. The Atrium is an enclosed private sanctuary on the left side of the home. The laundry closet and double door pantry are also in the kitchen. Washer and Dryer convey. Over-sized garage. The Primary bedroom is a showstopper; The bedroom is huge and has access to the pool. The primary bedroom walk-in closet is a dream that you must see! Bathroom has granite countertops and double vanity in the dressing area with double door mirrors as the second entrance to the amazing walk-in closet. The step-down shower and toilet are in a separate room that overlooks the atrium. Roof with gutters 2011, AC 2005. The 3 sliders throughout the home are new. 200amp General Electric Panel Box with copper wiring. Plumbing PVC/CPVC. Community has lake access to Lake Florence. There is a community dock, picnic tables, and a basketball court for the resident's enjoyment. Can't build on empty lot across the street from the community on Grand Rd. The HOA owns this property. This home is truly remarkable. You will think the same as you take a tour.

3306 Fishermans Cove, Winter Park
$550,000
3 Beds ⋅ 2 Baths ⋅ Brookshire Heights 1st Add SubDv. ⋅ 32792 Zip Code
Charming one-story ranch home walking distance to Brookshire Elementary. Located on a .20-acre lot, this 3-bedroom 1.5 bath, home has 1,352 sq ft., including a screen porch conversion adding sq ft. Kitchen has been completely remodeled with stainless appliances, poured concrete counters, tile backsplash and double ovens. All new vinyl plank flooring throughout. New roof in 2022. New exterior paint. Fantastic location close to shopping, dining, parks, Advent Health, The Wellness Center, and Cady Way pool and trail. Additionally, a short drive to Rollins College, Full Sail University, Winter Park Pines golf course and Baldwin Park. Top-rated Winter Park schools. Great opportunity to add or build new. Welcome home!

2492 Brookshire Avenue, Winter Park
$415,000
3 Beds ⋅ 2 Baths ⋅ Hyde Park SubDv. ⋅ 32792 Zip Code
Location, Location, Location! Welcome to Hyde Park! This lovely home in Winter Park offers a blend of amenities and classic charm. The home boasts an open layout, creating spacious living which is great for entertaining and everyday living. A cozy wood-burning fireplace adds warmth and charm to the living space. New roof installed in 2018, new HVAC system in 2022, freshly painted exterior and interior. The kitchen is equipped with a gas stove for simple to gourmet meals and a large dining area with abundant sunlight. The Hyde Park neighborhood offers additional amenities such as a community dock on Lake Florence for fishing, boating, or skiing, a playground, tennis courts and basketball courts. This property has public water and sewer, as well as natural gas. This convenient location puts you in close proximity to shopping, major highways, and desirable schools, adding to its appeal. The combination of modern updates, functional spaces, and neighborhood amenities, makes this home an attractive option for anyone seeking a comfortable and convenient lifestyle.

3063 Ash Park Loop, Winter Park
$420,000
3 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code
Don’t miss this beautifully maintained, move-in ready 3-bedroom, 2-bath gem in the highly desirable Winter Park area — and best of all, there’s no HOA! Step into the updated kitchen, complete with solid wood cabinetry, granite countertops, stainless steel appliances, and a wine fridge — perfect for cooking and entertaining. The kitchen seamlessly flows into a spacious great room, where sliding glass doors open to a large covered lanai overlooking a fully fenced backyard — ideal for relaxing evenings or lively gatherings. The primary suite features double closets and a spacious en-suite bathroom with a walk-in shower and dual vanities—ceramic tile flooring and elegant woodwork throughout the home, combining style and durability in every room. Centrally located with quick access to major highways, top shopping and dining spots, and community events. Zoned for highly rated English Estates Elementary, Tuskawilla Middle, and Lake Howell High. This is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods. Schedule your showing today!

2259 King Johns Court, Winter Park
$620,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code
Welcome to 2855 Lion Heart Dr, Winter Park — a beautifully remodeled home that seamlessly combines modern comfort with an unbeatable location. This move-in ready residence features a brand-new kitchen with smart stainless steel appliances, completely updated bathrooms, new luxury flooring throughout, and an open-concept layout perfect for entertaining. Major upgrades include a new roof (2025) and new water heater. Situated just minutes from Winter Park Pines Golf Course, Cady Way Trail, tennis and pickleball courts, community pool, parks, shopping, and Winter Park Hospital, it’s also conveniently close to Rollins College and Full Sail University. Located on a quiet, tree-lined street with sidewalks for walking or biking, zoned for highly rated Winter Park schools, and with an optional HOA, this property is a perfect choice for families, professionals, or investors alike.

2855 Lion Heart Road, Winter Park
$460,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Improved Price! Welcome to your private "nest" on Little Wren. Nestled among the trees, this modern masterpiece is located directly next to a wide open green space and also backs to a private wooded area giving you beautiful, natural, unobstructed views. The home's modern architecture style is evident from the moment you approach with its striking front door acting as a key focal point. Featuring 3 bedrooms, 2.5 bathrooms, with an abundance of double pane, low E windows, the open concept floorplan allows you to maximize livable space and entertaining options that fit your lifestyle. The flooring featured on the main floor is luxury vinyl providing ease of use and care. The covered patio, extending the length of the rear property, provides maximium private views of the foliage and is a sanctuary for you to enjoy nature. The kitchen features a designer glass backsplash, 42" cabinetry, with an abundance of storage including large pantry closet, stainless appliances, and granite counters. Upstairs you are greeted by a 'bonus area' that can be your office area with a 'birds nest' view of the greenspace, or quiet area to enjoy a good book! The 3 bedrooms are split - giving ample privacy to all. The laundry area is located upstairs and comes with washer and dryer, plus custom cabinetry that maximize your storage needs. Both upstairs bathrooms feature upgraded granite counters - leaving no detail left out! Finally, the owner's suite is beautiful with its expansive ceilings, large windows, and custom-designed walk-in closet. The Enclave at Hawks Crest is centrally located in Winter Park. The community features a resort style pool, clubhouse, picnic area, parks, and playground. You will love returning home in the evening to your sanctuary among the city! Roof-2019!, HVAC-2019!, Electrical-2019!, Plumbing-2019! Welcome Home.

1628 Little Wren Lane, Winter Park
$396,477
3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code
PRICED TO SELL! NEW ROOF, NEW INSULATION, NEW SPRINKLER PUMP, NEW AC WIRING, NEW SOD IN THE REAR, NEW BREAKER PANEL INSTALLED, backyard cleared, porch set up to for get togethers/Super Bowl parties etc. Here we have a 3 bedroom 2 bath single family home located in a (B) rated school district. This turnkey home is ready for its next owners. Perfect first home or upgrade to a new area with good schools. Centrally located with access to major highways. This home has been tastefully decorated and cared for. Entering the home you see the living room followed by the kitchen and a second living area. Home has a state of the art nest thermostat allowing you to control the temperature from your phone. You then encounter 2 guest bedrooms big enough for full size beds. Entering the dining room you can look through the plantation shutters for a nice view of the back yard porch area of the home. The master bedroom fits a king size bed and features a spacious walk-in closet. The master bathroom is updated with sink and glass shower enclosure. Out back you have a screened in porch all wired for tv and entertaining. Past the porch you have a sizable back yard for gardening and or entertaining. Bring your offers!!

7543 Dockside Street, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ Arrowhead Cove SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Beautiful remodeled pool home. Luxury vinyl plank flooring throughout the entire home with tile in the bathrooms. Spacious living area with open concept floorplan. Upgraded kitchen with stainless steel appliances, granite counters, large kitchen island/bar, and closet pantry. Bathrooms both updated. Primary bathroom has large walk-in shower with dual sinks. 2 bedrooms with nice-sized walk-in closets. Oversized 24'x20' garage. Large 20'x16' screened porch leads to the swimming pool. High fence surrounds spacious backyard. Plenty of room for entertaining in this home. Brand new HVAC system installed in 2025. Roof replaced in 2022. Electric upgraded in 2009. Plumbing upgraded in 2015. New irrigations system in 2025. Just minutes from Publix, Target, Walmart Super center, and plenty of shopping and restaurants. Easy drive into downtown Winter Park, highway 436, highway 417, and UCF. Plus zoned for great Winter Park area schools. What's not to love?!?! Let's make a deal.

7584 Lodge Pole Trail, Winter Park
$630,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code
Welcome home to the Winter Park Pines with its tree-lined streets and where the mailman still delivers to your door! Nestled on a large corner lot, this beautifully and meticulously renovated 3-bedroom, 2-bathroom (PLUS AN OFFICE) home is an entertainer’s dream, perfectly blending comfort, functionality, and style. Step inside to discover a chef’s kitchen that will impress even the most discerning cook. Featuring exquisite quartzite countertops, custom cabinetry, a freestanding island, and thoughtful touches like a built-in microwave, pull-out spice rack, and sliding cabinet organizers, this space is both stunning and highly functional. The adjacent breakfast bar comfortably seats three, while the expansive dining area with custom built-in bench seating is perfect for hosting family and friends. A sun-filled garden window makes morning coffee a true delight. Flowing seamlessly from the kitchen, the spacious living and sitting areas provide the ideal layout for everyday living and entertaining. Tucked behind charming barn doors is a versatile office/guest space, complete with a pull-out sofa bed—perfect for visitors or remote work. All three bedrooms are thoughtfully located on the opposite side of the home for added privacy. One features a Murphy bed, offering flexible space for a home office or guest suite. The primary suite includes dual closets and a luxurious ensuite bath with a large double vanity and a sleek, glass-enclosed shower. Step outside and enjoy your own private oasis—a backyard built for year-round enjoyment! Lounge by the pool and spa, gather around the firepit, or practice your short game on your personal putting green. Low-maintenance artificial turf ensures more time enjoying, less time working. Just minutes from Cady Way Pool, tennis and pickleball courts, playgrounds, Ward Park, and top-rated schools and colleges (Full Sail, Valencia, Rollins, UCF), this home offers unmatched access to both leisure and lifestyle. With nearby grocery stores, dining, shopping, and the Advent Health Wellness Center, everything you need is right at your doorstep. Don’t miss this rare opportunity to own a home that offers the perfect blend of indoor elegance and outdoor living. Schedule your private showing today—this gem won’t last long! ROOF - 2022 HVAC - 2022 PLUMBING - 2016 WATER HEATER - 2023

2707 Prince John Road, Winter Park
$392,500
3 Beds ⋅ 2 Baths ⋅ Cedar Ridge Unit 2 SubDv. ⋅ 32792 Zip Code
This 3-bedroom, 2-bathroom residence is situated on a corner lot, offering an inviting and comfortable living space. A notable feature of this property is the BRAND NEW ROOF and WATER HEATER, ensuring peace of mind for years to come. The split floor plan enhances both privacy and functionality. The master bedroom boasts a walk-in closet and a private ensuite bathroom. On the opposite side of the home are two generously sized bedrooms accompanied by a full bathroom. The eat-in kitchen is ideal for casual dining and family meals. The spacious living and dining room areas feature sliding glass doors that open onto a large screened-in porch, providing a seamless indoor-outdoor living experience. The screened-in porch overlooks a large yard, providing ample opportunities for outdoor activities and gardening. The property includes a two-car garage, equipped with a hurricane-proof door for added security and convenience. Ideally located, this charming home is near shopping, dining, and numerous other amenities, making it the perfect blend of comfort and convenience. This home is filled with potential. Do not miss the opportunity to make this lovely corner lot residence your own and enjoy the best of quiet neighborhood living.

2100 Shirewood Court, Winter Park
$335,000
3 Beds ⋅ 2 Baths ⋅ Suburban Homes SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. *** Price Improvement*** This one is a must see!! Welcome Home!! NEW ROOF, UPDATED KITCHEN, SEMINOLE COUNTY SCHOOLS. RV Carport Upgrade! This comfortable 3 Bedroom, 2 Bathroom Winter Park home sits on an oversized lot with no HOA, offering the perfect blend of privacy and freedom to make it your own. Zoned for Seminole County Schools! Step inside to FRESH PAINT (2024), NEW CARPET (2024), A BRAND-NEW ROOF (2025), ensuring comfort from day one. The electrical system includes an UPDATED PANEL BOX, providing peace of mind for years to come, while MODERN CEILING FANS throughout enhance both style and efficiency. The kitchen has been completely reimagined with STUNNING GRANITE COUNTERTOPS, and a STYLISH TILE BACKSPLASH, all designed to create a fresh, contemporary space. Love the outdoors? The expansive fenced-in backyard is perfect for pets, gardening, or hosting gatherings, while the screened-in back porch offers a relaxing retreat. A spacious two-car garage and an RV carport provide ample room for all your vehicles and toys. Nestled in a desirable Seminole County neighborhood, this home is close to Top-Rated Schools, beautiful parks, and an array of dining and shopping options, with easy access to major highways for a smooth commute. With modern upgrades, abundant outdoor space, and a fantastic location, this move-in-ready gem is ready for you to call it home!

5144 Orange Avenue, Winter Park
$400,000
3 Beds ⋅ 2 Baths ⋅ Goldenrod Place SubDv. ⋅ 32792 Zip Code
Great Opportunity. Nestled on an oversized lot at the end of a peaceful cul-de-sac, this charming home offers the perfect blend of privacy and comfort. The spacious feel of the location provides a serene and tranquil setting, making it the ideal place to relax and unwind on your huge Patio overlooking wonderful backyard ! As you step inside, the warm and cozy atmosphere welcomes you. The home's inviting ambiance is ready for new owners . Enjoy living 7.5 miles from downtown Winter park with easy access to dining, shopping and recreational options. The Primary suite is a true retreat, offering a a updated en-suite bath and Additional bedrooms provide plenty of space for family or guests, ensuring everyone feels at home. Outside, the expansive backyard provides an oasis for outdoor living,. Fully fenced and Large Shed for all your extra Storage needs in addition to 2 car garage. Tons of Storage, Split floor plan , CBC Const. , Thermal Windows and Metal Roof for peace of mind.

5144 Goldenrod Place Road, Winter Park
$434,900
3 Beds ⋅ 2 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code
Pool Home! Whole House Solar!! No HOA!!! This 3 bedroom, 2 bathroom pool home offers a split plan bedroom arrangement and open-concept gathering areas that lead out to a spacious screen-enclosed porch that faces the pool. The absence of a pool cage allows for landscape & gardening opportunities along with cannonballs at a moment’s notice. Enjoy fun in the sun and night swims next to the stone firepit for the ultimate staycation vibes. Grab some sleeping bags while you’re at it. Updates include 2024 attic insulation; 2023 solar; 2022 pool pump; 2021 painted kitchen cabinets; 2017 pool resurface; 2016 washer, dryer, replace two front windows.

5441 Justine Way, Winter Park
$400,000
3 Beds ⋅ 2 Baths ⋅ Hyde Park SubDv. ⋅ 32792 Zip Code
Under contract-accepting backup offers. Welcome home! This well maintained home is located in the quaint, Winter Park neighborhood of Hyde Park. Located on a quiet, cul de sac street, this home offers a desirable split floor plan with 3 spacious bedrooms. The primary bedroom and 3rd bedroom both have generously sized walk in closets. A spacious living room bathed in natural light, features a large windows that flood the space with warmth and brightness. The room is anchored by a stunning, gas fireplace, adding both charm and coziness, creating the perfect ambiance for relaxation. A bright and airy sunroom extends off the back of the home, offering panoramic views of the lush backyard. This serene space is perfect for relaxing, reading, or entertaining while surrounded by the natural beauty of the outdoors. Hyde Park offers tennis courts, basketball courts a playground area and a community dock overlooking the lake! This home is just minutes from Winter Parks downtown park avenue, Rollins College and UCF as well as a variety of restaurants and shops including the newly renovated Winter Park Village. Easy access to the 417 as well as Trinity Prep and Park Maitland pre school. Schedule your private tour today! AC-2016, ROOF-2021, PLUMBING-2022, WATER HEATER- 2022. Gas used for stovetop, fireplace and water heater.

3021 Little Cypress Cove, Winter Park
$200,000
3 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 08 SubDv. ⋅ 32792 Zip Code
HUGE PRICE REDUCTION! We are proud to bring to market this incredibly private END UNIT condo within the Hidden Oaks community. The unit offers three bedrooms (all upstairs), two full bathrooms (upstairs) and one half bathroom (downstairs), two reserved parking spots, upgraded wood-look ceramic tile, upgraded light fixtures, upgraded bathroom mirrors and upgraded fans throughout, upgraded thick granite countertop in kitchen, wood cabinets with upgraded hardware, eating space in kitchen, interior laundry, upgraded complete stainless steel appliance package, newer A/C (2019), upgraded vanities in the full bathrooms, upgraded tile in second bathroom, private fenced patio perfect for entertaining all within close proximity to Full Sail University, the University of Central Florida and Valencia College as well as many major Central Florida employers.

3251 Oak Lake Place Unit 135, Winter Park