Winter Park FL Real Estate & Homes for Sale

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Beds:
5
Baths:
7.00
Sq.Ft.:
7,278
Status:
Active
MLS#:
O6319674
Type:
Single Family
Subdivision:
Maitland Shores
Lot size:
0.69 Acres
Year built:
2008
A broker reciprocity listing Courtesy: FORTUNE INTERNATIONAL REALTY 305-400-6393
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ADDITIONAL INFORMATION

Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all set on almost 3/4 acre of beautifully landscaped canal-front lot with direct access to the coveted Lake Maitland and Winter Park Chain of Lakes. Spanning an impressive 7,278 square feet, this two-story masterpiece rises 40 feet and is designed for both grand-scale entertaining and luxurious everyday living. Upon entry, you're greeted by soaring ceilings and elegant architectural details that set the tone for the home’s sophisticated style. With five expansive bedrooms—all featuring en-suite bathrooms—and six full baths plus a powder room, the home offers both comfort and privacy for family and guests. Two bedroom suites are located on the main level, ideal for multigenerational living or hosting overnight visitors, while the upper level includes three additional bedroom suites, a fully equipped theater room, a study room and a spacious game or playroom. The heart of the home is the gourmet kitchen, where solid wood cabinetry, rich granite countertops, and Viking appliances come together to create a true culinary haven. The adjacent family room features one of the home’s three fireplaces and invites cozy gatherings or relaxed evenings overlooking the lush outdoor living space. The formal living and dining areas are equally impressive, offering elegant backdrops for holiday celebrations or intimate dinner parties. Step outside to discover a true private oasis. The resort-style backyard boasts a saltwater heated pool and spa with all-new equipment, a summer kitchen, and a dedicated pool bathroom—perfect for effortless indoor-outdoor living. The entire property is fenced with newly installed gates, ensuring both privacy and security. From the manicured landscaping to the serene waterfront setting, every detail has been thoughtfully curated to elevate the experience of lakeside living. For boating enthusiasts, the property includes a private boathouse, a dock with an automatic lift, and a 2 jetski dock—all providing seamless access to Lake Maitland and the entire Winter Park Chain of Lakes. Whether you're setting off for an early morning paddle, an afternoon on the water, or simply enjoying the sunset from your dock, this home offers an unrivaled connection to the natural beauty. Additional features include a 5-car garage, 2 laundry rooms, dual staircases, all-new AC units, a comprehensive security system, and three wood-burning fireplaces that add charm and warmth throughout the home. Every inch of this residence has been impeccably maintained and thoughtfully updated, offering peace of mind and modern convenience without sacrificing its classic elegance. 2211 Azalea Place is more than just a home—it’s a lifestyle. This is a rare opportunity to own a one-of-a-kind estate in one of Winter Park’s most sought-after locations, where quiet sophistication meets waterfront luxury.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,895
Status:
Active
MLS#:
O6320741
Type:
Single Family
Subdivision:
Orwin Manor Westminster Sec
Lot size:
0.16 Acres
Year built:
2025
A broker reciprocity listing Courtesy: GOLDEN GROUP REALTY LLC 407-990-5905
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers the perfect blend of timeless architecture and contemporary design, offering 5 bedrooms, 4 bathrooms, and nearly 2,900 sqft of refined living space. Step inside to discover: • 10-ft ceilings & 8-ft solid-core doors • Wide-plank luxury vinyl flooring throughout • Gourmet kitchen with quartz countertops, custom cabinetry, stainless steel appliances & oversized island • Elegant electric fireplace and expansive great room • Built-in wine cellar discreetly tucked under the stairs • Downstairs guest suite for added privacy Upstairs, the primary suite impresses with pool views and a spa-style bath: dual vanities, soaking tub, walk-in shower, and a generous closet. Three additional bedrooms include a Jack & Jill layout plus one with a private en-suite. A large upstairs laundry room adds convenience. Outside, your private backyard oasis awaits: • In-ground pool, fully landscaped • Summer kitchen with built-in grill • Covered patio for year-round entertaining Located just minutes from Park Avenue, this home offers walkability, top-rated schools, cultural landmarks, boutique shops, and dining. A rare opportunity to own new construction in one of Central Florida’s most iconic neighborhoods. Schedule your private tour today — this home defines the Winter Park lifestyle. Seller is offering up to 1% toward buyer’s closing costs, along with a 15% discount on title insurance.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,263
Status:
Active
MLS#:
O6319233
Type:
Single Family
Subdivision:
Osceola Summit
Lot size:
0.35 Acres
Year built:
1968
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake Osceola for paddle boarding, fishing, swimming or just to enjoy the view!! This home has only had one owner and is uniquely positioned not to see a next-door neighbor to your left or right!! Embrace the mid century modern style of this home or it is priced to be a tear down to build your dream home around the other multi million dollar homes. Nestled in the heart of highly sought-after Winter Park, this spacious 4-bedroom, 2.5-bath home offers over 3,260 square feet of living space on an oversized .35 acre lot with gorgeous lake views—ideal for enjoying sunsets from a future second-story balcony or out your current kitchen window!! The 4 bedrooms are very generous in size, have ample natural light and each one has oversized closets. The bathrooms have been updated with style in mind. The luxury vinyl floors were recently installed along with new kitchen appliances. Featuring a distinctive Mansard-style roof, this residence boasts strong architectural character and a versatile layout designed for modern living. Inside, you’ll find new luxury plank flooring, large windows that invite abundant natural light, and generously sized rooms with ample closet and storage space. Home offers a lot of character and charm with the present architectural features of a Chicago brick wall, ceiling accent beams and for the art lover a huge paneled art gallery wall!! The home includes two separate living areas, a formal dining room, an eat-in kitchen, and an office area with abundant storage and desk work space —perfect for work-from-home needs, student study session or family organization. The 2-car garage adds both storage and convenience and has a large utility closet inside the garage to stay organized. While the home is ready for your personal touch, it presents a rare chance to customize and elevate a spacious property in a top-rated school district, just minutes from parks, shopping, dining, and lakefront recreation. Whether you're looking to renovate, invest, expand upward, or build your dream home — the potential here is truly exceptional.

Beds:
5
Baths:
6.00
Sq.Ft.:
4,955
Status:
Active
MLS#:
O6302616
Type:
Single Family
Subdivision:
Green Oaks Rep 02
Lot size:
0.39 Acres
Year built:
2017
A broker reciprocity listing Courtesy: SCANLON REALTY GROUP LLC 305-905-0496
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ADDITIONAL INFORMATION

One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly positioned on a prime over-sized corner lot, the home blends transitional architecture with modern elegance. Sunlight fills the open layout through expansive sliding doors, creating effortless indoor-outdoor flow. The main living area seamlessly connects a formal living room and spacious dining area to the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and Sub-Zero and Wolf appliances. A cozy family room with fireplace provides a relaxed yet stylish gathering space. The private downstairs primary suite opens directly to the lanai, saltwater pool and features a spa-style bath. A secondary ground floor bedroom is perfect for guests or multigenerational living. Upstairs, enjoy a spacious loft with custom bar, leading to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a full-house generator, a newly added semi-circular driveway that enhances curb appeal and functionality, and three newer A/C units with re-engineered, high-efficiency ductwork to ensure optimal climate control throughout the home. The outdoor living space is equally impressive, offering a saltwater heated pool and spa with cascading waterfall, elegant stone decking, ambient lighting, and a covered summer kitchen—ideal for year-round entertaining. A rare 3-car garage completes this exceptional home. All just moments from the shops, dining, and charm of downtown Winter Park.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,153
Status:
Active
MLS#:
O6316445
Type:
Single Family
Subdivision:
Lake Florence Preserve
Lot size:
0.67 Acres
Year built:
2019
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront residence offers a serene retreat within an intimate gated enclave of just 28 homes. A setting that feels private and peaceful that is increasingly hard to find. Designed for both everyday comfort and effortless entertaining, the thoughtfully planned 4-bedroom, 3.5-bath layout includes a dedicated office, formal dining room and a desirable three-way split floor plan that provides flexibility and privacy for today’s lifestyle. At the heart of the home, the gourmet kitchen blends beauty and function with quartz countertops, a substantial center island, natural gas cooktop, 42" solid wood cabinetry, walk-in pantry, and a generous butler’s pantry—perfect for hosting or simply enjoying the flow of daily living. Rich wood flooring carries throughout the home connecting the kitchen seamlessly to the light-filled family room and casual dinette area. The primary suite is a true lakefront sanctuary featuring peaceful water views, two walk-in closets and a spa-inspired bath with dual sinks and an oversized shower with dual shower heads. Many upgrades are to be found through out this home such as an extra oversized storage closet, crown molding, custom mud room off of the laundry room, high ceilings, tray accents and abundant natural light to enhance the home’s relaxed, refined feel. Outdoors, the property transforms into a private lakefront escape. Enjoy sweeping water views, a sparkling pool and spa, custom rock waterfall, screened-in lanai and a fully fenced yard framed by tall privacy hedges and mature trees—ideal for quiet evenings or weekend gatherings. Direct lake frontage and access to a nearby community dock complete the lifestyle experience. A three-car garage with a separate AC wall unit offers added versatility—perfect for a workshop, home gym, or additional storage. Thoughtfully positioned, this home represents a rare opportunity to own a lakefront retreat that delivers serenity, lifestyle and value—all within close proximity to shopping, dining and top-rated schools in a prime location!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,066
Status:
Active
MLS#:
O6314262
Type:
Condo
Subdivision:
Colonies
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: JASON MITCHELL REAL ESTATE FLO 754-307-0607
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ADDITIONAL INFORMATION

Welcome to 3057 Aaron Burr Ave #2, a beautifully updated 2-bedroom, 2-bathroom condo in the desirable Colonies community. Whether you're looking for a stylish home or a fantastic investment opportunity, this property checks all the boxes! Step inside to find brand-new stainless-steel appliances, granite countertops, and spacious walk-in closets. The open layout creates a bright and inviting atmosphere, perfect for relaxing or entertaining. Enjoy the new balcony, offering a peaceful outdoor retreat. Plus, with community amenities like a pool and playground, you’ll have everything you need for a comfortable lifestyle. Prime Location! Conveniently located near UCF, Valencia College, and Full Sail University, with easy access to shopping, dining, and major highways—making commuting a breeze! Don’t miss out on this incredible opportunity—schedule your private showing today!

Beds:
1
Baths:
1.00
Sq.Ft.:
645
Status:
Active
MLS#:
O6315656
Type:
Condo
Subdivision:
Lakeside Manor Apts Condo
Lot size:
0.05 Acres
Year built:
1969
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living room with dining space. The tidy kitchen with matching all white appliances is clean as a whistle. You'll love the large utility is where you'll find the air conditioner, hot water heater and plenty of shelving. The bathroom has new vanity (2025), mirror and light fixture (2025), and newer toilet. You'll find the bedroom spacious with a large double closet. Ceiling fans in living and bedroom. Location in the community is handy, with assigned parking space just steps away and easy access to the quiet courtyard. You'll love the lakefront outdoor space including pool, club house, tons of manicured green space, over-water covered seating on the new dock, boat launch and slips. Close to shopping and dining in Winter Park, easy access to highways. This community is everything people come to Florida to find!

Beds:
2
Baths:
2.00
Sq.Ft.:
953
Status:
Active
MLS#:
O6314817
Type:
Condo
Subdivision:
Stratford A Winter Park Condo
Year built:
1973
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling cabinetry, granite countertops, and stainless steel appliances. Both spacious bedrooms sit near the entry, with the primary suite offering a walk-in closet and a sleek ensuite bath with a glass-front shower and floating vanity—mirrored in the newly updated guest bath as well. Enjoy low-maintenance living with access to resort-style community amenities including two pools, tennis courts, and a gym—all in a prime location! Schedule your private showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,770
Status:
Active
MLS#:
O6314734
Type:
Single Family
Subdivision:
Winter Park Village
Lot size:
0.18 Acres
Year built:
2018
A broker reciprocity listing Courtesy: FORTUNE INTERNATIONAL REALTY 305-400-6393
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ADDITIONAL INFORMATION

Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining. Step inside to discover an open-concept layout that seamlessly connects the kitchen, dining, and living areas. The kitchen features brand-new appliances, quartz countertops, shaker-style cabinetry, a classic subway tile backsplash, and a large island ideal for gathering. Elegant new light fixtures and a built-in wet bar elevate the space with a touch of sophistication. The first-floor primary suite is a serene retreat, offering two closets and a well-appointed en-suite bathroom complete with a soaking tub and separate walk-in shower. Upstairs, a spacious loft opens to a walk-out balcony and is accompanied by three additional bedrooms and two full bathrooms – perfect for family and guests. Storage is abundant with three walk-in closets, a double closet, and a convenient under-stair space. Additional highlights include a two-car garage with an epoxy floor, a screened patio for year-round enjoyment, and a fenced backyard oasis ideal for relaxation or entertaining. Freshly painted and surrounded by all-new professional landscaping with an irrigation system, this home offers exceptional curb appeal. Located just minutes from Park Avenue’s shopping and dining, Rollins College, the Winter Park Chain of Lakes, and zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High School—this property blends luxury, location, and lifestyle.

Beds:
5
Baths:
6.00
Sq.Ft.:
6,502
Status:
Active
MLS#:
O6312768
Type:
Single Family
Subdivision:
Windsong Preserve Point 43/76
Lot size:
1.94 Acres
Year built:
2013
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve and 407' of pristine waterfront. The main house offers over 6,500 sf of luxurious living space and a modern and open floorplan with a great room for entertaining, a gourmet kitchen with double islands and high-end Miele and Thermador appliances, a temperature-controlled wine vault, a home office/den, a gym/flex space, and a first-floor owner's retreat. Upstairs are three oversized guest bedrooms, each with an en suite bath, and a bonus room with built-ins. La Cantina accordion-style glass doors in the great room open to the wraparound covered lanai which can be enjoyed year-round thanks to the retractable screens, a dual-sided fireplace, multiple ceiling fans, an outdoor kitchen, and panoramic views of the infinity pool and spa and of course Lake Berry. A detached one bedroom, one bath guest house with living room and kitchenette is perfect for extended family and guests, or even an au pair, as it has its own private entrance. Electricity has been installed down to the shoreline to provide for a future, powered boathouse and lift, and for anyone who wants to take advantage and boat or ski on Lake Berry's 76 acres of fresh water. A detailed list of the home's specs and upgrades is available upon request; however, some notable features include a full house generator, two tankless hot water heaters, 4-HVAC units, natural gas, a heated saltwater system for the pool and spa, a 3-car garage with motor court, and more. Located within the prestigious Windsong neighborhood, residents enjoy exclusive use of two community pools, a splash pad, community parks and playground, walking trails, multiple lakefront overlooks, fishing, and HOA boat access. Downtown Winter Park, Park Avenue, Rollins College, Downtown Orlando, Advent Health, and Orlando Health are all within a 15-minute drive. Homes of this significance hardly ever come on the market and are extremely rare to find. Showings are by appointment only for qualified buyers.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,837
Status:
Active
MLS#:
TB8387465
Type:
Townhouse
Subdivision:
Via Lago/hanging Moss Ph 1
Lot size:
0.04 Acres
Year built:
2007
A broker reciprocity listing Courtesy: FLAT FEE MLS REALTY 813-642-6030
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ADDITIONAL INFORMATION

Location! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, 3 Bedroom Town Home with a Garage in the VIA LAGO GATED community?? ABSOLUTELY! Meticulously maintained and spacious town home is just waiting for its new owner! Elegant brick paver driveway and entryway greet you as you pull up. The downstairs is open, light and bright. The beautifully appointed kitchen has plenty of cabinets and counter space and opens to the family room and dining room. With a breakfast bar, Corian counter tops and wood cabinets--it's perfect for entertaining! Updated lighting fixtures and flooring throughout the home. Enjoy your morning coffee or evening beverage on your private, screened in lanai. All 3 bedrooms are upstairs, and the large master bedroom has a HUGE walk-in closet! The master bath has a relaxing garden tub and separate shower and double vanity sinks. The secondary bedrooms are at the far end of the hall and the laundry room is also upstairs for added convenience. Via Lago has a gated dog walk area and a playground. This community is ideally located near excellent Winter Park public schools, UCF, Full Sail, Baldwin Park, Downtown Orlando and all major roadways. It's the perfect place to live, play and enjoy the Florida lifestyle!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,474
Status:
Active
MLS#:
TB8388549
Type:
Single Family
Subdivision:
Maitland Shores First Add
Lot size:
0.21 Acres
Year built:
2008
A broker reciprocity listing Courtesy: THE SHOP REAL ESTATE CO. 727-593-7777
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ADDITIONAL INFORMATION

Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find luxurious plank flooring flowing through the entryway, family room, and guest bedrooms, complemented by polished marble in the formal living room and opulent primary suite. The interior showcases meticulous craftsmanship with recessed lighting, custom cabinetry, and coffered ceilings that add architectural charm. At the heart of the home lies a gourmet chef’s kitchen, a culinary dream featuring sleek custom cabinetry, a stylish farmhouse sink, a practical pot filler, and top-of-the-line stainless steel appliances, perfect for both everyday meals and grand entertaining. Outside, a covered lanai invites relaxation, while the sparkling pool with its tranquil waterfall and soothing hot tub creates a private oasis perfect for unwinding or hosting gatherings. The meticulously landscaped backyard, framed by lush greenery, offers a serene retreat for outdoor enjoyment. Soaring vaulted ceilings enhance the airy, open feel throughout the home. Located near the esteemed Rollins College and vibrant Park Avenue, this property is nestled in a charming neighborhood, offering both prestige and access to Winter Park’s finest dining, shopping, and cultural attractions. With a paved parking area, a two-car garage, and dual-zone AC for year-round comfort, this exquisite home is as practical as it is beautiful. Don’t miss the opportunity to own this Winter Park masterpiece, where timeless elegance meets modern luxury. Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln—a true gem ready to become your forever home.

Beds:
2
Baths:
1.00
Sq.Ft.:
710
Status:
Active
MLS#:
O6311340
Type:
Condo
Subdivision:
Lake Killarney Condo
Lot size:
0.23 Acres
Year built:
1960
A broker reciprocity listing Courtesy: FLORIDA DREAMS REALTY GRP INC 407-654-9992
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ADDITIONAL INFORMATION

Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property or dream home!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,939
Status:
Active
MLS#:
O6309509
Type:
Single Family
Subdivision:
Laurel Spgs
Lot size:
0.32 Acres
Year built:
1973
A broker reciprocity listing Courtesy: ALORA REALTY GROUP INC 407-790-9605
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ADDITIONAL INFORMATION

Step into your dream home located in the charming Winter Park, Florida. This stunning property boasts 3 bedrooms and 2 bathrooms, perfect for a growing family or those who love to entertain. As you enter, you are greeted by a cozy fireplace, ideal for chilly Florida evenings. The spacious living room flows seamlessly into the gourmet kitchen, complete with granite countertops and stainless steel appliances. But the real showstopper is the backyard oasis. Relax and unwind in your own private pool, surrounded by lush landscaping and no back yard neighbors, providing the ultimate in privacy and tranquility. Looking for a bit of fun? Head to the game room, perfect for hosting game nights or watching the big game. Not only is this home an entertainer's paradise, but it also offers quiet neighbors and a serene atmosphere, making it the perfect place to escape the hustle and bustle of everyday life. Don't miss out on the opportunity to own this slice of paradise in Winter Park. Schedule your showing today and fall in love with your new forever home.

Beds:
1
Baths:
1.00
Sq.Ft.:
678
Status:
Active
MLS#:
TB8384159
Type:
Condo
Subdivision:
Stratford A Winter Park Condo
Year built:
1973
A broker reciprocity listing Courtesy: HOMECOIN.COM 888-400-2513
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ADDITIONAL INFORMATION

1 bed, 1 bath condo in Winter Park

Beds:
3
Baths:
3.00
Sq.Ft.:
1,803
Status:
Active
MLS#:
O6303931
Type:
Townhouse
Subdivision:
Windward Square Sec 1
Lot size:
0.09 Acres
Year built:
1978
A broker reciprocity listing Courtesy: WRA BUSINESS & REAL ESTATE 407-512-1008
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ADDITIONAL INFORMATION

Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for those seeking comfort, convenience and quality of life. Located in one of the most sought-after areas of Winter Park, with an excellent location, close to schools, shops, restaurants, parks and much more! The community offers a complete infrastructure with a swimming pool, playground, sidewalks for walking and a family environment ideal for all ages. Don't miss this chance to live well! Schedule your visit and come see your new home!

Open House:

Sunday, 2/8 1:00-3:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,804
Status:
Active
MLS#:
O6304495
Type:
Single Family
Subdivision:
Galloway Place Rep
Lot size:
0.19 Acres
Year built:
1948
A broker reciprocity listing Courtesy: FLORIDA HOMES REALTY & MORTGAGE 904-996-9115
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ADDITIONAL INFORMATION

***Price Adjustment *** Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on a private lot in the heart of Winter Park, moments from Rollins College, Park Avenue, and Winter Park Hospital. Just a short walk provides coveted access to the Winter Park Chain of Lakes, bring your paddle board or canoe. Step inside the spacious formal living room with a gas fireplace and original hardwood floors. The updated kitchen with Carrara quartz countertops, quality wood cabinetry, a large pantry and ample storage opens to the dining and sunrooms. A wall of French and glass doors in the sunroom—spanning the length of the home—creates a seamless indoor-outdoor connection to the covered patio and beautifully landscaped garden. Paver walkways through lush greenery, guide you to a tranquil cabana, a serene retreat perfect for both relaxation and hosting guests. The primary suite is a peaceful retreat offering direct access to both the interior and exterior through elegant French doors. It features an updated ensuite bath and a spacious cedar-lined walk-in closet, combining luxury with thoughtful functionality. A spacious and functional split floor plan ensures privacy, with two generously sized guest bedrooms located on the opposite side of the home. Each room showcases rich hardwood floors, plantation shutters, and walk-in closets. A beautifully renovated guest bath adds style and comfort, making it ideal for family or visitors. The attached single car garage with washer, dryer and a circular drive offers ample parking and easy access. The freshly painted interior (2025) is a blank canvas for your vision! This home is a perfect blend of classic charm and modern updates. The busy street is actually a benefit, offering exceptional privacy and allowing for easy exits in either direction with typically less than a 3-minute wait. Fix426 improvements starting Spring 2026. Schedule your showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,307
Status:
Active
MLS#:
O6301489
Type:
Single Family
Subdivision:
Parklando 03
Lot size:
0.23 Acres
Year built:
2007
A broker reciprocity listing Courtesy: JW GASTON LLC 321-239-5540
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ADDITIONAL INFORMATION

The only home priced under $2MM that has over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Completely remodeled in late 2022, this home radiates warmth and sophistication. Solid light oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape.The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,031
Status:
Active
MLS#:
O6298927
Type:
Townhouse
Subdivision:
Hidden Oaks Condo Ph 08
Lot size:
1.43 Acres
Year built:
1984
A broker reciprocity listing Courtesy: GLOBAL ENTERPRISE REALTY GROUP 321-281-8781
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ADDITIONAL INFORMATION

THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESTLED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING QUARTZITE COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGERATOR AND MICROWAVE/CONVECTION OVEN. BEAMED CIELING THAT FLOWS TO THE BEAUTIFUL LAMINANTE WOOD FLOORS. LOVELY DESIGNED MASTER AND QUEST BATHROOMS WITH STAINLESS STEELE FIXTURES AND WOOD LAMINATE CIELING FANS IN MASTER BEDROOM, LIVING ROOM AND FAMILY ROOM. NEWER ROOF. UPDATED PLUMBING, NEW ELECTRICAL UPDATES AND NEW AC HANDLER & CONDENSER. WONDERFULLY LANDSCAPED TO GIVE ULTIMATE CURB APPEAL. THIS HOME IS APPROXIMATELY 10 MINUTES FROM DOWNTOWN ORLANDO, APPROXIMATELY 15 MINUTES TO ORLANDO INTERNATIONAL AIRPORT, APPROXIMATELY 10 MINUTES TO RETAIL SHOPPING AND RESTUARANTS, APPROXIMATELY 15 MINUTES TO VALENCIA STATE COLLEGE, APPROXIMATELY 25 MINUTES TO UCF AND APPROXIMATELY 30 MINUTES TO DISNEY WORLD.

Beds:
2
Baths:
2.00
Sq.Ft.:
956
Status:
Active
MLS#:
O6297570
Type:
Condo
Subdivision:
Lakeside Manor Apts Condo
Lot size:
0.05 Acres
Year built:
1969
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water is included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to boat slips (based on availability, charge is $30/month), a boat ramp, a sparkling pool, a welcoming clubhouse, and mature landscaping that enhances the serene environment. Outdoor enthusiasts will appreciate the multiple barbeque grills and tables, ideal for courtyard or lakeside dining. Additional amenities include two on-site laundry rooms, on-site storage, and convenient proximity to key destinations. COA approval is required. The application fee is $85.00. Situated in Winter Park, the community is less than 10 minutes from Winter Park Village, Maitland, and Downtown Winter Park, about 10 minutes from College Park, and approximately 15 minutes from Downtown Orlando and Lake Mary. This prime location ensures easy access to shopping, dining, entertainment, and the vibrant city lifestyle.

Beds:
2
Baths:
2.00
Sq.Ft.:
949
Status:
Active
MLS#:
O6290188
Type:
Condo
Subdivision:
Lachen House Condo
Year built:
1969
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

FIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN HOUSE – AVAILABLE FOR RENT OR PURCHASE! This is your chance to secure a highly coveted ground floor unit in one of Winter Park's most desirable locations. Available for rent at $3,800/month or purchase at $635,000 with quick move-in or quick closing possible! This stunning 2-bedroom, 2-bath condo has been completely remodeled from top to bottom, featuring sleek new laminate flooring, bright recessed lighting throughout, and a gorgeous gourmet kitchen perfect for entertaining. Both bedrooms are generously oversized with abundant closet space, and a charming private courtyard off the back bedrooms offers a peaceful outdoor retreat to enjoy year-round. Ground floor living means unparalleled convenience – no stairs, no elevators, just easy access every day. Plus, enjoy your own reserved, covered parking space for ultimate comfort and protection. Location doesn't get better than this! Situated just one block from iconic Park Avenue and beautiful Lake Osceola, you'll be immersed in the heart of Winter Park's vibrant lifestyle. Stroll down brick-lined streets to world-class restaurants, boutique shopping, art museums, cultural events, and the prestigious Rollins College campus – all within walking distance. This is high-walkability living at its finest, with endless attractions and amenities right at your doorstep. Opportunities like this are incredibly rare. Inquire immediately – this ground floor gem won't last long!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,114
Status:
Active
MLS#:
O6290084
Type:
Single Family
Subdivision:
Cortland Park
Lot size:
0.19 Acres
Year built:
1981
A broker reciprocity listing Courtesy: EXP REALTY LLC 888-883-8509
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ADDITIONAL INFORMATION

Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a sparkling swimming pool, and a spa, all enclosed for privacy by a PVC fence. Step inside this inviting three-bedroom, two-bath split floor plan home, and you're instantly captivated by the expansive view of the grand living area, the enclosed lanai, and the serene pool beyond. The residence boasts a move-in-ready condition with a host of recent upgrades, including a new roof, elegant Brazilian Rosewood floors in the living area, and durable, health-conscious quarry tile floors in the kitchen, bath, and hallways. The heart of the home, the kitchen, has been reimagined with new cabinetry and state-of-the-art appliances. Both the master and secondary bathrooms are refreshed with new vanities and modern shower doors. Additional comforts include new carpeting, vinyl flooring in select areas, ample storage with large walk-in closets, an entry hall closet, and a generous linen storage space. The thoughtful touches extend to new door hardware and upgraded lighting throughout, enhancing the overall aesthetic and functionality. Imagine retracting the 3way sliding glass doors that connect the grand living area to the lanai, and you're living the quintessential inside-outside Florida lifestyle. This home is so light and airy that no daytime lighting is required. All of this located by Lake Mizell, part of the sought after Winter Park chain of lakes. Where you can enjoy the incredible views while taking a tranquil walk along the Lake. Don't miss the opportunity to own this true neighborhood gem in Winter Park, where luxury living and convenience meet.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,230
Status:
Active
MLS#:
O6285927
Type:
Condo
Subdivision:
Goldenrod Villas Condo
Lot size:
0.03 Acres
Year built:
1984
A broker reciprocity listing Courtesy: REALTY TECH INC 407-332-9757
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ADDITIONAL INFORMATION

Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining family and friends. Come and make it your own. The HOA maintains building exterior, roof, and exterior landscape maintenance. The Community features enjoyable sparkling swimming pool and clubhouse. Great location! Conveniently located to nearby shopping, schools, banks, medical centers, and restaurants as well as easy access to major highways. Don't miss it. Priced to sell. Will Not Last!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,149
Status:
Active
MLS#:
O6285607
Type:
Condo
Subdivision:
Waterfall Cove At Winter Park
Lot size:
0.41 Acres
Year built:
1966
A broker reciprocity listing Courtesy: PRIMESTATE REALTY, INC. 407-850-9494
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ADDITIONAL INFORMATION

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

Beds:
5
Baths:
7.00
Sq.Ft.:
6,406
Status:
Active
MLS#:
O6282425
Type:
Single Family
Subdivision:
Comstock Park
Lot size:
0.36 Acres
Year built:
2024
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator, that offers nearly 770 square feet of multi-use space. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


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Winter Park Real Estate

Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.

The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.

Winter Park Weather

The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.

Winter Park Map

Winter Park Real Estate Market Conditions

  • Median sales price

    $500,000
    25.3%
    change since last quarter
  • # Active listings

    294
    30-day change

Winter Park Schools and Demographics

Education near Winter Park, FL

City County
High School Graduates 96.78 89.47
College Degree - 2 year 9.01 11.45
College Degree - 4 year 62.48 35.7
Graduate Degree 17.77 9.12
Expenditures per Student 12,701 12,701
Students per Teacher 17.3 17.3

Elementary Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Aloma Elementary School PK - 05 528 15.5 32792
Aspire Academy Charter KG - 05 111 8.5 32804
Audubon Park Elementary School PK - 05 1,182 14.8 32814
Brookshire Elementary School PK - 05 632 12.9 32792
Dommerich Elementary School PK - 05 603 15.1 32751
Eastbrook Elementary School PK - 05 809 14.2 32792
Fern Creek Elementary School PK - 05 326 12.1 32803
Hillcrest Elementary School PK - 05 463 14.5 32803
Hungerford Elementary School PK - 05 283 13.5 32751
Killarney Elementary School KG - 05 444 14.8 32789
Lake Silver Elementary School PK - 05 688 12.3 32804
Lake Sybelia Elementary School PK - 05 600 13.3 32751
Lakemont Elementary School KG - 05 656 14.6 32792
Orlando Science Elementary Charter KG - 05 482 15.1 32804
Princeton Elementary School PK - 05 488 13.2 32804

Middle Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Glenridge Middle School 06 - 08 1,415 18.4 32814
Maitland Middle School 06 - 08 909 18.9 32751
Robert E Lee Middle 06 - 08 1,034 17.2 32804

High Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Edgewater High School 09 - 12 1,782 20 32804
Lake Howell High School 09 - 12 2,229 19.1 32792
Winter Park High School 09 - 12 3,069 18.7 32792
Workforce Advantage Academy Charter 09 - 12 238 47.6 32803

Ungraded Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
* Aloma High Charter School 09 - 12 510 42.5 32792
* Winter Park Education Center 11 - 12 0 32789
Broward Science Charter School UG - UG 0 32804
Central Florida Leadership Academy Charter 06 - 12 189 15.8 32803
Gateway 06 - 12 63 3.7 32804
Hospital Homebound PK - 12 229 4 32804
La Amistad School KG - 12 48 9.6 32751
Orlando Science Middle High Charter School 06 - 12 555 15.4 32804
Pace Center for Girls 06 - 12 34 6.8 32803
Silver Star Center 06 - 12 25 2.5 32804
Winter Park Tech AE - AE 0 32789

Demographics near Winter Park, FL

City County
Neighborhood Type Suburban
Population 29,672 1,409,949
Population Density 3,393 1,562
Median Age 45.3 35.7
People per Household 2.3 2.9
Median Household Income 88,688 65,784
Average Income per Capita 67,032 33,498

Real estate near Winter Park