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Winter Park FL Real Estate & Homes for Sale

332 Properties Found

The median home value in Winter Park, FL is $480,000. This is higher than the county median home value of $318,000. The national median home value is $308,980. The average price of homes sold in Winter Park, FL is $480,000. Approximately 56% of Winter Park homes are owned, compared to 33% rented, while 11% are vacant. Winter Park real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Winter Park real estate agent to arrange a tour today!
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Beds:
3
Baths:
3.00
Sq.Ft.:
3,653
Status:
NEW LISTING
MLS#:
O6284417
Type:
Single Family
Subdivision:
SYLVAN LAKE SHORES
Lot size:
0.42 Acres
Year built:
2000
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK, 407-545-6430
View additional info

Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don't miss the opportunity to make this lake front home yours. Schedule your private showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,295
Status:
NEW LISTING
MLS#:
O6291369
Type:
Condo, Townhouse
Subdivision:
CEDARWOOD VILLAGE 1
Lot size:
0.04 Acres
Year built:
1981
A broker reciprocity listing Courtesy: MLSB THE BUREAU POWERED BY CAROM REALTY, 407-284-3488
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Welcome to this beautifully renovated 2-bedroom, 2-bathroom townhouse located in the desirable Cedarwood Village community of Winter Park. This 1,295 sq ft home seamlessly blends modern updates with classic charm, offering a comfortable and stylish living space. The heart of this home boasts a brand-new kitchen equipped with modern appliances, sleek countertops, and ample cabinet space, perfect for culinary enthusiasts. High-grade laminate flooring extends throughout the living areas, providing durability and a contemporary aesthetic, while the entire interior has been freshly painted in neutral tones, creating a bright and inviting atmosphere. Both bathrooms have been thoughtfully updated with modern fixtures and finishes, enhancing both functionality and style. The open-concept living and dining areas feature vaulted ceilings and skylights, filling the space with natural light and offering a welcoming environment for relaxation and entertainment. Residents of Cedarwood Village enjoy access to a community pool, clubhouse, and well-maintained common areas, enhancing the overall living experience. The association fee covers exterior maintenance, landscaping, and access to community amenities. Situated in Winter Park, this townhouse offers proximity to a variety of shopping, dining, and entertainment options. The area is known for its excellent schools and vibrant community atmosphere, making it a sought-after location for families and professionals alike. Don't miss out on this incredible opportunity"schedule your private showing today!

Open House:

Saturday, 3/22 12:00-2:00PM

More Open House Info >

Beds:
1
Baths:
1.00
Sq.Ft.:
884
Status:
NEW LISTING
MLS#:
O6290860
Type:
Condo, Townhouse
Subdivision:
PHILLIPS CIRCLE REP
Year built:
1960
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
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Tucked away just two blocks from Park Avenue, this one bedroom, one bathroom corner unit places you in the heart of downtown Winter Park"steps from acclaimed restaurants, charming shops, and the iconic boat tour on Lake Osceola. Situated on the second floor of Building 6 with convenient elevator access, this light filled condo has brand new carpet in the living areas and bedroom, creating a fresh and cozy feel. The kitchen features granite countertops, a built-in oven, glass cooktop, stainless steel refrigerator, and recently painted blue, solid wood cabinetry that adds a fun pop of color to the space. A dedicated dining area is located just off the kitchen and includes sliding glass doors that open to a small private balcony overlooking Morse Blvd"perfect for enjoying your morning coffee. Off the living room, an enclosed sunroom offers bonus living space with abundant natural light, motorized custom blinds, and upgraded windows for improved energy efficiency and sound insulation. The oversized bedroom offers space for a sitting area and features motorized shades for added comfort and privacy. A convenient door allows you to close off the bedroom "ideal for when guests are visiting and need access to the bathroom without entering the bedroom. The unit also comes with one assigned parking space in the garage, additional storage, and the peace of mind that HOA covers electric, water, sewer, trash, building insurance, pool maintenance, landscaping, and on-site management. Whispering Waters is a lakefront community on beautiful Lake Osceola, with water access available to residents"bring your kayak, soak in the serene views, or enjoy a sunset by the water. Whether you're seeking a full-time residence or a part-time getaway, this home offers effortless, low-maintenance living"just lock and leave. Bonus: Since the current owner is under 55, the next buyer can be too (only 85% of residents need to meet the 55+ age requirement). Call today to schedule your private showing!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,066
Status:
NEW LISTING
MLS#:
O6286150
Type:
Condo, Townhouse
Subdivision:
COLONIES
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: REALTY HUB, 888-900-1801
View additional info

Priced to sell! This updated 1st Floor, 2 bed, 2 bath unit, with luxury tile (faux wood) floors and updated amenities, is a great starter home or investment property. Freshly painted and cleaned, ready to move in!The monthly HOA fee include amenities, water & trash pick up, Exterior and ground maintenance. As a resident of the Colonies subdivision, you'll enjoy access to a host of exclusive amenities, including a sparkling community pool, perfect for cooling off on hot summer days or lounging in the sun with a good book as well as tennis courts, dog park and a clubhouse. Conveniently located just moments from the vibrant shops, restaurants, and cultural attractions of downtown Winter Park, as well as top-rated schools and parks, this coveted unit offers the ultimate in luxury living with all the conveniences of modern-day life at your fingertips. Don't miss your opportunity to experience the epitome of luxury living in Winter Park. Schedule your private showing today and make your dream of owning this unit a reality.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,014
Status:
NEW LISTING
MLS#:
A4644849
Type:
Single Family
Subdivision:
CAROLYN ESTATES
Lot size:
0.25 Acres
Year built:
1982
A broker reciprocity listing Courtesy: MINK REALTY, 502-716-6151
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Welcome to 1776 E Cheryl Dr, located on a quiet cul-de-sac in desirable Winter Park. The home offers a split plan with 4 bedrooms and 2 bathrooms. The living room has a beautiful stone fireplace. It has a separate indoor laundry room and an attached 2-car garage. Notes of interests include a fully renovated guest bathroom (2018), fully renovated kitchen (2023), new roof and gutters (2021), house replumb (2023) and home exterior paint (2024) and new interior paint throughout the home. Outside you will find a beautiful screened in pool to enjoy the Florida sun. It also has a covered area where you can enjoy outside dining. There is ample room on the .24 square foot lot to have a garden or enjoy lawn games. Located in Winter Park, this home is conveniently situated near a variety of shopping, dining, and entertainment options. The home is in the perfect location as there is a short commute to three top-rated Seminole County schools.. With easy access to major highways and public transportation, commuting to work or school is a breeze. Additionally, the neighborhood is known for its friendly atmosphere and sense of community. Don't miss out on the chance to make this lovely property your own!.

Open House:

Saturday, 3/22 12:00-2:00PM

More Open House Info >

Beds:
5
Baths:
4.00
Sq.Ft.:
2,910
Status:
NEW LISTING
MLS#:
O6285510
Type:
Single Family
Subdivision:
TEMPLE TERRACE
Lot size:
0.41 Acres
Year built:
1954
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC
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Stunning fully remodeled Winter Park bungalow featuring a 500 square foot detached guest house. This charming residence is perfectly positioned on a rare oversized .41-acre double lot and has been completely transformed, offering a harmonious blend of modern luxury and timeless elegance. The main house features 4 bedrooms and 2.5 baths while the guest house features a living room, bedroom, kitchenette, and a full bathroom. Step inside and you are immediately greeted by a bright, spacious open floor plan. Designed for effortless entertaining, this home features a sleek modern wet bar complete with an under counter ice maker, additional dishwasher, and wine fridge! The gourmet kitchen is a true masterpiece, featuring top-of-the-line stainless steel appliances, upgraded countertops, a walk-in pantry, a large butcher block center island, tile backsplash, and loads of custom cabinetry. There is even a pass-through window to a bar area on the covered lanai. The luxurious primary suite provides a serene escape, designed as a private retreat where you can unwind in ultimate comfort. It boasts an impressive closet and a spa-inspired en-suite bath, complete with a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Outside, the home continues to impress with its private backyard oasis provided by the rare double lot. A sparkling screened in pool, set against lush landscaping, serves as the centerpiece of the expansive patio area. In addition, the beautifully landscaped yard holds a custom fire pit, elevated covered wooden lanai and garden boxes to create the perfect setting for relaxation and gatherings. There is also a spacious covered deck, and a large storage shed. Last but not least, your guest will love the privacy provided by the detached guest house overlooking the pool. Jump on your golf cart and within minutes you're transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don't miss the opportunity to make this unique Winter Park home yours!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,578
Status:
NEW LISTING
MLS#:
O6290118
Type:
Condo, Townhouse
Subdivision:
WHISPERWOOD CONDO
Lot size:
0.1 Acres
Year built:
1974
A broker reciprocity listing Courtesy: CREEGAN GROUP, 407-622-1111
View additional info

One or more photo(s) has been virtually staged. Welcome to this charming two bedroom, two and a half bathroom condo in the heart of Winter Park. This home offers a spacious and functional layout with a half bath on the first floor, perfect for guests, and an interior laundry room for added convenience. The living room features a cozy fireplace, creating a warm and inviting atmosphere. Two sliding glass doors on the first floor lead out to the expansive, fenced-in paver backyard ideal for outdoor relaxation or entertaining. The custom kitchen is a chef's dream, featuring beautiful maple cabinets with crown molding, sleek granite countertops, and high end Frigidaire stainless steel appliances. Tile flooring throughout the living areas and new luxury vinyl upstairs provide both style and durability. Upstairs, you'll find the primary bedroom, offering a private sanctuary with a stand-up shower, a spacious walk in closet, and a screened-in porch that overlooks a serene, lush green space. The generously sized second bedroom and a well appointed bathroom, featuring a luxurious Jacuzzi tub, complete the upper level. Additionally, there's an oversized storage room for all your extra needs. Exterior features include an oversized carport with a sun porch and extra storage space. The HOA includes exterior maintenance, pest control, as well as access to the community pool and clubhouse. Ideally located in Winter Park, this condo offers a peaceful setting while being just minutes away from local restaurants, shopping centers, major roadways, and top-rated schools. This condo is the perfect blend of comfort, style, and convenience, making it a must-see in Winter Park!

Beds:
4
Baths:
6.00
Sq.Ft.:
5,097
Status:
NEW LISTING
MLS#:
O6289739
Type:
Single Family
Subdivision:
STONEHURST ESTATES
Lot size:
0.5 Acres
Year built:
2001
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle.The red brick faade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light.Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas range, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating.The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms.Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room.The private, fenced-in backyard oasis includes a two-story covered brick patio with a summer kitchen, a breathtaking saltwater pool and heated spa with water features, and lush landscaping accented by a three-tier fountain and fire pit area; this outdoor space is truly magical and not easily replicated in Winter Park!A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above"ideal for a gym or studio.This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home"it's a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,525
Status:
NEW LISTING
MLS#:
O6290615
Type:
Single Family
Subdivision:
SPRINGVIEW
Lot size:
0.23 Acres
Year built:
1984
A broker reciprocity listing Courtesy: ORLANDO EXPERT REALTY LLC, 321-274-6991
View additional info

Welcome to this meticulously updated and **FULLY FENCED POOL HOME**, reflecting exceptional pride in ownership and featuring numerous thoughtful upgrades, all nestled in the desirable Winter Park area with **NO HOA** and a **NEW METAL ROOF (2022) ** This home is ideally situated on a **QUIET CUL-DE-SAC**, offering additional privacy and tranquility. The **SOLID BLOCK CONSTRUCTION** ensures durability and long-term peace of mind, providing the home's overall structural integrity. It offers 3 bedrooms, 2 bathrooms, and **A VERSATILE BONUS ROOM** with a closet on the ground floor, perfect for a home office, a 4th bedroom, or extra storage, adapting effortlessly to your needs.As you step inside, you'll be greeted by a bright, inviting living room, with new plantation shutters and tile flooring throughout. The open layout effortlessly transitions into the dining area, where French doors lead to the backyard, ideal for seamless indoor-outdoor living.The modern kitchen features warm wood cabinetry, stainless steel appliances, a stylish glass tile backsplash, and a cozy nook area, perfect for casual meals or enjoying your morning coffee. Upstairs, all the bedrooms have been updated with beautiful wood floors, giving the home a fresh, contemporary feel. The remodeled bathrooms combine both style and function, offering comfort for your daily routines.Step outside to your private backyard retreat: an entertainer's dream and **SPACE GALORE!**The sparkling swimming pool, resurfaced in 2024 and color-changing pool lights, is the centerpiece of this expansive backyard, offering the perfect spot to relax and cool off on warm Florida days. The fully fenced yard ensures complete privacy, with no rear neighbors. For outdoor dining or relaxation, the shaded gazebo on the concrete pad provides a cozy retreat, complete with a built-in charcoal grill, Bluetooth sound system, and hanging lights, creating the ideal setting for evening meals or entertaining guests.The yard has been freshly landscaped with new sod and includes an efficient well-powered irrigation system, ensuring the space stays lush and green year-round while helping to reduce utility costs. For added convenience, a storage shed offers ample space for tools and outdoor equipment, keeping everything organized and accessible. With plenty of space, you can easily add a swing set, garden beds, or a fire pit to enhance your outdoor oasis. Additional upgrades include new gutters, new insulation (2020), and a new garage door with updated features (2023) and alarm system, giving you peace of mind for years to come.Located nearby schools and shopping, this home offers the perfect balance of convenience and comfort. This is a rare opportunity to own a meticulously updated home in the desirable Winter Park area. Don't miss your chance to make this exceptional property yours, schedule your private tour today!

Beds:
1
Baths:
1.00
Sq.Ft.:
549
Status:
NEW LISTING
MLS#:
O6289736
Type:
Condo, Townhouse
Subdivision:
COLONIES
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: CASTLE & COTTAGE REALTY LLC, 407-620-9405
View additional info

Charming Studio Condo Near UCF & Full Sail - Ideal Investment or Cozy Retreat!Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to maintain. Enjoy a bright and open layout, a well-equipped kitchen, and a full bathroom, all designed for convenience and efficiency. Step outside to your private covered patio, where you can relax while overlooking the serene courtyard setting.Whether you're looking for a low-maintenance home or a smart investment opportunity, this condo checks all the boxes. Schedule your showing today!

Open House:

Saturday, 3/22 10:00-2:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
2,563
Status:
NEW LISTING
MLS#:
O6289847
Type:
Single Family
Subdivision:
DUBSDREAD HEIGHTS
Lot size:
0.16 Acres
Year built:
2020
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295
View additional info

Discover modern living at its finest in this stunning contemporary home in the heart of Winter Park! Built in 2020, this spacious four-bedroom, 2.5-bath residence offers over 2,500 square feet of beautifully designed living space ideal for families of all sizes. The first floor features a bright, open-concept kitchen with sleek finishes, a large island and ample storage, seamlessly flowing into a spacious living area, and ideal for family gatherings and entertaining. Upstairs, the luxurious primary suite offers a private retreat with a large en-suite bath, while three additional bedrooms provide plenty of space for guests, or a home office. At top of the stairs, you'll find a versatile loft space, ideal for a playroom, media area or additional lounge. Step outside to enjoy the expansive backyard, complete with a large privacy fence, offering plenty of space for families and pets to play or to host outdoor gatherings. This home is in a prime location, only a short distance to Dubsdread Golf Course. It's also just minutes from Park Avenue, College Park and downtown Orlando, offering easy access to dining, shopping and entertainment. Plus, with quick access to Interstate 4, commuting anywhere in Central Florida is effortless. This home is a rare find. Don't miss your chance to make it yours, schedule your showing today.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,114
Status:
NEW LISTING
MLS#:
O6290084
Type:
Single Family
Subdivision:
CORTLAND PARK
Lot size:
0.19 Acres
Year built:
1981
A broker reciprocity listing Courtesy: EXP REALTY LLC, 407-204-1111
View additional info

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:
8
Baths:
8.00
Sq.Ft.:
3,600
Status:
NEW LISTING
MLS#:
O6284382
Type:
Duplex, Multi-Family
Subdivision:
SLOVAK VILLAGE
Lot size:
0.45 Acres
Year built:
1979
A broker reciprocity listing Courtesy: FLORIDA ONE REAL ESTATE LLC, 407-599-7070
View additional info

Welcome to 160 Moyses Road, an exciting investment opportunity to own two two-story townhouse duplexes all on one property in a desirable Winter Park location. You read that right - there are four units. No HOA. Each building has two two-story units. On the ground floor, each unit comprises a living room, a kitchen, a 1/2 bathroom, and a laundry room. Upstairs, each has two good-sized bedrooms with nice closets and one full bathroom. Each unit offers an attached carport and a storage closet. For ease of being the landlord, the utilities are all metered separately. The property offers lots of privacy, and the lot across the street is vacant. The lot measures 98' by 200'. Residents will love that assigned schools are top-rated in the area - Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High. The property is just a few minutes' drive from downtown Winter Park, close to coffee shops, restaurants, supermarkets, movie theaters, and schools. It is mid-way between I-4 and SR 417, so you can easily access everything in Central Florida, including downtown Orlando, the theme parks, the beaches, and Orlando International Airport.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,020
Status:
NEW LISTING
MLS#:
O6285553
Type:
Condo, Townhouse
Subdivision:
WINTER PARK WOODS CONDO
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: EXP REALTY LLC
View additional info

Welcome to this spacious and modern 2 bedroom, 2 bathroom condominium located in Winter Park, FL, just minutes from Full Sail University, Baldwin Park, shopping, and entertainment. This property is the perfect fit for a first-time home buyer or a great rental opportunity for $1600 monthly. Huge Rental Market in this area! Upon entering the unit, you'll be greeted by an open floor plan, with a large living room. The kitchen features newer appliances and a bar top big enough for three . There is plenty of cabinet and counter space, as well as built-in storage. The master bedroom features an ensuite bathroom. The second bedroom is well-sized and adjacent to the second full bathroom. Both bathrooms are in good condition. Additional features of the unit include a large laundry room with plenty of storage, central air conditioning, and a back patio. Don't miss out on the opportunity to call this condominium home. Schedule your showing today!

Open House:

Wednesday, 3/19 12:00-2:00PM

More Open House Info >

Beds:
4
Baths:
4.00
Sq.Ft.:
3,140
Status:
NEW LISTING
MLS#:
O6288366
Type:
Single Family
Subdivision:
BROOKSHIRE HEIGHTS 1ST ADD
Lot size:
0.2 Acres
Year built:
2018
A broker reciprocity listing Courtesy: PALMANO GROUP RE BROKERAGE LLC, 321-214-1211
View additional info

Welcome to 2536 Brookshire Ave, a spacious 4-bedroom, 3.5-bath modern farmhouse located in the heart of Winter Park. The open floor plan enhances connectivity throughout, with a first-floor primary suite featuring generous his and her closets. Designer lighting and plumbing fixtures, custom interior paint, 8-foot doors, and wood-like tile floors create a cohesive design.Enjoy additional space upstairs with a loft that has the potential to be converted to a 5th bedroom.All bedrooms are pre-wired for cable and CAT 6, with surround sound in the main living areas and speaker wiring on the back porch. The gourmet kitchen features custom white shaker cabinetry with soft-close doors and drawers, an oversized granite island, and designer pendant lighting. Stainless steel appliances, including an induction cooktop and refrigerator, complement the space. A built-in pantry and under-cabinet lighting with integrated outlets add functionality.The primary suite includes a walk-in shower enclosed in custom glass, a freestanding soaking tub, and dual solid wood vanities with ample storage. Smart technology features include a motorized retractable screen lanai, a Lutron smart exterior lighting system, a MyQ smart garage door opener, and a Schlage smart front door lock with coded entry access on all exterior doors. The home is wired for Ethernet, and a Ring doorbell adds security.The spacious garage offers remote access. Built for efficiency and durability, the home features foam-insulated block walls, Low-E windows, a fully fenced backyard, a sprinkler system, and a radiant barrier roof. Two 15 SEER AC units and a programmable thermostat provide climate control.Located within one of Winter Park's top-rated school districts, this home is just minutes from Park Avenue, offering upscale shopping, dining, and entertainment.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,309
Status:
NEW LISTING
MLS#:
O6289193
Type:
Single Family
Subdivision:
WINTER PARK PINES
Lot size:
0.2 Acres
Year built:
1963
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC, 407-645-4321
View additional info

Beautifully updated and FURNISHED 3-bedroom, 2-bath home in the desirable Winter Park Pines neighborhood is truly move-in ready! Fully renovated in 2019, the home boasts a range of high-end features, including hardwood flooring, designer fixtures, custom crown molding, and 5.25" baseboards throughout the majority of the home. Open floor plan is an inviting space for both living and entertaining. Wonderful chef's kitchen, complete with Quartz countertops, large island, floor-to-ceiling cabinetry with under-cabinet lighting, soft-close doors and drawers, and stainless steel appliances, including fridge, convection oven, dishwasher, microwave, and dry bar. Skylights and double-pane windows flood the space with natural light.The spacious living and dining areas flow seamlessly. Multiple sitting areas. Large walk-in pantry, mudroom and laundry room. Great room / game room, or home office, features French doors that open onto a screened-in porch, ideal for relaxing. Outdoor patio, dry shed and privacy provided by the lush landscaping and fencing.The primary bedroom is a retreat, and features a stunning, large frameless shower, custom dual vanity with quartz countertops, and an oversized walk-in closet. Two additional bedrooms are generously sized, offering views of the front and side yards, and share an improved bathroom.This home is packed with upgrades including a new water heater (2024), new roof (2023), newer indoor electrical panel, and re-plumbing completed in 2017, along with a 2016 HVAC system. A well for 3- zoned irrigation, providing free water for your landscaping. Located just minutes from the Winter Park Pines Golf Course, Cady Way Bike Trail, pool, pickleball/tennis courts, playground, sports fields, and shopping, as well as Winter Park Hospital, this home offers the perfect blend of convenience and luxury. Zoned for Winter Park schools, with an optional HOA, it's an excellent investment opportunity as well. Close to Rollins College and Full Sail. Enjoy mature, green trees, sidewalks for biking and walking in this charming and sought-after neighborhood.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,466
Status:
NEW LISTING
MLS#:
O6288258
Type:
Single Family, Ranch
Subdivision:
BROOKSHIRE HEIGHTS
Lot size:
0.25 Acres
Year built:
1958
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY, 407-695-2066
View additional info

Incredible opportunity to own a beautifully updated POOL home in Winter Park... just a block from Top-rated Brookshire Elementary School! Situated on an oversized lot with 2-car garage, this home offers the perfect blend of function, design, and comfort- boasting Mid-Century Modern vibes! As you enter through the beautiful double glass doors, you are greeted by an expansive foyer that flows seamlessly into the dining room and open-concept kitchen; all of which has been tastefully updated with meal prep and entertaining in mind!! Fully equipped with all appliances, the kitchen offers modern granite countertops & breakfast bar, and beautiful wood cabinetry with soft-close features, undermount lighting & glass-front display cabinets **PLUS great storage, prep space and excellent lighting! Off of the kitchen and dining room is a dedicated living/great room with TWO sets of French Doors to access the covered patio where you can take advantage of the Florida weather nearly year-round! The master bedroom sits at the back of the home for added privacy, and offers a walk-in closet, an en-suite shared bath, and French Doors that lead to a pavered patio that overlooks the backyard oasis (while providing just the right amount of natural light!). Outside you will enjoy the sparkling pool with stone-pavered deck nestled among the large, fully-fenced yard with plenty of space to play, garden, and relax! Roof and HVAC were replaced in 2014, Pool Pump replaced in 2018. All electrical panels have been updated.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,067
Status:
NEW LISTING
MLS#:
V4941401
Type:
Condo, Townhouse
Subdivision:
FOUR SEASONS CONDO
Lot size:
19.03 Acres
Year built:
1970
A broker reciprocity listing Courtesy: BETTER HOMES & GARDENS RE STAR, 321-868-5555
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FOUR SEASONS CONDO IN Winter Park is Centrally located. Great community with a clubhouse, a fitness center recently renovated, 3 swimming pools, tennis courts, and shuffleboard court. Close by you are only a short walk to Cady Way Park for baseball and soccer fields as well as other playgrounds. This 2 bedrooom/2 bath unit has been updated with laminate flooring, ceiling fans, all appliances including washer and dryer. Very close to Advent Health, Winter Park Hospital and all the shopping on Park Avenue, Rollins College, UCF, Valencia Communtiy College. 2 pets allowed :). THis is absolutely a prime location within Winter Park!

Beds:
2
Baths:
2.00
Sq.Ft.:
929
Status:
NEW LISTING
MLS#:
O6289768
Type:
Condo, Townhouse
Subdivision:
GALLERY AT WINTER PARK SEC 01
Lot size:
1.46 Acres
Year built:
1984
A broker reciprocity listing Courtesy: NONA LEGACY POWERED BY LA ROSA, 407-270-6841
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Welcome home to Winter Park! This corner, end unit is located on the second floor with a cozy fireplace and vaulted ceilings to create an open feeling. Tons of natural light fill the space. The large primary bedroom has a pool view, ensuite bath and walk-in closet. The split bedroom plan offers privacy and there is indoor laundry. This unit has eating space in the kitchen and solid countertops. The kitchen is open to the dining and living are for entertaining. Quartz countertops and new vanities in both baths. AC system 2024. The screened balcony overlooks the pool and lush landscaping. This community is well maintained with mature landscaping, tennis court, bike storage rack, pool and clubhouse. The Gallery at Winter Park is close to amenities on Aloma Ave, Advent Health Winter Park, Full Sail University, Rollins College the Cady Way trail and just a short distance from Park Avenue where you will find dining, shopping and Central Park. Schedule your private tour today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,046
Status:
NEW LISTING
MLS#:
O6289998
Type:
Single Family
Subdivision:
KENILWORTH SHORES SEC 04
Lot size:
0.21 Acres
Year built:
1964
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO, 407-622-2122
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Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue's top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef's kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel appliances. Each bathroom has been modernized with sleek, contemporary finishes, while the spacious primary suite offers a private retreat with a beautifully updated ensuite. Outside, the fully fenced backyard provides a perfect space for relaxation or entertaining, and the two-car garage offers ample storage with easy access to the main living areas. Situated in a prime location with convenient access to I-4 and SR-417, this home blends modern elegance with unbeatable convenience. Don't miss your chance to experience Winter Park living at its best"schedule your showing today!

Open House:

Sunday, 3/23 12:00-2:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,088
Status:
NEW LISTING
MLS#:
O6287695
Type:
Condo, Townhouse
Subdivision:
ANDALUCIA APTS
Lot size:
0.61 Acres
Year built:
1972
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
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Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor unit is located on corner of Swoop and Interlachen, steps from the Winter Park 9 Golf Course and Park Avenue! Beautiful views, glassed in porch overlooking stunning landscape. This unit offers high ceilings, open, updated kitchen to living areas, sunroom (enclosed porch) large primary suite and guest room. Two full baths. Large utility room. Designer lighting. Open floor plan, light and bright! A/C 2018. The charming Andalucia complex, which consists of only 20 units, offers access to a lovely covered patio downstairs, an elevator, courtyard, and a community laundry room. The community also provides a private storage room for this unit. The roof was replaced in 2024. The exterior was painted, and new gates were installed in 2018. One covered parking space is included. Additional guest parking is available in the rear. The condo fee covers water, sewer, Spectrum WiFi and cable TV, landscaping and exterior maintenance, garbage, insurance on the exterior building, and reserves. Please note: No pets or rentals allowed. Call today for your private viewing of this special unit.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,801
Status:
NEW LISTING
MLS#:
O6289327
Type:
Condo, Townhouse
Subdivision:
GRAYSON SQUARE
Lot size:
0.05 Acres
Year built:
2023
A broker reciprocity listing Courtesy: LPT REALTY, LLC
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Nestled in the coveted Grayson Square community of highly desired Winter Park, FL, 2037 Canny Cove Lane is a contemporary 3-bedroom, 2.5-bath townhome built in 2023. The open-concept layout features a stylish kitchen with stainless steel appliances, quartz countertops, and ample storage, seamlessly flowing into the spacious gathering room. The owner's suite offers a private retreat with an en-suite bathroom, complemented by two additional bedrooms and a shared full bath. Located in a gated community with amenities like a gorgeous pool and high-speed internet and cable, this property provides serene living with access to the neighboring grass space as a maintenance free yard, and side entry, full two car garage and easy access to local attractions, dining, shopping, and major highways.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,627
Status:
NEW LISTING
MLS#:
O6289675
Type:
Single Family
Subdivision:
BEL AIRE PINES
Lot size:
0.23 Acres
Year built:
1981
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS, 407-629-4420
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**This property qualifies for a closing cost credit up to $6,600 through the Seller's preferred lender.**Welcome home to this 3-bedroom, 2-bathroom home located in the highly desirable Winter Park community of Bel Air Pines. Offering the perfect blend of modern amenities and classic style, this home is sure to check the boxes and more! The front screened-in porch with its charming arched detailing invites you to relax and enjoy the Florda breeze. As you enter the foyer, you'll see the hallway to your right connecting all three bedrooms and both updated bathrooms. The open concept living and dining areas are perfect for entertaining, with plenty of natural light and a seamless flow for gatherings. The kitchen around the corner features updated white cabinetry, stainless steel appliances, and quartz countertops, offering both style and functionality. Sliding glass doors open from the living area to the backyard, extending your space for indoor-outdoor living. The spacious backyard is the perfect space to store your RV, trailer, or boat with an 8-foot privacy fence surrounding. Recent upgrades include new windows and sky lights, replumbed and new breaker box in 2015, soffit and gutters and facia and new hot water heater in 2020, all new exterior lights, and the attic has R18 pest repellent insulation. Zoned for winter Park High School, this amazing location offers amazing dining and shopping being close to Downtown Winter Park and Orlando and easy access to major highways. Schedule your private showing today!

Beds:
2
Baths:
1.00
Sq.Ft.:
912
Status:
NEW LISTING
MLS#:
O6288240
Type:
Condo, Townhouse
Subdivision:
WINDWARD SQUARE SEC 2
Lot size:
0.05 Acres
Year built:
1977
A broker reciprocity listing Courtesy: CREEGAN GROUP, 407-622-1111
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Don't miss out on a great opportunity to own a SINGLE-STORY, LOW HOA townhouse in Winter Park's popular Windward Square community. Imagine yourself enjoying any of its three pools, tennis courts, BBQ area, or outdoor reading benches AND being located a mere 5 minutes from grocery shopping and dining esablishments. More shopping, dining, and opportunities to just relax and watch busy shoppers are available nearby, in Winter Park's downtown Park Avenue district. This two-bedroom, no carpet unit offers a living/dining room combo with beautiful morning light. In addition to its smartly situated full bathroom, a separate sink and dressing area is available in the master bedroom, for owner convenience. Walk-in closets are found in both bedrooms, and the townhouse has a designated laundry closet, too (washer and dryer convey). Sliding patio doors open to a fully-fenced backyard, affording privacy and the ability to garden, BBQ, or watch Fido play. An exterior storage closet provides space for yard or hobby items you own. You will love the 3-car parking pad right in front of your unit. No more searching for visitor parking spots! Just around the corner you'll find the clubhouse and all the community amenities that give Windward Square its "easy living" reputation. Schedule your private showing today!ROOF: 2023HVAC: 2023

Beds:
5
Baths:
5.00
Sq.Ft.:
4,912
Status:
NEW LISTING
MLS#:
O6289369
Type:
Single Family
Subdivision:
COMSTOCK PARK
Lot size:
0.34 Acres
Year built:
2003
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Nestled on a serene, brick-paved street in the heart of Winter Park, this elegant 5-bedroom, 3.2-bathroom pool home is situated on a stunning oversized lot. Custom-built in 2003, it offers a thoughtful floor plan that adapts beautifully to any lifestyle. From the moment you arrive, this home welcomes you with timeless charm and a sense of warmth. Inside, expansive windows, rich wood flooring, and exquisite millwork create an atmosphere of sophistication. Upon entering, you're greeted by breathtaking views of the lushly landscaped backyard, complete with a sparkling pool and spa. The main level features a luxurious primary suite with picturesque views of the outdoor retreat. The primary bath is a sanctuary, offering dual sinks, a jacuzzi tub, a separate shower with dual showerheads, dual walk-in closets, and a private water closet. Adjacent to the suite is a dedicated home office, ideal for remote work or quiet study. Perfect for hosting, the spacious dining room is ready for memorable gatherings. The chef's kitchen is a true centerpiece, outfitted with custom Busby cabinetry, GE Monogram appliances, a 6-burner gas cooktop with dual ovens, and a cozy breakfast nook that overlooks the backyard. The kitchen opens seamlessly to the family room, creating a welcoming space for everyday living and entertaining. French doors from the family room, living room, and primary bedroom provide effortless access to the backyard. The outdoor space is a true escape, featuring a sparkling pool and spa, lush greenery, and a custom summer kitchen, perfect for enjoying time with family and friends. Upstairs, four generously sized bedrooms are paired with Jack-and-Jill bathrooms, each offering dual sinks and a shared tub or shower. A cozy loft area adds flexibility to the second floor. Above the 3-car garage, a spacious bonus room doubles as a theater or playroom, and is equipped with additional storage space. Lovingly maintained by its original owner, this pristine home combines elegance and convenience, with walkability to Phelps Park, the YMCA, Interlachen Country Club, and Park Avenue. It's a rare find in one of Winter Park's most desirable neighborhoods.

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