32792 Homes For Sale in Winter Park, FL | Real Living Real Estate Solutions | Real Living Real Estate Solutions

Winter Park FL Real Estate & Homes for Sale

190 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!
Learn more about Winter Park Real Estate.


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Beds:
2
Baths:
3.00
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
View additional info

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!

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
View additional info

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!.

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:
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!

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
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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

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.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
View additional info

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
View additional info

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
View additional info

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!

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
View additional info

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
View additional info

**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
View additional info

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:
3
Baths:
2.00
Sq.Ft.:
1,409
Status:
NEW LISTING
MLS#:
O6289597
Type:
Single Family, Ranch
Subdivision:
WINTER PARK ESTATES
Lot size:
0.28 Acres
Year built:
1958
A broker reciprocity listing Courtesy: CENTURY 21 CARIOTI, 407-354-0074
View additional info

Welcome to this charming 3-bedroom, 2-bathroom single-story home, perfectly located in highly sought-after Winter Park. Situated on a beautiful corner lot, this property offers the ultimate in convenience and charm, with the added bonus of NO HOA! Ideal for first-time homebuyers or investors, this home boasts low-maintenance tile and laminate flooring throughout. The spacious living room is the heart of the home, featuring a cozy fireplace, a striking brick accent wall, and high ceilings that create an open and inviting atmosphere. The living area seamlessly flows into the dining room, which offers stunning views of the private backyard through glass sliders"perfect for indoor-outdoor living. The well-equipped kitchen includes all appliances, making it easy to move right in. Both bathrooms are beautifully designed with pedestal sinks and tiled surfaces for a sleek, clean look. The oversized 2-car side-entry garage is a standout feature, with high ceilings, a laundry room, and a dedicated workroom, offering plenty of storage and potential for projects. Conveniently located just minutes from Rollins College, Winter Park Pines Golf Course, Cady Way Trail, Downtown Winter Park and Park Avenue you'll be surrounded by parks, shops, restaurants, and venues. This home is also zoned for top-rated schools, making it an ideal choice for families. Additional highlights include brand-new garage doors and openers (2025), AC and Air Handler (2022) and Washer and Dryer are included. This home offers an incredible opportunity in one of Winter Park's most desirable locations"schedule your showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,020
Status:
Active
MLS#:
O6289538
Type:
Condo, Townhouse
Subdivision:
WINTER PARK WOODS CONDO
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: NEXTHOME DIVERSIFIED
View additional info

Auction Property. Online auction ENDS MARCH 24, 2025 at 11 AM EST on Federa. Discover this charming 2-bedroom, 2-bathroom condo offering a wonderful opportunity to reside in a desirable Orlando neighborhood. An auction deposit is required to bid, which will be applied to the sale price of the winning bid. Sold As-is. No showings. Explore more details and register for the auction through the Federa Home App.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,121
Status:
Active
MLS#:
S5122502
Type:
Single Family
Subdivision:
PELICAN BAY
Lot size:
0.57 Acres
Year built:
1984
A broker reciprocity listing Courtesy: TRANSCEND REALTY, 407-518-7653
View additional info

A True Gem on the Lake!If you've been dreaming of owning a lakefront property with a Winter Park address, this is your chance! This stunning 4-bedroom, 2.5-bathroom home in the tranquil Pelican Bay Subdivision is move-in ready and full of charm.As you approach, you'll be greeted by lush landscaping. Step through the double front doors into a welcoming foyer with beautiful wood floors and modern accents. An elegant oak staircase with iron rails leads you upstairs to three spacious bedrooms, a loft, a bathroom, and a private patio.The heart of the home lies downstairs, where you'll find a modern kitchen with upgraded appliances, granite countertops, and wood cabinets. A large island/breakfast bar overlooks the family room, where you can take in breathtaking lake views. Enjoy formal gatherings in the separate dining and living rooms, each offering plenty of space and comfort.The downstairs primary suite boasts serene lake views and features exquisite built-in cabinets, renovated master bath with dual sinks, a large glass-enclosed walk-in shower, and an expansive walk-in closet.The screened-in lanai is the perfect place to relax or entertain, with a jacuzzi, wet bar, and plenty of counter space. Whether it's morning coffee, afternoon relaxation, or evening sunsets, you'll love the view of the lake all day long. The dock is an ideal spot for fishing, relaxing, or simply enjoying the tranquil surroundings.Major renovations to the home were done in 2017 including mostly new new windows throughout, dock, all bathrooms and flooring. New roof installed in 2021.This home truly has it all. Don't miss out"schedule a tour today!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,598
Status:
Active
MLS#:
O6288234
Type:
Single Family
Subdivision:
CYPRESS RESERVE
Lot size:
0.21 Acres
Year built:
1998
A broker reciprocity listing Courtesy: LPT REALTY, LLC, 877-366-2213
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Your Dream Home Awaits!Imagine a home that blends luxury, comfort, & convenience that's exactly what you'll find at 5325 Cypress Reserve Pl in Winter Park's exclusive gated community Cypress Reserve.This move-in-ready 5-bedroom masterpiece isn't just a house it's a lifestyle upgrade. With a heated pool & spa, 3-car garage, newly installed roof, and spacious layout, this home offers everything you could want.From the moment you pull into the driveway, you'll notice the attention to detail. Pristine landscaping, fresh upgrades, newly installed sealed pavers, & a welcoming curb appeal that sets the tone for the beauty inside. - 5 spacious bedrooms - perfect for family, guests, or a home office.- Grand first-level primary suite - trey ceilings, fireplace, ensuite master bathroom, 2 closets, & private pool access.- 4 additional bedrooms, 2 full baths & a large loft upstairs - ideal for office, a game room or movie room.- Multi-purpose living spaces - formal dining & living rooms, great room, breakfast nook, & open-concept kitchen.- Main floor laundry room.- Chef's Kitchen for Culinary Creativity- Expansive countertops & ample cabinetry for plenty of prep & storage space.- Large island & breakfast bar to engage with family & guests while cooking.- Open layout overlooking the family room for seamless togetherness.- Whether hosting a dinner party or enjoying a quiet breakfast, this kitchen is the heart of the home.- Backyard Oasis - Your Private Resort- Heated, screened-in pool & spa enjoy year-round with solar heating & ambient lighting.- Lush landscaping & serene outdoor space ideal for unwinding after a long day. - Outdoor wet bar & dining area perfect for entertaining.- Two fireplaces + a heated pool Florida winters never looked better!-Float in the pool while streaming your favorite show, sip a cocktail as the sun sets, or take a nap in the shade"your backyard is a staycation destination.- Prime Location Convenience at your door step.- Easy Commute - Quick access to 417 & major roads for stress-free travel.- Shopping & Dining - Minutes from Park Avenue, Winter Park Village, & top restaurants.- Top Schools Nearby - Zoned for highly rated Seminole County Schools, plus UCF, Rollins, & Full Sail.- World-Class Healthcare - Close to Advent Health Winter Park & Orlando Health.- Outdoor Lifestyle - Steps from Cross Seminole Trail, ideal for biking & jogging.- Move-In Ready with Major Upgrades- 7/2020 Roof - Long-lasting durability.- Newer A/C Units 12/20- Efficient cooling for Florida summers. UV Lamp installed 12/23 on main floor unit.- Newer Driveway Pavers - Sealed & treated for long-term appeal.- Newer Solar Panels - Eco-friendly & heats the pool & spa.- Newer 80-Gallon Water Heater - Perfect for a busy household.- All new upstairs & master bedroom windows installed 4/23.- All new toilets with soft-close lids replaced 4/23.- New bathroom lighting.4/23- New powder room vanity and sink 4/23The Opportunity of a Lifetime!This home isn't just a place to live it's where you thrive. With its spacious layout, modern upgrades, and unbeatable location, 5325 Cypress Reserve Pl is an investment in your happiness and future.Schedule Your Private Showing Today! Homes in Cypress Reserve rarely become available"don't miss this one!

Beds:
4
Baths:
2.00
Sq.Ft.:
2,124
Status:
Active
MLS#:
O6288881
Type:
Single Family
Subdivision:
WRENWOOD HEIGHTS
Lot size:
0.21 Acres
Year built:
1972
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE REALTY, 407-977-7600
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Welcome to 4991 Tangerine Ave in the heart of Winter Park! This charming 4-bedroom, 2-bathroom home offers comfortable living with no carpet throughout"perfect for easy maintenance. The spacious family and dining room combination provides an open and inviting layout, ideal for gatherings. A large, air-conditioned Florida room adds even more flexibility, ensuring plenty of space for entertaining. The generously sized bedrooms offer comfort and versatility to fit your needs. Step outside to your beautiful backyard oasis, featuring a sparkling pool and additional yard space for relaxation or recreation. With no HOA and zoning for top-rated schools, this home is a rare find in a fantastic location. Don't miss this incredible opportunity!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,050
Status:
Active
MLS#:
O6289464
Type:
Single Family
Subdivision:
BROOKSHIRE HGTS 1ST ADD
Lot size:
0.2 Acres
Year built:
1959
A broker reciprocity listing Courtesy: HOME WISE REALTY GROUP, INC., 407-712-2000
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Great house in sought after neighborhood. The home is close to Brookshire Elementary, Winter Park High, Cady Way trail, Cady Way pool, and Showalter Home has an inviting front porch with swing, storm door with decorative front door, open floor concept for family room, dining room and kitchen. The screened in back porch overlooks a nice fenced in yard. This home won't last long.

Open House:

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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,867
Status:
Active
MLS#:
O6289177
Type:
Single Family
Subdivision:
GREENVIEW AT WINTER PINES
Lot size:
0.2 Acres
Year built:
1979
A broker reciprocity listing Courtesy: HOPKEY REALTY, 407-454-1217
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Experience luxury living in this stunning 3-bedroom, 2-bathroom pool home perfectly positioned on the 3rd hole of the golf course in Winter Park. Thoughtfully upgraded with designer details, this home blends elegance and comfort. A beautifully tiled walkway leads to an inviting interior featuring crown moldings, wood-look porcelain flooring, energy-efficient LED lighting, and stylish fixtures throughout. To the right, a versatile office/flex space with custom built-ins offers the potential for a 4th bedroom filled with natural light. The chef's dream kitchen boasts custom soft-close cabinets with pull-out shelves, stainless steel appliances, and a massive island with extra storage, perfect for entertaining. Flowing into the family room with built-in cabinetry, a wood-burning fireplace, and surround sound, this space seamlessly connects to the expansive patio and sparkling pool with waterfall, all protected by golf ball-resistant screens and windows. The living room features built-in cabinets for additional storage and functionality. French doors create a smooth indoor-outdoor transition, ideal for gatherings. The primary suite features an extra seating area, a large converted walk-in closet (originally the 4th bedroom), and an en-suite with warm-toned tile, a walk-in shower, and designer fixtures. The additional bedrooms offer ample space, new carpeting with a 25-year warranty, and generous closets. Spray foam insulation between the trusses enhances energy efficiency and comfort year-round. For peace of mind, the home includes exterior security cameras, fresh exterior paint, an expanded concrete driveway, and a new state-of-the-art water heater. Major updates include a roof (2013), AC (2017), and full repipe (2024). Located in an area with top-rated schools, this home is perfect for families. Conveniently across from Cady Way Trail and near the Golf & Country Club, which is owned by Winter Park and hosts community events, a restaurant, and a bar, this home offers easy access to downtown Winter Park and Baldwin Park's top restaurants, entertainment, and attractions. Don't miss this exceptional opportunity"schedule your private tour today!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,134
Status:
Active
MLS#:
O6288728
Type:
Single Family
Subdivision:
BROOKSHIRE HEIGHTS 3RD ADD
Lot size:
0.18 Acres
Year built:
1962
A broker reciprocity listing Courtesy: CORCORAN PREMIER REALTY, 407-965-1155
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A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040 sqft. Exuding luxury in a modern setting and with stunning curb appeal, this TURNKEY residence with high-end finishes features 3 bedrooms and 2 bathrooms. At the heart of the home is the expansive OPEN PLAN CONCEPT kitchen and living room with plenty of natural light which flows into the dining room area and large family room with sliding patio doors providing access to the tiled COVERED PATIO and sizeable backyard. The GOURMET KITCHEN is a chef's dream including brand new appliances, ample cabinetry, sprawling central island with countertop seating, quartz countertops and tile backsplash. There is a conveniently located laundry room which leads to the ATTACHED GARAGE with automatic door opener. The driveway also provides extra space for parking. The primary bedroom is a well-appointed, true retreat with views of the yard and has a large CUSTOM walk-in closet and in addition a secondary closet as well as an impressive ensuite bathroom consisting of separate vanities and a walk-in shower. Each of the other additional two bedrooms are well-proportioned with well sized closet spaces both served by a beautiful bathroom with vanity sink and large walk-in shower. OTHER HIGHLIGHTS TO NOTE are new windows and doors, new Carrier a/c, new tankless water heater, new electrical panel, new plumbing, new LED lighting throughout the home as well as new front yard landscaping. Seamlessly blending the outdoor with the indoor, enjoy Florida lifestyle at its finest. The huge backyard is a COMPLETELY FENCED IN PRIVATE OASIS and has plenty of room to add a dream pool should a future project be in your sights. LOCATION, location, location! NO HOA's! This property is only a couple of blocks away and zoned for top rated schools. Also conveniently located to a ton of amenities - nearby shopping centers, dining & entertainment options, Park Ave, Baldwin Park, Ward Park, the Cady Way Bike Path, Cady Way pool, sports such as Winter Park Pines Golf Club and close to Full Sail, UCF & Valencia colleges. Orlando International Airport and highways 417, 436, and I-4 for easy access to anywhere in the greater Orlando area. DON'T MISS OUT, see the 3D tour, video or schedule your private showing today!

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