Winter Park FL Homes for Rent

Sort Results:
151–175 of 299 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 of 12    Prev | Next
Type:
Single Family
Sq.Ft.:
4,600
Status:
Active
Beds:
4
Lot size:
1.1 Acres
Year built:
1969
Baths:
5.00
MLS#:
O6251960
Subdivision:
Forest Hills

ADDITIONAL INFORMATION

Discover this exquisite lakefront property located in the heart of Winter Park! Nestled on over an acre with more than 125 feet of water frontage, this home offers breathtaking views and absolutely stunning sunsets. As you step through the front door, you’re greeted by captivating lake views that flow from front to back. The spacious foyer leads to a charming living room, complete with a brick wood-burning fireplace. This area seamlessly transitions into the Florida room, an entertainer’s paradise featuring a wet bar, seating area and pool table, with easy access to a full bathroom that is equipped with a steamer shower. Open the French doors to reveal a tranquil outdoor oasis, where mature landscaping ensures privacy for the heated spa, creating a resort-like atmosphere in your own backyard. The heart of the home is a state-of-the-art chef's kitchen, boasting a large island, oversized GE refrigerator, Thermador dual ovens, elegant custom cabinetry, granite countertops, and a cozy breakfast nook. The spacious formal dining and living rooms offer beautiful lake views and lead out to a tranquil front terrace. For those who work from home, a private office on the main floor with a lake view provides an ideal and serene workspace. The large family room is perfect for everyday gatherings and is conveniently located next to a half bath. Upstairs, the primary suite overlooks the lake and features a walk-in closet and ensuite bathroom with a standalone Jacuzzi tub and separate shower. Two additional bedrooms share a full bath, while a generous fourth bedroom serves as a secondary primary suite with its own ensuite and walk-in closet. The property includes a paver circular driveway leading to a side-entry two-car garage. Cross the brick paved road to a sprawling lakefront lawn, leading to a private boat dock with a lift, perfect for enjoying all the water activities. Located on Lake Sue, a private ski lake, this home is just minutes from Park Avenue's shopping and dining, Downtown Orlando, Baldwin Park, playgrounds, parks and excellent public schools. Don’t miss the opportunity to make this stunning lakefront home your own!

Type:
Single Family
Sq.Ft.:
2,762
Status:
Active
Beds:
4
Lot size:
0.31 Acres
Year built:
1960
Baths:
4.00
MLS#:
O6251187
Subdivision:
Timberlane Shores

ADDITIONAL INFORMATION

Welcome home to this beautiful home located in the highly desirable Timberlane Shores. Situated on almost 1/3 of an acre, this corner lot home has endless possibilities. The 4- bedroom, 3.5 bath home has over 2700 sq feet of living space, including separate guest quarters that consist of 2 bedrooms and 1 shared bath, perfect for extended family, teens, or simply to have privacy for guests. As you enter the home, you will notice the large open concept that includes both dining and living space. The gourmet kitchen features white quartz countertops, 42-inch espresso cabinets, stainless steel appliances, and a large island that can accommodate 3 barstools. The master bedroom has an ensuite bath with a large walk-in shower, marble tile and textured subway tile in a tub/shower combo. The secondary bedroom in the main part of the home functions as a second master bedroom and also has an ensuite bathroom. A very private and serene patio area from which to watch the birds and hear tranquil sounds of nature, can be found through the living room sliders. The home’s 2-car garage is spacious and offers a tremendous amount of storage. This unique home is surrounded by multi-million-dollar homes, so there is also the opportunity to tear this down and build a brand-new home on the lot. Close to downtown and Winter Park Village and Park Avenue is less than 2 miles away. Beautiful parks, walking/bike trail and dog park are within walking distance. You don’t want to miss this one!

Type:
Single Family
Sq.Ft.:
3,215
Status:
Active
Beds:
4
Lot size:
0.19 Acres
Year built:
2013
Baths:
4.00
MLS#:
O6252394
Subdivision:
Enclave At Aloma

ADDITIONAL INFORMATION

Move in Ready **Seller Financing Available**Motivated Seller** Conveniently located gated community. Spacious and Open Floor Plan. Private fenced back yard that backs to conservation. Lots of Upgrades, Crown Molding on entire 1st floor, flooring is engineered hardwood throughout including bedrooms, tile in the baths, carpet in the bonus room for sound control. Large kitchen with quartz countertops that opens into large family room, Formal Living and Dining, Den/Office, and Half Bath on first floor. The large bedrooms are on the second floor with a split plan. The Primary suite includes a spacious bath and walk in closet. Bedrooms 2 & 3 have an attached shared bath and include an activity desk in the hallway. The 4th bedroom is off the bonus area and adjoins the 3rd bath. Large Bonus Area upstairs too. See the Photos, 3D Virtual Walk through, and Floor Plans.

Type:
Condo
Sq.Ft.:
1,374
Status:
Active
Beds:
3
Lot size:
0.15 Acres
Year built:
1986
Baths:
3.00
MLS#:
O6251997
Subdivision:
Winter Park Pines Condo

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. **WATCH 3D TOUR and REAL Walkthrough VIDEO!** Welcome to this exquisite two-story villa-style condominium in Winter Park! Situated at 543 Warrenton Rd, this 3-bedroom, 3-bath home with a little less than 1,400 SqFt provides the perfect combination of comfort and convenience. Nestled in a serene neighborhood adorned with majestic, towering trees. NEW ROOF, mostly all NEW FLOORING. Upon entering, you will be welcomed by a spacious living area featuring a charming BRICK corner FIREPLACE and HIGH CEILINGS with 2 SKYLIGHT WINDOWS. The 1st FLOOR boasts a PRIMARY BEDROOM with an en-suite bathroom with a shower, complete with DUAL SINKS and a generous size closet. The kitchen is bright and airy, offering ample space for cooking and entertaining + a convenient BREAKFAST BAR. STAINLESS STEEL appliances and a large sliding door that lets the beautiful sunlight in. Step outside to enjoy the front private COURTYARD and fenced-in REAR PATIO , NO REAR NEIGHBORS. The washer and dryer are located in the 2nd bathroom on the 1st floor. The second and third bedrooms are located upstairs and share a 3rd bathroom with a TUB and shower combo. Additional amenities include a one-car garage with guest parking for added convenience. Conveniently located near all the essentials, including Publix/Walmart/Walgreens/Home Depot (5 minutes), Downtown Winter Park (10 minutes), Winter Park Golf Course (3 minutes), Full Sail University (1min), Baldwin Park (7 minutes), 408 and 417 highways (less than 10 minutes away), UCF (15mins) and Downtown Orlando (14 minutes). This unit is in pristine condition and ready for immediate occupancy. Please be aware that rentals are only allowed on a 10% max neighborhood capacity basis meaning there may be a wait list. At the moment the property must be occupied by the owner. Don't let this amazing opportunity pass you by!

Type:
Townhouse
Sq.Ft.:
1,755
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
2020
Baths:
3.00
MLS#:
O6251457
Subdivision:
Enclave At Hawks Crest

ADDITIONAL INFORMATION

Welcome to this beautifully updated 3-bedroom, 2.5-bathroom gem! Built in 2020 and located in highly sought after Hawks Crest, a private gated community, this home offers luxury, comfort and every modern convenience. This home has been taken from builder grade to custom upgrades though out! You'll enter through a bright and airy foyer and be greeted by a spacious living area adorned with crown molding and LED recessed lighting, creating an inviting atmosphere. The kitchen is a chef’s dream, equipped with brand new stainless steel appliances, including a Samsung oven with an air fryer, and a Samsung Bespoke dishwasher and microwave and LG refrigerator. Enjoy the added benefit of a reverse osmosis filtration system for clean drinking water right at your fingertips. Upstairs you will find the spacious primary bedroom with ensuite, two additional bedrooms and a hall bath. The expansive primary bedroom features an en-suite bathroom with new custom sliding shower doors and a separate private water closet for added privacy. CUSTOM CLOSETS THROUGHOUT THE HOME, along with tailored shelving in the laundry room and pantry, provide ample storage solutions! Step outside to the back patio, where you can take in the views of the serene nature conservation area with a cup of coffee to start the perfect day or a glass of wine to unwind. The extended driveway and garage storage rack hanging system add to the home’s practicality and maximizes space and organization. This gated community offers fantastic amenities, including a resort-style pool, playground, parks, and picnic areas, all with low monthly HOA fees (which include cable and internet). Perfectly situated just a 2-minute walk from the new Park Maitland Preschool and a 5-minute drive to Trinity Prep, one of Central Florida's premier private middle/high school. Also near the entrance of the community is Foxtail Coffee, Kelly’s Homemade Ice Cream, and Ravenous Pig restaurant. You will find this community is centrally located, as you are just 10 minutes from the thriving downtown Winter Park and easy access to all major highways. Don't miss your chance to own this immaculate home—schedule your showing today! ROOF - 2020, HVAC - 2020, PLUMBING - 2020, ELECTRIC - 2020

Type:
Condo
Sq.Ft.:
803
Status:
Active
Beds:
1
Lot size:
10.07 Acres
Year built:
1974
Baths:
1.00
MLS#:
S5114398
Subdivision:
Colonies

ADDITIONAL INFORMATION

Completely remodeled, come enjoy this amazing 1 bedroom 1 bathroom condo in winter park. Close to UCF, Full Sail University and centrally located to shopping malls, major highways, restaurants and theme parks. Just 11 minutes from Orlando international Airport. COMPLETELY REMODELED BRAND NEW A/C, NEW FLOORS, NEW BASEBOARDS, NEW VANITY, NEW TOILET, NEW PAINTING, NEW APPLIANCES, WASHER AND DRYER INCLUDED, NEW KITCHEN COUNTERTOP, NEW CABINETS. If you are looking for something affordable and a completely remodeled place to call home, this is it...or if you are looking to add a new apartment to your portfolio this apartment can be rented for $1450/ month. Make your appointment quick this apartment is ready to move in.

Type:
Condo
Sq.Ft.:
927
Status:
Active
Beds:
2
Lot size:
0.02 Acres
Year built:
1973
Baths:
2.00
MLS#:
O6251967
Subdivision:
Stratford A Winter Park Condo

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Introducing a charming 2-bedroom, 2-bathroom condominium for sale in the desirable Stratford at Winter Park community. This residence combines comfort and convenience, featuring a tiled foyer, kitchen, and bathrooms. The entire unit has been updated with new carpeting and fresh paint, creating a fresh and inviting atmosphere. The kitchen features white cabinetry, and there is additional dining space in a cozy breakfast nook. The expansive living room opens to a private balcony that provides stunning views of the beautifully landscaped interior courtyard and swimming pool. Both bedrooms boast large closets, with the master bedroom featuring an upgraded tiled shower in the ensuite bathroom. BRAND NEW A/C SYSTEM! UPGRADED ELECTRICAL PANEL! BRAND NEW CARPETING AND PAINT! Enjoy the convenience of included water service and recreational facilities, allowing you more time to savor the community amenities. The well-maintained Stratford community offers residents access to ample parking, two swimming pools, lighted tennis courts, a fitness room, a car wash area, and a clubhouse. Included in your HOA dues is water service; internet service with Spectrum; and a laundry with 2 washers and 2 dryers at no charge. This condo is ideally located just 5 minutes from the chic Park Avenue, close to downtown Winter Park, Rollins College, UCF, and Full Sail University. A variety of local eateries and stores are conveniently located just a short walk away. This property not only provides a comfortable living space but also offers a vibrant lifestyle in one of Winter Park’s most sought-after communities. Whether you’re a first-time homebuyer or looking to downsize, this condo presents a perfect opportunity to own a piece of Winter Park charm. Schedule your viewing today and come see why this should be your next home!

Type:
Single Family
Sq.Ft.:
1,760
Status:
Active
Beds:
3
Lot size:
0.23 Acres
Year built:
1953
Baths:
2.00
MLS#:
L4948316
Subdivision:
Northwood Terrace

ADDITIONAL INFORMATION

** MUST SEE! ** Lease and lease-to-own options with seller financing are available. Don’t miss this fantastic investment opportunity or put the final touches on this beautiful 3-bedroom, 2-bathroom home situated on a .23-acre corner lot. This property features an upgraded septic tank, fresh paint, a 2016 roof, new gutters, and fascia, making it a great choice for those looking to move in or enhance its value. With its prime location and recent upgrades, this home is ready for a personal touch. Act fast—opportunities like this don’t last long! Contact me for more details or to schedule a showing!

Type:
Condo
Sq.Ft.:
840
Status:
Active
Beds:
2
Lot size:
0.22 Acres
Year built:
1990
Baths:
2.00
MLS#:
W7869224
Subdivision:
Lancelot/winter Park

ADDITIONAL INFORMATION

Welcome to this beautifully updated 2 bedroom/ 2 bath  first floor condo.  This open floor plan has tiled flooring throughout the common areas, along with granite counter tops in the kitchen and bathrooms. The energy efficient AC is less than a year old (12/2023)!  Included appliances are: Washer, dryer, stove, microwave, dishwasher, and refrigerator are all less than 5 yrs old. The garbage disposal is also new.  The interior boasts thoughtful details like ceiling fans, window blinds and drapes. The building is newly painted 2024, with new roof 2023.  Included in HOA is  water, trash, outside maintenance and private pool.  This condo is conveniently located just minutes from top rated schools, Full Sail, UFC, great dining spots, and major highways.  Don't miss the opportunity to own this beautiful condo in a central location.

Type:
Condo
Sq.Ft.:
1,536
Status:
Active
Beds:
2
Year built:
1986
Baths:
3.00
MLS#:
O6249823
Subdivision:
Killarney Bay Condo

ADDITIONAL INFORMATION

Largest unit at Killarney Bay, set up as a town home -bedrooms upstairs town house with large screened in area back pooch, new washer and dryer - wood floors throughout, close to Winter Park Village - complex is a small great location with great access to I-4 - Killarney Bay sits on Lake Killarney with private pool overlooking. Only 5 rental units are allowed at KB at any given time. Super clean and ready for new owner. Beautiful wood ceilings in main living areas and wood floors and stairway! tastefully done. Current tenant has flexibility in moving.

Type:
Single Family
Sq.Ft.:
2,342
Status:
Active
Beds:
3
Lot size:
0.52 Acres
Year built:
1952
Baths:
2.00
MLS#:
O6250417
Subdivision:
Lords Sub

ADDITIONAL INFORMATION

Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.

Type:
Single Family
Sq.Ft.:
1,440
Status:
Active
Beds:
3
Lot size:
0.75 Acres
Year built:
1959
Baths:
2.00
MLS#:
O6249965
Subdivision:
Winter Park Manor

ADDITIONAL INFORMATION

Welcome to 2821 Chantilly Avenue Winter Park FL 32789! A unique opportunity to own this .75 acre lot and the ONLY home on Lake Vella. Classic 3/2 bungalow with lake views zoned for Dommerich, Maitland & Winter Park High. Large back yard offers room to expand, renovate existing home or build new. Great location just minutes to Park Avenue. Extras include: updated electric panel, 2017 AC, updated plumbing & 24x12 backyard shed. WELCOME HOME!

Type:
Single Family
Sq.Ft.:
1,898
Status:
Active
Beds:
3
Lot size:
0.14 Acres
Year built:
1950
Baths:
3.00
MLS#:
O6250649
Subdivision:
Carver Town

ADDITIONAL INFORMATION

Welcome to this stunning modern, custom-built home in the heart of Winter Park, FL! This beautifully remodeled 3-bedroom, 2.5-bath residence offers 1,898 sq ft of inviting living space. The home features an eat-in kitchen with custom bench seating, earthy wood-tone cabinets, a large waterfall island, and elegant countertops. Sleek black appliances perfectly complement the modern design. All bedrooms are located on the second floor, with the primary suite boasting cool contemporary lines, a walk-in shower, double sink vanity with quartz countertops, and plenty of natural light. The suite also includes a spacious walk-in closet, fully built-in for optimal organization. The home’s outdoor space is equally impressive, with gorgeous landscaping that enhances the fenced, private yard—perfect for entertaining guests or enjoying quiet moments with loved ones. The 1-car wide garage extends two cars deep, providing ample storage, while the paved driveway offers room to securely store a boat or RV behind the fence. With only two original block walls retained, the rest of the home is entirely new, including updated sewer pipes, plumbing, electrical systems, and a fully installed irrigation system. Located in an excellent A+ rated school district, this home is just minutes from Winter Park Hospital, Park Avenue, Rollins College, museums, galleries, shopping, restaurants, and major highways—everything you need is close by. Call today to schedule your private showing and make this dream home yours! Pool renderings are only showed as an illustration of what is possible and can be built for additional cost.

Type:
Single Family
Sq.Ft.:
5,072
Status:
Active
Beds:
5
Lot size:
0.33 Acres
Year built:
2008
Baths:
6.00
MLS#:
O6250411
Subdivision:
Maitland Shores First Add

ADDITIONAL INFORMATION

Gorgeous Winter Park home beautifully curated with designer details and recently featured in June’s “Orange Appeal” and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of Art. This elegant transitional French Provincial residence is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This designer home has been significantly enhanced inside and out by the current owner and is in “brand new condition.” The home features 5,100 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms, 1 half bathroom, 3 car garage, pool, patio, outdoor shower and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with lacquered walls and 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include new slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine new iron French doors, new ebony-stained oak hardwood floors, lacquered walls, newly renovated master bath and two ensuite baths. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School.

Type:
Condo
Sq.Ft.:
1,365
Status:
Active
Beds:
2
Lot size:
0.01 Acres
Year built:
1974
Baths:
2.00
MLS#:
S5114106
Subdivision:
Whisperwood Condo

ADDITIONAL INFORMATION

Stop Looking!!! Gorgeous and Fully updated two-bedroom, two-story condo with spacious fully fenced backyard! Yes, Condo with backyard and screened lanai in Highly desired Winter Park area. Zoned for top-rated schools and just minutes from UCF, Full Sail, and Downtown Orlando! Condo is a very well maintained condo. Kitchen updated with granite counter tops and stainless steel appliances. You will find additional dining space in the living/dining room combo! Step out back and enjoy the spacious screened lanai! The upstairs boasts two enormous bedrooms with nice closet space, a full bath with extended granite vanity, and extra linen storage in the hallway! Main bedroom features a screened-in BALCONY and Walk- in closet. Exterior features include an oversized carport with spacious storage unit.Great condo for owner occupant or investment property!

Type:
Single Family
Sq.Ft.:
1,078
Status:
Active
Beds:
3
Lot size:
0.24 Acres
Year built:
1924
Baths:
2.00
MLS#:
O6249839
Subdivision:
Suburban Homes

ADDITIONAL INFORMATION

Welcome to this adorable 3-bedroom, 2-bathroom cottage-style home, perfectly situated in a prime location with no HOA! Immaculate and move-in ready, this charming property features a cozy front porch that invites you to sit back and relax. Step inside to find bright, comfortable living spaces with easy-to-maintain laminate and tile flooring throughout. The kitchen offers a warm, inviting atmosphere with an eat-in space, perfect for casual dining. The home also boasts a large yard, providing plenty of room for outdoor activities. Located just minutes from Rollins College, UCF, and Full Sail University, this property is ideal for those seeking a great investment opportunity. Plus, Airbnb is allowed, making it an excellent choice for those looking to generate rental income. Don’t miss out on this fantastic home in a highly desirable area!

Type:
Single Family
Sq.Ft.:
3,399
Status:
Active
Beds:
4
Lot size:
0.24 Acres
Year built:
2022
Baths:
4.00
MLS#:
O6250342
Subdivision:
Winter Park Village

ADDITIONAL INFORMATION

This exquisite, custom-designed residence blends impeccable architectural details with unparalleled craftsmanship, in the highly sought Winter Park Village. With Pella windows and natural stone accents throughout, this home showcases a Poggenpohl gourmet kitchen featuring Wolf and Sub-Zero appliances, cascading countertops, and natural hardwood floors. A unique double primary suite layout offers two luxurious primary bedrooms, each with its own expansive executive powder room. The upper suite opens onto a private outdoor terrace, perfect for enjoying views of the lush outdoor oasis, which includes a heated luxury pool and spa, completed by an outdoor summer kitchen featuring Miele appliances. This home boasts two-story concrete-filled walls, steel joists, and composite steel decking, with a waterproof concrete roof. A stunning floating staircase leads to the second level, which includes the second primary suite with a spacious executive powder room, plus two additional bedrooms and an expansive custom walk-in closet. The interiors are bathed in natural light, compliments of the soaring 20' ceilings and an open, airy layout. Handcrafted luxury elements, including a bespoke entry door and Clopay modern garage doors, make a bold first impression. Additional highlights include elegant lighting, stunning automated window coverings, innovative hidden appliances, pristine landscaping and so much more. This masterpiece offers beauty and style with full functionality and the very best of everything. Just steps from the Vias, K-12 educational zoning all Winter Park. This part of the Village is in the process of transforming into an extension of Temple Road, and a great time to buy in to this luxurious community before the property values skyrocket. Truly photos and words do not begin to describe this Architectural Brilliance, come out and explore this gem where you will be greeted by Astro the Robot.

Type:
Single Family
Sq.Ft.:
2,717
Status:
Active
Beds:
4
Lot size:
0.24 Acres
Year built:
1995
Baths:
4.00
MLS#:
O6253346
Subdivision:
Lost Creek

ADDITIONAL INFORMATION

Welcome to your Winter Park dream home! This stunning 4-bedroom, 3.5-bathroom residence offers a spacious open floor plan, a gourmet kitchen with updated counters (2022), a luxurious master suite, and a backyard oasis perfect for entertaining. The outdoor living space features a private heated saltwater pool with a new screen enclosure (2022) and brand new pool equipment (pump, filter, chlorinator, and heater, all 2023). The outdoor kitchen boasts a Jenn-Air cooktop, a retractable screen dining area, and a separate half bath and outdoor shower. Recent upgrades include a new roof (2021), plumbing (2022), solar panels (2022), new downstairs carpet (2022), a vinyl privacy fence (2023), outdoor shed, and plantation shutters throughout. Situated on almost a quarter-acre corner lot in a beautiful, well-cared-for neighborhood with Seminole County Schools, this well-maintained home offers easy access to 417, is less than 20 minutes from the famous Park Avenue with some of the best shops and restaurants in the city, and 25 minutes from the airport. Schedule your showing today!

Type:
Single Family
Sq.Ft.:
1,940
Status:
Active
Beds:
4
Lot size:
0.16 Acres
Year built:
1952
Baths:
3.00
MLS#:
O6247628
Subdivision:
Carver Town First Add

ADDITIONAL INFORMATION

This stunning property in historic Winter Park offers an excellent price point and is ideally situated near Park Avenue’s shops and restaurants, Rollins College, Winter Park Village, Winter Park Farmer's Market, and Hannibal Square. Completely renovated in 2021, this 4 bedroom, 3 bathroom home has been thoughtfully appointed with double primary suites, each with ensuite bathrooms and large closets. Split from these primary suites are 2 additional ample sized bedrooms and a full bathroom. The open floor plan boasts contemporary updates throughout, including light wood-like tile floors, LED recessed lighting and fresh paint. The kitchen is a chef's dream, featuring quartz countertops, a designer tile backsplash, stainless steel appliances, and a 5-burner gas stove complete with a pot filler. The primary ensuite bathroom is a luxurious retreat, showcasing dual vanities, an oversized tiled shower with multiple shower heads, and a built-in bench. The bathrooms are bright and fresh with contemporary black and white tile accents. Enjoy an expansive back yard with a large paved patio, perfect for entertaining. This home can also serve as an excellent investment opportunity for your Rollins student! Schedule your private showing today! HVAC - 2017 ROOF - 2021

Type:
Single Family
Sq.Ft.:
1,301
Status:
Active
Beds:
3
Lot size:
0.13 Acres
Year built:
1991
Baths:
2.00
MLS#:
O6251052
Subdivision:
Bridgewater Ph 2

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. SOLAR PANELS WILL BE PAID OFF AT CLOSING!! Welcome to this move-in ready Winter Park pool home, tucked away in a peaceful cul-de-sac! This gem has been thoughtfully updated with significant renovations, including a composition shingle roof (2019), custom gutters with in-ground drain lines (2019), a Trane HVAC with hurricane slab foundation (2019), rebuilt pool pump and chamber (2019), and fresh landscaping with new sod (2019). Exterior updates include siding and paint (2021). This home features 3 bedrooms, 2 bathrooms, and a sparkling pool perfect for family relaxation and backyard BBQs. Step inside through the inviting screened front porch to an open floor plan with vaulted ceilings and abundant natural light. The living areas boast tile flooring throughout, leading to an open kitchen with a breakfast bar and freshly painted cabinets offering extra storage. Unwind in the spacious master suite with a private en-suite bath, featuring a tiled shower and updated vanity. Two additional generously sized bedrooms and a full bath with a tub/shower combo complete the interior. Enjoy ultimate privacy in the fully fenced backyard, beautifully landscaped and featuring an open-air pool—ideal for entertaining or peaceful relaxation. To top it off, the home is equipped with a solar panel system (2022). Located in the highly sought-after Lake Howell High School district, this home is conveniently close to Park Avenue, Rollins College, local dining, shopping, and the 417 Expressway. With a low HOA of just $15/month in a private and safe community, this property won’t be on the market for long. Schedule your showing today and submit your offers—don’t miss out on this beautiful home!

Type:
Condo
Sq.Ft.:
1,612
Status:
Active
Beds:
2
Lot size:
0.04 Acres
Year built:
1985
Baths:
2.00
MLS#:
O6247851
Subdivision:
Cedarwood Village 1

ADDITIONAL INFORMATION

A charming 2-bedroom, 2-bath condo with an upstairs loft, perfect as a 3rd bedroom or home office. The loft features two built-in desks, cabinets, and shelves for ample storage and functionality. Family-owned since pre-construction, this home includes thoughtful extras throughout. The living room and dining room are separated by a built-in divider with additional storage. The enclosed back patio offers built-in storage and a closet housing the water heater with additional storage space. While the condo could use a little sprucing up, it’s priced to allow you to customize it to your taste. Enjoy a low-maintenance lifestyle with lawn care included. Community amenities feature newly resurfaced tennis courts, a pool, a clubhouse, and great dog-walking areas. Located in a quiet, extremely well-maintained neighborhood with a highly-rated school district. The unit comes with two assigned parking spaces conveniently located in front. An ideal blend of comfort, convenience, and potential awaits!

Type:
Townhouse
Sq.Ft.:
2,265
Status:
Active
Beds:
3
Lot size:
0.04 Acres
Year built:
2018
Baths:
4.00
MLS#:
O6248828
Subdivision:
Mondrian/winter Park Twnhms

ADDITIONAL INFORMATION

Introducing an exceptional opportunity at The Mondrian Winter Park, a stunning waterfront community featuring 30 contemporary townhomes elegantly situated along the serene shores of Lake Killarney. This remarkable residence is truly a standout, showcasing top-tier finishes that exemplify both quality and value. As you enter, you'll be greeted by fresh interior paint and updated flooring that enhance the home's modern appeal. Enjoy the added comfort of privacy shades, stylish light fixtures, and ceiling fans that enhance the overall ambiance. The chef-inspired kitchen is a culinary dream, equipped with a natural gas cooktop and a wine refrigerator, perfect for entertaining. Retreat to the luxurious master suite, which offers a walk-in glass shower, a separate water closet, and ample closet space for all your storage needs. Your own personal oasis awaits on the expansive rooftop terrace, complete with a hot tub spa, grilling station, and generous lounge area, ideal for hosting gatherings or relaxing under the stars. With soaring 10'6" ceilings on the second level and expansive storefront-style windows, natural light floods the living space, creating a bright and inviting atmosphere. Each of the three spacious bedrooms comes with its own bath, ensuring privacy and comfort for family members or guests. Nestled in the heart of beautiful Winter Park, just north of downtown Orlando, this luxury enclave offers an unparalleled lifestyle. Experience breathtaking views of Lake Killarney from the newly constructed dock or unwind in the lakeside Pavilion as you watch the sunset. For those who enjoy water activities, a private boat slip is available for purchase, allowing you to cruise across the lake to visit Trader Joe’s or enjoy a meal at Shake Shack. Outdoor enthusiasts will appreciate the community’s kayak and paddleboard racks, providing easy access for fishing, exercising, or simply soaking in the tranquil waters. Nearby, Winter Park Village boasts a variety of shopping and fine dining options, while the vibrant Farmer’s Market and renowned Enzian Theater offer an array of local culture and entertainment. Discover the ultimate blend of luxury, comfort, and convenience at The Mondrian Winter Park—where every detail is meticulously crafted for your enjoyment and every moment holds the potential for adventure. Welcome to your new home.

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.26 Acres
Baths:
MLS#:
O6248801
Subdivision:
Garden Acres 2nd Rep Of Blk E

ADDITIONAL INFORMATION

Over a quarter acre of cleared land is ready for you to build your Winter Park dream home. Conveniently located near the Advent Health Hospital Orlando, other medical offices, Park Avenue for finding great shops and restaurants, and Downtown Orlando. Easy to drive to major roads (17-92/Mills Avenue, Colonial Drive, and I-4). Enjoy living in a great community in a fantastic location!

Type:
Condo
Sq.Ft.:
1,040
Status:
Active
Beds:
2
Lot size:
1.09 Acres
Year built:
1971
Baths:
2.00
MLS#:
O6248526
Subdivision:
Village Winterset Inc

ADDITIONAL INFORMATION

Price Improvement! Welcome to the luxury of Winter Park condo living, just steps from the world famous Park Avenue! You will be delighted to step into elegance in this charming first-floor condo with 9' ceilings in the highly sought-after Villages of Winterset Condominiums. Picture this – a simple stroll from your doorstep leads you to Park Avenue's enticing shopping and dining delights, the Morse Museum's cultural treasures, the vibrant energy of Rollins College, the refreshing greenery of the Winter Park Golf course, and the convenience of Sun Rail's commuter train. Immerse yourself in the charm of Central Park, where art festivals, concerts, movies, and events unfold right before your eyes. The Winterset mid-rise building offers key-secured access and a convenient call box for welcoming visitors. The lobby extends a warm welcome with a lounge area, perfect for unwinding or greeting your guests. Indulge in the pristine amenities of this well maintained community – a generously sized private pool, sun deck, and a grilling area designed for your leisure. Now, let's talk about this freshly painted gem of a corner unit – bathed in natural light and adorned with stunning travertine floors. The fully remodeled kitchen (2024) features granite countertops, new cabinets, all new stainless steel appliances and overlooks the spacious dining space. The open-concept dining into living room leads you to the open-entry sunroom that features energy-efficient impact-resistant sliding glass doors that overlooks a paved patio and lush greenery. Both of the bedrooms feature brand new carpet and beautiful plantation shutters that offer privacy and energy efficiency. The welcoming primary suite, boasts a walk-in closet and elegant make-up vanity with a large walk-in tile shower, big enough for two! The guest bath exudes charm with warm wood cabinetry and a tub/shower combo. Live the carefree lifestyle you've been dreaming of in this exclusive Winter Park haven, surrounded by multi-million dollar condos and homes. A property like this will not be available long. Call for your private showing today!

Type:
Condo
Sq.Ft.:
1,165
Status:
Active
Beds:
3
Lot size:
19.03 Acres
Year built:
1970
Baths:
2.00
MLS#:
O6248464
Subdivision:
Four Seasons Condo

ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. I’m excited to share an incredible opportunity that you won’t want to miss—a spacious 3-bedroom, 2-bath condo in Winter Park at a fantastic price. Imagine closing on your new home before the Holidays! This rare find comes with all appliances included, even the washer and dryer, making your move-in seamless. The community is packed with amenities, featuring three pools, tennis courts, laundry rooms, and a pet-friendly environment. Plus, the clubhouse has just been remodeled to include a brand-new fitness room for your convenience. Four Seasons was designed with you in mind—blending traditional charm with a warm community feel that truly feels like home. Inside the condo, you’ll be impressed by the large rooms and thoughtful details such as remodeled Bathrooms, new windows and sliding door wall, an abundance of closets and even a outdoor storage closet. This quiet first-floor unit boasts great views and a spacious floor plan that invites comfort. Located within the city limits of Winter Park often referred to as its best-kept secret—you’re just minutes away from downtown Orlando’s vibrant parks, entertainment options, fine dining experiences, and top-notch shopping. Educational institutions like Rollins College, Full Sail University, and UCF are also nearby. Enjoy casual conversations with neighbors by the pool or simply relax in the serene environment of beautiful Winter Park. With a low HOA fee of only $430 covering water, trash removal, sewer services, pest control, building insurance and more—this is an opportunity you can’t afford to overlook. Winter Park schools are highly regarded too: Brookshire Elementary School / Glenridge Middle School / Winter Park High School. Let’s make your dream of owning this wonderful condo come true!

Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 of 12    Prev | Next
151–175 of 299 properties displayed
Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2025, My Florida Regional MLS DBA Stellar MLS.



Winter Park Real Estate

The median home value in Winter Park, FL is $496,000. This is higher than the county median home value of $369,000. The national median home value is $338,100. The average price of homes sold in Winter Park, FL is $496,000. Approximately 59.56% of Winter Park homes are owned, compared to 29.54% rented, while 10.9% are vacant. Winter Park real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Winter Park real estate agent to arrange a tour today!

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 Real Estate Market Conditions

  • Median sales price

    $496,000
    25.3% change since last quarter
  • # Active listings

    299
    30-day change

Winter Park Schools and Demographics

Education near Winter Park, FL

Metric 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

School 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

School 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

School 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

School 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

Metric 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