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

Winter Park FL Real Estate & Homes for Sale

238 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.


1–25 of 238 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 of 10    Prev | Next
Beds:
3
Baths:
2.00
Sq.Ft.:
2,169
Status:
NEW LISTING
MLS#:
O6200234
Type:
Single Family
Subdivision:
TIMBERLANE SHORES
Lot size:
0.28 Acres
Year built:
1958
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Don't miss this charming and updated home, situated on an expansive 12,000-square-foot corner lot, in the highly sought-after Timberlane Shores neighborhood! Boasting an inviting open floor plan and starting with the living space offering stunning engineered wood floors, crown molding and a big window bay, that invites natural light to illuminate the space. The refreshed kitchen complete with a built-in breakfast nook, an abundance of white cabinetry with granite counters and stainless appliances, seamlessly flows into the family room, featuring an electric fireplace and cozy window seating with wonderful views of the spacious lanai entertainment space and the screened-in saltwater pool. The owner's retreat is a haven of tranquility with a lovely renewed en-suite bath and direct access to the pool, while the generously sized secondary bedrooms boast walk-in closets. A perfect laundry room offers plenty of additional storage & built in ironing center. Complementing the rest of the features of this special home is the convenience of the oversized two-car garage with workshop/hobby area. The curb appeal and exterior are enviable displaying a lush landscape with enchanting flowering gardens, recently re-sodded backyard & charming playhouse. Recent improvements include a new 2023 roof, new HVAC 2022, along with replaced windows, interior doors, and baseboards. The added bonus is the superior Winter Park Schools! With all these fabulous highlights combined, this home promises an exceptional living experience!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,085
Status:
NEW LISTING
MLS#:
O6200307
Type:
Condo, Townhouse
Subdivision:
WINTER PARK WOODS CONDOMINIUM ASSOCIATION, INC.
Lot size:
0.13 Acres
Year built:
1974
A broker reciprocity listing Courtesy: HEROES REAL ESTATE GROUP LLC, 407-947-6420
View additional info

This updated and super clean property would be perfect as an income generating investment property or resident for a student being that it's located near multiple universities, Full Sail University, Rollins College, Barry Law School, UCF, Stratford, and Keiser University. Nestled in a sought-after Winter Park area and school district. This residence has only had 1 renter since updated in 2020, with new toilets (2024), new A/C in (2020), floors, paint and counter tops (2020). New sliding glass doors and balconies just off the living room and master bedroom, both face a beautiful green space for you to create your own private oasis let's in lots of natural light too. This home has all the upgrades from vinyl plank floors throughout the main living space and tile in the bathrooms. There is a washer and dryer connection with extra storage just outside and off the main balcony. This community also has a lovely park with a nice playground, a pool and clubhouse. HOA also includes water, sewer and trash.

Open House:

Saturday, 5/11 11:30-1:30PM

Beds:
3
Baths:
3.00
Sq.Ft.:
3,217
Status:
NEW LISTING
MLS#:
O6202026
Type:
Single Family
Subdivision:
CLOISTER GROVE SUB
Lot size:
0.2 Acres
Year built:
1952
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295
View additional info

Nestled in the heart of The Vias, this Mediterranean Masterpiece encompasses 3,217 SF of beauty and elegance for your enjoyment of living. Dating back to 1953, this iconic home rests on a corner lot, offering captivating views of Lake Knowles. A stately entrance greets you with a large open living and dining space adorned with a beautiful gas fireplace and hardwood floors. Continue your journey through the first floor to find your incredible gourmet kitchen accompanied by custom cabinetry, Viking gas range, Marble backsplash, Quartz countertops, stainless steel appliances, a warming drawer, oversized walk-in pantry, and an abundance of natural light illuminating the space perfectly. The main floor features a guest suite, a full bathroom, a spacious laundry room, and an office that leads to the private backyard. The owner's suite beckons you with its grandeur and features French doors that lead to a large, covered balcony overlooking Lake Knowles and an ensuite bath boasting a glass-enclosed shower, dual vanities, two custom walk-in closets, and a clawfoot tub where you can soak and take in some of the best views Winter Park has to offer. A second private staircase leads to an additional guest ensuite, providing seclusion and luxurious living quarters for your family or guests. The enclosed backyard offers low-maintenance landscaping and also features a gas generator for additional peace of mind. Revel in the glorious views of the sunrise over Lake Knowles and enjoy being situated perfectly, just a short golf cart ride from Park Avenue shops and restaurants, the Winter Park Racquet Club, and walking distance to Kraft Azalea, Phelps Park, and the Winter Park YMCA. An exclusive respite, this home represents the epitome of Winter Park living at its finest.

Open House:

Saturday, 5/11 2:00-4:00PM

Beds:
4
Baths:
5.00
Sq.Ft.:
3,478
Status:
NEW LISTING
MLS#:
O6200787
Type:
Single Family
Subdivision:
DIXIE TERRACE
Lot size:
0.23 Acres
Year built:
2003
A broker reciprocity listing Courtesy: HOMEVEST REALTY, 407-897-5400
View additional info

Step into a world of unmatched luxury and meticulous detail in this stunning custom-built home located in the heart of Winter Park. This home spans two levels of exquisite living spaces designed for comfort and entertainment, featuring four bedrooms, three full bathrooms, two half bathrooms, and a large bonus room. As you enter, the grand foyer invites you into a voluminous layout, accented by Brazilian Cherry hardwood floors, extensive crown molding, and plantation shutters that add a touch of elegance to the 10-foot high ceilings. The formal living and dining rooms provide an impeccable setting for hosting, complemented by a gourmet kitchen that's sure to impress with its high-end stainless steel appliances, including a 48" gas stove, granite countertops, and an island with a built-in wine cooler, making it perfect for any culinary adventure. The family room, anchored by a cozy gas fireplace and French doors, opens to a lush tropical oasis with mature landscaping ensuring privacy with high hedging surrounding the property. Here, a screened pool and spa create a serene retreat with a pool bathroom and surround sound system for ultimate relaxation and entertainment. The ground floor primary suite is a true sanctuary, featuring two California Closets, a hand-painted tray ceiling, and direct outdoor access through beautiful French doors. The opulent en-suite bathroom offers a whirlpool tub, a separate shower with multiple shower heads, and a vanity mirror with a built-in TV for a spa-like experience. Upstairs, the additional bedrooms include a second primary suite with a dressing room and another bedroom with an en-suite bathroom. A spacious bonus room on this floor serves ideally as a game room or home theater, adding to the home's luxurious appeal. Located in a highly sought-after neighborhood and a prime location that provides easy access to top-rated schools, boutique shopping, fine dining, and cultural venues, making it a perfect blend of luxury living and convenience. This home is not just a residence but a statement of luxury, exclusivity, and a testament to the careful craftsmanship in one of Florida's most sought-after neighborhoods. Schedule your private showing today and enjoy the best of both worlds - a private haven and a splendid venue for entertaining guests. Welcome to your new home in Winter Park, designed for those who desire the very best in life.

Beds:
2
Baths:
2.00
Sq.Ft.:
840
Status:
NEW LISTING
MLS#:
O6202969
Type:
Condo, Townhouse
Subdivision:
LANCELOT/WINTER PARK
Lot size:
0.22 Acres
Year built:
1990
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY, 407-352-1040
View additional info

Newly remodeled 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with large windows brings in plenty of natural light. The main living areas boasts of wood laminate tile flooring and granite countertops in the kitchen. The bathrooms have been updated with sleek fixtures and modern design elements. Nearby, you will find top A-rated schools and several dining and shopping centers making this location very convenient for everything you need. There is also a community pool and the HOA includes trash, water, and the exterior maintenance of the property. Don't miss out on this great opportunity, schedule a viewing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,764
Status:
NEW LISTING
MLS#:
O6202560
Type:
Single Family
Subdivision:
KENILWORTH ESTATES 1ST ADD
Lot size:
0.26 Acres
Year built:
1960
A broker reciprocity listing Courtesy: EXPLORE FLORIDA REALTY SERVICES LLC, 407-982-9709
View additional info

Location! Location! Location! A short drive to Renown Rollin College, Park Ave and Advent Health Hospitals! Close to downtown Orlando, theme parks, Fullsail, UCF! Walking distance to Baldwin Park and Cody Trails. Enjoy signature food and drinks from Winter Park popular restaurants and bars! Enjoy family time at theme parks and Millenia Mall through easy and close access to I-4. Live like locals and move into your dream home today! As you walk in the main door, you will be amazed by its warm welcoming theme of modern floorings and wall colors. A spacious office room on the right and can be used as the third bedroom with a spacious floor plan. Sparkling modern pool in front of your eyesight as you open a clear glass double sliding door. A covered outdoor porch for you to relax and enjoy fresh drinks and snacks while enjoying ocean blue pool view. Spacious kitchen cabinet space for your cooking supplies. Luxurious kitchen cabinets and modern stainless top line Samsung appliances for preparing a delicious meal! While looking out kitchen window, you will be amazed by its garden and seaware-sounding yard scenery. Have you ever dreamt what your dream home should be? Here is: Brand-new double-pin windows, modern kitchen cabinets, luxury quartz countertop, classy light fixtures, luxury water-proof vinyl flooring, porcelain tiles, brand-new interior, and exterior paints, re-piped in 2022 and brand-new roof and gutters in 2023. Be ready to live in a move in-ready 4 bedrooms, 2 full bath, and breath-taking Winter Park Pool home, while enjoying all Florida sunshine and outdoor biking, jogging, and golfing at Winter Park Pine. Come to see your dream home today!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,160
Status:
NEW LISTING
MLS#:
S5104475
Type:
Single Family
Subdivision:
TANGLEWOOD SEC 3 REP
Lot size:
0.24 Acres
Year built:
1957
A broker reciprocity listing Courtesy: LA ROSA REALTY KISSIMMEE, 407-930-3530
View additional info

Discover the perfect gem in Winter Park with no HOA or CDD fees! This fully remodeled home is conveniently located minutes from downtown Winter Park, top-rated restaurants, shopping centers, Rollins College, and the SunRail. It features beautiful, bright porcelain tiles throughout, a newly updated kitchen, and freshly painted walls. The property boasts three bedrooms, a large backyard, a closed garage, and abundant natural light, ideal for entertaining and enjoying time with friends and family. Additionally, there are two backyard sheds, perfect for storage; one includes a bio-toilet. Recent upgrades include a new electrical panel and air conditioning system in 2022, and the plumbing was completely redone in 2023. The home also features a gas water heater and up-to-date termite treatment around the house. For those with an RV, there is a parking space and an electrical hookup. The property is fully fenced, offering privacy and security. Explore the endless possibilities with this stunning home. Call today to schedule your private tour. This could be your dream home! (Some pictures are one year old)

Beds:
2
Baths:
1.00
Sq.Ft.:
851
Status:
NEW LISTING
MLS#:
O6202273
Type:
Condo, Townhouse
Subdivision:
LAKESIDE MANOR APTS CONDO
Lot size:
0.1 Acres
Year built:
1969
A broker reciprocity listing Courtesy: SAND DOLLAR REALTY GROUP INC, 407-389-7318
View additional info

A HIDDEN GEM. Relax in the park-like central courtyard or poolside on the lake. Close and easy access to I-4. This 2 bedroom, 1 bath condo is a first-floor end unit in a lovely community located on Lake Killarney. It has newer Pella Energy-Efficient windows which provide sound reduction and lower electric bill. The bathroom has been renovated to include a walk-in shower. Plumbing was replaced in 2018. The kitchen has newer refrigerator, cabinets, countertops & backsplash. A well-maintained Laundry room is just steps away. Minutes from Winter Park Village, Trader Joes, Park Avenue and Rollins College. This is a NO PETS community and has rental restrictions. No rentals for the first 2 years, Primary residents only for the first 2 years, then minimum 1-year rentals. HOA application fee, transfer fee.

Beds:
5
Baths:
6.00
Sq.Ft.:
3,731
Status:
NEW LISTING
MLS#:
O6202078
Type:
Single Family
Subdivision:
ORANGE GROVE SUB
Lot size:
0.22 Acres
Year built:
2024
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK, 407-545-6430
View additional info

Pre-Construction. To be built. Discover the epitome of luxury and wellness with this breathtaking new construction home designed by Urban Perch and nestled in the heart of Winter Park, one of Central Florida's most coveted neighborhoods. 1791 Taylor Avenue is available pre-construction and features a spacious 3,731 square foot layout with four bedrooms, six bathrooms, and a versatile study (with walk-in closet), that can easily serve as a fifth bedroom or home office.The home's striking facade sets a stunning precedent for its interior, where elegance meets exceptional design. Inside, you'll find a state-of-the-art kitchen boasting Monogram appliances, sleek cabinetry and custom paneling, and dramatic quartzite countertops. This chef's paradise is perfect for entertaining, seamlessly connecting to an expansive living area highlighted by a minimalist fireplace and abundant natural light.Each bedroom is thoughtfully designed to offer maximum comfort and privacy, accompanied by modern bathrooms that resemble a spa retreat. The primary suite indulges with a lavish bathroom, featuring dual vanities, a large soaking tub, and a luxurious walk-in shower.Step outside to your private backyard oasis, complete with a pristine swimming pool and thoughtfully designed outdoor kitchen. The outdoor space is designed to be a serene retreat, promoting a healthy and relaxed lifestyle.Living in Winter Park means enjoying a high walkability score with proximity to an array of top-rated restaurants, boutiques, and cultural attractions. The neighborhood is renowned for its charming atmosphere and community spirit, making it an ideal place for those seeking a balance of tranquility and city conveniences.This home is not just a residence but a statement of luxury and wellness, designed to enhance your lifestyle with every detail thoughtfully planned out. Prepare to be captivated by its beauty and functionality"a truly exquisite property waiting to be called home. View detailed design and inspiration deck at https://urbanperchhomes.com/1791-taylor-avenue-winter-park-fl-32789-custom-home/

Beds:
4
Baths:
4.00
Sq.Ft.:
2,902
Status:
NEW LISTING
MLS#:
O6201350
Type:
Single Family
Subdivision:
CYPRESS RESERVE
Lot size:
0.33 Acres
Year built:
1997
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY, 407-695-2066
View additional info

This is your perfect opportunity to live in the Established, Beautifully Manicured Gated community of Cypress Reserve in Winter Park! When you drive up to the home, notice the Beautiful canopy of trees. This home boasts a 3-way split floorplan with 4 Bedrooms and 2 baths downstairs, half bath in the pool area and a Loft which be used as another bedroom with a closet AND it's own Full Bath upstairs, not to mention the gorgeous pool and patio area! When you walk in the front door, your gaze takes you up to the Cathedral High Ceilings and then the Spacious 21' x 17' Family Room with a Fireplace. 2018 Roof and 2021 HVAC! The seller is the original owner and has taken great care of this home. This home is ready for you to make it your own! It is conveniently located to SR 417, lots of restaurants and shopping! Please schedule your appointment today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,289
Status:
NEW LISTING
MLS#:
O6202180
Type:
Single Family
Subdivision:
WINTER PARK PINES
Lot size:
0.21 Acres
Year built:
1968
A broker reciprocity listing Courtesy: LEERDAM PROPERTIES INC., 407-740-0993
View additional info

Nestled in the heart of a vibrant community, this charming residence offers the perfect blend of comfort, style, and convenience. Step inside and discover a haven of modern living, where every detail has been meticulously crafted to create an inviting atmosphere.From the moment you enter, you're greeted by airy, light-filled spaces ideal for relaxation and entertaining. The open floor plan seamlessly connects the living, dining, and kitchen areas, providing ample room for gatherings with family and friends.The Kitchen is the heart of the home, the kitchen is a chef's delight, featuring sleek countertops, stainless steel appliances, and plenty of storage space. Whether you're whipping up a quick meal or preparing a feast, this kitchen has everything you need to unleash your culinary creativity.Pamper yourself in the luxurious bathrooms, complete with elegant fixtures, modern finishes, and spa-like amenities. Indulge in a soothing soak in the bathtub or refresh in the spacious walk-in shower - the choice is yours.Step outside and discover your own private oasis, where lush landscaping and mature trees create a peaceful setting for outdoor enjoyment. Whether you're hosting a barbecue on the patio or simply relaxing in the sunshine, the backyard is the perfect place to unwind and recharge.The home is conveniently located in Winter Park Pine, this home offers easy access to everything you need for a fulfilling lifestyle. Whether you're commuting to work, exploring the local shops and restaurants, or simply enjoying a leisurely stroll through the neighborhood, you'll love the convenience of this prime location.Don't miss your chance to make this stunning property your own - schedule a showing today and experience the epitome of modern living at 754 Gilbert Rd.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,361
Status:
NEW LISTING
MLS#:
O6201554
Type:
Single Family
Subdivision:
CHARMONT
Lot size:
0.22 Acres
Year built:
2007
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295
View additional info

Step into timeless elegance and modern luxury with this meticulously renovated Mediterranean-style home nestled in the historic charm of Winter Park. As you enter through the inviting blue, iron-detailed door, you're greeted by the artisanal beauty of Moroccan Zellige hand-painted tiles, guiding you into the sunlit dining room adorned with a custom Moroccan arch and vintage crystal chandelier. Entertain easily with the adjacent butler pantry, boasting bespoke cabinetry, marble counters, and a dual-zone wine fridge, all seamlessly blending sophistication and functionality. The heart of the home lies in the open-concept kitchen/living area, where high-end Thermador appliances, including a 60-inch dual fuel range, elevate culinary experiences. Walnut countertops and polished nickel fixtures complement white shaker cabinets, while a breakfast banquette offers a cozy spot for casual dining or gathering with loved ones. Retreat to the master wing, where plush carpeting and crown molding set a serene tone. A cerulean-blue door beckons you into the master bathroom oasis, featuring herringbone-laid porcelain tile, marble countertops, and a spa-like shower and luxurious bathtub. A custom-built closet system with an impeccable display case ensures organization meets elegance. The first-floor office exudes warmth with classic wooden beams and French doors, while the adjacent powder room delights with hand-painted Moroccan Zellige flooring and Schumacher wallpaper. Upstairs, three spacious secondary bedrooms each boast ensuite full bathrooms and exquisite wood floors, providing comfort and privacy for family or guests. Outside, the lush turfed yard invites al fresco dining amidst fragrant blooms of hydrangeas, crepe myrtles, camellias, and jasmine, creating a private oasis for relaxation. Embrace the coveted Winter Park lifestyle with convenient access to the Baldwin Fitness Trail, Lake Sue, local shops, and coffee spots, all while basking in the tranquility of this idyllic neighborhood. Discover the perfect blend of historic charm and modern luxury in this exquisite home"a true sanctuary in the heart of Winter Park.

Open House:

Saturday, 5/11 11:00-2:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
987
Status:
NEW LISTING
MLS#:
G5081725
Type:
Single Family
Subdivision:
STANSBURY ESTATES
Lot size:
0.15 Acres
Year built:
1956
A broker reciprocity listing Courtesy: REAL BROKER, LLC, 407.279.0038
View additional info

Welcome to your dream home in the heart of Winter Park! This charming bungalow has been fully renovated and completed upgraded from top to bottom, blending modern amenities with classic charm. Located between College Park and Winter Park, this home offers convenience, comfort, and style. The master suite has a walk-in closet and luxurious en-suite bathroom with a walk-in shower. The brand new kitchen includes granite countertops, stainless steel appliances, and custom cabinetry. There are 2 additional bedrooms along with a fully updated guest bathroom. Also included is the all-new paver driveway providing ample parking space, and a freshly custom-built fence that aesthetically pleases the eye, while ensuring privacy, security, and charm. Last but not least the custom-built pergola out in the front of the home is the finishing touch for the entire ensemble. Please present highest and best offers to listing agents email. There were already offers on the home prior to it hitting the market! OPEN HOUSE SATURDAY 5/11 11a-2p!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,362
Status:
NEW LISTING
MLS#:
O6201572
Type:
Single Family
Subdivision:
BEL AIRE PINES
Lot size:
0.18 Acres
Year built:
1983
A broker reciprocity listing Courtesy: REDFIN CORPORATION, 407-708-9747
View additional info

Welcome to your newly updated Winter Park sanctuary! This meticulously maintained home is truly turnkey, offering a seamless transition for its fortunate new owners. As you step inside, you're greeted by a beautifully landscaped exterior and a spacious layout filled with impressive upgrades.Environmental consciousness meets practicality with the recent addition of a NEW HVAC, NEW GUTTERS, DRAINAGE SYSTEM, SOLAR PANELS, and GARAGE INSULATION. UPGRADED ELECTRICAL PANEL, TANKLESS WATER HEATER and UTILITY SINK have all been added for convenience and peace of mind. Not only does this enhance the home's eco-friendliness, but it also promises long-term cost savings.Inside, the split floor plan ensures privacy and comfort for all. The versatile sunroom at the rear of the home invites creativity, serving as a flexible space for living, dining, working, or unwinding.Step into your private backyard retreat, boasting a beautiful saltwater pool"a refreshing oasis for hot summer days. The expansive deck provides an ideal setting for weekend gatherings, whether it's for BBQs or realizing your outdoor kitchen dreams.Every detail has been meticulously attended to, from the mature landscaping to the ample storage for lawn and garden essentials. Inside, the upgrades continue, including luxurious engineered wood flooring throughout and a top-of-the-line R.O. Water Treatment System. Upgraded bathrooms and kitchen, along with new lighting fixtures, showcase the home's modern elegance.Conveniently located just minutes away from UCF, Full Sail University, Park Ave boutiques, downtown Orlando, and the Orlando International Airport, this home offers both indulgence and convenience. With an optional HOA fee of just $40/year and easy access to major highways, including 408, 417, and I-4, this Winter Park gem is sure to attract eager buyers. Don't miss out on the opportunity to make this stunning pool home your own!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,214
Status:
NEW LISTING
MLS#:
O6201966
Type:
Condo, Townhouse
Subdivision:
KILLARNEY BAY CONDO
Lot size:
0.13 Acres
Year built:
1986
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Welcome to lakefront living at its best! This lovely direct lakefront condominium is nestled on the shores of Lake Killarney with breathtaking views from almost every room. This unit was the original model featuring 2 bedrooms, 2.5 baths, Cathedral ceilings throughout, crown molding and a spacious screened in balcony overlooking the lake. The balcony is the perfect spot to enjoy your morning coffee or a cocktail in the evening while watching all that nature has to offer. The floor plan has a nice open feel with a generous great room for living/dining and showcases a lovely wood burning fireplace. The kitchen is so spacious featuring granite countertops, stainless steel appliances, wood cabinets, breakfast nook and two openings so you can enjoy the view while cooking. The generous primary bedroom has incredible lake views, two closets, a door to the balcony and a spacious bathroom with a large updated shower and dual sinks. There is also a full attic with easy access where you can store all your holiday dcor. The secondary bedroom is an en suite featuring a spacious vanity and tub. Enjoy the convenience of an indoor laundry closet with room for a full-size washer and dryer, and a beautiful powder bath is located just off the living room. Many recent updates include; all new luxury vinyl flooring, all new hardware, designer lighting and mirrors, entire interior painted, ceiling fans and new dishwasher. HVAC (2018) and Water Heater (2019). Killarney Bay is tucked away off the beaten path; however, it is one of the most walkable locations in the area being only one block from the newly updated Winter Park Village with all its wonderful shops and restaurants, and many more restaurants and shopping along N. Orlando Ave, including Publix and Trader Joe's. Do not miss this opportunity to live in this beautiful waterfront community featuring a community dock and pool along the lake. There are only a handful of lakefront units and they do not come up very often.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,331
Status:
NEW LISTING
MLS#:
O6200958
Type:
Condo, Townhouse
Subdivision:
WINDWARD SQUARE SEC 1
Lot size:
0.08 Acres
Year built:
1976
A broker reciprocity listing Courtesy: METROPOLIS R.E. SOLUTIONS, LLC, 407-282-1600
View additional info

Introducing Windward Square and Winter Park living under $300k! This meticulously updated townhome offers modern living at an affordable price. With a NEW ROOF installed in 2022 AND NEW HVAC , this turnkey property ensures peace of mind. Enjoy privacy with a charming front porch and fenced backyard, perfect for relaxation or entertaining. The spacious primary bedroom features a fireplace, walk-in closet, and en-suite bathroom, while the additional bedrooms offer ample space. Plant enthusiasts will appreciate the private atrium, adding a touch of greenery to the home. Complete with a shed in the backyard, this cozy abode has everything you need. With HOA fees under $100 per month, residents have access to a community pool just steps away. Situated in a prime location close to Winter Park's finest amenities, this home is a must-see!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,422
Status:
NEW LISTING
MLS#:
O6198477
Type:
Single Family
Subdivision:
WRENWOOD UNIT 3 3RD ADD
Lot size:
0.19 Acres
Year built:
1980
A broker reciprocity listing Courtesy: THE REAL ESTATE COLLECTION LLC, 407-656-7814
View additional info

Welcome to your beautiful Winter Park retreat with NO HOA!This fully renovated residence offers 3 bedrooms, 2 bathrooms, a 2-car garage, and comes complete with a newly screened back patio and an expansive backyard.Every aspect of this home has been meticulously remodeled. The home features freshly painted interior and exterior and beautiful new flooring throughout. Essential components like the HVAC, Roof, and Windows have been replaced, ensuring peace of mind for the new owner.The heart of the home lies in its newly designed open-plan kitchen, creating an inviting atmosphere with new cabinets, beautiful butcher block countertops, and an added island providing extra storage. Ample space adjacent to the kitchen allows for a sizable dining area, perfect for gatherings. As you continue to the spacious great room you are greeted by a beautiful stone fireplace and wood mantel, creating a cozy place for relaxing. New lighting fixtures illuminate the space throughout, complemented by freshly done ceilings. Step outside to relax on the newly painted back patio, surrounded by freshly landscaped grounds in front and back.With close proximity to restaurants, retail, and a short drive to the vibrant Park Avenue, residents have easy access to a variety of shopping and dining options. Additionally, the convenient distance to Trinity Prep and the nearby Cross Seminole Trail offers opportunities for education and outdoor activities. With its modern updates and attention to detail, this Winter Park home presents an exceptional opportunity for those seeking a high-quality and well-maintained living space in a desirable location.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,726
Status:
NEW LISTING
MLS#:
O6200647
Type:
Single Family
Subdivision:
BENNINGTON
Lot size:
0.2 Acres
Year built:
2002
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY, 407-696-8000
View additional info

WOW FACTOR!!! Absolutely stunning POOL home and rare find in Winter Park FL with 3 car garage under 650K. Welcome to your 4 bedrooms 2 bathrooms home with 3 car garage oasis. This showstopper features a Resort style backyard with a screened in pool, built-in bar & kitchen! Every corner of this home has been meticulously maintained and oozes elegance. Stunning features include beautiful luxury plank flooring softly flowing throughout the house and a gorgeous NEW KItchen with extended Quartz countertops, waterfall edge and full backsplash, built-in oven, and cooktop with a POT FILLER for the home chef! The Shaker style kitchen cabinetry offers a ton of storage and a sleek look, along with a cozy Bar area and stackable full sized washer and dryer. The comfortable home floor plan features a three-way split, ideal for everyone. The owners used the front bedroom as a dining room, so the door frame has been widened. The patio slider was upgraded for noise reduction and energy savings. The unreal BACKYARD paradise will absolutely blow you away!!!! A custom pool with a waterfall and fountain is just a few years old and features color changing lighting, built-in-speakers in the ceiling, the roof and gutters are only 3 years old, and the pool enclosure was expanded last year with brand new pavers. The perimeter of the home has pavers added as well for optimal entertaining space. The exterior of the home was painted last year with premium Sherwin Williams paint. Owners replaced the front sod in 2023 and the property has a functioning irrigation system with numerous zones for front and back, not to mention is fully fenced in for pet lovers! Exceptional neighborhood with low HOA. Come and see this beautiful home before it's gone!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,350
Status:
NEW LISTING
MLS#:
O6202067
Type:
Single Family
Subdivision:
WINTER PARK ESTATES
Lot size:
0.21 Acres
Year built:
1958
A broker reciprocity listing Courtesy: LPT REALTY, 877-366-2213
View additional info

Location! Location! Location! Here is your perfect chance to buy a home in Winter Park for under $375k! As well as being in Winter Park, this home backs up to a city easement which further backs up to the wooded area of the private Interlachen Country Club Golf course. NO REAR NEIGHBORS and optional HOA! With a little TLC, this 3 bedroom, 1.5 bath home provides endless opportunities. This approximately 1350 sq ft rancher sitting on a generous 0.2 acre lot with mature landscaping, is just the retreat you've been looking for! Winter Park offers serene parks, picturesque walking trails, and lush greenery right at your doorstep, you'll feel a world away while still being just moments from all the amenities and attractions the area has to offer. Downtown Park Ave is just mins away, as well as access to the highways. Whether you're enjoying a leisurely stroll through the neighborhood or unwinding in your own private backyard oasis, you'll love coming home to this peaceful paradise.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,028
Status:
NEW LISTING
MLS#:
O6200815
Type:
Single Family
Subdivision:
FREMAR
Lot size:
0.21 Acres
Year built:
2006
A broker reciprocity listing Courtesy: EXP REALTY LLC, 888-883-8509
View additional info

Step into a realm of timeless elegance and modern luxury with this custom-built Mediterranean-style estate in the heart of Winter Park. From the moment you enter, a grand foyer welcomes you with Turkish Travertine stone and wood floors, setting the tone for the exquisite craftsmanship and attention to detail that defines every corner of this home. The soaring 12-foot ceilings adorned with intricate molding create a sense of grandeur, while the spacious open floor plan bathes the interiors in natural light. Delight in the seamless integration of technology and comfort, with an intercom system, built-in speakers throughout, and electronic blackout curtains for effortless ambiance control. Indulge your senses in the culinary haven of the gourmet kitchen, boasting state-of-the-art stainless steel appliances, white cabinets, granite countertops, and a Butler's pantry with a wine refrigerator and bar area. The kitchen flows seamlessly into the family room, where a wood-burning fireplace with a gas starter invites cozy gatherings. The master bedroom suite is a sanctuary of luxury, featured in Florida Home Magazine for its custom-designed bath. Enjoy backlit floor-to-ceiling mirrors, a floating tub, a self-cleaning smart toilet with a bidet, a custom Barclay tub with a black matte exterior, Brizo hardware finished in Brilliance Polished Gold, and bathroom floor tiled in an oversized chevron pattern by Crossville in Ice White. The black and white penny round tiled shower floor is laid in a throwback diamond pattern, complemented by a Kuzco LED chandelier. Entertain in style with outdoor amenities that rival a five-star resort. Lounge by the heated saltwater pool and spa, practice your putting skills on the mini-golf green, or retreat to the Nikki Beach cabana for a moment of relaxation. The summer kitchen with a tongue and groove wood ceiling is perfect for al fresco dining, while the outdoor shower adds a touch of indulgence. Every detail has been carefully curated to enhance your lifestyle, from the custom-built closet systems to the self-cleaning smart toilet with a bidet. Enjoy the convenience of a surveillance system, electronic private gated access, and a Mosquito NIX misting system for outdoor comfort. Escape to your tropical oasis with this highly energy-efficient natural gas home equipped with Velux solar-powered skylights with an acoustic rain sensor that automatically closes the skylight at the first sign of rain. The average utility bill is $560 a month. The property also features premium artificial grass and a premium landscaping and lighting package throughout the entire property. Enjoy the serenity of no rear neighbors and indulge in the luxury of your private retreat. This Winter Park estate is not just a home; it's a masterpiece of design and functionality, offering a lifestyle of unparalleled luxury. Don't miss your chance to experience the epitome of gracious living in one of Florida's most coveted neighborhoods.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,812
Status:
NEW LISTING
MLS#:
O6199613
Type:
Single Family
Subdivision:
KILLARNEY CIRCLE
Lot size:
0.22 Acres
Year built:
2001
A broker reciprocity listing Courtesy: SOTERA LIVING, 407-725-9660
View additional info

FEATURED ON HOUSE HUNTERS LAKEFRONT EDITION! Indulge in the epitome of LAKEFRONT luxury living on the shores of stunning Lake Killarney. Nestled within the vibrant heart of Winter Park, this exceptional residence offers a serene retreat on the largest private lake in Winter Park. Lake Killarney, a cherished gem, spans 259 acres of pristine, ski-able waters, ensuring exclusive tranquility for residents, with no access for non-residents. Convenience meets sophistication with this prime location, mere minutes from premier amenities including Whole Foods, Trader Joe's, REI, and the charming boutiques of Park Avenue Winter Park. Downtown Orlando, Maitland, Lake Mary, and the upscale shopping paradise of the Mall at Millenia are all within effortless reach, promising a lifestyle of unparalleled convenience. Step inside this bespoke custom home and be captivated by its distinctive features. With 10-foot ceilings, designer finishes throughout, and a meticulously crafted kitchen and baths, every detail exudes elegance. Boasting 3 bedrooms and a versatile loft that can easily transition into a fourth bedroom, along with 2.5 baths, this residence caters to every need. Embrace outdoor bliss with a dark bottom swimming pool, a private BOAT DOCK complete with a cradle, and lifts for both jet skis and paddle boards, ensuring effortless access to the water. Lavish low maintenance backyard landscaping with luxury turf surrounds the pool & lake, creating a picturesque oasis for relaxation and entertainment. Additional highlights include an upstairs balcony offering panoramic lake views, a secluded private courtyard, a spacious 2-car garage, and deluxe amenities such as a wine cooler, mini-fridge, and wet bar in the master suite. Granite and marble adorn the countertops and showers, while an oversized tub in the master bath provides the ultimate in indulgence. With an unrivalled level of craftsmanship and attention to detail, this home offers a lifestyle of unparalleled luxury. The value of this exquisite property surpasses its asking price, making it a wise investment in a rapidly appreciating area. Envision a life spent lounging by the pool, paddle boarding on the lake, or cruising to Hillstone for a waterfront dining experience. Create lasting memories with family and friends in your own slice of paradise at 580 Ololu Drive. Experience the epitome of lakeside living and make this dream home yours today.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,582
Status:
NEW LISTING
MLS#:
O6200824
Type:
Single Family
Subdivision:
TANGLEWOOD SEC 3 REP
Lot size:
0.21 Acres
Year built:
1956
A broker reciprocity listing Courtesy: BHHS FLORIDA REALTY, 407-876-2090
View additional info

Welcome to 1852 Maywood Road, a charming 4 bedroom 2 bathroom home, just under 1,600 SqFt, nestled in Winter Park! Featuring a NEWER ROOF (2021), NEWER A/C (2021), and a NEWER HOT WATER HEATER. Let's take a look through this captivating home: As you step through the front door, you're greeted by the inviting ambiance of a spacious family room with luxury vinyl plank flooring. The generously sized kitchen boasts ample cabinetry space, beautifully tiled backsplash, and plenty of counter space. With its open layout, the kitchen seamlessly transitions into the dining area, perfect for casual family meals and entertaining. The primary suite offers a serene retreat, while the additional bedrooms provide versatility for guests, home offices, or hobbies. Outside, the charm continues with a large yard and screened-in covered patio, offering a tranquil oasis for outdoor relaxation. Conveniently located in Winter Park, this home offers easy access to a wide variety of shopping, popular and trendy restaurants to dine, and access to parks, ensuring that all of life's essentials are just moments away. Don't miss your chance to make 1852 Maywood Road your new home! Schedule your private tour today and discover the perfect blend of comfort, style, and convenience!

Beds:
1
Baths:
1.00
Sq.Ft.:
645
Status:
NEW LISTING
MLS#:
O6201816
Type:
Condo, Townhouse
Subdivision:
LAKESIDE MANOR APTS CONDO
Lot size:
0.05 Acres
Year built:
1969
A broker reciprocity listing Courtesy: MARKET CONNECT REALTY LLC, 407-250-4708
View additional info

Explore the serene beauty of this hidden gem situated on the picturesque shores of spring fed Lake Killarney in Winter Park's coveted 32789 area. Tucked away in a peaceful enclave, this charming 1 bedroom, 1 bath condominium offers 645 sq. ft. of cozy living space on the second floor of a quaint two story complex. Despite its tranquil surroundings, the property enjoys convenient access to I-4 and is nestled within a quiet, tree lined environment, providing residents with a serene retreat just moments away from major amenities and transportation routes. Lakeside Manor, renowned for its low HOA fees and strong HOA board, remains one of Winter Park's best kept secrets. The community boasts a clubhouse with a lakefront pool, perfect for relaxation or entertainment, along with onsite boat launch facilities, boat slips, and dockage, offering residents the opportunity to fully embrace the lakefront lifestyle. Reserved parking and onsite laundry facilities enhance convenience, while the ability to boat to popular local destinations such as Hillstone and Trader Joe's adds to the allure of this exceptional property. Discover the epitome of lakeside living in Winter Park-schedule a showing today to experience the tranquility and charm of Lakeside Manor firsthand.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,919
Status:
NEW LISTING
MLS#:
O6200506
Type:
Single Family
Subdivision:
WOODCREST UNIT 02
Lot size:
0.17 Acres
Year built:
1970
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY, 407-696-8000
View additional info

BE THE HAPPY INVESTOR OR THE WORRY FREE HOMEOWNER! WINTER PARK POOL HOME WITH THE MOST VALUE, UPGRADES AND INCLUSIVE IMRPOVEMENTS. THIS BEAUTIFUL PROPERTY IS A MOVE IN READY AND IN LIKE NEW CONDITIONS! ALL RECENT UPGRADES ARE DONE IN APRIL 2024 WHICH INCLUDES: NEW ROOF, 3.5 TONS HVAC, WATER HEATER, DOUBLED PANELED WINDOWS, INTERIOR/EXTERIOR DOORS, DESIGNER COLORS, FLOORINGS, BEAUTIFUL KITCHEN WITH LARGE DOUBLE-SIDED CLOSET, DRAWER AND GOLD VEINED SOLID SURFACE COUNTERTOP, PENDENT LIGHTS. THERE ARE ALSO NEW KITCHEN APPLIANCES, NEW MANTEL, EXPENSIVE IMPROVEMENTS ON BOTH BATHROOMS, LAMINATE FLOORS, INSIDE LAUNERY ROOM, SEPARATE LIVING ROOM. THERE IS NO OTHER WINTER PARK HOME LISTED FOR @296 PER SQ FT THAT OFFERS AS MANY IMRPOVEMENTS, UPGRADES AND BEING IN A CONVENIENT LOCATION, WINTER PARK SCHOOL SYSTEMS. BE A HAPPY HOME OWNER, OR SHREWD INVESTOR!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,822
Status:
NEW LISTING
MLS#:
O6199197
Type:
Single Family
Subdivision:
SANCTUARY AT ALOMA
Lot size:
0.48 Acres
Year built:
2014
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY, 407-647-1211
View additional info

This MOVE-IN-READY 4-bedroom home is tucked away on an oversized lot in a quiet gated community in east Winter Park.The property has an amazing backyard oasis, complete with an expansive lanai and a brick paver deck surrounding the gorgeous pool. There's lots of room to entertain, with a fenced-in yard that offers plenty of privacy and space for your playset, garden & more.The sliders on the lanai lead into a large great room open to the kitchen. The main living areas are flooded with natural light. The kitchen boasts stainless appliances, granite countertops, and a unique island with bonus seating. Need more space for guests at your housewarming party? You still have a full breakfast nook and a formal dining room off the foyer, too.The isolated primary suite overlooks the pool and includes a spa-like ensuite with marble tilework, a soaking tub, a glass shower, dual sinks, and a massive walk-in closet.The split floorplan puts two guest rooms and an updated full bathroom at the front of the floorplan. ANOTHER BONUS: The fourth bedroom has a seating area, attached bathroom, and private entrance on the lanai - all of which add up to a perfect in-law suite!The long driveway offers extra parking in front of the 3-car garage, and the laundry room has lots of storage!Sanctuary at Aloma puts you just minutes from Rts 417 & 426, and you'll be less than 5 miles from all the quaint shops & restaurants in downtown Winter Park. Twenty-five minutes to Orlando and one hour to the beach!

Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 of 10    Prev | Next
1–25 of 238 properties displayed


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 2017, My Florida Regional MLS

Winter Park FL Real Estate Listings Provided By:

Real Living Real Estate Solutions
7380 West Sand Lake Road #500
Orlando, FL 32819
Email Us | Visit our Real Estate Website

How may I help you?

Get property information, schedule a showing or find an agent





We respect your privacy