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2572 Fifeshire Drive, Winter Park
$875,000
4 Beds ⋅ 3 Baths ⋅ O6442325 MLS
Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after community. Offering more than 2,500 square feet of living space, this spacious residence features four bedrooms and two-and-a-half baths, with an open, comfortable layout designed for both everyday living and entertaining. The home has been thoughtfully updated and maintained over the years, blending timeless character with modern conveniences. The kitchen was beautifully remodeled in 2021 with new cabinetry, appliances, flooring and countertops, while the family room was enhanced with additional air-conditioning ducts and vents for added comfort. The second full bath was also remodeled in 2021 and the downstairs powder room received a stylish update in 2025.Significant improvements include new wood flooring downstairs and refinished and stained upstairs floors in 2019, a new HVAC system with an additional upstairs unit and complete ductwork replacement in 2020 and a customized primary closet in 2022. The primary suite continues to impress with a new porch door and a private balcony railing added in 2026. A new water heater was installed in 2023, while the main sewer line exiting the home was replaced in 2024. The garage is air-cooled. Outdoor living has been equally well considered, with a screened porch enclosure, a covered side patio, new fencing and refreshed landscaping creating inviting spaces to relax and entertain. Beyond the home itself, the location is exceptional, conveniently situated in a wonderful community with Cady Way pool and Cady Way trail, which spans 7.2 miles and connects to the Seminole Trail outdoor recreation. Highly regarded schools and easy access to the area’s everyday amenities. With its generous living spaces, extensive updates, inviting outdoor areas and prime corner-lot setting, this Brookshire Heights home offers an exceptional opportunity to enjoy a beautifully cared-for residence in a highly desirable location.

2572 Fifeshire Drive, Winter Park

2345 Brookshire Avenue, Winter Park
$825,000
3 Beds ⋅ 3 Baths ⋅ O6439369 MLS
Welcome to this beautiful Winter Park home where a flagstone, ivy-lined entry sets the tone for the inviting spaces found within. Tucked away on a private .21-acre lot, this 3-bedroom, 3-bathroom home offers 2,488 square feet of thoughtfully designed living space with vaulted ceilings, multiple living areas, and an effortless flow that makes everyday living and entertaining feel natural. From the moment you arrive, the lush new landscaping and charming entry create a warm first impression, while the spacious interior offers plenty of room for family and friends to gather, relax, and enjoy time together. Inside, the home's multiple living areas provide exceptional flexibility, creating inviting spaces for entertaining, casual gatherings, or simply relaxing with family. The kitchen serves as a natural gathering point, featuring white shaker cabinetry, granite countertops, brand-new stainless-steel appliances, a convenient coffee/wine bar, and a breakfast bar with seating for four. Whether hosting friends for dinner or enjoying a quiet morning together, the layout offers space for every occasion. The primary suite, thoughtfully added in 2017, is a private retreat designed for both comfort and relaxation. A dedicated sitting room or office provides additional flexibility, while the spacious walk-in closet offers abundant storage. The expansive ensuite bathroom delivers a true spa-like experience, featuring a large tiled shower with multiple shower heads and a frameless glass enclosure, creating a luxurious place to unwind at the end of the day. A dual vanity with elegant marble countertops and a separate water closet complete this serene retreat. A secondary bedroom with its own ensuite bathroom provides additional comfort and privacy for guests or family members. All bathrooms have been updated, and the bedrooms feature brand-new carpet, while recessed lighting and ceiling fans throughout add to the home's comfort. Step outside to enjoy the privacy of the fully fenced backyard, with fencing replaced in 2025, a brand-new deck, and beautiful new landscaping. The outdoor space offers another inviting setting for relaxing, entertaining, or enjoying Florida's year-round lifestyle. Beyond the home, the location places you just steps from Brookshire Elementary and close to the Cady Way pool, playground, beach volleyball, tennis and pickleball courts, Cady Way Trail, and Winter Park Pines Golf Course. You'll also enjoy convenient access to UCF, Rollins College, Full Sail University, AdventHealth Winter Park, and Crosby Wellness Center, with Orlando International Airport approximately 25 minutes away. With its welcoming entry, versatile living spaces, spa-inspired primary retreat, private setting, and exceptional Winter Park location, this home offers an ideal backdrop for gathering, relaxing, and making memories with family and friends. ROOF(S) - Main - 2022, Family Room - 2019, Primary Suite - 2017 HVAC - 2021 MINI-SPLIT - 2026

2345 Brookshire Avenue, Winter Park

2383 Sun Valley Circle Unit 2383, Winter Park
$234,900
2 Beds ⋅ 2 Baths ⋅ O6440965 MLS ⋅ 15 BLDG.
Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood flooring along with updated vanity with granite counters along with a separate tub and shower. Secondary bedroom has laminate flooring along with updated vanity and granite countertops. Ceramic tile throughout the rest of the home as there is no carpet. French doors leading out to the oversized screen enclosed covered patio overlooking lush landscaping with no direct rear neighbor.  2 assigned parking spaces directly in front of the unit.There is also a small courtyard just outside the kitchen. Community features a recently remodeled pool, clubhouse and tennis courts. Winter Park location benefits include easy access to Full Sail University, UCF, Valencia College, Park Avenue filled with famous restaurants and boutique shopping.

2383 Sun Valley Circle Unit 2383, Winter Park

311 E Morse Boulevard Unit 1-5, Winter Park
$2,475,000
3 Beds ⋅ 3 Baths ⋅ O6441437 MLS ⋅ Bldg. Number 1 BLDG.
Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two blocks from Park Avenue. Residence 1-5 is located on the quiet, private NE corner of the Whispering Water complex, and it offers the largest floor plan within Whispering Waters at 2,316 sq. ft. under A/C (plus two step-out balconies). This light-filled residence offers an open floor plan and raised ceiling heights. From the moment you enter, you are drawn to the breathtaking lake views and understated elegance of this spacious home. The lakefront great room includes a large living area with adjacent bar and dining areas. The living area opens to the kitchen allowing the lake view to be enjoyed in all main living areas. The kitchen has been updated with white wood cabinetry, a built-in stainless Bosch oven, Bosch glass induction cooktop, Bosch microwave, Subzero refrigerator with two freezer drawers and two additional built-in refrigerator drawers. The custom mirrored backsplash adds a luxury feel, and the flexible center console provides additional work space. The primary suite offers a large walk-in closet and en-suite bathroom with a large walk-in shower, custom floating vanity and elegant fixtures. Bedroom #2 includes two closets and is directly across the hall from a large full bathroom with tub/shower. The 3rd bedroom is currently configured as a large Family Room and includes built-in cabinetry, a private door to the South hallway, two closets and an adjacent alcove ideal for office space. In the photos you'll see a floor plan virtually depicting bedroom #3 with a wall and doorway to the main hallway and living areas. Bathroom #3 is just across the hall and features a large walk-in shower. Wait, there's more! Residence 1-5 includes your own covered boat slip (#1). The entire residence features new seagrass floor covering in all the main living areas. This neutral, organic flooring makes for the perfect contemporary, elegant foundation for your furnishings and for showing off your own custom carpets and rugs. Additional features include plantation shutters throughout, additional storage closet in the garage, and a designated parking space in the gated under-building garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. Residence 1-5 is the jewel of Whispering Waters. This home provides the very finest of Lakefront "lock and Leave" living in the heart of Winter Park. All measurements are approximate and Buyer to verify all dimensions. Please see attached Disclosures and Governing Documents.

311 E Morse Boulevard Unit 1-5, Winter Park

7476 Woodburn Court Unit 38, Winter Park
$170,000
2 Beds ⋅ 3 Baths ⋅ O6434437 MLS ⋅ 38 BLDG.
Terrific townhome in the Hidden Oaks community featuring an updated interior and its own private, fenced patio! Step inside to a bright and spacious living/dining area with beautiful wood laminate flooring and a convenient wet bar. The galley-style kitchen includes a breakfast area, along with a laundry closet equipped with a full-size washer and dryer. Upstairs, you'll find two spacious bedrooms, including one with an oversized walk-in closet. Additional storage is available under the stairs and in the A/C closet. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities! Enjoy community amenities, including a refreshing pool! Conveniently located just off Goldenrod Rd, with easy access to E Colonial, 408, and 417 for a quick commute and nearby everyday conveniences. Full Sail University is just 1.8 miles away, Valencia College is 4.5 miles away, and UCF is only 6.2 miles away!

7476 Woodburn Court Unit 38, Winter Park

1250 S Denning Drive Unit 127, Winter Park
$245,000
2 Beds ⋅ 2 Baths ⋅ O6439854 MLS ⋅ F BLDG.
Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite countertops, a white subway tile backsplash and stainless steel appliances, including a refrigerator, range, microwave and dishwasher. A pass-through to the dining area incorporates built-in cabinetry, glass-front display storage and additional counter space. The dining area flows into the living room, where sliding glass doors open to a screened-in porch overlooking the community pool and landscaped grounds. The primary bedroom features natural light from a pool-facing window, built-in closet storage and an en-suite bath with a walk-in shower and white tile surround. A second bedroom provides flexible space for a variety of uses, while the second full bath offers a tub and shower combination. Additional features include a newer water heater, updated plumbing fixtures and convenient access to the community laundry room just outside the residence. From 1250 South Denning Drive, Residence 127 offers proximity to Mead Botanical Garden, Rollins College, Park Avenue, Azalea Park, Seven Oaks Park and Winter Park dining and retail.

1250 S Denning Drive Unit 127, Winter Park

2657 Exuma Way, Winter Park
$285,000
3 Beds ⋅ 2 Baths ⋅ O6437751 MLS ⋅ 2657 BLDG.
Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite countertops and all-new stainless steel appliances. The spacious primary suite includes a walk-in closet and private en suite bath with a walk-in shower. Two additional bedrooms and a full bath offer ample room for everyone. Tile flooring throughout provides easy maintenance and durability. Enjoy time relaxing outdoors on the covered patio in the privacy of the fenced backyard. Additional recent updates include a new roof, all-new Low-E energy-efficient windows, and a new vanity, toilet, and faucets in the guest bath. Residents enjoy access to the community pool and clubhouse, along with a prime location close to shopping, dining, entertainment, and major roadways. EV parking with outlet for your charger. With its combination of recent upgrades, community amenities, and sought-after Winter Park address, this is the perfect place to call home.

2657 Exuma Way, Winter Park

151 N Orlando Avenue Unit 242, Winter Park
$269,000
2 Beds ⋅ 1 Baths ⋅ O6437574 MLS ⋅ Lake Killarney Condominiums BLDG.
Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

151 N Orlando Avenue Unit 242, Winter Park

222 Lewfield Circle, Winter Park
$189,900
2 Beds ⋅ 2 Baths ⋅ O6436344 MLS ⋅ 10 BLDG.
One or more photos was virtually staged. This 2 Bedroom, 2 Bath, 953 SF Winter Park condo in the amazing Stratford community offers a comfortable, functional floor plan complemented by fresh interior paint, updated flooring, and a 2026 HVAC system. The spacious living area features a ceiling fan and sliding glass doors that bring in natural light and open to a covered balcony, creating an easy extension of the indoor living space. The adjacent dining area provides flexibility for everyday meals or additional living space. The kitchen features wood cabinetry, generous counter space, tile flooring, and stainless steel refrigerator, while an in-unit laundry closet adds everyday convenience. Bedrooms feature updated flooring, neutral finishes, ceiling fans, and ample natural light. A large walk-in closet with extensive shelving and storage helps keep everything organized, while the bathroom includes a tiled walk-in shower and vanity storage. Freshly touched up throughout and offering a practical layout with comfortable living spaces, this Winter Park condo is ready for its next chapter.

222 Lewfield Circle, Winter Park

285 Lewfield Circle Unit 285, Winter Park
$147,000
1 Beds ⋅ 1 Baths ⋅ O6435396 MLS ⋅ Lewfield 285 BLDG.
Virtually Staged. LOCATION, CONVENIENCE, AND EASY LIVING IN WINTER PARK! This move-in-ready first-floor, 1-bedroom, 1-bath condo features an open living and dining area, wood flooring throughout the main living areas, tile flooring in the primary bedroom, a private screened-in balcony, a fully equipped kitchen, and a stackable washer and dryer. Conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando, with easy access to shopping, dining, and major highways. Community amenities include two pools, a tennis court, fitness center, and clubhouse. HOA includes water, trash, internet, pest control, exterior maintenance, and grounds care. A great opportunity to enjoy a low-maintenance lifestyle in a highly convenient Winter Park location.

285 Lewfield Circle Unit 285, Winter Park

623 Grenadine Court Unit 623, Winter Park
$194,900
2 Beds ⋅ 2 Baths ⋅ O6434195 MLS ⋅ 623 BLDG.
PRICE ADJUSTMENT! Welcome to this Desirable Winter Park Villas Condo FIRST FLOOR 2 BEDROOM, 2 FULL BATH, 1037 square feet, featuring NEW AIR CONDITIONING SYSTEM and BRAND NEW CARPET freshly installed! EXCELLENT LOCATION walking or bike riding distance to FULL SAIL UNIVERSITY and easy access to UCF! Ideally located in rear of community with ample open parking. Your spacious Kitchen features ample counter space and abundant cabinetry, kitchen sink window with view of front door entry and parking area. Kitchen has a closet pantry and there is an opening to Dining Room with Bar Seating area. Dining Room has views to backyard and a Wet Bar with unique Sink Closet feature. Family Room has a fireplace and views of outside greenery. In hallway off entry is your Washer/Dryer closet and they are both included in the sale. The Primary Bedroom is large with walk in closet, full bathroom with tub shower combo and two vanities. The Secondary Bedroom features back yard views and built in closet and easy access to hallway full second bath. Outside you'll love the covered patio and lawn area for lounging or gardening outside. Off the patio is a storage closet for the Water Heater. Winter Park Villas amenities include community pool, fitness center and tennis courts. Seller is offering a One Year Assurant Home Warranty covering all the appliances included. Located in Winter Park School District and easy access to Orlando International Airport! Call for to see it today, priced under $200,000 location can't be beat! Property may be under audio/visual surveillance.

623 Grenadine Court Unit 623, Winter Park

2857 Clever Lane, Winter Park
$394,500
3 Beds ⋅ 3 Baths ⋅ O6434185 MLS ⋅ 2857 BLDG.
Talk about VALUE! Almost brand new and move in ready CORNER townhome in Winter Park! This beautiful 3 bedroom 2.5 bathroom home with just under 1,800 sq. ft. offers a large 2 car garage, light and bright living spaces, clean and modern designer features, and comes equipped with a full kitchen appliance package and washer/dryer. The first floor offers expansive living spaces with enough room for a dining area and family room. All of which flow seamlessly into the open kitchen. With white cabinets and Quartz counter tops, the kitchen is a show stopper! The entire first level is adorned with tile and offers a half bathroom and access to the covered back porch. Just up the stairs, you will find all of your bedrooms and full bathrooms. The primary bedroom and en suite bathroom are ample in size and also offer a large walk in closet. Both secondary bedrooms are down the hall and share a large full bathroom. The small gated community of townhomes offers a community pool and serene pond. HOA includes cable! Make sure to put this on your must see list!

2857 Clever Lane, Winter Park

1287 Verdant Glade Place, Winter Park
$735,000
4 Beds ⋅ 4 Baths ⋅ O6434086 MLS
Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park

311 E Morse Boulevard Unit 4-5, Winter Park
$895,000
2 Beds ⋅ 2 Baths ⋅ O6432808 MLS ⋅ Building 4 BLDG.
Experience the best of downtown Winter Park living at Whispering Waters, a desirable 55+ lakefront community ideally located on beautiful Lake Osceola and just a short stroll from iconic Park Avenue. Priced BELOW APPRAISED VALUE, this rare third-floor mid-century modern condo combines an unbeatable location, spacious living, and an easy, low-maintenance lifestyle. Step inside to a bright, inviting interior filled with natural light from multiple floor-to-ceiling windows. The spacious living and dining areas overlook tranquil waterfall ponds and beautifully landscaped grounds, creating a peaceful retreat in the heart of Winter Park. A versatile bonus space is perfect for a home office, den, reading room, or creative space. The expansive owner’s suite offers a private sitting area, dual closets, pool access, and a spacious bath with a relaxing jetted tub. The generously sized secondary bedroom features its own cozy reading nook and dual closets—ideal for guests or additional living space. Convenience is built right in with private in-unit washer and dryer hookups, secure underground parking with a deeded space, and elevator access. Even better, the monthly association DUES INCLUDE ELECTRIC, WATER, GAS, SEWER & TRASH, helping make everyday living refreshingly simple. Residents also enjoy an on-site property manager, additional laundry facilities, a community clubhouse, sparkling pool, and beautiful lakefront surroundings. Leave the car at home and enjoy the boutiques, cafés, restaurants, museums, and events of Park Avenue, stroll through Central Park, catch the SunRail or Amtrak, or enjoy nearby Rollins College and Winter Park’s highly rated public golf course. With its PRIME LAKEFRONT SETTING, WALKABLE PARK AVENUE LOCATION, UTILITIES INCLUDED & LOW-MAINTENANCE LIFESTYLE, this condo offers a RARE OPPORTUNITY to enjoy one of Central Florida’s most sought-after communities. COME DISCOVER THE LIFESTYLE THAT MAKES WHISPERING WATERS AND WINTER PARK SO SPECIAL—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park

2477 Tahoe Circle Unit 2477, Winter Park
$247,000
2 Beds ⋅ 2 Baths ⋅ O6432904 MLS ⋅ 2477 BLDG.
Virtually Staged. ALL NEW PRICE!!!!!! LIVE THE WINTER PARK LIFESTYLE! STYLE, SPACE & LOCATION—THIS ONE HAS IT ALL! Welcome to Cedarwood Village, where easy living meets one of Winter Park’s most desirable locations, just minutes from the charm, dining, shopping, and entertainment of Downtown Winter Park and Park Avenue. This beautifully maintained 2-bedroom, 2-bath residence with an enclosed bonus room offers a spacious, light-filled floor plan designed for both comfortable everyday living and entertaining. Vaulted ceilings enhance the open living and dining areas, while the generously sized kitchen features newer appliances, abundant cabinet and counter space, plus room for a cozy breakfast table. Retreat to the oversized primary suite, complete with two large closets and sliding glass doors opening to the bonus room. The renovated primary bath adds a touch of luxury with an updated vanity and impressive custom walk-in shower. The guest bedroom offers its own sliding glass doors leading to the front patio, creating a bright and inviting space for family or overnight guests. The updated guest bath adds convenience with a washer and dryer neatly tucked away in the closet. One of the home's best features is the enclosed bonus room, offering valuable additional living space that's perfect for a home office, den, reading retreat, hobby room, or simply a relaxing place to unwind. Enjoy the Florida lifestyle without leaving the neighborhood! Cedarwood Village offers a sparkling community pool, two tennis courts, and clubhouse for residents to enjoy. And then there’s the LOCATION! Shopping, restaurants, medical facilities, and everyday conveniences are all close by, with easy access to major roadways and the boutiques, sidewalk cafés, restaurants, parks, and unmistakable charm of Park Avenue and Downtown Winter Park just minutes away. More than a home—it’s a Winter Park lifestyle. Come see why Cedarwood Village is such a special place to call home!

2477 Tahoe Circle Unit 2477, Winter Park

283 Sandlewood Trail Unit 3, Winter Park
$279,000
2 Beds ⋅ 3 Baths ⋅ O6431475 MLS ⋅ 2 BLDG.
Virtually Staged. MOVE IN READY in Winter Park with nearly $30,000 in recent upgrades and improvements! This beautifully updated 2 bedroom, 2.5 bathroom condo in Sandlewood Creek offers a bright, open layout, conservation views and a quiet community setting in an incredibly convenient location. The main level features a spacious open living and dining area with plenty of room to create separate gathering and dining spaces while maintaining an easy flow throughout the home. The updated kitchen features white cabinetry, granite countertops, stainless steel appliances and a breakfast bar overlooking the living and dining space. A convenient half bath, interior laundry, washer and dryer included, and an additional downstairs storage closet complete the first floor. Step outside to the screened rear porch overlooking conservation, creating a peaceful outdoor space with added privacy. Upstairs, the primary bedroom features a private en suite bathroom, while the second bedroom is located near the additional full bath. A small landing separates the two bedrooms and includes an additional upstairs storage closet, providing valuable extra space for linens, seasonal items or everyday storage. Nearly $30,000 in recent upgrades and improvements include vinyl flooring and baseboards upstairs completed in September 2023, an updated kitchen with cabinetry, countertops and stainless steel appliances in 2023, AC installed in January 2024, roof is 2021, washing machine replaced in 2024, fresh interior paint and new downstairs baseboards completed in July 2026, plus a 2018 water heater. Sandlewood Creek is an established community with a community pool and one assigned parking space. Maitland Community Park is located directly behind the community and connects to additional park space, offering convenient access to trails and outdoor recreation. Park Avenue and Downtown Winter Park are approximately 10 minutes away, putting shopping, dining and entertainment within easy reach. With its extensive recent improvements, conservation setting, screened porch, multiple storage areas and convenient Winter Park location, this home is truly move in ready.

283 Sandlewood Trail Unit 3, Winter Park

1122 Wildmeadow Run, Winter Park
$660,000
4 Beds ⋅ 3 Baths ⋅ O6429492 MLS
Welcome to a premier opportunity in the the coveted Winter Park. This beautifully maintained 4-bedroom, 2.5-bathroom home is located in The Meadows – an alcove in the gated Hawks Crest community – and offers buyers a turn-key opportunity to crack into the Winter Park market. With 1,770 square feet of thoughtfully designed living space, this home strikes the perfect balance between functionality and flow, featuring a living/dining combination anchored by the kitchen in the heart of the home. The central dining configuration is equally suited for quiet evenings or effortless entertaining, while the living room offers versatility as a spacious indoor retreat, or an indoor-outdoor oasis, complimented by the glass sliders. Before entering the primary suite, find three secondary rooms - two guest bedrooms and an office - along with a full guest bathroom and a powder bath, making every day living hassle-free and providing ample privacy. In the primary en-suite, unwind and enjoy the pleasures of a spacious retreat featuring an over-sized walk-in shower. This home is only 4 years young, so newer appliances and core components provide peace of mind, and an upgraded Tesla level 2 charger makes it fully equipped to suit every homeowner's needs. This home is just a short walk to the community amenities which include a clubhouse, pool, fitness center, turf lawn with a putting green, playground, dog park, and a private community dock on to Lake Howell. The 24-hour gated community provides peace of mind, all within easy reach of A-rated Seminole County schools (Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High), major employment corridors, the Orlando International Airport, and everything that Orlando has to offer. This is the kind of opportunity that doesn't come along often. Contact us to schedule your private tour today!

1122 Wildmeadow Run, Winter Park

7413 Belle River Court Unit 3, Winter Park
$214,900
3 Beds ⋅ 3 Baths ⋅ O6430667 MLS ⋅ 7413 BLDG.
MOTIVATED SELLER...Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is Sure to Impress with Quartz Countertops, Stainless Steel Appliances, and A Sliding Glass Door That Opens to a Private Patio—Perfect for Relaxing or Entertaining. Upstairs, You'll Find All Three Bedrooms and Two Full Bathrooms, including a Generously Sized Primary Suite with a Walk-In Closet and Large Front-Facing Windows That Fill the Room with Natural Light. Residents of Hidden Oaks Enjoy a Peaceful Setting with Access to a Community Swimming Pool, Assigned Parking, And Plenty of Guest Parking. Ideally Located Just Minutes from Major Highways 408 And 417, This Home Is Only 4 Minutes from Full Sail University, Minutes from the University of Central Florida (UCF), Downtown Orlando, and Conveniently Close to Valencia College, Rollins College, Winter Park Shopping and Dining, Restaurants, and Everyday Conveniences. The Property Is Also Zoned for Highly Desirable Winter Park Schools, Making It an Excellent Choice for Homeowners and Investors Alike. Don't Miss This Move-In-Ready Opportunity in One of the Area's Most Convenient Locations!

7413 Belle River Court Unit 3, Winter Park

1000 S Semoran Boulevard Unit 302, Winter Park
$97,000
1 Beds ⋅ 1 Baths ⋅ O6428713 MLS ⋅ 302 BLDG.
Virtually Staged. 2018 AC, ROOF REPLACED BY HOA WITHIN THE LAST 3 YEARS ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully designed layout featuring a generous living area, an oversized bedroom, and a large bathroom. The charming kitchen offers ample cabinet and counter space, creating an inviting space for both everyday living and entertaining. Step outside to your private balcony, the perfect place to enjoy your morning coffee or relax at the end of the day. The home's separate exterior entrance adds an extra level of convenience and privacy. Enjoy low-maintenance living with HOA dues that cover water, trash, exterior maintenance, and roof replacement. The community recently completed a roof replacement, providing added peace of mind for the new owner. Residents also enjoy access to the community pool, perfect for cooling off on warm Florida days. Conveniently located near UCF, Valencia College, Waterford Lakes Town Center, Orlando International Airport, major highways including SR 408 and SR 417, shopping, dining, and entertainment, this home is also zoned for highly desirable schools. Whether you're a first-time homebuyer, someone looking to downsize, or an investor seeking a well-maintained property in a prime East Orlando location, this condominium offers an outstanding opportunity. Schedule your private showing today!

1000 S Semoran Boulevard Unit 302, Winter Park

2475 Tahoe Circle, Winter Park
$268,000
2 Beds ⋅ 2 Baths ⋅ O6428082 MLS ⋅ Na BLDG.
Turnkey Living in the Heart of Winter Park! Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner. Inside, you'll find a thoughtfully designed floor plan with spacious living and dining areas, a well-appointed kitchen, and two generously sized bedrooms and bathrooms designed for comfort and functionality. Whether you're relaxing at home or entertaining friends and family, this inviting layout makes everyday living effortless. Step outside and enjoy the exceptional community amenities, including a sparkling swimming pool and tennis courts, perfect for enjoying Florida's year-round sunshine. Whether you're a first-time homebuyer, downsizing, seeking a second home, or looking for an investment opportunity, this property offers incredible versatility. Ideally located in desirable Winter Park, you'll be just minutes from shopping, dining, entertainment, major highways, UCF, Full Sail University, Downtown Winter Park, and Downtown Orlando, making commuting and enjoying Central Florida's best attractions a breeze. Don't miss your opportunity to own this beautifully updated, turnkey home in one of Central Florida's most sought-after communities! All room measurements, HOA information, square footage, and property details are deemed reliable but not guaranteed and should be independently verified by the buyer and buyer's agent.

2475 Tahoe Circle, Winter Park

1000 S Semoran Boulevard Unit 305, Winter Park
$115,000
1 Beds ⋅ 1 Baths ⋅ O6428044 MLS ⋅ 1000 BLDG.
Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas, creating a bright and inviting space for everyday living and entertaining. A set of French doors leads to the screened-in porch, providing the perfect spot to enjoy your morning coffee or unwind after a long day. The spacious bedroom features a large walk-in closet, offering plenty of storage. This condo also includes one assigned parking space, along with additional guest parking for visitors. Residents enjoy access to a community pool and onsite laundry facilities, adding to the convenience of low-maintenance living. Ideally located just minutes from SR 408, the University of Central Florida (UCF), shopping, dining, restaurants, and entertainment, this condo offers an unbeatable combination of comfort, convenience, and value. Whether you're searching for a primary residence or a smart investment opportunity in a high-demand area, this Central Florida gem is one you won't want to miss!

1000 S Semoran Boulevard Unit 305, Winter Park

2033 Canny Cove, Winter Park
$389,000
3 Beds ⋅ 3 Baths ⋅ O6426457 MLS ⋅ 2033 BLDG.
Seller offering up to $10,000 toward buyer closing costs and prepaids! Discover stylish, low-maintenance living in this beautifully designed townhome in Winter Park’s gated Grayson Square community. The inviting open-concept layout connects the kitchen, dining, and living areas, creating an ideal space for entertaining or relaxing at home. Stainless steel appliances, gray cabinetry, and quartz countertops give the kitchen a fresh, modern finish. Upstairs, the spacious primary suite features a walk-in closet and a private ensuite bath with dual sinks and quartz countertops. Two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Enjoy your morning coffee or unwind in the evening on the covered lanai, with the added appeal of a cul-de-sac location. The HOA includes landscaping, exterior maintenance and high-speed internet, making everyday living easier. No CDD adds to the value! Conveniently located near SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and Seminole County schools nearby. Winter Park’s renowned Park Avenue is just a short drive away. Comfort, convenience, and an attractive seller contribution make this home an opportunity worth exploring—schedule your showing today!

2033 Canny Cove, Winter Park

7450 Wynnewood Square Unit 189, Winter Park
$170,000
2 Beds ⋅ 3 Baths ⋅ O6425486 MLS ⋅ Na BLDG.
***Price Improvement*** This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the upstairs boasts beautiful laminate wood flooring—no carpet here! Both bedrooms are located upstairs, each with its own ensuite bathroom and additional storage above the mirrors. Downstairs, you'll find ample space for entertaining or simply relaxing, enhanced by the convenience of a wet bar. Located just minutes from UCF and Full Sail University, this condo is perfect for anyone looking to enjoy the vibrant local community without the long commute! With shopping, dining, and recreational activities nearby, you'll have everything you need right at your fingertips. Don’t miss out on this fantastic opportunity—schedule a showing today!

7450 Wynnewood Square Unit 189, Winter Park

1418 Lone Feather Trail, Winter Park
$699,500
4 Beds ⋅ 3 Baths ⋅ O6417341 MLS
Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park

2450 Grand Teton Circle Unit 2450, Winter Park
$250,000
3 Beds ⋅ 2 Baths ⋅ O6418973 MLS ⋅ 2450 BLDG.
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park
$279,900
2 Beds ⋅ 2 Baths ⋅ O6421422 MLS ⋅ 19 BLDG.
Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park

1000 S Semoran Boulevard Unit 306, Winter Park
$138,000
1 Beds ⋅ 1 Baths ⋅ R4911525 MLS ⋅ 3 BLDG.
Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other amenities. Water and sewer is though HOA fees , nice bonus for tenants. This condo home is investment property with a long term tenant but can be ready for an owner occupant Current tenant is under market rent… opportunity to make some changes here. Schedule a showing today!

1000 S Semoran Boulevard Unit 306, Winter Park

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