Winter Park Homes with Pool Community Features

Winter Park Homes with Pool Community Features

Welcome to Winter Park, Florida—a picturesque city that perfectly blends small-town charm with vibrant urban living. Nestled just north of Orlando, Winter Park is renowned for its lush landscapes, stunning lakes, and a rich cultural scene that captivates residents and visitors alike. With its tree-lined streets, historic architecture, and a delightful array of dining and shopping options, Winter Park is a place where community and convenience come together harmoniously.

One of the standout features of Winter Park is its exceptional homes with pool community options. Imagine stepping out of your beautifully designed home to a private oasis where you can relax and unwind by your own sparkling pool. These communities are thoughtfully designed to enhance your lifestyle, offering amenities that cater to both relaxation and recreation. Whether you’re hosting a summer barbecue, enjoying a quiet evening swim, or engaging in family fun, having a pool right at your doorstep transforms everyday living into a vacation-like experience.

In addition to the allure of poolside living, Winter Park boasts a wealth of recreational opportunities. From the scenic beauty of the Chain of Lakes to the vibrant Winter Park Farmers’ Market, there’s always something to explore. The city is also home to an array of art galleries, museums, and the esteemed Rollins College, which adds to the cultural richness of the area.

If you’re looking for a home that embodies luxury and leisure in a community that feels like a close-knit family, Winter Park’s homes with pool community features are the perfect choice. Come discover the charm and elegance of Winter Park—your dream home awaits!

Newest Winter Park Homes with Pool Community Features

6 Beds ⋅ 5 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most coveted premium lots, featuring a larger lot line, wooded HOA land behind the property, and serene views toward Lake Howell. The thoughtfully designed floor plan offers two primary suites, one on each level, plus a dedicated office, a theater room, a loft, and a three-car tandem garage with built-in shelving and a workbench. Designer finishes include Restoration Hardware and Pottery Barn chandeliers, plantation shutters, crown molding, motorized blinds, app-controlled LED trim lighting, and custom built-ins throughout the home. The resort-style backyard features a saltwater, solar-heated pool, expansive pool deck, motorized Sunpro awnings, landscape lighting, and lanai market lights—perfect for entertaining or relaxing in complete privacy. Additional upgrades include a custom entertainment center with an electric fireplace, a Sony theater system and projector in the media room, a water softener, gutters, and extensive custom storage solutions by Inspired Closets throughout the home. The hot tub, Paradise Grill, and custom workout equipment are also available for negotiation, offering the opportunity to make this already exceptional home truly turnkey for your lifestyle. Hawks Crest residents enjoy an impressive collection of community amenities, including a resort-style pool, splash pad, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. With highly regarded private schools nearby—including Park Maitland School, The Geneva School, Trinity Preparatory School, and The Master’s Academy—along with the exceptional shopping and dining of Park Avenue, this coveted Winter Park location truly offers the best of convenience, lifestyle, and luxury. Every box has been checked. From the premium homesite to the designer finishes, custom upgrades, resort-style pool, and thoughtful details throughout, this is a home where everything has already been done—just move in and enjoy.

1257 Wading Waters Circle, Winter Park

2 Beds ⋅ 2 Baths ⋅ Lancelot/Winter Park SubDv. ⋅ 32792 Zip Code

This is exactly what you are looking for! Adorable 2/2 close to Full Sail and UCF. Tons of shopping and restaurants and convenient to the 417 and the 408. Location makes this perfect for a primary residence or investment property. Split floor plan ideal for roommates. Walk to Full Sail. 15 minutes to downtown Orlando and approximately 30 minutes to most attractions. Exceptionally well taken care of and only needs your personal touches to make it a really cute home. Seller will offer an appliance package and a 1 year home warranty with the right contract. What are you waiting for come and get it!!

3651 N Goldenrod Road Unit C109, Winter Park

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

Hawk's Crest is a care free resort style master planned community in Winter Park, Florida. With it's Modern style architecture, this 3 bedroom, 2 1/2 bathroom townhome is meticulously maintained with an HOA that covers more than most. While driving through the community you will pass the community pool and recreation area which is conveniently nestled at the end of Bantam Way. The curb appeal of the paver driveway and home design will make you feel you are home. Inside you will be greeted by a foyer before entering the home itself. On the main floor you will find a half bathroom/ guest bathroom, tile flooring throughout, excellent natural light, living room, dinette, and the statement kitchen sure to please. The kitchen boast granite counter tops, shaker style cabinets, a extra large kitchen island with a breakfast bar, ample size walk-in pantry, refrigerator 2026, all other appliances 2021, new and upgraded kitchen hardware, newer faucet, and newer large single basin sink. Upstairs you will find all the bedrooms, inside laundry room and both full bathrooms, The primary suite is an ample 20 x 15 with trey ceiling, en-suite bathroom, and walk in closet with a custom closet organizer. The en-suite bathroom is highlighted by a dual vanity sink, granite countertops, shaker style cabinets, and shower stall. Both additional bedrooms are an impressive 15 x 12 with walk in closets. The inside laundry room has upgraded cabinets. Out back you will find a quiet covered rear patio with space for seating, a grill, and more. Other highlights to mention include the tesla electric charger in the garage and freshly added cabinets and granite countertops in the drop zone just off the inside garage entrance. Community common areas include a resort style pool with covered social gathering area and a community playground. The HOA covers the cable, internet, community pool, exterior building maintenance, common area maintenance and more. Hawk's Crest is just minutes to Park Avenue Winter Park, 417, UCF, shopping, restaurants and much more. Just a short walk to the out-parcel building in the front of the community you will find local favorites like Foxtail coffee, Kelly's Ice cream, and the Park Maitland School. Don't miss this opportunity. These townhomes go quickly.

1521 Bantam Way, Winter Park

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will appreciate the home's refined modern aesthetic, clean architectural lines, and thoughtfully curated finishes. Brand new flooring creates a seamless sense of elegance throughout, while sleek new cabinetry, contemporary finishes, and new premium appliances, and new quartz counters is suited for dinning or entertaining! Through sliding glass doors lies the crown jewel: a sparkling, screened in-ground pool surrounded by a luxury private patio! Spend time hosting barbecues under the covered lanai or relaxing in the warm afternoon sun! Yard is fully fenced! Private backyard featuring a plenty sitting areas and a brand-new fire pit for wonderful outdoor gatherings! Whether you are doing morning exercise or watching the sunset by the water, it delivers a peaceful resort living! Living in this renown Winter Park Pine neighborhood with No HOA, yet easy access to golf courses, biking trails and parks, community amenities, Advent hospital, Park Ave, Rollin College and Baldwin Park! Renown school districts and convenient locations! Don't miss out on this rare find—call now to see it in person!

274 N Ranger Boulevard, Winter Park

2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code

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 an enclosed sunroom 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

3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to the Enclave at Hawks Crest, where this modern 3-bedroom, 2.5-bath townhome gives you 1,755 square feet of space without a long list of things to maintain. A paver driveway, two-car garage, and clean exterior make a great first impression, and inside, high ceilings and plenty of natural light keep the main level feeling open and bright. The kitchen sits right in the middle of it all with a large island, stainless steel appliances, and a walk-in pantry, opening naturally to the dining and living areas. Out back, sliding doors lead to a covered, screened patio overlooking greenspace, giving you a little breathing room without a backyard to take care of. Upstairs, the primary suite is spacious with a tray ceiling, large walk-in closet, and ensuite bath with dual sinks and a tiled shower. Two additional bedrooms sit at the opposite end of the hall, along with a second full bath and, thankfully, the laundry room is upstairs too. This home has been meticulously maintained by its original owner since 2021. The HOA handles the exterior and landscaping, and the gated community includes a resort-style pool, playground, and dog park. Zoned for A-rated Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High, and you're just minutes from Park Avenue, with Kelly's Ice Cream and Foxtail Coffee a short walk from your front door. Low maintenance, high convenience, and Winter Park right outside your door. Call today for your private showing!

2349 Shadowland Loop, Winter Park

2 Beds ⋅ 2 Baths ⋅ Parkview Village SubDv. ⋅ 32792 Zip Code

VALUE OPPORTUNITY IN WINTER PARK! Welcome to 3020 Antique Oaks Circle #129, a spacious 2-bedroom, 2-bath FIRST-FLOOR CONDO offering approximately 1,018 square feet in the conveniently located Parkview Village community in Winter Park, FL 32792. If you have been searching for an affordable Winter Park condo, investment property, renovation opportunity, first-floor condo or 2-bedroom condo in Winter Park, this property deserves your attention. The functional floor plan offers generous living space, two full bathrooms, an interior laundry area and the convenience of first-floor living. Parkview Village offers desirable community amenities including a COMMUNITY POOL, SPA, TENNIS COURTS and recreational areas, creating an appealing combination of location, convenience and value. LOCATION IS A MAJOR HIGHLIGHT! Enjoy easy access to Semoran Boulevard/436, Aloma Avenue, University Boulevard, Downtown Winter Park, Park Avenue, Rollins College, UCF and major Central Florida roadways. Shopping, restaurants, grocery stores and everyday conveniences are close by, making this an excellent option for buyers looking for a Winter Park condo close to dining, shopping, entertainment and employment centers. The property is currently served by Aloma Elementary School, Glenridge Middle School and Winter Park High School. Buyers are encouraged to independently verify current school zoning and assignments with Orange County Public Schools. IMPORTANT VALUE OPPORTUNITY: The property has known mold present in the kitchen area that requires professional remediation, and the asking price has been positioned to reflect the property's current condition and the work needed. This creates an opportunity for a buyer who is prepared to complete the necessary remediation and customize the property to their own style. Buyers are encouraged to perform their own inspections, obtain professional remediation evaluations and verify all property and association information. With a Winter Park address, first-floor location, 2 bedrooms, 2 full bathrooms, community amenities and convenient access to shopping, dining and major roadways, this condo offers significant potential for the buyer willing to address the existing condition. Bring your vision and take advantage of this affordable Winter Park condo opportunity!

3020 Antique Oaks Circle Unit 129, Winter Park

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239 acre lake that is perfect for sailing, motor boating and skiing. The lush courtyard, lakeside pool, clubhouse and gazebo, updated dock and private boat ramp make this a serene place to enjoy the best of Central Florida in a noisy world. This one bedroom condo is in original condition, with 3 year old A/C unit, and is ready for your personal touches to make it your own.

2500 Lee Road Unit 143, Winter Park

2 Beds ⋅ 2 Baths ⋅ Lancelot/Winter Park SubDv. ⋅ 32792 Zip Code

Just Reduced $10k!! Priced to sell, already rented, perfect for investor buyer. This 2nd floor end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. Stainless Appliances, including Refrigerator, Microwave, Flat top Range/oven, Dishwasher, full size front load washer and Dryer in Laundry Closet. Community features a pool/clubhouse. Excellent school zone which includes desirable Winter Park School High School, Glenridge Middle School, Aloma Elementary School. An ideal location that makes a Great Rental Investment property, already leased. Location, Location, Location... with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping. Call now for your private showing, will not last.

3651 N N Goldenrod Rd Road Unit #C205, Winter Park

3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 2 SubDv. ⋅ 32792 Zip Code

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

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

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

2 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

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

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