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Browse All Winter Park FL Between $300K - $400K Properties for Sale

$329,900
2 Beds 1 Baths Village Condo SubDv. 32789 Zip Code
Location.... Location.... Location.... First Floor Condo situated in the heart of Winter Park and walking distance to Park Avenue, Rollins College, Winter Park Village and Sun Rail. The condo has been recently renovated with new appliances, led lighting, wood, tile, and stone finishes and there are NO units above this one. You have access to a "new" private deck just right outside the unit back door to just relax and enjoy a quiet evening. No Condominium Assessments and All Major Building Components/Projects (Roof, Fencing, Driveway, Landscaping, Lighting, Painting) have been completed Within the Last 7 Years! This home is "wireless" from the doorbell to the electrical switches and ceiling lights which can be dimmed for a relaxing mood. It is set up on a Google Home Platform and can be controlled remotely. A nest thermostat, doorbell and a state of the art wireless Blue ADT alarm system that is self-monitored with backup capabilities to ensure notifications of events. There is a new all-in-one washer/dryer for a one-time load and done. The unlimited hot water system maintains constant temperature based on your convenient and easy dial setting and comfort. The kitchen has modern track lighting and granite counters. Custom white plantation shutters and crown molding throughout the home. There is one assigned parking space with ample parking for another vehicle and guest parking. The location in Winter Park is ideal and is located near the police and fire station. This home has everything you need to enjoy the Winter Park lifestyle and cultural events.

500 N Pennsylvania Avenue Unit E, Winter Park

$359,000
3 Beds 2 Baths Temple Terrace Annex SubDv. 32792 Zip Code
Under contract-accepting backup offers. HIDDEN GEM ALERT! A rare opportunity to own a move-in ready 3 bedroom 2 bathroom home located in the heart of Seminole County Winter Park with a huge backyard and no HOA at an affordable price! WOW!! Located on a large lot on a dead-end street, this "Old Florida" block construction ranch is a perfect starter home for any family or a great addition to an investment portfolio. The exterior is highlighted with great curb appeal with an extra wide paver driveway, mature landscaping, and paver front walkway and patio area. The interior consists of a bright and OPEN CONCEPT dining/kitchen/living space with ample room to relax or entertain. The kitchen boasts granite counters, solid wood cabinets, stainless steel appliances, eat-in island, and a closet style pantry. The master suite has a total of THREE CLOSETS and a spacious bathroom with updated vanity and tile shower. The opposite side of the SPLIT LAYOUT home contains two additional bedrooms and a recently updated full size bathroom. Outside is a massive fully fenced backyard with paver patio and shed for additional storage. Other features include: a spacious indoor laundry room, irrigation system for front lawn, 2014 roof, and 2018 HVAC. Zoned for great schools and centrally located only 15 minutes from downtown Orlando and 30 min from MCO airport this home is perfectly situated to meet YOUR needs! Opportunities at this price simply do not come on the market often! Book your private showing today!!

1935 Azalea Avenue, Winter Park

$350,000
3 Beds 2.5 Baths Vistas At Lake Howell SubDv. 32792 Zip Code
Under contract-accepting backup offers. Beautifully remodeled, 3 bedroom/2.5 bathroom, 2-story townhome in gated, Winter Park community!! This home is a stunner! Every inch has been updated with top-of-the-line features throughout! The chef's kitchen offers stainless appliances, real-wood cabinets, granite counters, and is open to the tiled living area, making hosting and family time a breeze. A glass slider door opens up to the fully screened-in back patio for indoor/outdoor living when the weather is nice. There is an updated, half-bath on the main floor. All bedrooms and both full bathrooms are upstairs, as well as a split bedroom layout, and upstairs laundry closet! The bathrooms were recently remodeled with brand new tub/showers, tiles, fixtures, vanities, lighting, and they even added smart, bluetooth exhaust bathroom fans/speakers! All new, neutral paint and blinds throughout the entire home, brand new carpet in all the bedrooms, a smart thermostat, and an attached 1-car garage for additional storage and covered parking...the sellers have really considered every detail! AC was replaced in 2023, water heater was replaced in 2019. All conveniently located in gated, Winter Park community zoned for A-rated schools, near to Full Sail, Park Ave, I-4, and endless shopping and dining options. Pack your bags, this home is completely turnkey and waiting for your family to move right in!

1512 Florentino Lane, Winter Park

$349,900
3 Beds 1 Baths N/A SubDv. 32792 Zip Code
Step into a piece of Winter Park history with this delightful residence at 7102 Easter St. Built in 1956, this home exudes timeless vintage charm, seamlessly blending classic character with modern potential. Boasting 3 spacious bedrooms, the property offers a cozy and inviting atmosphere that immediately feels like home. One of the standout features of this property is its impressive lot size. The generous outdoor space provides a rare opportunity in Winter Park, ideal for a myriad of activities and personal retreats. Imagine spending weekends hosting vibrant gatherings with family and friends in your expansive backyard, or enjoying serene moments of relaxation in your private outdoor oasis. There’s ample room for a flourishing garden, a play area, or even a peaceful sanctuary where you can unwind and reconnect with nature. The home itself showcases unique vintage details that add to its charm, offering a nostalgic touch while providing a solid foundation for contemporary updates. Whether you’re drawn to its historical appeal or the potential for creating your dream space, this property caters to both. Location is another key highlight of this property. Situated less than a mile from Full Sail University, it’s a perfect choice for those who value proximity to the campus. Additionally, the home is just 3 miles from the renowned Park Avenue in Winter Park, known for its vibrant dining, shopping, and cultural experiences. For those commuting to the University of Central Florida (UCF), the property is conveniently located just 5 miles away, making daily travel a breeze. With Winter Park’s renowned amenities, parks, and dining all within easy reach, this home offers the perfect blend of nostalgic appeal, modern convenience, and exceptional location. Don’t miss this unique opportunity to own a home that combines classic elegance with spacious living in one of Central Florida’s most desirable neighborhoods. Embrace the charm of yesteryear while enjoying the lifestyle of today at 7102 Easter St.

7102 Easter Street, Winter Park

$379,000
3 Beds 2 Baths Springview SubDv. 32792 Zip Code
Updated and well maintained Winter Park home! This 3 bedroom 2 bathroom 2 car garage home is move-in ready and has NO HOA. As you walk up you will be greeted by the new solid wood front door with a breathtaking decorative glass insert. Step inside onto the new wood-like, modern ceramic tile floors that expand throughout the entire home. The well appointed kitchen boasts gorgeous cherry wood cabinets, stainless steel appliances, granite countertops and a picturesque window with clear views of your serene backyard. This split plan model offers privacy for your primary suite and features a walk-in closet and an exquisitely updated ensuite. Enjoy the spa-like primary bathroom with granite countertops, cherrywood vanity and stone-like decorative floor to ceiling tile shower. The screened porch is perfect for relaxing, grilling and entertaining. The large backyard offers plenty of space to build your dream pool and/or store your boat/RV/quad/golf cart. Additional highlights include: New roof 2021, A/C 2019, re-plumbed 2021, fully painted interior (except the kitchen and primary suite) 2024, fully painted exterior 2023, Ceramic tiles 2024, kitchen and primary bathroom 2016, guest bathroom 2017, double pane windows 2016, water heater 2014 and screened porch 2021. Located in sought after Seminole County Winter Park just blocks from Lake Howell High School and minutes to shopping, entertainment, UCF and 417. Don't pass up on this one, schedule a showing today.

3031 Moss Valley Place, Winter Park

$350,000
3 Beds 2 Baths Villas Of Casselberry Ph 3 SubDv. 32792 Zip Code
Multiple Offers, PLEASE SUBMIT YOUR BEST OFFER BY MONDAY 8/26/2024 AT 12pm EST (NOON). This beautifully maintained 3-bedroom, 2-bathroom home offers outstanding curb appeal with meticulously landscaped grounds and stunning Crepe Myrtle trees. As you approach, you'll appreciate the attention to detail, including commercial-grade gutters and a Rain Bird irrigation system that keeps the landscaping vibrant year-round. Step inside to discover vaulted ceilings throughout, enhancing the spacious feel of this home. The neutral paint palette and abundance of natural light create a warm and inviting atmosphere. The functional kitchen features stainless steel appliances (updated in 2021), glass block accents, and a convenient passthrough window to the living room. The primary suite is a private retreat with a spacious walk-in closet, ceiling fan, and sliders leading to the 27' x 9' screened-in lanai, perfect for outdoor entertaining or relaxing in the serene environment. The primary en-suite bath has been updated with a new vanity and features new “wood-look” plank tile flooring and a stand-up shower. This home is equipped with modern conveniences including a fire suppression system, pre-wiring for an alarm system, and a new front door handle and lock. Additional features include a 1-car garage, a washer & dryer, and a BRAND NEW roof, 2023 HVAC system, and 2020 plumbing. Your low monthly HOA fee allows you access to a community pool and a serene lake with a covered dock and gazebo, perfect for relaxing or socializing. This location puts you in close proximity to Downtown Winter Park, Park Avenue, Rollins College, Full Sail University, UCF, and Valencia College. Easy access to 436 with plenty of shopping, dining, and entertainment options are just minutes away. This home is a true gem, combining thoughtful updates, prime location, and a warm, welcoming atmosphere. Don’t miss the opportunity to make it yours! ROOF - 2024, HVAC - 2023, PLUMBING - 2020, ELECTRIC - 1994.

3379 Hamlet Loop, Winter Park

$400,000
4 Beds 2 Baths Park Green SubDv. 32789 Zip Code
Under contract-accepting backup offers. Welcome home! This meticulously maintained townhome that DOES NOT SHARE WALLS!! This property offers the perfect blend of comfort and style. Step inside to find beautiful tile flooring throughout the main floor, entrance, and screened porch, complemented by plush carpeting on the staircase, loft, and upstairs bedroom. The kitchen is a chef's delight, featuring sleek quartz countertops, while the bathrooms boast durable Corian surfaces. With 10 ceiling fans thoughtfully placed throughout the house, including the garage and screened porch, you'll stay cool year-round. The home also features a new AC and roof, both just 3 years old, ensuring peace of mind for years to come. Safety is a priority with 2 hardwired smoke detectors and access panels to both showers. The upstairs bedroom is a private retreat, offering 2 spacious closets. Enjoy great savings with bulk Spectrum cable and internet included in the HOA fees. Additional features include an extra refrigerator in the garage, a water softener, and curtains for the screened porch. The outdoor spaces are just as impressive, with pavers in the front and back yards and a middle walkway between houses. The privacy-fenced backyard, adorned with a jasmine vine, offers a serene escape. Security is top-notch with a comprehensive system including window and door sensors and 4 security cameras, monitored by Orlando Security Center. The home was re-piped in 2023 and boasts Hardee board siding with Tex Cote paint, ensuring durability and curb appeal. With no rear neighbors and 3 gates (one at the front and two in the back), this home provides the perfect blend of privacy and convenience. The decorative front iron security door adds a touch of elegance to this already stunning property. Don't miss out on this exceptional home—schedule your showing today!

1236 Park Green Place, Winter Park

$369,000
4 Beds 2 Baths Woodcrest Unit 5 SubDv. 32792 Zip Code
Come see this charming 4/2 home in highly sought after Winter Park! Tucked away in a quiet neighborhood nestled between tall oak trees with NO HOA feels and plenty of space to grow. This adorable home has a master bedroom with 3 additional quaint bedrooms that can also be used for a home office, nursery, art room etc.! The dining room opens to a large living room space with natural lighting from large glass doors and ceiling fan in dining for nice ventilation and additional lighting. The kitchen has a lovely large window with natural light overlooking the huge back yard, wooden cabinets and nice tile flooring which runs throughout the dining and living room areas for easy cleanups. Showers in both the master and hallway bathrooms have newly remodeled. In addition to the one full car garage it boasts a large screened backyard porch providing additional living and/or entertainment space. The large fully fenced in backyard is a great play area for family and/or pets. It also provides ample opportunity for a home addition, pool or use the land to park your boat or a large RV. Roof and AC are 4-5 years old, inside and outside are freshly painted. Located in an A rated school district. Enjoy the convenience of being just minutes away from Rollins College, Park Avenue, Full Sail and the Orlando area via 417 and 436. This home is a perfect blend of convenience and charm with room to expand into the home of your dreams.

7439 Grand Avenue, Winter Park

$314,900
3 Beds 2 Baths Windward Square Sec 2 SubDv. 32792 Zip Code
Welcome to Winter Park with this lovely 3 bedroom 2 bath Townhome. It has been meticulously and tastefully renovated with new tile flooring in the Living Room, Kitchen, Bathrooms and hallways. Here’s what you’ll love about this home: Brand New Roof and Electrical Panel in August 2023, newly remodeled open concept layout floor plan. Enjoy sleek New appliances, Dishwasher, Stove, Refrigerator, Microwave, Brand new Contemporary cabinetry, and stylish quartz countertops all installed September 2023. Elegant newly renovated Bathrooms: Freshly renovated to provide a spa-like experience with modern fixtures and finishes. Vaulted Ceilings: Adding an airy and spacious feel to the living areas, enhancing the overall ambiance of the home. Open air atrium that brings in natural light throughout the house. And go ahead and look, but you won’t find one that has this large of a covered back screened porch with a outdoor flower garden and a fountain view. Also, there is a small front patio that can add to the outdoor living space. This unit is one of only a few that provide a Covered Carport parking to keep two cars out of the hot Florida sun. Located in desirable Winter Park neighborhood, offering convenience to local amenities, parks, and schools. Don’t miss out on this exceptional opportunity to own a home that combines contemporary updates with classic charm. Schedule your viewing today and discover all that 2641 Cayman Way provides!

2641 Cayman Way, Winter Park

$370,000
3 Beds 2 Baths Eastbrook Sub Unit 06 SubDv. 32792 Zip Code
Don't miss the opportunity to own your home in one of Winter Park's top-rated school districts! This property's backyard is oversized. The roof was installed in 2011, a NEW ELECTRICAL PANEL installed in 2015, and a NEW AC with UV light added in 2015. Newer water heater and water treatment! The windows in the house have also been updated. The backyard has been cleared by the homeowner and it's ready for your touch! There is a storage shed and the yard is FENCED. There's lots of patio space for entertaining or grilling. A stainless steel refrigerator and dishwashing machine have been added to the kitchen inside. The front patio garden is visible from a window above the sink, and SKYLIGHTS allow for an abundance of natural light There is also plenty of cabinet space, including unique cabinets that can be pulled down to reveal countertop appliances or pulled up for storage. There is a dining area off the kitchen with a large window overlooking the side yard. The original TERRAZZO floors are unique and add character to the main living areas. The living room is approximately 19x14 feet in size and has many windows as well as a large sliding glass door that looks out onto the beautiful backyard. The washer and dryer come with the sale. This home is close to popular Park Avenue, Rollins College, Full Sail University, the Cady Way Trail, and the Winter Park chain of lakes. Shopping, entertainment, dining, and other amenities are also available just outside the Eastbrook.

1656 Peruvian Lane, Winter Park

$324,900
3 Beds 2 Baths Cedarwood Village 1 SubDv. 32792 Zip Code
Welcome to your dream home in beautiful Winter Park, Florida! This charming 3-bedroom, 2-bathroom corner unit is perfectly situated within walking distance to a shopping center, providing convenience at your doorstep. Step inside to discover a meticulously maintained home featuring a brand new roof (2023), along with a new thermostat and fan installed in 2024. Enjoy optimal comfort with newly installed AC ducts and insulation from 2023. The entire home boasts fresh paint, brand new flooring, and two newly redone skylights in the living room, filling the space with abundant natural light. The kitchen is a chef’s delight with a brand new Whirlpool stainless steel refrigerator, a sleek black top range, a dishwasher, and dual sinks. Laundry is a breeze with a Whirlpool washer and dryer included. The primary bathroom has been updated with new tiles, safety bars, and stylish Moen faucets for a touch of modern elegance. The spacious rooms offer flexibility, with one room easily convertible into an office or den to suit your needs. Located in an area with top-rated A schools, this home is perfect for families. As a corner unit, it offers extra privacy and tranquility. Plus, with lawn maintenance included, you’ll never have to worry about cutting grass again. Enjoy the wonderful amenities this community has to offer, including resurfaced tennis courts, a recently resurfaced pool, and a clubhouse. Additionally, the home features a rear screened-in porch, perfect for relaxing and enjoying the outdoors without any hassle. Don’t miss the opportunity to make this move-in ready gem your own! Schedule a viewing today and experience the perfect blend of comfort, convenience, and contemporary living.

2384 Sun Valley Circle, Winter Park

$399,999
2 Beds 1 Baths Lake Killarney Condo SubDv. 32789 Zip Code
FULL LAKE FRONT VIEW, ONE OUT OF 6 UNITS WITH BEST VIEW IN LAKE KILLARNEY CONDO! Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability). Assigned parking space, community storage & mail just outside the back door. Walk to Trader Joe's, Hillstone's, Winter Park Village, Publix, movies, restaurants, shopping, etc. Bike or walk to Downtown Winter Park and Sunrail. Fully renovated unit with extra care to space planning. o Highest ceilings in the community. Solid bamboo wood flooring. Recessed lights. Surround sound & TV mount . Textured walls & ceiling . Custom trim . 4 panel sliding glass and transom windows looking over lakeview & lawn . Large renovated kitchen with glass tower cabinets . Drink bar and large island . Granite counters . Stainless steel appliances. Downlighting, under & over cabinet lighting o stainless steel appliances. End your day enjoy the lake views while making dinner. Shower cubbies & candle cubbie for baths . Italian space enhancing vanity . Upgraded fixtures . Frame mirrored medicine cabinet for hidden extra storage o Custom expanded master closet system. Community amenities include o Lakefront dock with boat slips o Private boat ramp o Lakeside pool & large lawn with Adirondacks o Grills & picnic tables o Paddle board / canoe / kayak racks o Bass fishing . Bike racks, shuffleboard . Assigned Parking space just outside the door . Storage Space o Gym, laundry rooms, community storage, and recycling. **Furniture is not inlcuded in the listing price**

151 N Orlando Avenue Unit 131, Winter Park

$399,999
4 Beds 2 Baths Eastbrook Sub Unit 8 SubDv. 32792 Zip Code
NEW PRICE!!! NEW ROOF!!! NEW HVAC!!! This established and desirable Winter Park neighborhood enjoys access to the excellent, top-rated Seminole County schools, with an elementary school just a half-mile away. Step into this welcoming, freshly painted Eastbrook home and be dazzled by the beautiful wood floors throughout the spacious living areas and bedrooms. To your right is the formal living room which flows easily into the dining room, and then into the galley-style kitchen, which features a gas stove. From the entry foyer you could go straight back to the large family room, with sliding glass doors into the HUGE Florida room. The Florida room overlooks a large, fenced back yard with tall, stately oak trees and mature landscaping. This is a great house for entertaining family and friends, with a circular flow connecting the living areas, kitchen and then the Florida room. The three secondary bedrooms are accessed from the family room, and share a bath. The primary bedroom is entered from the dining room, and enjoys the peace and privacy of being away from the family room and other bedrooms. This bedroom features a generous closet and en suite bath. The double garage has a spacious alcove for the washer and dryer. The gas water heater is also located there. The new HVAC is a 15-SEER Carrier heat pump, split system. This Winter Park location offers easy access to all major arteries, including the 417, the 408 and I-4. Don’t miss your chance to move into this Winter Park home and enjoy the complete peace of mind knowing you can just move right in and unpack your bags..

2437 Eastbrook Boulevard, Winter Park

$389,000
3 Beds 1.5 Baths Albert Lee Ridge SubDv. 32789 Zip Code
Under contract-accepting backup offers. Welcome to 2028 Albert Lee Parkway, located in the heart of Winter Park, FL. This home provides many updates including a newer roof and septic system installed in 2020, and also updated electrical panel installed in 2024. This large, open, one-story home, with extra living & storage space, large front porch and large covered patio in the back yard, is situated in a vibrant and desirable community, ideal for those seeking a blend of peaceful living and urban convenience. Nestled in a charming neighborhood, this property offers a tranquil setting with tree-lined streets. Winter Park is known for its historic charm, parks, and cultural richness. Enjoy the natural beauty of nearby Lake Baldwin, perfect for walks, jogs, dog park or picnics. Shopping & dining, Just minutes away from Park Avenue, you'll find an array of boutique shops, restaurants, and cafes. Close to Mead Botanical Garden and other local parks, providing opportunities for outdoor activities. The nearby Cady Way Trail is great for biking and hiking. Top-rated schools are within easy reach. You can also explore local museums, theaters, and art galleries nearby. Convenience, with easy access to major highways makes commuting to downtown Orlando and surrounding areas convenient. The Winter Park SunRail station is also close, offering public transportation options. This property offers a lifestyle of community and accessibility. Don’t miss the opportunity to make this property your own! For more information or to schedule a private showing, contact us today.

2028 Albert Lee Parkway, Winter Park

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