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Winter Park and Maitland

Winter Park and Maitland are two neighboring historic towns, well-located just to the north of Downtown Orlando. Winter Park is the most famous area in Central Florida for locals for having its well-known “Park Avenue” downtown district with high-end shopping, award-winning dining, and art galleries. Winter Park has its own chain of lakes with the historic Rollins College and multimillion-dollar homes located along with them, where you can even take a boat tour. The city is diverse in that it has modest, older homes next door to larger, ultra-luxury homes built more recently, which has risen the value of all properties in the area substantially, making it a very hot real estate market. Many buyers opt to renovate these older homes or completely tear them down to build the larger, more luxurious ones due to
the inherent land value.

Maitland is located just north of Winter Park and it too has lakes connected to the famous chain of lakes, with a mix of modest homes and luxury homes. Maitland is famous for its art & history museums, and sports & recreation complexes, such as the RDV Sportsplex. There are several office buildings here too, with many national corporate headquarters located here.

Under Construction. Rare opportunity for affordable new construction in Winter Park!  Construction has commenced!  You will love the convenience of being in the hub of activity near Advent Health, UCF Downtown Campus, Dr. Phillips Center, shopping and restaurants!  Park Avenue, Historic Dubsdread Golf Course, and the future Packing District are all within a 3-mile radius of this brand-new construction.  Watch your home being built from the ground up in one of the most desirable locations in Central Florida.  Price includes base price of home, lot, structural and designer upgrades.  Don't miss this amazing opportunity! Enjoy the benefits of a brand-new home, such as our 1-2-10 warranty and brand-new finishes. This new home packs quite a punch featuring 5-bedrooms, 3 full bathrooms, and a two-car detached garage. Contact our new homes specialist for more information on this specific home or to schedule an appointment.  Two brand new homes are being build side by side by Domain Homes and on track for a 2022 close! $789,990 Active

25 Stymie Place Winter Park, Florida

5 Beds 3 Baths 2,327 SqFt 0.150 Acres

Under Construction. Rare opportunity for affordable new construction in Winter Park!  Construction has commenced! Park Avenue, Historic Dubsdread Golf Course, and the future Packing District are all within a 3-mile radius of this brand-new construction.  PRIME LOCATION and a convenient commute to dining, shopping and entertainment!  Watch your home being built from the ground up in one of the best locations in Central Florida.  Price includes base price of home, lot, structural and designer upgrades.  Don't miss this amazing opportunity! Enjoy the benefits of a brand-new home, such as our 1-2-10 warranty and brand luxury finishes. Contact our new homes specialist for more information on this specific home or to schedule an appointment. $784,990 Active

27 Stymie Place Winter Park, Florida

5 Beds 3 Baths 2,327 SqFt 0.150 Acres

Incredible opportunity in the Heart of Winter Park. This charming 3 bedroom, 3 bath garden cottage is ready to be moved-in, renovated, or be the perfect site for your future dream home. Set back on one of Winter Park’s most popular drives, the home sits on an oversized 66x138 lot within walking distance to Lake Knowles, The Vias, and the Winter Park Racquet Club. Originally built in 1952 this bungalow has great bones and still features the original hardwood floors.  The open layout offers two bedrooms, two baths, the living/dining room, and kitchen at the front of the home. At the back is a very large 3rd bedroom with full bath and a separate entrance, which was previously added onto the home. If you don’t need a 3rd bedroom that’s okay, the space is well-suited to be used as a second tv room, playroom, home office or even an in-law suite. Landscaped and manicured to perfection the home takes full advantage of it’s curb appeal and is complimented by privacy hedging, stepping stones, gravel garden beds, fruit trees, tropical flowers, and even a playset with a swing, slide, and rock climbing wall. Additional highlights for this home include a new roof (2021), gated front courtyard, and circular drive. Zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High. $775,000 Active

1822 Temple Drive Winter Park, Florida

3 Beds 3 Baths 2,079 SqFt 0.210 Acres

Three bedroom, two full bath pool home with lake access in Dommerich Estates!  Situated on a corner lot with beautiful wood floors throughout, renovated kitchen with stainless steel appliances, quartz countertops, solid wood cabinetry, and a spacious dining room off the kitchen with large windows overlooking the backyard.  Bright and spacious living room with wood burning fireplace, cozy sitting area, and an even larger family room/bonus room with built-in shelves.  En-suite master suite offers two closets, shiplap, en-suite bath with pedestal sink and shower.  Updated hall bath with shower/tub serves the two additional bedrooms.  There is a flagstone sitting area and a brick paver pool deck that offer a relaxing atmosphere after a busy day.  The exterior of the home was just painted, double pane energy efficient windows throughout, replumbed, and an inside utility room with built-in shelving.  Take advantage of the optional HOA to have access to the neighborhood lake lot with a private boat ramp on Lake Minnehaha which feeds into the Winter Park Chain of Lakes!  Zoned for the best schools - Dommerich, Maitland Middle, and Winter Park High! $645,000 Active

1721 Cheyenne Trail Maitland, Florida

3 Beds 2 Baths 1,943 SqFt 0.220 Acres

Enter the Foyer that expresses character, comfort and a welcoming feeling is the perfect room to set the tone for this amazing home. Open floor plan with a Family room and dining room combo. Completely renovated kitchen with Wellborn maple cabinetry with 3 zone LED lighting, beautiful 36” Farm sink, granite counter tops, stainless steel appliances, cooktop, in wall oven and microwave, and porcelain tile flooring that looks like wood. Walk in pantry with custom 10 pane glass door with antique knob. Great room is spacious with built in shelving. Inside laundry with tile floors, large sink, quartzite counter tops, under cabinet LED lighting, Wellborn cabinets and broom closet. You also have enough room for a mud room area. Upgraded wood door to garage with tempered glass. Vaulted ceilings throughout. The Florida room has built in cabinets with granite counter tops. Upper cabinets are glass front with lighting. French door and 3 large windows for lots of natural light and a great view of the pool area and covered patio. Bedroom three off the Florida room had one of the closets converted into a workstation with a desk. Can easily be converted back. The bathroom updated with Wellborn Maple cabinets, dual sinks, quartzite counter tops, porcelain tub, and Carrera tile, and a backlit heated mirror. Primary bathroom renovated with an expansive zero step shower with rainfall shower head and wand. Added eye level windows to shower and separate toilet room. Dual sinks and separate vanity with Silestone counter tops Wellborn cabinetry, non-slip porcelain tile floors and matching walls, and two matching backlit heated mirrors. Adjacent to the Primary bedroom is an amazing Bonus room with double door entry that has 3 windows facing the East viewing the pool for lots of natural light, large custom closet, built in cabinets, oak flooring, and a window seat between bookshelves. The covered pool was converted to salt water in 2014. Energy saving variable speed pool pump was installed in 2014.  Cedar grilling station with an Integral Big Green Egg, copper sink, charcoal bin, and drawers that any grill master would enjoy. Complete privacy with fencing and shrubbery all around. There is a 6’ Utility easement located in the backyard. Cedar potting shed on the West of the home. There are two irrigated raised gardening beds. The two-car garage has large custom built tool cabinets with work surface. Have ample storage over garage door and over workbench. This home is hurricane ready with whole house backup infrastructure with a 12000-Watt propane/gas portable generator and custom hurricane shutters stored in the garage that allow light while protecting windows from damage. Generator powers air conditioner, water heater, and everything else in the home, except the dryer and stove. New roof installed 2020. Trane 5 ton a/c 2016. Rheem 50 gallon hybrid water heater 2015. Energy efficient double pane windows throughout. Infrared reflecting window film on East and West windows. LED can lightning throughout. Plumbing updated in 2020. House has two septic systems grey water and black water) Maitland will be connecting to city sewer in late 2023. New exterior paint 2022.  Septic was inspected and pumped 3 years ago. Sellers had a Home Inspection completed on August 5th.  Summary of inspection is in attachments. $645,000 Active

2523 Chippewa Trail Maitland, Florida

4 Beds 2 Baths 2,510 SqFt 0.210 Acres

Unbeatable location in the heart of Winter Park! This charming town is home to Park Avenue, Winter Park Golf Course, Rollins College, Winter Park Village, a SunRail station, and many unique and modern fine dining and eclectic shopping options. Imagine being able to walk to all that Winter Park has to offer whenever your heart desires and then coming home to a warm and inviting haven tucked away in a shaded lot. Surrounded by mature landscaping, this 3 bedroom, 2 bathroom residence features a well-designed floor plan with elegant finishes and a sun-drenched Florida room. A comfortable living room welcomes you with the formal dining area to the right. A passthrough window peeks into the kitchen, with a counter for bar seating or to serve meals with ease. The gourmet kitchen provides an elegant place to prepare meals boasting granite countertops, stainless steel appliances, single basin sink with pulldown faucet, dark wood cabinetry, and tile backsplash. From the kitchen, step through a French door entry to the sun-washed Florida room. Currently being used as a playroom, this flex space can be converted to a relaxing seating area, game room, or office. An inviting owner’s suite offers a warm haven to retire at the end of the day, boasting a plank ceiling and ensuite bathroom. Two additional comfortable bedrooms and a full bathroom complete the floor plan. Outside, double sliding glass doors lead to a large, fenced backyard with mature trees offering naturally shaded areas. Relax by the fire pit on the paved area on chilly nights. There’s room for a garden, shed, or pool, if you wish! Situated in a fantastic location and zoned for a top rated school district, this lovely home is just waiting for your personal touches. Don’t miss this rare opportunity! $639,000 Active

973 Wilma Avenue Winter Park, Florida

3 Beds 2 Baths 1,000 SqFt 0.170 Acres

1939 home was moved from PARK AVE many years ago. NOW IN MAITLAND bordering WINTER PARK. INCLUDES  1/16 ownership of LAKE LOT. A Must remodel piece of HISTORY with 82 YEARS OF CHARACTER. Arched high ceilings along with a fireplace in the formal living room. Florida room is surrounded by glass sliding doors that open to a wooden patio with French doors, countless windows, gracious screened front porch and additional awning covered porches surrounding the home and huge master bedroom. LARGE DEVELOPERS have purchased most all properties surrounding this 3 BED 2BATH ESTATE. Area across street is transforming to 1ST CLASS  RAVAUDAGE COMMUNITY, LARGE HIGH-RISE LUXURY APARTMENTS, RESTAURANTS AND OFFICES, in one of the most sought after areas. Use your imagination to make this a estate your dream home. 4 football fields distance away, A luxury apartments developer purchases 3 acres 02/22/2021 for $8,905,000.00 that’s $742,000 per 1/4 acre. This is a winning deal. $525,000 Active

113 Gem Lake Drive Maitland, Florida

3 Beds 2 Baths 1,538 SqFt 0.240 Acres

WINTER PARK TOWNHOUSE - This is the perfect home for entertaining.  This well maintained and updated townhome features a light and bright open living room and kitchen area with access to the patio area which has a direct connect gas grill.  Floor to ceiling windows with plantation shutters, slate floors, fireplace and ceiling fan are all part of the living room which opens directly to the kitchen featuring wood cabinets, granite countertops, Thor gas cooking range set in an open breakfast bar.  Two Master Suites with updated bathrooms featuring granite countertops with dual sinks.  Barn door style doors on shower.  Upstairs Master Suite features a garden tub, separate walk-in shower area with door, dual sinks set in a granite countertop.  The third bedroom features doors that lead you to an open balcony. All bedroom closets and hall closets have built in shelving.  New tile roof to be installed.  Please call and ask for a copy of all the upgrades for this home I guarantee you will be impressed. $525,000 Active

970 Aragon Avenue Winter Park, Florida

3 Beds 2 Baths 1,680 SqFt 0.050 Acres

LOCATION LOCATION LOCATION! This lovely Winter Park home has it all and is ready for every lifestyle in this sought after pocket of homes. Baldwin Park Dog Park, and Playground at the end of the street. As close to Baldwin Park as you can get (0.7 miles away from downtown BP along trail) without the added taxes and HOA fees of Baldwin Park. Enjoy the big beautiful trees in the huge corner lot. Beautiful marble counters throughout the kitchen and large island overlooking the open living space. This home is a basketball players dream with custom Basketball half court while still having plenty of fully fenced yard space, PLUS side yard big enough for boat, trailer or vehicle storage! This home is currently set-up as a 2 bedroom 2 bath. Right now the owner uses the Florida room as additional closet space but this space would make a great office or sitting area. There is also a unique basement space which could be a perfect wine cellar, office, workshop, storage or just extra space. There is access to the outside from finished cellar too! This is truly a one-of-a-kind property! $525,000 Active

1843 Barker Drive Winter Park, Florida

3 Beds 2 Baths 1,697 SqFt 0.290 Acres

Location, location, location! Located in trendy Winter Park across from Lake Killarney. This is your opportunity to live the Winter Park lifestyle near Park Avenue and Downtown Winter Park’s cobblestone streets with a fabulous array of eateries, pubs, boutiques, and services all within a 5- minute drive.  With Rollins College nearby, the investment opportunity can’t be missed! Tons of potential:  it can be converted back to a duplex where you could live on one side and rent out the other or multigenerational living or separate MOTHER-IN-LAW SUITE. If you need options with lots of bedrooms for a home-office or gym this one-of-a-kind property is for you! The main part of the property features 4-bedrooms and 2-bathrooms, spacious living room & dining combination plus an enclosed patio and laundry room. The second side of the house contains a living room, kitchenette with dining area, 2-bedrooms and 1-bathroom. NEW in 2021 ROOF, Paint and Carpet. This unique property is ready for your finishing touches.  Fall in love with the huge, fenced back yard that is a gardeners dream or room for the gang to run and play. Less than 10 minutes to Winter Park Village with arts and cultural events, farmers market plus nearby golf courses, parks and lakes.  When you’re ready to adventure out I-4 is five minutes away, Downtown Orlando 15 minutes, and area Theme Parks & Attractions within 30 minutes.  Bring your creativity to this dream location! $519,900 Active

2600 Euston Road Winter Park, Florida

6 Beds 3 Baths 3,145 SqFt 0.280 Acres

** New Roof 5/2022  Plumbing Re-pipe 8/2022** Amazing Location.  Don't miss this Winter Park property before it is gone.  Brand new interior paint. Why rent, when you can own this perfectly, located property. FREESTANDING MIXED USE BUILDING in PRIME WINTER PARK LOCATION (1 Block South of Fairbanks & 2 Blocks West of 17-92). Walking Distance to Shopping Center & Bank. Excellent Access to I-4 & Minutes to Park Avenue, Restaurants, Shopping & Florida Hospital Orlando. Open Reception Area, Very Large Open Office Area, Kitchen/Break Area, 3 Private Restrooms, Storage Areas. Windows in All Offices. Front & Side Entrances to the Building. Building Signage and Street Signage Allowed.  Parking in front Concrete Block Building with Fenced Rear Yard. Well Known Street & Neighboring Properties are Doctor Offices, Lawyer Offices, Interior Designer, Contractors, Financial Co., etc. $499,000 Active

1450 Gene Street Winter Park, Florida

3 Beds 3 Baths 2,080 SqFt 0.170 Acres

Amazing Winter Park/Lake Killarney Location!  Sit on your front porch swing and enjoy the beautifully landscaped yard with Magnolia trees and Almond trees that are in bloom and smell heavenly right now!  Walk into your open and bright living areas with trendy concrete floors, lots of architectural features and a wood burning fire place.  The charming kitchen opens up to the dining area with views of the large fenced backyard. Upstairs you will find three huge bedrooms with wood floors and a separate area that could be used as an office, playroom or fourth bedroom.  All drapes, washer/dryer and furniture stay!  Roof replaced 2018.  View Lake Killarney from your front yard! Easy access to I-4 for commute time. $499,000 Pending

2418 Euston Road Winter Park, Florida

3 Beds 3 Baths 2,048 SqFt 0.270 Acres

*Bring your boat, your RV, your utility trailers, No HOA you may park in the side yard! 4 bedroom 3.5 bath 2 car garage home situated on 1/2 acre in Winter Park!! This is truly a rare and unique find. New roof, water heater, exterior paint, Well maintained has easy care/allergy free ceramic tile flooring throughout and a practical floorplan, great for entertaining! Cozy up next to the fireplace and read a good book. This home has a generator, fire alarm system, and sprinklers.   Great shopping, churches schools and restaurants are close by. In addition, it is convenient to the University of Central Florida, Full Sail University, Rollins College, Oviedo Marketplace, and all of the attractions by way of the 417 expressway. Bike/Jogging trails are nearby as well. Whether your destination is Winter Park, Winter Springs, or Oviedo, this home is in the perfect location for you. $499,000 Pending

1554 Dodd Road Winter Park, Florida

4 Beds 4 Baths 2,110 SqFt 0.500 Acres

This beautiful one-story house is located in the family oriented Tanglewood neighborhood of Winter Park, nestled on a tree-lined street. The home features 4 nice sized bedrooms with all new carpet, 2 updated bathrooms with granite countertop vanities.  An open updated Kitchen features stainless steel appliances and granite countertops. Relax in a spacious living room complete with a fireplace, or a large adjacent bonus room, both with ample windows looking out into the lush, fenced backyard. No details have been overlooked in this ready-to-move-in charming house. A large garage with an attached half bath and laundry area provides plenty of storage options. Located close to shopping and restaurants, this must-see house won't last long. Seller will be putting NEW ROOF on home prior to closing $499,000 Active

1926 Linden Road Winter Park, Florida

4 Beds 3 Baths 1,920 SqFt 0.240 Acres