Homes for Sale near Jenkins Middle School

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  /39

  $899,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,448 Sq Ft

  501 E Oakland Ave, Winter Garden, FL 34787

  One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue

  Erica Diaz HOMEVEST REALTY

  501 E Oakland Ave, Winter Garden, FL 34787
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  /46

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  2690 Bobcat Chase Blvd, Oakland, FL 34787

  Love Where You Live — in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one of Central Florida’s most sought-after communities near Winter Garden, where modern living meets natural serenity. This immaculate 3-bedroom, 2-bath home with a 2-car garage backs to peaceful conservation land—so you’ll enjoy privacy, stunning views, and no rear neighbors. Built in 2019 and cared for like new,

  Marnetta Arnett LPT REALTY, LLC

  2690 Bobcat Chase Blvd, Oakland, FL 34787
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  /3

  $75,000

  • Land
  • 0.11 Acre
  • $681,818 per Acre

  121 S Nixon St, Oakland, FL 34760

  If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

  Ramon Morales SANCTUM REALTY PROFESSIONALS LLC

  121 S Nixon St, Oakland, FL 34760
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  /52

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 2,548 Sq Ft

  1428 Union Club Dr, Winter Garden, FL 34787

  Welcome to Oakland Park, Winter Garden’s premier Golf Cart District — where timeless architecture, front-porch living, and modern design come together just steps from the West Orange Trail and charming downtown Winter Garden. This home exudes curb appeal with its classic front porch that invites you to relax and take in the neighborhood’s vibrant, walkable atmosphere. Inside, the open-concept

  Matt McKee COMPASS FLORIDA LLC

  1428 Union Club Dr, Winter Garden, FL 34787
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  /36

  $268,900

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft

  651 J W Jones Rd, Winter Garden, FL 34787

  *****Sellers motivated! Sellers will consider closing assistance to Buyer(s).***** Welcome Home! Bicyclists and nature lovers will appreciate being just minutes from West Orange Trail. Let the stresses of the day melt away as you step into this beautiful residence in the highly sought-after Winter Garden. Relax on the screened front porch as you soak in the peaceful atmosphere. Inside, the

  David Seeley EXIT REALTY TRI-COUNTY

  651 J W Jones Rd, Winter Garden, FL 34787
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  /17

  $174,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  344 Eron Way Unit 12, Winter Garden, FL 34787

  PRICE DROP!! BUYER MAY BE ELIGIBLE FOR 5% DOWN, NO PMI, SPECIAL 4.75% RATE ON THIS HOME!!! This two bed, two bath villa home offers low maintenance living near downtown Winter Garden. Walk into an open concept living area with two large windows giving plenty of natural light. New floors throughout. The kitchen offers solid wood cabinets, granite, and stainless steel appliances. The primary

  Marcus Moffatt MOFFATT

  344 Eron Way Unit 12, Winter Garden, FL 34787
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  /44

  $675,000

  • 4 Beds
  • 3 Baths
  • 2,650 Sq Ft

  529 Johns Landing Way, Oakland, FL 34787

  Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary

  Denise Pellegrino REAL BROKER, LLC

  529 Johns Landing Way, Oakland, FL 34787
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  /14

  $385,000

  • Land
  • 0.29 Acre
  • $1,327,586 per Acre

  610 Simeon Rd, Oakland, FL 34787

  Presenting a rare opportunity to purchase a 0.29-acre residential lot in the highly sought-after Town of Oakland. This unincorporated property offers exceptional flexibility, no HOA restrictions and agricultural zoning. Conveniently located just steps from the scenic West Orange Trail, the Oakland Nature Preserve, and downtown Oakland. Enjoy the peaceful surroundings amongst the oak trees and

  Blaine Dooley REGENCY REAL ESTATE LLC

  610 Simeon Rd, Oakland, FL 34787
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  /26

  $649,900

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft

  326 Largovista Dr, Oakland, FL 34787

  Welcome to your dream home in the highly sought-after Johns Landing community! This immaculate 4-bedroom, 3-bathroom residence offers a perfect blend of elegance, comfort, and convenience—nestled in the heart of charming Oakland, FL. From the moment you step inside, you’ll be greeted by soaring ceilings, abundant natural light, and an open-concept layout ideal for both entertaining and everyday

  Chris Sanford EXP REALTY LLC

  326 Largovista Dr, Oakland, FL 34787
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  /13

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,010 Sq Ft

  618 Foster Ave, Winter Garden, FL 34787

  Newly renovated INCOME PRODUCING 3-bedroom, 2-bathroom home nestled in the heart of downtown Winter Garden! Hop onto your golf cart or take a few moments' walk towards numerous shops, restaurants, the local farmer's market and all of the other charm that downtown has to offer. This home has been fully renovated with brand new roof, interior paint, luxury vinyl plank flooring, new appliances,

  Jenna Palmero COLDWELL BANKER REALTY

  618 Foster Ave, Winter Garden, FL 34787
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  /35

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  2090 Standing Rock Cir, Oakland, FL 34787

  Price reduced to $585,000 on this Stunning Home in Oakland Trails!This immaculate 3-bedroom, 2.5 bath home blends thoughtful upgrades with a warm, inviting layout. From the moment you walk in, pride of ownership is evident. The bright, open living area features built-in HEOS speakers, perfect for entertainment. The chef’s kitchen will impress with 42" wood cabinetry, granite countertops,

  Tim Boon CREEGAN GROUP

  2090 Standing Rock Cir, Oakland, FL 34787
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  /21

  $610,000

  • 5 Beds
  • 4 Baths
  • 3,903 Sq Ft

  219 Largovista Dr, Oakland, FL 34787

  Investor Special! Located in the highly desirable, gated lakefront community of Johns Landing. This spacious 5-bedroom, 4-bathroom pool home offers nearly 4,000 sq. ft. of living space (excluding garage) and features two upstairs primary suites, additional bedrooms with a loft and bathroom, plus a downstairs guest/in-law suite. The layout also includes formal living and dining rooms, an open

  Gnesa Fray INTERMIX REAL ESTATE INC

  219 Largovista Dr, Oakland, FL 34787
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  /24

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,154 Sq Ft

  711 Burch Ave, Winter Garden, FL 34787

  Welcome to this lovely 3-bedroom, 2-bath home, just minutes from the heart of Downtown Winter Garden. Freshly painted inside and out, with a brand-new kitchen countertop, it feels fresh, modern, and move-in ready. The layout is cozy and practical—perfect for families or anyone looking to enjoy all the charm and convenience of Winter Garden living.One great bonus is the additional room with

  Carina Davis LAKESIDE REALTY WINDERMERE INC

  711 Burch Ave, Winter Garden, FL 34787
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  /56

  $619,900

  • 5 Beds
  • 4 Baths
  • 3,449 Sq Ft

  229 Largovista Dr, Oakland, FL 34787

  **NEW PRICE – MUST-SEE LUXURY POOL HOME!** Prepare to fall in love with this stunning 5-bedroom, 4-bathroom home located in the exclusive gated community of *Johns Landing*. Offering nearly 3,500 sq. ft. of meticulously designed living space, this home is the perfect blend of elegance, comfort, and Florida living at its finest! From the moment you step inside, you'll be captivated by the beauty

  Richard Lokhnauth RL LUXURY REAL ESTATE

  229 Largovista Dr, Oakland, FL 34787
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  /29

  $471,900

  • 4 Beds
  • 2.5 Baths
  • 2,017 Sq Ft

  2435 Standing Rock Cir, Oakland, FL 34787

  Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a turnkey away from being yours! 4 bed, 2.5 bath, the primary bed in the second level. The landscape perfectly accentuates your front porch. Step inside your fully upgraded home; complete with luxury upgrades ranging from lighting, designer finishes, and brand-name appliances. Up the

  Celestino De Cicco CENTRAL FLORIDA REALTY

  2435 Standing Rock Cir, Oakland, FL 34787
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  /15

  $28,900

  • 2 Beds
  • 2 Baths
  • 782 Sq Ft

  560 Royal Oak Dr N Unit 192, Winter Garden, FL 34787

  Fully renovated manufactured home with NEW roof and NEW A/C!!! 2 Bedrooms / 2 Bathrooms, Tile floors throughout, Fresh paint, move-in ready, Large backyard deck, Quiet neighborhood in a great location, Close to downtown Winter Garden, shopping, dining, and hospitals. Priced to sell fast! Message now to schedule a showing! FIRE SALE!!! ONE WEEK ONLY!!!! $40,000!!!! SALE END AUGUST 10 2025!!!!

  Isabel Dalgleish Four Star Homes, Inc.

  560 Royal Oak Dr N Unit 192, Winter Garden, FL 34787
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  /15

  $88,500

  • 2 Beds
  • 2 Baths
  • 1,144 Sq Ft

  1020 Hyde Park Cir Unit 140, Winter Garden, FL 34787

  Spacious 2 Bed, 2 Bath Manufactured Home. Do not miss this opportunity to own a well maintained, move in ready manufactured home in one of Winter Gardens most sought after 55plus gated Community! Features included Large 2 bedroom, 2 bathroom layout, well-maintained interior and exterior, move-in ready condition, located in a quiet, secure, pet-friendly, gated community, convenient to shopping,

  Isabel Dalgleish Four Star Homes, Inc.

  1020 Hyde Park Cir Unit 140, Winter Garden, FL 34787
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  /11

  $895,000

  • Land
  • 1.03 Acres
  • $868,932 per Acre

  529 N Pollard St, Winter Garden, FL 34787

  Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your oasis—a timeless farmhouse, a classic Southern

  Matthew Burks CORCORAN PREMIER REALTY

  529 N Pollard St, Winter Garden, FL 34787
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  /24

  $1,250,000

  • Land
  • 0.82 Acre
  • $1,524,390 per Acre

  552 Walker St, Oakland, FL 34760

  Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your personal oasis—whether that’s a timeless farmhouse, a

  Alexis Anderson REGENCY REAL ESTATE LLC

  552 Walker St, Oakland, FL 34760
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  /3

  $374,900

  • Land
  • 0.24 Acre
  • $1,562,083 per Acre

  1215 Ridge Lake Way, Winter Garden, FL 34787

  LOT 247: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1215 Ridge Lake Way, Winter Garden, FL 34787
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  /3

  $449,900

  • Land
  • 0.23 Acre
  • $1,956,087 per Acre

  1203 Ridge Lake Way, Winter Garden, FL 34787

  LOT 244: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

  Tracey McFadden OAK AVENUE REAL ESTATE LLC

  1203 Ridge Lake Way, Winter Garden, FL 34787
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  /14

  $420,000

  • Land
  • 0.26 Acre
  • $1,615,385 per Acre

  1161 Prado Ln, Oakland, FL 34787

  Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal

  Alexis Anderson REGENCY REAL ESTATE LLC

  1161 Prado Ln, Oakland, FL 34787
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  /58

  $1,899,999

  • 4 Beds
  • 3 Baths
  • 2,535 Sq Ft

  1136 Brick Rd, Winter Garden, FL 34787

  Don’t miss this rare opportunity to own almost 5 acres in the heart of downtown Winter Garden. Privacy at its best yet just a short golf cart ride to downtown for your restaurants retail therapy and fun, YES IT IN THE GOLF CART DISTRICT! 2019 custom built home sits on 4.89 acres of privacy. Two separate driveways lead to this beautiful home. This two-story home currently is a 3 bed 2 bath with

  Alison Wheatley WHEATLEY REALTY GROUP

  1136 Brick Rd, Winter Garden, FL 34787
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  /8

  $69,999

  • Land
  • 0.28 Acre
  • $249,996 per Acre

  0 Killarney Cove Dr, Winter Garden, FL 34787

  This is a group of 3 lots for sale; they can all be purchased or sold individually. They're side by side. The lots have canal access to Lake Apopka. They will need to be cleaned out due to the overgrowth. Right off of highway 50 just minutes to the turnpike onramp for quick access anywhere in the Orlando area. Tax ID 19 22 27 0000 00 043 is first on the left, middle Lot is Tax ID 19 22 27 0000 00

  Carl Mataushek REAL ESTATE FIRM OF ORLANDO

  0 Killarney Cove Dr, Winter Garden, FL 34787
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  /16

  $2,130,760 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,992 Sq Ft

  1146 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Heather Spirazza REGENCY REAL ESTATE LLC

  1146 Prado Ln, Oakland, FL 34787
• 

  

  /17

  $2,238,120 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,204 Sq Ft

  1173 Prado Ln, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

  Alexis Anderson REGENCY REAL ESTATE LLC

  1173 Prado Ln, Oakland, FL 34787
• 

  

  /5

  $2,995,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 5,144 Sq Ft

  312 Briley Ave, Oakland, FL 34760

  Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully

  Carolina Dumit CORCORAN PREMIER REALTY

  312 Briley Ave, Oakland, FL 34760
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  /7

  $1,700,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,909 Sq Ft

  1207 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours

  Chris Herlihy NEW HOMES REAL ESTATE, INC.

  1207 Ridge Lake Way, Winter Garden, FL 34787
• 

  

  /15

  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  1244 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Introducing the Hamlin model by Element Home Builders—a stunning 4,859 square-foot residence designed for luxurious living and modern comfort. With 6 spacious bedrooms and 5.5 beautifully appointed bathrooms, this home offers ample space for families of all sizes and lifestyles.Step inside and experience an open-concept layout that combines elegance with

  Alexis Anderson REGENCY REAL ESTATE LLC

  1244 Water Maple Dr, Oakland, FL 34787
• 

  

  /15

  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  1238 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family living and entertaining. Enjoy seamless transitions between the gourmet kitchen, dining, and living areas, perfect for

  Heather Spirazza REGENCY REAL ESTATE LLC

  1238 Water Maple Dr, Oakland, FL 34787
• 

  

  /15

  $2,175,000 New Construction

  • 5 Beds
  • 8 Baths
  • 4,433 Sq Ft

  1232 Water Maple Dr, Oakland, FL 34787

  Pre-Construction. To be built. Presenting the Citrus plan by Element Home Builders—a spacious home designed for modern living. With 5 bedrooms and 5 bathrooms, and 3 powder bathrooms, this expansive layout provides the perfect combination of comfort, style, and functionality. Every inch of this home is thoughtfully designed to create ample space for both private retreats and vibrant social

  Alexis Anderson REGENCY REAL ESTATE LLC

  1232 Water Maple Dr, Oakland, FL 34787
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  /5

  $1,996,500 New Construction

  • 4 Beds
  • 4 Baths
  • 4,557 Sq Ft

  1258 Ridge Lake Way, Winter Garden, FL 34787

  Pre-Construction. To be built. Welcome 1258 Ridge Lake Way, nestled in the final phase of the sought-after Oakland Park community. This custom-built modern farmhouse by RCB Homes offers a perfect blend of style and comfort. Spanning just under 6,280 square feet, this two-story residence features four spacious bedrooms and four luxurious bathrooms, providing ample space for relaxation and

  Matt McKee COMPASS FLORIDA LLC

  1258 Ridge Lake Way, Winter Garden, FL 34787
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  /46

  $650,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,448 Sq Ft

  634 Burch Ave, Winter Garden, FL 34787

  Seller offering $7,500 towards buyer’s closing costs & pre-paids and/or an interest rate buy-down! Welcome to your dream home - NEW CONSTRUCTION with NO HOA in the heart of Downtown Winter Garden’s GOLF CART DISTRICT - where small-town charm meets modern living. This newly built home is packed with thoughtful design and high-end finishes. Step inside to wide plank luxury vinyl floors, an airy

  Ken Pozek REAL BROKER, LLC

  634 Burch Ave, Winter Garden, FL 34787
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  /15

  $1,975,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  1149 Dr, Oakland, FL 34787

  Pre-Construction. To be built. Welcome to the Clementine Floorplan by Element Home Builders – A Stunning New Home in Oakland's Premier Community!Discover your dream home with the Clementine Floorplan, a thoughtfully designed residence nestled in Oakland's newest, most sought-after community. This spacious, modern home combines elegance, functionality, and comfort to create the perfect

  Blaine Dooley REGENCY REAL ESTATE LLC

  1149 Dr, Oakland, FL 34787
• 

  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,895 Sq Ft

  Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

  AR Homes Builder

  884 Tilden Oaks Trail Unit 37615294, Winter Garden, FL 34787
• 

  $1,675,000 New Construction

  • 5 Beds
  • 5 Baths
  • 4,819 Sq Ft

  166 Hammock Preserve Loop, Oakland, FL 34787

  AR Homes Builder

  166 Hammock Preserve Loop, Oakland, FL 34787
• 

  $1,975,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,596 Sq Ft

  The Clementine Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36498057, Oakland, FL 34760
• 

  $2,175,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,433 Sq Ft

  The Citrus Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36480892, Oakland, FL 34760
• 

  $2,295,000 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,859 Sq Ft

  The Hamlin Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36487597, Oakland, FL 34760
• 

  $2,150,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,388 Sq Ft

  The Blossom Plan at The Grove, Oakland, FL 34760

  Element Home Builders Builder

  15752 E Oakland Ave St Unit 36481095, Oakland, FL 34760

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