2,243

Rolling Hills Homes

Section Image
  • /39

    $229,990 Pending

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    920 Kings Estate Rd, Saint Augustine, FL 32086

    Under contract-accepting backup offers. Welcome to 920 Kings Estate Rd in St. Augustine—an updated and well-maintained 2-bedroom, 1-bath home offering exceptional value andfuture upside. Situated on an oversized corner lot of nearly half an acre, this property provides ample room for storage, expansion, orcustomization to suit your needs. The home features a durable metal roof and has

    Viral Doshi, PA. AMETHYST PROPERTY ADVISORS LLC

    920 Kings Estate Rd, Saint Augustine, FL 32086
  • /40

    $345,000 Sold Feb 02, 2026

    421 Chamberlain Dr, Saint Augustine, FL 32086

    • 3 Beds
    • 2 Baths
    • 1,335 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $258/SF
    • 93 Days On Market

    Current Estimated Value $339,929

    Last Listing Agent Paul Wenglowsky Keller Williams Realty Atlantic Partners St Augustine

    421 Chamberlain Dr, Saint Augustine, FL 32086
    • /33

      Est $326,226 Not Listed For Sale

      228 Ashby Landing Way, Saint Augustine, FL 32086

      • 3 Beds
      • 2 Baths
      • 1,463 Sq Ft
      • Built 2017
      228 Ashby Landing Way, Saint Augustine, FL 32086

      Last Sold Summary

      • 7% Below List Price
      • $239/SF
      • 3 Days On Market
      • Last Sold Price $350,000
      • Aug 14, 2023

      Last Listing Agent Chloe Goble MAXREV, LLC

  • /30

    $199,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    2665 Hispanola Ave, Saint Augustine, FL 32086

    Fresh, clean, and completely move-in ready! This 2-bedroom, 2-bath home in beautiful St. Augustine sits on a spacious lot in a fantastic location. Inside, you'll love the freshly painted interior, new flooring (no carpet), updated ductwork, and natural light from newer skylights. The durable metal roof adds long-term peace of mind. Enjoy indoor-outdoor living with a large glass-enclosed cooled

    Bailey Martin STA SUNRISE REALTY

    2665 Hispanola Ave, Saint Augustine, FL 32086
  • /58

    $430,000 Sold Mar 04, 2026

    228 Fox Water Trail, St. Augustine, FL 32086

    • 4 Beds
    • 2 Baths
    • 2,067 Sq Ft
    • Built 2018

    Last Sold Summary

    • 1% Below List Price
    • $208/SF
    • 17 Days On Market

    Current Estimated Value $432,084

    Last Listing Agent Ciara Ward RE/MAX BLUE COAST

    228 Fox Water Trail, St. Augustine, FL 32086
    • /31

      Est $342,331 Not Listed For Sale

      252 Ashby Landing Way, Saint Augustine, FL 32086

      • 3 Beds
      • 2.5 Baths
      • 2,090 Sq Ft
      • Built 2018
      252 Ashby Landing Way, Saint Augustine, FL 32086

      Last Sold Summary

      • 1% Below List Price
      • $166/SF
      • 4 Days On Market
      • Last Sold Price $346,000
      • Dec 11, 2024

      Last Listing Agent DJ DellaSala DJ & Lindsey Real Estate

  • /17

    $170,000

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    420 S Villa San Marco Dr Unit 304, Saint Augustine, FL 32086

    Relax in this well-kept 2-bedroom, 2-bath condo at Villa San Marco. The open layout with a smart split floor plan gives you plenty of space to relax or entertain. You'll love the private enclosed balcony -- perfect for morning coffee or unwinding with friends. Low HOA fees cover water, sewer, and garbage, so you can focus on what matters most. Plus, you're just minutes from shopping, dining,

    AARON MCMENAMY FLORIDA COASTAL JACKSONVILLE

    420 S Villa San Marco Dr Unit 304, Saint Augustine, FL 32086
  • /30

    $234,900 Sold Jan 09, 2026

    187 Whitland Way, Saint Augustine, FL 32086

    • 2 Beds
    • 2.5 Baths
    • 1,211 Sq Ft
    • Built 2018

    Last Sold Summary

    • $194/SF
    • 6 Days On Market

    Current Estimated Value $233,800

    Last Listing Agent Brad Barfield One Sotheby's - Downtown

    187 Whitland Way, Saint Augustine, FL 32086
    • /55

      Est $444,939 Not Listed For Sale

      638 Deer Crossing Rd, St. Augustine, FL 32086

      • 4 Beds
      • 2 Baths
      • 1,981 Sq Ft
      • Built 2018
      638 Deer Crossing Rd, St. Augustine, FL 32086

      Last Sold Summary

      • 5% Below List Price
      • $237/SF
      • 19 Days On Market
      • Last Sold Price $469,000
      • Mar 01, 2024

      Last Listing Agent Brittany Licari REALTY EXCHANGE, LLC

  • /7

    $189,000

    • Land
    • 1.23 Acres
    • $153,659 per Acre

    00 Kings Estate Rd, Saint Augustine, FL 32086

    Vacant Lot in St. Augustine – Close to the Historic District! An opportunity to build your dream home on this vacant lot located just moments away from St. Augustine's historic district. This lot offers a perfect blend of serene living and vibrant city life, making it an ideal spot for your future home. Situated in the heart of St. Augustine, this lot is just a short drive from the historic

    howard hughes Coastal Realty Pros LLC

    00 Kings Estate Rd, Saint Augustine, FL 32086
  • /50

    $368,000 Sold Sep 05, 2025

    222 Green Turtle Ln, St. Augustine, FL 32086

    • 3 Beds
    • 2 Baths
    • 1,729 Sq Ft
    • Built 2015

    Last Sold Summary

    • $213/SF
    • 20 Days On Market

    Current Estimated Value $374,962

    Last Listing Agent Scott Hum RE/MAX SPECIALISTS

    222 Green Turtle Ln, St. Augustine, FL 32086
    • /33

      Est $391,640 Not Listed For Sale

      598 Deer Crossing Rd, St. Augustine, FL 32086

      • 4 Beds
      • 2 Baths
      • 1,797 Sq Ft
      • Built 2018
      598 Deer Crossing Rd, St. Augustine, FL 32086

      Last Sold Summary

      • 4% Below List Price
      • $226/SF
      • 72 Days On Market
      • Last Sold Price $407,000
      • Feb 16, 2024

      Last Listing Agent Matthew Territo KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE

  • /26

    $374,900

    • 3 Beds
    • 2 Baths
    • 1,546 Sq Ft

    153 Little Owl Ln, Saint Augustine, FL 32086

    A wonderful neighborhood with nice amenities at an affordable price. Ten years young. 3BR/3BA gently lived in home. Beautiful wood look tile encompasses the main living areas and master bedroom. Large master bath with walk in shower; double oversized vanity and walk in closet. The split floor plan provides the two guest bedrooms and bath their own privacy space. Formal dining is located adjacent

    Jane Wolfe Coldwell Banker Premier Properties (A1A Beach)

    153 Little Owl Ln, Saint Augustine, FL 32086
  • /25

    $375,000 Sold Mar 26, 2026

    709 Deer Crossing Rd, Saint Augustine, FL 32086

    • 4 Beds
    • 3 Baths
    • 1,925 Sq Ft
    • Built 2016

    Last Sold Summary

    • 10% Below List Price
    • $195/SF
    • 129 Days On Market

    Current Estimated Value $386,437

    Last Listing Agent Lorraine Manna Exp Realty

    709 Deer Crossing Rd, Saint Augustine, FL 32086
    • /2

      Est $124,495 Not Listed For Sale

      2365 Dobbs Rd, Saint Augustine, FL 32086

      2365 Dobbs Rd, Saint Augustine, FL 32086

      Last Sold Summary

      • 25% Below List Price
      • 7 Days On Market
      • Last Sold Price $165,000
      • Jan 28, 2025

      Last Listing Agent Justin Noe AGILE GROUP REALTY

  • /19

    $1,100,000

    • Land
    • 5.09 Acres
    • $216,110 per Acre

    0 Rolling Hills Dr Unit 260130, St. Augustine, FL 32086

    5 Acre Parcel with Flexible Use. Opportunity to acquire a 5-acre parcel in a rapidly expanding area of St. Augustine, located adjacent to Epic Village and surrounded by continued commercial and residential growth. With convenient access to SR-207, US-1, and SR-312, this property offers excellent long-term potential. The parcel is currently zoned Open Rural (OR), which allows for a wide range of

    Amy Taylor Endless Summer Realty

    0 Rolling Hills Dr Unit 260130, St. Augustine, FL 32086
  • /45

    $210,000 Sold Aug 27, 2025

    91 Whitland Way, Saint Augustine, FL 32086

    • 3 Beds
    • 2.5 Baths
    • 1,499 Sq Ft
    • Built 2017

    Last Sold Summary

    • 16% Below List Price
    • $140/SF
    • 3 Days On Market

    Current Estimated Value $251,874

    Last Listing Agent Ali Burchfield Watson Realty Corp (A1A)

    91 Whitland Way, Saint Augustine, FL 32086
    • /44

      Est $260,000 Not Listed For Sale

      27 Buckley Ct, Saint Augustine, FL 32086

      • 2 Beds
      • 2 Baths
      • 1,341 Sq Ft
      • Built 2017
      27 Buckley Ct, Saint Augustine, FL 32086

      Last Sold Summary

      • $194/SF
      • 33 Days On Market
      • Last Sold Price $260,000
      • Apr 10, 2025

      Last Listing Agent Justin Petrucci Beach State Realty

  • /29

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,505 Sq Ft

    725 Cypress Rd, Saint Augustine, FL 32086

    Rare opportunity in St. Augustine Beach! Enjoy over 1.5 acres of partially cleared, lushly landscaped land with no HOA, a true find this close to the coast. Tucked away on a quiet street with only 10 homes, this property offers privacy, space, and endless potential. Property highlights are this 3 Bedrooms, 2 Bathrooms, 1,500+ sq ft home. Two 12x30 ft sheds with electricity — ideal for a workshop,

    Marian Schneider RE/MAX PRIME PROPERTIES

    725 Cypress Rd, Saint Augustine, FL 32086
  • /32

    $185,000 Sold Mar 06, 2026

    410 S Villa San Marco Dr Unit 106, Saint Augustine, FL 32086

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft
    • Built 2004

    Last Sold Summary

    • $171/SF
    • 13 Days On Market

    Current Estimated Value $198,724

    Last Listing Agent Trudy Padilla KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE

    410 S Villa San Marco Dr Unit 106, Saint Augustine, FL 32086
    • /29

      Est $274,353 Not Listed For Sale

      81 Buckley Ct, Saint Augustine, FL 32086

      • 3 Beds
      • 2.5 Baths
      • 1,499 Sq Ft
      • Built 2017
      81 Buckley Ct, Saint Augustine, FL 32086

      Last Sold Summary

      • 16% Below List Price
      • $217/SF
      • 14 Days On Market
      • Last Sold Price $325,000
      • Oct 30, 2023

      Last Listing Agent DJ DellaSala DJ & LINDSEY REAL ESTATE

  • /28

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    127 Ashby Landing Way, Saint Augustine, FL 32086

    Beautiful 3/2 Waterfront Ranch Home. Built in 2017 and looks NEW inside and out. Located in the Sub of Ashby Landing. Fantastic LOCATION very close to Shopping, Restaurants, Theater, Schools, and More! Water fountain is located directly behind home with perfect view and gentle sound. Recently outside paint, seamless gutters, sealed foundation. Ceiling Fans throughout. Cathedral ceiling in Great

    JIM WAULDRON Coldwell Banker Premier Properties (A1A Beach)

    127 Ashby Landing Way, Saint Augustine, FL 32086
  • /80

    $359,000 Sold Mar 24, 2026

    157 N Churchill Dr, Saint Augustine, FL 32086

    • 2 Beds
    • 2 Baths
    • 1,508 Sq Ft
    • Built 2006

    Last Sold Summary

    • 2% Below List Price
    • $238/SF
    • 53 Days On Market

    Current Estimated Value $356,494

    Last Listing Agent Andrew Birchall Birchall and Company Real Estate

    157 N Churchill Dr, Saint Augustine, FL 32086
    • /48

      Est $377,569 Not Listed For Sale

      309 Mystic Castle Dr, Saint Augustine, FL 32086

      • 3 Beds
      • 2 Baths
      • 1,511 Sq Ft
      • Built 2011
      309 Mystic Castle Dr, Saint Augustine, FL 32086

      Last Sold Summary

      • $250/SF
      • 12 Days On Market
      • Last Sold Price $377,000
      • Apr 30, 2025

      Last Listing Agent ADRIENNE LORD STAGED TO SELL REALTY

  • /58

    $599,000

    • 5 Beds
    • 4.5 Baths
    • 3,266 Sq Ft

    50 Sandy Palm Trail, St. Augustine, FL 32086

    Stunning 5BR/4.5BA 2024-built home! Featuring modern design, spacious layout and premium finishes throughout. Located in the heart of Saint Augustine near SR 312 & 207! Just 8 minutes to downtown, 12 minutes to the beach, and 4 miles to I-95. Enjoy versatile flex spaces, a gorgeous owner's suite with super shower upgrade, tandem 3-car garage, fully fenced yard, waterfront & conservation views and

    Bethany Gerecke STA REALTY

    50 Sandy Palm Trail, St. Augustine, FL 32086
  • /40

    $160,000 Sold Apr 27, 2026

    2242 Twin Fox Trail, Saint Augustine, FL 32086

    • 3 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • Built 1995

    Last Sold Summary

    • 20% Below List Price
    • $93/SF
    • 76 Days On Market

    Last Listing Agent Beth Robinson Berkshire Hathaway Homeservices Florida Network Realty

    2242 Twin Fox Trail, Saint Augustine, FL 32086
    • /23

      Est $229,706 Not Listed For Sale

      55 Moultrie Village Ln, Saint Augustine, FL 32086

      • 3 Beds
      • 2.5 Baths
      • 1,384 Sq Ft
      • Built 2013
      55 Moultrie Village Ln, Saint Augustine, FL 32086

      Last Sold Summary

      • 2% Above List Price
      • $163/SF
      • 204 Days On Market
      • Last Sold Price $225,000
      • Oct 21, 2024

      Last Listing Agent ALLISON JOHNSTON OPENDOOR BROKERAGE, LLC.

  • /35

    $167,900

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    415 S Villa San Marco Dr Unit 205, Saint Augustine, FL 32086

    **Motivated Seller**Location, Location! This efficient 2 bedroom 2 bath unit shows that it has been well maintained and the highly-desirable Villa San Marco community is a wonderful and meticulously-maintained community as well! Enjoy all the conveniences of resort style living with a clubhouse, pool and gym. Its central location is just minutes to our historic downtown as well as the sugar sand

    Gloria Worley Century 21 St Augustine Properties

    415 S Villa San Marco Dr Unit 205, Saint Augustine, FL 32086
  • /28

    $380,000 Sold Nov 07, 2025

    924 S Garden Lake Dr, Saint Augustine, FL 32086

    • 3 Beds
    • 2 Baths
    • 2,429 Sq Ft
    • Built 2007

    Last Sold Summary

    • 5% Below List Price
    • $156/SF
    • 126 Days On Market

    Current Estimated Value $380,222

    Last Listing Agent Caitlin Daugherty One Sotheby's Int (A1A Beach)

    924 S Garden Lake Dr, Saint Augustine, FL 32086
    • /19

      Est $223,357 Not Listed For Sale

      61 Moultrie Village Ln, Saint Augustine, FL 32086

      • 3 Beds
      • 2.5 Baths
      • 1,384 Sq Ft
      • Built 2013
      61 Moultrie Village Ln, Saint Augustine, FL 32086

      Last Sold Summary

      • 3% Below List Price
      • $166/SF
      • 166 Days On Market
      • Last Sold Price $230,000
      • Nov 12, 2024

      Last Listing Agent ALLISON JOHNSTON OPENDOOR BROKERAGE, LLC.

  • /29

    $169,900 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    410 S Villa San Marco Dr Unit 203, Saint Augustine, FL 32086

    Discover low-stress, low-maintenance living in this clean 2-bed, 2-bath condo in popular Villa San Marco. The open, split bedroom layout keeps the living area bright and usable, with each bedroom having its own full bath for privacy. A screened balcony just off the living room adds extra space for morning coffee, pets, or plants. Monthly costs stay predictable here: the HOA covers water, sewer,

    Trudy Padilla KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE

    410 S Villa San Marco Dr Unit 203, Saint Augustine, FL 32086
  • /17

    $235,000 Sold Apr 09, 2026

    209 Whitland Way, Saint Augustine, FL 32086

    • 2 Beds
    • 2.5 Baths
    • 1,211 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Below List Price
    • $194/SF
    • 26 Days On Market

    Current Estimated Value $242,000

    Last Listing Agent Cole Slate KELLER WILLIAMS ST JOHNS

    209 Whitland Way, Saint Augustine, FL 32086
    • /28

      Est $210,316 Not Listed For Sale

      305 S Villa San Marco Dr Unit 207, St. Augustine, FL 32086

      • 3 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 2004
      305 S Villa San Marco Dr Unit 207, St. Augustine, FL 32086

      Last Sold Summary

      • $167/SF
      • 117 Days On Market
      • Last Sold Price $210,000
      • Jan 21, 2025

      Last Listing Agent Jennifer Hayes COMPASS FLORIDA LLC

  • /35

    $265,000 Under Contract

    • 2 Beds
    • 2.5 Baths
    • 1,341 Sq Ft

    78 Buckley Ct, Saint Augustine, FL 32086

    Welcome to this well-maintained 2 bed, 2.5 bath townhome in the heart of St. Augustine. Featuring a comfortable, functional layout with abundant natural light, this home is ideal for both everyday living and entertaining. Updated LVP flooring runs throughout both upstairs and downstairs for a modern, cohesive feel. The covered patio with additional pavers offers a private outdoor space to relax

    Kelly Rogers COLDWELL BANKER VANGUARD REALTY

    78 Buckley Ct, Saint Augustine, FL 32086
  • /57

    $353,500 Sold Dec 30, 2025

    38 Green Turtle Ln, Saint Augustine, FL 32086

    • 4 Beds
    • 2 Baths
    • 1,916 Sq Ft
    • Built 2016

    Last Sold Summary

    • 29% Below List Price
    • $184/SF
    • 301 Days On Market

    Current Estimated Value $365,513

    Last Listing Agent Shane Radcliff Realty Exchange Commercial/Residential Brokerage

    38 Green Turtle Ln, Saint Augustine, FL 32086
    • /24

      Not Listed For Sale

      2216 Twin Fox Trail, St. Augustine, FL 32086

      • 3 Beds
      • 2 Baths
      • 1,242 Sq Ft
      • Built 1989
      2216 Twin Fox Trail, St. Augustine, FL 32086

      Last Sold Summary

      • $200/SF
      • 60 Days On Market
      • Last Sold Price $248,000
      • Nov 08, 2024

      Last Listing Agent Hanna Pennington MOMENTUM REALTY

  • /39

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,451 Sq Ft

    284 N Churchill Dr, Saint Augustine, FL 32086

    284 N Churchill is the kind of place that just makes life easy. Fully move-in ready and well cared for, with updated flooring and kitchen countertops, vaulted ceilings, and a cozy fireplace that makes the space feel open and inviting. The screened lanai overlooking the pond is perfect for morning coffee or winding down after a beach day. Big-ticket updates are already done too, including a 2018

    Kiara Nicolette Endless Summer Realty

    284 N Churchill Dr, Saint Augustine, FL 32086
  • /33

    $325,000 Sold Sep 02, 2025

    484 Ashby Landing Way, St. Augustine, FL 32086

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 2018

    Last Sold Summary

    • $229/SF
    • 11 Days On Market

    Current Estimated Value $322,525

    Last Listing Agent Diana O'Keefe XCELLENCE

    484 Ashby Landing Way, St. Augustine, FL 32086
    • /18

      Est $373,371 Not Listed For Sale

      71 Sandy Palm Trail, St. Augustine, FL 32086

      • 3 Beds
      • 2 Baths
      • 1,509 Sq Ft
      • Built 2024
      71 Sandy Palm Trail, St. Augustine, FL 32086

      Last Sold Summary

      • 2% Below List Price
      • $254/SF
      • 46 Days On Market
      • Last Sold Price $382,840
      • Sep 30, 2024

      Last Listing Agent Sabrina Lozada PULTE REALTY OF NORTH FLORIDA, LLC.

  • /28

    $229,900 Pending

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    920 Kings Estate Rd, Saint Augustine, FL 32086

    For sale by trustee. Home is freshly renovated on a 0.4 acre lot. Car port as well as RV port. There is a storage unit in the back. Home is currently in a land trust and can be acquired through the trust, subject to existing mortgage. Please bring any offers for consideration

    VIRAL DOSHI AMETHYST PROPERTY ADVISORS LLC

    920 Kings Estate Rd, Saint Augustine, FL 32086

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