# 100 OAK Drive, Annapolis, MD 21403 > **TL;DR:** 4bd/3ba single family, $769,900 ($345/sqft), built 1975, 2,229 sqft. > Fireplace, A/C. Est. $4,143/mo. Listed 74 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $769,900 | | Price/sqft | $345 | | Bedrooms | 4 | | Bathrooms | 3 full | | Square Feet | 2,229 | | Year Built | 1975 | | Lot Size | 12,602 sqft (0.29 acres) | | Stories | 2 | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 74 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $3,893 | | Estimated Insurance | $225 | | HOA | $25 | | **Total** | **$4,143** | ## Key Amenities - Fireplace - A/C ## Property Highlights - Built in 1975 - 0.29 acre lot - 2 stories - 1 parking spaces - Fireplace ## Description ### Agent Description Price Improvement! Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures, and along with a new staircase railing. The inviting fireplace has been refaced on the lower level, creating a stylish focal point in the living space. The home also offers a versatile den/office and a one-car garage. Enjoy Hillsmere's community amenities including private sandy beaches on the South River, a private marina with boat slips and direct access to the South River, boat ramps, waterfront pavilions, a community swimming pool, playgrounds, volleyball courts, and picnic areas. Whether you're boating, kayaking, fishing, or simply taking in the waterfront scenery, this community offers an unmatched coastal lifestyle. Conveniently located just minutes from historic downtown Annapolis, Quiet Waters Park, shopping, and dining, this exceptional home combines extensive recent updates with one of the area's most desirable waterfront communities. Don't miss the opportunity to make this beautifully renovated home your own. ## Location - **Address:** 100 OAK Drive, Annapolis, MD 21403 - **County:** ANNE ARUNDEL - **Neighborhood:** HILLSMERE ESTATES - **Coordinates:** 38.93786, -76.49145 - **Google Maps:** https://www.google.com/maps?q=38.93786,-76.49145 ## Listing Agent - **Name:** Lauren R Dorsey · **License:** 617663 - **Brokerage:** Innovative Properties, Inc. - **Phone:** (410) 268-8400 - **Broker Phone:** (410) 268-8400 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/100-Oak-Dr_Annapolis_MD_21403_M50502-57241?f=listhub&s=TRENDPA&m=MDAA2149498&c=propsimple) ## Photos ![100 OAK Drive - Photo 1](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f1306286480r.jpg) ![100 OAK Drive - Photo 2](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3776016523r.jpg) ![100 OAK Drive - Photo 3](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f704743003r.jpg) ![100 OAK Drive - Photo 4](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f786320076r.jpg) ![100 OAK Drive - Photo 5](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2908899629r.jpg) ![100 OAK Drive - Photo 6](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2928145111r.jpg) ![100 OAK Drive - Photo 7](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f10587534r.jpg) ![100 OAK Drive - Photo 8](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3859205087r.jpg) ![100 OAK Drive - Photo 9](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2652988811r.jpg) ![100 OAK Drive - Photo 10](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2500318745r.jpg) ![100 OAK Drive - Photo 11](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3863715343r.jpg) ![100 OAK Drive - Photo 12](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3753854227r.jpg) ![100 OAK Drive - Photo 13](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f702301091r.jpg) ![100 OAK Drive - Photo 14](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3306260627r.jpg) ![100 OAK Drive - Photo 15](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3664440804r.jpg) ![100 OAK Drive - Photo 16](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2870300289r.jpg) ![100 OAK Drive - Photo 17](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3257059156r.jpg) ![100 OAK Drive - Photo 18](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2368288295r.jpg) ![100 OAK Drive - Photo 19](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3522158669r.jpg) ![100 OAK Drive - Photo 20](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2729029883r.jpg) ![100 OAK Drive - Photo 21](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f19933523r.jpg) ![100 OAK Drive - Photo 22](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2996216792r.jpg) ![100 OAK Drive - Photo 23](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f36572825r.jpg) ![100 OAK Drive - Photo 24](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2618501788r.jpg) ![100 OAK Drive - Photo 25](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f4160746635r.jpg) ![100 OAK Drive - Photo 26](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f1774504420r.jpg) ![100 OAK Drive - Photo 27](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f911206575r.jpg) ![100 OAK Drive - Photo 28](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3702556878r.jpg) ![100 OAK Drive - Photo 29](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3110157020r.jpg) ![100 OAK Drive - Photo 30](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3397720737r.jpg) ![100 OAK Drive - Photo 31](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2908130167r.jpg) ![100 OAK Drive - Photo 32](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2560640318r.jpg) ![100 OAK Drive - Photo 33](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f1539278501r.jpg) ![100 OAK Drive - Photo 34](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f304849980r.jpg) ![100 OAK Drive - Photo 35](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3051007339r.jpg) ![100 OAK Drive - Photo 36](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f471215349r.jpg) ![100 OAK Drive - Photo 37](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2579959249r.jpg) ![100 OAK Drive - Photo 38](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2591622930r.jpg) ![100 OAK Drive - Photo 39](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3802257924r.jpg) ![100 OAK Drive - Photo 40](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f190134652r.jpg) ![100 OAK Drive - Photo 41](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2104720648r.jpg) ![100 OAK Drive - Photo 42](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f1508262742r.jpg) ![100 OAK Drive - Photo 43](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f138397080r.jpg) ![100 OAK Drive - Photo 44](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f519244440r.jpg) ![100 OAK Drive - Photo 45](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f793271801r.jpg) ![100 OAK Drive - Photo 46](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f2735826326r.jpg) ![100 OAK Drive - Photo 47](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3953589124r.jpg) ![100 OAK Drive - Photo 48](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f1722506445r.jpg) ![100 OAK Drive - Photo 49](http://lh.rdcpix.com/ef3e6da442cf3190c04e03d8a5c0889cl-f3089859357r.jpg) --- **MLS#:** MDAA2149498 | **Updated:** 2026-09-16 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/100-oak-drive-annapolis-md-21403-a2149498) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/100-oak-drive-annapolis-md-21403-a2149498#listing", "url": "https://www.propertysimple.ai/listing/100-oak-drive-annapolis-md-21403-a2149498", "name": "100 OAK Drive, Annapolis, MD 21403", "description": "Price Improvement! Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures, and along with a new staircase railing. The inviting fireplace has been refaced on the lower level, creating a stylish focal point in the living space. The home also offers a versatile den/office and a one-car garage. 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