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$576,000
4 Beds ⋅ 4 Baths
Owner Says Sell!!! Make Offer Today!!! Discover your slice of paradise in the heart of Annapolis! This exceptional property combines two complete homes with productive fruit trees, creating the ultimate in flexible living. It is Opened up to be one home but with little work you can close off to make this two separate living areas. Main Home (3BR/2BA): Beautiful hardwood floors flow through the large living room and bedrooms, while the spacious kitchen with Island connects to a separate dining area - perfect fro daily living and entertaining. Three comfortable bedrooms and two full baths complete this well designed space. You can close off addition very easily and make it a true In-Law suite or a nice rental apartment for extra income. In-Law suite Addition (1BR/2BA - 1200 sq ft): This isn't just and addition - It's a complete second home! Features include a large living room, Full eat-in kitchen, bedroom, two full baths, and generous laundry room. The crown jewel? An incredible 8x28 Sunroom with natural gas fireplace - your year round sanctuary with garden views. Separate entrance ensures complete privacy. Step outside to your personal orchard featuring mature pear, apple, cherry, plum and chestnut trees, plus established grapevines. Imagine morning coffee in the sunroom or out the back patio surrounded by blooming fruit trees and harvesting your own fresh produce each season. Entertaining made effortless with a sprawling 650 sq ft deck - perfect for everything from intimate dinners to large gatherings. The outdoor space flows seamlessly with nature's bounty at your fingertips. Two separate driveways ensure privacy and convenience, with circular drive serving the main house (multiple car capacity) and a dedicated 4 - car driveway for the In-law suite. Storage and workspace solved with a generous 12x24 detached garage and 8x14 shed - plenty of room for vehicles, tools, hobbies and seasonal storage. Prime Annapolis location puts you in the heart of Maryland's historic capital where waterfront charm continues to fuel demand and properties remain strong. Just a mile from downtown Annapolis for all your dining and shopping needs. Walk to Truxtun park and the Pip Moyer center that houses a gym, basketball courts, and an indoor track. You can also walk to the newly renovated tennis court and Pickleball courts with lights. Around the corner is the Truxtun park pool, Public Boat ramp and fishing pier.

399 Hilltop Lane, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$480,000
4 Beds ⋅ 3 Baths
Spacious and thoughtfully updated, this 4-bedroom, 2.5-bath single-family home offers comfort, functionality, and modern improvements throughout. Over the past two years, the property has seen numerous upgrades, including a new rear privacy fence, concrete walkway, expansive Trex deck with dual staircases, luxury vinyl plank flooring in the primary bedroom, and an updated walk-in shower on the main level. The large eat-in kitchen serves as the heart of the home and features a wood-burning fireplace, creating the perfect space for gathering and entertaining. The private lower-level primary suite provides a peaceful retreat with added separation from the main living areas. Outside, enjoy the backyard setup and generous off-street parking, offering both convenience and flexibility. With a blend of recent updates, ample living space, and inviting indoor and outdoor features, this home is move-in ready and designed for everyday living and entertaining alike.

209 Garden Gate Lane, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

$395,000
3 Beds ⋅ 1 Baths
A rare opportunity to own a lovingly maintained home in a prime Annapolis location, just minutes from Downtown Annapolis, shopping, dining, waterfront attractions, and major commuter routes. This home has remained in the same family since it was originally built and is being offered to the market for the very first time, showcasing true pride of ownership throughout. Properties with this kind of history and care rarely become available. Inside, you’ll find a fully renovated interior featuring brand new luxury plank vinyl flooring, fresh paint throughout, an upgraded bathroom, and a bright, clean feel from top to bottom. The kitchen includes brand new appliances, including a refrigerator, oven/range, and microwave. A brand new washer and dryer are also included for added convenience. Major system updates provide peace of mind, including an upgraded furnace with an active service contract, replaced electrical panel, and a roof that is less than 10 years old. Outside, enjoy a large yard perfect for entertaining, gardening, or relaxing, complete with a brand new white fence surrounding the yard for added charm, privacy, and functionality. The home also offers a full unfinished basement, providing endless possibilities for storage, workshop space, or future finishing potential. A truly move-in-ready home with modern updates, and a fantastic location in the heart of Annapolis—this is one you won’t want to miss.

114 Roselawn Road, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: .

$380,000
4 Beds ⋅ 2 Baths
Semi-detached residence of 2 homes on over 1/2 acre offers several unique opportunities - live in 1 house and rent the other, rent both homes (#1180 rent $1200 & #1182 rent $850 - both monthly), combine 2 houses - as well as extend the footprint onto 1/2 acre lot, tear down the structure and build new modern home. Built in 1942, 2 structures total 1,364 finished square feet. Both homes are open floor plans with front porches. (Details under rooms is total for both buildings.) Building #1182 is open LR - Kit with wood floors in living room area, 2 BRs have carpet, combo washer/dryer (new Sept 2025). Building #1180 includes table space kitchen with 2 windows, all essential appliances, including dishwasher, spacious sunny (windows on 2 sides) living room - dining room with carpeting, 2 Bedrooms plus attic with windows. Long level backyard offers privacy, gardening and space for outdoor activities, plus storage shed. Located close to all Eastport and downtown Annapolis amenities - marinas, restaurants, parks and pubs, as well as easy access to major highways. Note that legal lot number for both builidngs is #1182, but each building using its own number for convenience.

1182 Tyler Avenue, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$375,000
4 Beds ⋅ 2 Baths
One level living at its finest this rancher offers and updated kitchen with granite tops, On demand gas hot water heater and AC all new in the last year. Primary bath currently being updated, warm pellet stove for those cool winter nights

106 Roselawn Road, Annapolis

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: .

$360,000
2 Beds ⋅ 1 Baths
Welcome to 122 Roselawn Road, a beautifully renovated single-family home in the heart of Annapolis, MD. This 2-bedroom, 1-bathroom gem offers the perfect blend of modern upgrades and timeless charm. Step inside to discover fresh finishes and an open layout, making this home warm and inviting. Enjoy cooking in the gourmet kitchen featuring stainless steel appliances, ample cabinet space, and sleek countertops. The cozy living spaces are perfect for relaxing or entertaining guests. The large fenced backyard for outdoor gatherings, or creating your dream garden. Prime location situated in a peaceful neighborhood, yet close to shopping, dining, and everything Annapolis has to offer. This home is ready for you to move in and start creating memories Schedule your showing today and make 122 Roselawn Road your new address!..

122 Roselawn Road, Annapolis

Listing courtesy of Simms and Associates. Contact:

Selling Office: .

$350,000
3 Beds ⋅ 2 Baths
+++ATTENTION ATTENTION+++ARE YOU LOOKING FOR A REHAB PROJECT?+++ THIS COULD BE THE ONE YOU HAVE BEEN WAITING FOR THEN!+++FULL PROJECT WAITING FOR YOU IN ANNAPOLIS+++MINUTES FROM DOWNTOWN ANNAPOLIS - KNOWN FOR IT'S MANY SELECTIONS OF RESTAURANTS , DIVERSE SHOPPING BOUTIQUES, AND NIGHTLIFE+++SHOPIING, SCHOOLS and PLACES OF WORSHIP NEARBY+++THIS 2 LEVEL SPLIT FOYER ALSO OFFERS AN INGROUND POOL+++KITCHEN ONLY HAS DATED CABINETS, NO appliances+++BATHROOMS ARE IN DISREPAIR, ALONG WITH SO MANY OTHER AREAS+++INVESTORS AND OWNER OCCUPANTS ARE WELCOME TO VIEW+++REAR DECK and DECK Steps are a HAZARD+++

391 Hilltop Lane, Annapolis

Listing courtesy of Taylor Properties. Contact:

Selling Office: .

$325,000
3 Beds ⋅ 1 Baths
Tucked away on a quiet street in an established neighborhood, this home is perfect for a first-time buyer, or downsizer looking for a place to make their own. Investors, this would be a wonderful rental property! The freshly painted living room and kitchen, along with new carpet and kitchen tile, provide a welcoming starting point while leaving room to add your personal style over time. Step outside and you’ll find a fully fenced, expansive backyard—ideal for outdoor play, summer cookouts, and relaxing evenings around the firepit. The built-in brick BBQ is ready for your next gathering. Conveniently located near Quiet Waters Park, local marinas, shopping, Pip Moyer Recreation Center, and historic downtown Annapolis, this home offers both comfort and opportunity in a location that’s hard to beat. Come take a look and imagine the possibilities!

120 Roselawn Road, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: .